Supporting Information

Size: px
Start display at page:

Download "Supporting Information"

Transcription

1 Supporting Information Kamaly et al /pnas SI Materials and Methods Materials. Ac2-26 peptide (AMVSEFLKQAWFIENEEQEYV- QTVK) was purchased from Tocris Biosciences. Zymosan A was purchased from Sigma-Aldrich. Alexa Fluor 647 cadaverine (disodium salt) and FITC Annexin-V were purchased from Invitrogen. The Col IV-targeting peptide sequence (KLWVLPKGGGC) and the scrambled Ac2-26 peptide sequence (WLKQKFQESVE- QIAYVMENATEFEV) were purchased from Mimotopes. Carboxy-terminated poly(lactic-co-glycolic acid)-b-polyethyleneglycol (PLGA) [50:50 poly(dl-lactide-coglycolide) ( dl/g)] was purchased from Lactel Absorbable Polymers. The heterobifunctional PEG polymers NH 2 -PEG-COOH and HO-PEGmaleimide (molecular weight of 3,400) were purchased from Laysan Bio Inc. 1-Ethyl-3-(3 dimethylaminopropyl)carbodiimide hydrochloride (EDC), N-hydroxysuccinimide (NHS), N,N-diisopropylethylamine (DIEA), and all other solvents and chemicals were purchased from Sigma-Aldrich. 1 H NMR spectra were recorded on a Bruker AVANCED-400 NMR spectrometer. Ac2-26 quantification measurements were carried out on a Nanodrop UV- Vis spectrometer. Peptide-encapsulated NPs were prepared using the nanoprecipitation method. The NP sizes and ζ-potentials were obtained by quasi-electric laser light scattering using a ZetaPALS dynamic light-scattering detector (15 mw laser, incident beam 1/4 676 nm; Brookhaven Instruments). Electron microscopy (EM) was performed at the Harvard Medical School EM facility on a Tecnai G 2 Spirit BioTWIN EM. Synthesis of PLGA-PEG-COOH (1). Dry dichloromethane (DCM) (1 ml) was added to 50:50 poly(dl-lactide-coglycolide) ( dl/g) (100 mg, mmol), and to this was added EDC (4.41 mg, mmol) dissolved in dry DCM (0.5 ml), and the reaction was stirred for 10 min. Subsequently, NHS (2.65 mg, 0.023) was dissolved in dry DCM (0.5 ml) and added to the reaction, and the reaction was stirred at room temperature (RT) for 60 min. The solution was then added dropwise into MeOH (50 ml), the resultant precipitate was centrifuged (3,000 g for 5 min), the supernatant was decanted, and the pellet was dissolved in DCM (1 ml) and then further washed (two times). The pellet was then dried under vacuum for 90 min after which it was dissolved in dry CHCl 3 (1 ml). To this was added heterobifunctional NH 2 -PEG-COOH (9.52 mg, mmol) dissolved in dry CHCl 3 (0.5 ml), followed by the addition of DIEA (3.62 mg, mmol), and the reaction was stirred for 12 h at RT. The copolymer was then precipitated by dropwise addition into cold diethylether/methanol (15:35 ml) and centrifuged (3,000 g for 5 min). The supernatant was decanted, and the pellet redissolved in CHCl 3 (1 ml), precipitated, and washed further (three times) and dried under vacuum to yield 1 (yield 80%). Polymer characterization: 1 H NMR (400 MHz, CDCl 3 ): δ 5.22 (m, (-OCH(CH 3 ) CONH-)), 4.82 (m, (-OCH 2 COO-)), 3.63 (s, (-CH 2 CH 2 O-), 1.58 (d, (-OCH(CH 3 )CONH-) ppm. Synthesis of PLGA-PEG-Mal (2). The PLGA-PEG-COOH diblock polymer 1 (100 mg, mmol) was dissolved in DCM (1 ml); to this was added EDC (4.03 mg, mmol) in dry DCM (0.5 ml), and the reaction stirred for 10 min. Subsequently, NHS (2.42 mg, 0.021) was dissolved in dry DCM (0.5 ml) and added to the reaction. The reaction was left to stir at RT for 60 min. The solution was then added dropwise into MeOH (50 ml), the resultant precipitate was centrifuged (3,000 g for 5 min), the supernatant was decanted, and the pellet was dissolved in DCM (1 ml) and then further washed (two times). The pellet was then dried under vacuum for 90 min after which it was dissolved in dry CHCl 3 (1 ml). To this was then added heterobifunctional HO-PEG-maleimide (8.84 mg, mmol) dissolved in dry CHCl 3 (0.5 ml), followed by DIEA (3.36 mg, mmol), and the reaction was stirred for 12 h at RT. The copolymer was then precipitated by dropwise addition into cold diethylether/methanol (15:35 ml) and centrifuged (3,000 g for 5 min). The supernatant was decanted, and the pellet was redissolved in CHCl 3 (1 ml), precipitated and washed further (three times) and dried under vacuum to yield 2 (yield 65%). Polymer characterization: 1 H NMR (400 MHz, CDCl 3 ): δ 6.69 (-HC = CH-), 5.20 (m, (-OCH(CH 3 )COO-), 4.80 (m, (-OCH 2 COO-)), 4.27 (-NCH 2 CH 2 -), 3.64 (s, (-CH 2 CH 2 O-), 2.5 (-NCH 2 CH 2 -CONH-), 1.56 (-OCH(CH 3 )CONH-) ppm. Synthesis of PLGA-PEG-Col IV Targeting Polymer (3). To the synthesized PLGA-PEG-Mal 2 (81.7 mg, mmol) dissolved in dry DMF (1 ml) was added the Col IV-targeting peptide sequence (H-KLWVLPKGGGC-NH 2, 2.36 mg, mmol) that was previously dissolved in dry DMF (1 ml). To this was added Et 3 N (2.31 mg, mmol), and the reaction was stirred at RT for 24 h. The solution was then added dropwise into cold MeOH (100 ml), and the resultant precipitate was centrifuged (3,000 g for 5 min), the supernatant decanted, and the pellet was further washed (three times). The pellet was then dried under vacuum to yield 3 (yield 67%). Polymer characterization: 1 H NMR (400 MHz, CDCl 3 ): δ PLGA-PEG-Mal: 5.21 (m, (-OCH(CH 3 )COO-)), 4.82 (m, (-OCH 2 COO-)), 4.29 (-NCH 2 CH 2 -), 3.64 (s, (-CH 2 CH 2 O-), 1.58 (-OCH(CH 3 )CONH-), peptide peaks: 8.02 (sharp s), 7.52, (s) (m), (m), (m), 4.99 (s), (m), 4.30 (m), (m), 2.17 (s), (m), (m), (m) ppm. Synthesis of PLGA-Alexa 647 (4). Dry DCM (1 ml) was added to 50:50 Poly(DL-lactide-coglycolide) ( dl/g) (100 mg, mmol); to this was added EDC (4.41 mg, mmol) in dry DCM (0.5 ml), and the reaction was stirred for 10 min. Subsequently, NHS (2.65 mg, 0.023) was dissolved in dry DCM (0.5 ml) and added. The reaction was stirred at RT for 60 min. The PLGA-NHS activated polymer was precipitated with 20 ml of cold 1:1 MeOH/Et 2 O mixture and centrifuged at 2,700 g for 10 min to remove residual EDC/NHS. The washing and centrifugation steps were repeated twice, and the polymer was then dried under vacuum for 90 min to remove residual solvents. After drying, PLGA-NHS was dissolved in DCM (1 ml) followed by the addition of Alexa 647 cadaverine (3.50 mg, mmol) dissolved in dry DCM (0.5 ml), followed by the addition of DIEA (3.62 mg, mmol), and the reaction was stirred for 12 h at RT. The polymer was then precipitated with 20 ml of cold 1:1 MeOH/ Et 2 O mixture and centrifuged at 2,700 g for 10 min. The washing was repeated twice more, and the product dried under vacuum (to obtain a blue polymer compound). The supernatant was decanted, and the pellet was redissolved in CHCl 3, precipitated, washed further (three times), and dried under vacuum to yield 4 (yield 95%). Polymer characterization: 1 H NMR (400 MHz, CDCl 3 ): δ PLGA peaks: 5.21 (m, (-OCH(CH 3 )CONH-)), 4.83 (m, (-OCH 2 COO-)), 1.59 (d, (-OCH(CH 3 )CONH-) ppm. 1of5

2 Fig. S1. Schematic of polymer synthesis. The diblock PLGA-PEG polymer was synthesized by first activating the carboxy distal end of 50:50 poly(dl-lactidecoglycolide) ( dl/g) with EDC and NHS conjugation crosslinkers in DCM, followed by conjugation with the heterobifunctional NH 2 -PEG-COOH in the presence of DIEA. The copolymer was then precipitated and washed with diethylether/methanol and dried under vacuum to yield 1. The Col IV peptideconjugated targeting polymer (PLGA-PEG-Col IV) was synthesized by initially coupling the heterobifunctional HO-PEG-maleimide to PLGA to form an ester bond. The polymer was then precipitated and washed with diethylether/methanol and dried under vacuum to yield 2. PLGA-PEG-Mal (2) was then conjugated to the free thiol on the cysteine of the KLWVLPKGGC peptide sequence via thiol-maleimide chemistry in DMF with triethylamine (Et 3 N) and subsequently precipitated and washed with cold methanol to yield 3. The diblock PLGA-Alexa 647 was synthesized by conjugating Alexa 647 cadaverine to poly(dl-lactidecoglycolide under conditions similar to those used to synthesize 1. 2of5

3 Fig. S2. Synthesis scheme for PLGA-PEG-COOH and associated 1 H NMR (chemical shifts of residual diethyl ether solvent are shown in gray, 7.26; CDCl 3 ). 3of5

4 Fig. S3. Synthesis of PLGA-PEG-Mal and associated 1 H NMR spectrum (chemical shifts of residual diethyl ether solvent are shown in gray) 4of5

5 Fig. S4. Synthesis of PLGA-PEG-Col IV targeting polymer and associated 1 H NMR. Enlarged area shows aromatic peaks corresponding to the tryptophan side chain of the conjugated peptide sequence. Fig. S5. Synthesis scheme for PLGA-Alexa 647 polymer. (Note: the Alexa 647 structure is proprietary.) 5of5

A supramolecular approach for fabrication of photo- responsive block-controllable supramolecular polymers

A supramolecular approach for fabrication of photo- responsive block-controllable supramolecular polymers Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information A supramolecular approach for fabrication of photo- responsive

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of Poly(dihydroxystyrene-block-styrene) (PDHSt-b-PSt) by the RAFT

More information

Supporting Information

Supporting Information Supporting Information of Appointed exploding microcapsules as drug carriers By Jing Zhang, Cao Li, Ya Wang, Ren-Xi Zhuo and Xian-Zheng Zhang * Materials Propargyl alcohol (PA-OH), dextran (M w ~20 k &

More information

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL

More information

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated

More information

Self-Assembly of Single Amino acid-pyrene Conjugates with Unique Structure-Morphology Relationship

Self-Assembly of Single Amino acid-pyrene Conjugates with Unique Structure-Morphology Relationship Electronic Supplementary Material (ESI) for Soft Matter. This journal is The Royal Society of Chemistry 2017 Self-Assembly of Single Amino acid-pyrene Conjugates with Unique Structure-Morphology Relationship

More information

Supporting Information

Supporting Information Supporting Information Syntheses and characterizations: Compound 1 was synthesized according to Scheme S-1. Scheme S-1 2 N N 5 i N 4 P Et Et iii N 6 ii P Et Et iv v, vi N N i) Fmoc-Su, DIPEA, Acetone;

More information

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow

More information

Supporting Information

Supporting Information Supporting Information Tuning Supramolecular Structure and Functions of Peptide bola-amphiphile by Solvent Evaporation-Dissolution Anhe Wang,, Lingyun Cui,, Sisir Debnath, Qianqian Dong, Xuehai Yan, Xi

More information

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 2. A solution of Rhodamine B (14.2 g, 30.0 mmol) in CH 2 Cl 2 (40 ml) was treated with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 g, 30.0 mmol) and TEA (4.21 ml, 3.03 g, 30.0

More information

Supporting information. Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor

Supporting information. Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor Supporting information Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor Toni Mäkelä, a Elina Kalenius a and Kari Rissanen a* a University of Jyvaskyla, Department of Chemistry, Nanoscience

More information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for

More information

Revisiting the complexation between DNA and polyethylenimine when and where S S linked PEI is cleaved inside the cell

Revisiting the complexation between DNA and polyethylenimine when and where S S linked PEI is cleaved inside the cell Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B. This journal is The Royal Society of Chemistry 214 Revisiting the complexation between DNA and polyethylenimine when and where

More information

Supplementary Information. Rational Design of Soluble and Clickable Polymers Prepared by. Conventional Free Radical Polymerization of

Supplementary Information. Rational Design of Soluble and Clickable Polymers Prepared by. Conventional Free Radical Polymerization of Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Supplementary Information Rational Design of Soluble and Clickable Polymers Prepared by

More information

Supporting Information

Supporting Information Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,

More information

Supporting Information

Supporting Information Supporting Information UCST or LCST? Composition-Dependent Thermoresponsive Behavior of Poly(N-Acryloylglycinamide-co-Diacetone Acrylamide) Wenhui Sun, Zesheng An*, Peiyi Wu * Experimental Materials Glycinamide

More information

Magnetic nanoparticle-supported proline as a recyclable and recoverable ligand for the CuI catalyzed arylation of nitrogen nucleophiles

Magnetic nanoparticle-supported proline as a recyclable and recoverable ligand for the CuI catalyzed arylation of nitrogen nucleophiles Magnetic nanoparticle-supported proline as a recyclable and recoverable ligand for the CuI catalyzed arylation of nitrogen nucleophiles Gagan Chouhan, Dashan Wang and Howard Alper* Centre for Catalysis

More information

Supplementary Information. "On-demand" control of thermoresponsive properties of poly(n-isopropylacrylamide) with cucurbit[8]uril host-guest complexes

Supplementary Information. On-demand control of thermoresponsive properties of poly(n-isopropylacrylamide) with cucurbit[8]uril host-guest complexes upplementary Information "n-demand" control of thermoresponsive properties of poly(n-isopropylacrylamide) with cucurbit[8]uril host-guest complexes Urs Rauwald, Jesús del Barrio, Xian Jun Loh, and ren

More information

O-Allylation of phenols with allylic acetates in aqueous medium using a magnetically separable catalytic system

O-Allylation of phenols with allylic acetates in aqueous medium using a magnetically separable catalytic system Supporting information for -Allylation of phenols with allylic acetates in aqueous medium using a magnetically separable catalytic system Amit Saha, John Leazer* and Rajender S. Varma* Sustainable Technology

More information

Ring-Opening Polymerization of N-Carboxyanhydrides Initiated by a Hydroxyl Group

Ring-Opening Polymerization of N-Carboxyanhydrides Initiated by a Hydroxyl Group SUPPRTING INFRMATIN Ring-pening Polymerization of N-Carboxyanhydrides Initiated by a Hydroxyl Group Špela Gradišar, Ema Žagar, and David Pahovnik* National Institute of Chemistry, Department of Polymer

More information

Supporting Information

Supporting Information Supporting Information Synthesis of a new class of ribose functionalized dinucleotide cap analogues for biophysical studies on interaction of cap-binding proteins with the 5 end of mrna. Karolina Piecyk,

More information

Supplementary Information

Supplementary Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary Information A Novel Single-Side Azobenzene-Grafted Anderson-Type Polyoxometalate

More information

Synthesis of Peptide-Grafted Comb Polypeptides via Polymerisation of NCA-Peptides

Synthesis of Peptide-Grafted Comb Polypeptides via Polymerisation of NCA-Peptides Supporting Information to Synthesis of Peptide-Grafted Comb Polypeptides via Polymerisation of NCA-Peptides Hiroshi Enomoto, Benjamin Nottelet, Soultan Al Halifa, Christine Enjalbal, Mathieu Dupré, Julien

More information

Development and Validation of a Fluorescence Method to. Follow the Build-up of Short Peptide Sequences on Solid. 2D Surfaces

Development and Validation of a Fluorescence Method to. Follow the Build-up of Short Peptide Sequences on Solid. 2D Surfaces Supporting Information for Development and Validation of a Fluorescence Method to Follow the Build-up of Short Peptide Sequences on Solid 2D Surfaces Mischa Zelzer a* David J. Scurr, Morgan R. Alexander,

More information

Supplementary Material:

Supplementary Material: Supplementary Material: Water soluble amphiphilic gold nanoparticles with structured ligand shells Oktay Uzun, Ying Hu, Ayush Verma, Suelin Chen, Andrea Centrone, and Francesco Stellacci* Department of

More information

Highly efficient P-N nickel(ii) complexes for the dimerisation of ethylene

Highly efficient P-N nickel(ii) complexes for the dimerisation of ethylene Highly efficient P-N nickel(ii) complexes for the dimerisation of ethylene Antoine Buchard, Audrey Auffrant, Christian Klemps, Laurence Vu-Do, Leïla Boubekeur, Xavier F. Le Goff and Pascal Le Floch* Laboratoire

More information

Hyperbranched Poly(N-(2-Hydroxypropyl) Methacrylamide) via RAFT Self- Condensing Vinyl Polymerization

Hyperbranched Poly(N-(2-Hydroxypropyl) Methacrylamide) via RAFT Self- Condensing Vinyl Polymerization Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2016 Hyperbranched Poly(N-(2-Hydroxypropyl) Methacrylamide) via RAFT Self- Condensing Vinyl

More information

Amphiphilic diselenide-containing supramolecular polymers

Amphiphilic diselenide-containing supramolecular polymers Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2014 Amphiphilic diselenide-containing supramolecular polymers Xinxin Tan, Liulin Yang, Zehuan

More information

Supporting Information for. PNA FRET Pair Miniprobes for Quantitative. Fluorescent in Situ Hybridization to Telomeric DNA in Cells and Tissue

Supporting Information for. PNA FRET Pair Miniprobes for Quantitative. Fluorescent in Situ Hybridization to Telomeric DNA in Cells and Tissue Supporting Information for PNA FRET Pair Miniprobes for Quantitative Fluorescent in Situ Hybridization to Telomeric DNA in Cells and Tissue Orenstein, et al Page S2... PNA synthesis procedure Page S3...

More information

ESI. Core-Shell Polymer Nanoparticles for Prevention of GSH Drug Detoxification and Cisplatin Delivery to Breast Cancer Cells

ESI. Core-Shell Polymer Nanoparticles for Prevention of GSH Drug Detoxification and Cisplatin Delivery to Breast Cancer Cells Electronic Supplementary Material (ESI) for Nanoscale. This journal is The Royal Society of Chemistry 2015 ESI Core-Shell Polymer Nanoparticles for Prevention of GSH Drug Detoxification and Cisplatin Delivery

More information

Self-Healing Polymers with PEG Oligomer Side Chains. Based on Multiple H-Bonding and Adhesion Properties

Self-Healing Polymers with PEG Oligomer Side Chains. Based on Multiple H-Bonding and Adhesion Properties Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Self-Healing Polymers with PEG Oligomer Side Chains Based on Multiple

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION DOI: 10.1038/NCHEM.2201 Highly emissive platinum(ii) metallacages Xuzhou Yan, 1 Timothy R. Cook, 2 Pi Wang, 1 Feihe Huang,,1 and Peter J. Stang,3 1 Center for Chemistry of High-Performance & Novel Materials,

More information

Acid-Base Bifunctional Shell Cross-Linked Micelle Nanoreactor for One-pot Tandem Reaction

Acid-Base Bifunctional Shell Cross-Linked Micelle Nanoreactor for One-pot Tandem Reaction Supporting Information Acid-Base Bifunctional Shell Cross-Linked Micelle Nanoreactor for One-pot Tandem Reaction Li-Chen Lee, a# Jie Lu, b# Marcus Weck, b * Christopher W. Jones a * a School of Chemical

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Nanoparticle-to-vesicle and nanoparticle-to-toroid transitions of ph-sensitive

More information

Electronic Supplementary Information for New Journal of Chemistry

Electronic Supplementary Information for New Journal of Chemistry Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015 Electronic Supplementary Information

More information

Supporting Information

Supporting Information Supporting Information Precision Synthesis of Poly(-hexylpyrrole) and its Diblock Copolymer with Poly(p-phenylene) via Catalyst-Transfer Polycondensation Akihiro Yokoyama, Akira Kato, Ryo Miyakoshi, and

More information

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

Electronic Supplementary Material

Electronic Supplementary Material Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly

More information

Vitamin E-Labeled Polyethylenimine for in vitro and in vivo Gene Delivery

Vitamin E-Labeled Polyethylenimine for in vitro and in vivo Gene Delivery Supporting Information Vitamin E-Labeled Polyethylenimine for in vitro and in vivo Gene Delivery Jinxing Liu, Mengke Feng, Duanwei Liang, Jiali Yang, Xinjing Tang* State Key Laboratory of Natural and Biomimetic

More information

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide 217 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide O O Cl NH 3 NH 2 C 9 H 7 ClO (166.6) (17.) C 9 H 9 NO (147.2) Classification Reaction types and substance classes reaction of

More information

Supporting information

Supporting information Supporting information Imidazolium end-functionalized poly(l-lactide) for Efficient Carbon Nanotube Dispersion. Franck Meyer, a Jean-Marie Raquez, a Olivier Coulembier, a Julien De Winter, b Pascal Gerbaux,

More information

Synthesis of 2 ) Structures by Small Molecule-Assisted Nucleation for Plasmon-Enhanced Photocatalytic Activity

Synthesis of 2 ) Structures by Small Molecule-Assisted Nucleation for Plasmon-Enhanced Photocatalytic Activity Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Synthesis of Au@UiO-66(NH 2 ) Structures by Small Molecule-Assisted

More information

Supporting Information. Surface Functionalized Polystyrene Latexes using Itaconate based Surfmers

Supporting Information. Surface Functionalized Polystyrene Latexes using Itaconate based Surfmers Supporting Information Surface Functionalized Polystyrene Latexes using Itaconate based Surfmers Saheli Chakraborty and S Ramakrishnan* Department of Inorganic and Physical Chemistry Indian Institute of

More information

Experimental Section

Experimental Section White Light Emitting Lanthanide Metallogels with Tunable Luminescence and Reversible Stimuli-Responsive Properties Pangkuan Chen, Qiaochu Li, Scott Grindy, and Niels Holten-Andersen* Department of Materials

More information

HIV anti-latency treatment mediated by macromolecular prodrugs of histone deacetylase inhibitor, panobinostat

HIV anti-latency treatment mediated by macromolecular prodrugs of histone deacetylase inhibitor, panobinostat Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 206 Supporting information HIV anti-latency treatment mediated by macromolecular prodrugs of

More information

Electronic Supplementary Information. Jiani Wang, Lei Zhang, Qiong Qi, Shunhua Li* and Yunbao Jiang

Electronic Supplementary Information. Jiani Wang, Lei Zhang, Qiong Qi, Shunhua Li* and Yunbao Jiang Electronic Supplementary Information Specific ratiometric fluorescent sensing of Hg 2+ via the formation of mercury(ii) barbiturate coordination polymers Jiani Wang, Lei Zhang, Qiong Qi, Shunhua Li* and

More information

Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril

Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril SUPPORTING INFORMATION Drastically Decreased Reactivity of Thiols and Disulfides Complexed by Cucurbit[6]uril Lidia Strimbu Berbeci, Wei Wang and Angel E. Kaifer* Center for Supramolecular Science and

More information

An efficient one pot ipso-nitration: Structural transformation of a dipeptide by N-terminus modification

An efficient one pot ipso-nitration: Structural transformation of a dipeptide by N-terminus modification Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supporting information An efficient one pot ipso-nitration: Structural transformation of a

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using

More information

Aziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine

Aziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information (ESI) Aziridine in Polymers: A Strategy to Functionalize

More information

Supplementary Information

Supplementary Information Supplementary Information (1) Synthesis and Characterization Figure S1. 1 H-NMR of 3 (400 MHz; CDCl3; rt). Figure S2. 13 C-NMR of 3 (100 MHz; CDCl3; rt). S2 8000 7500 7000 6500 6000 5500 5000 4500 4000

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION DOI: 10.1038/NCHEM.2303 Light-controlled self-assembly of non-photoresponsive nanoparticles Pintu K. Kundu, 1 Dipak Samanta, 1 Ron Leizrowice, 1,2 Baruch Margulis, 1,3 Hui Zhao, 1 Martin Börner, 1,4 T.

More information

Electronic Supporting Information for

Electronic Supporting Information for Electronic Supporting Information for An efficient long fluorescence lifetime polymer-based sensor based on europium complex as chromophore for the specific detection of F -, CH 3 COO - -, and H 2 PO 4

More information

Tunable Visible Light Emission of Self-Assembled Rhomboidal Metallacycles

Tunable Visible Light Emission of Self-Assembled Rhomboidal Metallacycles Tunable Visible Light Emission of Self-Assembled Rhomboidal Metallacycles J. Bryant Pollock,* Gregory L. Schneider, Timothy R. Cook, Andrew S. Davies, Peter J. Stang* Department of Chemistry, University

More information

Thiol-reactive amphiphilic block copolymer for coating gold nanoparticles with neutral and functionable surfaces

Thiol-reactive amphiphilic block copolymer for coating gold nanoparticles with neutral and functionable surfaces Supporting information for: Thiol-reactive amphiphilic block copolymer for coating gold nanoparticles with neutral and functionable surfaces Hongwei Chen 1,*, Hao Zou 1,2, Hayley J. Paholak 1, Masayuki

More information

Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex

Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition

More information

Supporting Information for: End-capping ROMP Polymers with Vinyl. Lactones

Supporting Information for: End-capping ROMP Polymers with Vinyl. Lactones Supporting Information for: End-capping RMP Polymers with Vinyl Lactones Stefan Hilf, Robert H. Grubbs and Andreas F.M. Kilbinger * Institut für rganische Chemie, Johannes Gutenberg-Universität Mainz,

More information

A Thermoregulated Phase-Separable Chiral Pt Nanocatalyst for Recyclable Asymmetric Hydrogenation of α-ketoesters

A Thermoregulated Phase-Separable Chiral Pt Nanocatalyst for Recyclable Asymmetric Hydrogenation of α-ketoesters Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information (ESI) for A Thermoregulated Phase-Separable Chiral Pt Nanocatalyst

More information

4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester

4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester NP 4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester NaEt C 10 H 18 4 Na C 2 H 6 C 8 H 12 3 (202.2) (23.0) (46.1) (156.2) Classification Reaction types and substance

More information

One-pot synthesis of dual functional peptides by Sortase A-mediated on-resin cleavage and ligation

One-pot synthesis of dual functional peptides by Sortase A-mediated on-resin cleavage and ligation Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 One-pot synthesis of dual functional peptides by Sortase A-mediated on-resin cleavage

More information

A Poly(ethylene glycol)-supported Quaternary Ammonium Salt: An Efficient, Recoverable, and Recyclable Phase-Transfer Catalyst

A Poly(ethylene glycol)-supported Quaternary Ammonium Salt: An Efficient, Recoverable, and Recyclable Phase-Transfer Catalyst Supplementary Information for A Poly(ethylene glycol)-supported Quaternary Ammonium Salt: An Efficient, Recoverable, and Recyclable Phase-Transfer Catalyst Rita Annunziata, Maurizio Benaglia, Mauro Cinquini,

More information

Supporting information

Supporting information Supporting information Temperature and ph-dual Responsive AIE-Active Core Crosslinked Polyethylene Poly(methacrylic acid) Multimiktoarm Star Copolymers ` Zhen Zhang,*,, and Nikos Hadjichristidis*, School

More information

Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property

Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property Supporting Information for: Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property Wen-Bin Jia, Hao-Wei Wang, Long-Mei Yang, Hong-Bo Lu, Lin Kong, Yu-Peng

More information

Supporting information

Supporting information Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2015 Supporting information Porosity induced emission: exploring color-controllable

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,

More information

Selective total encapsulation of the sulfate anion by neutral nano-jars

Selective total encapsulation of the sulfate anion by neutral nano-jars Supporting Information for Selective total encapsulation of the sulfate anion by neutral nano-jars Isurika R. Fernando, Stuart A. Surmann, Alexander A. Urech, Alexander M. Poulsen and Gellert Mezei* Department

More information

Supporting Information

Supporting Information Supporting Information Azo Polymer Janus Particles and Their Photoinduced Symmetry-Breaking Deformation Xinran Zhou, Yi Du, Xiaogong Wang* Department of Chemical Engineering, Laboratory of Advanced Materials

More information

Chemical synthesis (see also reaction scheme, bold underlined numbers in this text refer to the bold underlined numbers in the scheme)

Chemical synthesis (see also reaction scheme, bold underlined numbers in this text refer to the bold underlined numbers in the scheme) Supplementary Note This section contains a detailed description of the chemical procedures and the characterization of products. The text is followed by a reaction scheme explaining the synthetic strategies

More information

Supporting Information for Polybenzimidazolium Salts: A New Class of. Anion-Conducting Polymer

Supporting Information for Polybenzimidazolium Salts: A New Class of. Anion-Conducting Polymer Supporting Information for Polybenzimidazolium Salts: A ew Class of Anion-Conducting Polymer Owen D. Thomas, Kristen J. W. Y. Soo, Timothy J. Peckham, Mahesh P. Kulkarni and Steven Holdcroft* Department

More information

Supporting Information. Self-assembled nanofibers from Leucine Derived Amphiphiles as Nanoreactors for Growth of ZnO Nanoparticles

Supporting Information. Self-assembled nanofibers from Leucine Derived Amphiphiles as Nanoreactors for Growth of ZnO Nanoparticles Supporting Information Self-assembled nanofibers from Leucine Derived Amphiphiles as Nanoreactors for Growth of ZnO Nanoparticles Karen T. Johnson, Theodore E. Gribb, Evan M. Smoak, and Ipsita A. Banerjee*

More information

Supporting Information

Supporting Information Supporting Information Responsive Prodrug Self-Assembled Vesicles for Targeted Chemotherapy in Combination with Intracellular Imaging Hongzhong Chen, Huijun Phoebe Tham,, Chung Yen Ang, Qiuyu Qu, Lingzhi

More information

Supramolecular hydrogen-bonded photodriven actuators based on an azobenzenecontaining

Supramolecular hydrogen-bonded photodriven actuators based on an azobenzenecontaining Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2017 Supporting Information Supramolecular hydrogen-bonded photodriven actuators

More information

1,1,3,3-Tetramethylguanidine-Promoted Ring-Opening Polymerization of N-Butyl N-Carboxyanhydride Using Alcohol Initiators

1,1,3,3-Tetramethylguanidine-Promoted Ring-Opening Polymerization of N-Butyl N-Carboxyanhydride Using Alcohol Initiators Supporting Information 1,1,3,3-Tetramethylguanidine-Promoted Ring-Opening Polymerization of N-Butyl N-Carboxyanhydride Using Alcohol Initiators Brandon A. Chan, Sunting Xuan, Matthew Horton, and Donghui

More information

Supporting Information

Supporting Information Supporting Information Incorporation of a Sugar Unit into a C C N Pincer Pd Complex Using Click Chemistry and Its Dynamic Behavior in Solution and Catalytic Ability toward the Suzuki Miyaura Coupling in

More information

Supporting Information. Solid-Phase Synthesis of Symmetrical 5,5 -Dinucleoside Mono-, Di-, Tri-, and Tetraphosphodiesters

Supporting Information. Solid-Phase Synthesis of Symmetrical 5,5 -Dinucleoside Mono-, Di-, Tri-, and Tetraphosphodiesters Supporting Information S1 Solid-Phase Synthesis of Symmetrical 5,5 -Dinucleoside Mono-, Di-, Tri-, and Tetraphosphodiesters Yousef Ahmadibeni and Keykavous Parang* Department of Biomedical and Pharmaceutical

More information

A "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media

A turn-on coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media A "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media Styliani Voutsadaki, George K. Tsikalas, Emmanuel Klontzas, George E. Froudakis, and Haralambos E.

More information

Hydrophobic Ionic Liquids with Strongly Coordinating Anions

Hydrophobic Ionic Liquids with Strongly Coordinating Anions Supporting material Hydrophobic Ionic Liquids with Strongly Coordinating Anions Hasan Mehdi, Koen Binnemans*, Kristof Van Hecke, Luc Van Meervelt, Peter Nockemann* Experimental details: General techniques.

More information

Functionalization of the Aryl Moiety in the Pincer Complex. (NCN)Ni III Br 2 :

Functionalization of the Aryl Moiety in the Pincer Complex. (NCN)Ni III Br 2 : Electronic Supporting Information For : Functionalization of the Aryl Moiety in the Pincer Complex (NCN)Ni III Br 2 : Insights on Ni III -Promoted Carbon-Heteroatom Coupling Jean-Philippe Cloutier and

More information

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information A synthetic strategy for the preparation of sub-100nm functional

More information

Electronic Supplementary Information. Selective detection of Al 3+ and citric acid with a fluorescent amphiphile

Electronic Supplementary Information. Selective detection of Al 3+ and citric acid with a fluorescent amphiphile Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Selective detection of Al 3+ and citric

More information

Multifunctional silica nanoparticles modified via silylateddecaborate

Multifunctional silica nanoparticles modified via silylateddecaborate Supporting information Multifunctional silica nanoparticles modified via silylateddecaborate precursors Fatima Abi-Ghaida, [a,b,c] Sébastien Clément, [a] Ali Safa, [b] Daoud Naoufal* [b,c] and Ahmad Mehdi*

More information

Tunable thermo-responsive water-dispersed multi walled. carbon nanotubes

Tunable thermo-responsive water-dispersed multi walled. carbon nanotubes Tunable thermo-responsive water-dispersed multi walled carbon nanotubes Gaojian Chen, Peter M. Wright, Jin Geng, Giuseppe Mantovani, and David M. Haddleton* Department of Chemistry, University of Warwick,

More information

Synthesis and characterization of innovative well-defined difluorophosphonylated-(co)polymers by RAFT polymerization

Synthesis and characterization of innovative well-defined difluorophosphonylated-(co)polymers by RAFT polymerization Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 205 Supporting Information Synthesis and characterization of innovative well-defined difluorophosphonylated-(co)polymers

More information

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde

More information

Supporting Information

Supporting Information Supporting Information Microcapsules with three orthogonal reactive sites Brian P. Mason, Steven M. Hira, Geoffrey F. Strouse, D. Tyler McQuade*, Department of Chemistry and Chemical Biology, Cornell University,

More information

Supporting Information Solid Phase Synthesis of Ultra-Photostable Cyanine NIR dye library

Supporting Information Solid Phase Synthesis of Ultra-Photostable Cyanine NIR dye library Supporting Information Solid Phase Synthesis of Ultra-Photostable Cyanine IR dye library Raj Kumar Das, a Animesh Samanta, a Hyung-Ho Ha, b and Young-Tae Chang a,c * a Department of Chemistry & MedChem

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some

More information

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 S1 Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 David Bézier, Sehoon Park and Maurice Brookhart* Department of Chemistry, University of North Carolina at Chapel Hill,

More information

Supporting Information for

Supporting Information for Supporting Information for Visible-Light Induced Thiol Ene Reaction on Natural Lignin Hailing Liu and Hoyong Chung * Department of Chemical and Biomedical Engineering, Florida State University, Tallahassee,

More information

Absorbance (a. u.) Wavelength (nm) Wavelength (nm) Intensity (a. u.) Wavelength (nm) Wavelength (nm)

Absorbance (a. u.) Wavelength (nm) Wavelength (nm) Intensity (a. u.) Wavelength (nm) Wavelength (nm) Intensity (a. u.) Absorbance (a. u.) a UV UV b Wavelength (nm) Wavelength (nm) UV UV Wavelength (nm) Wavelength (nm) Supplementary Figure 1. UV-Vis absorbance spectral changes of (a) SP-Gal (left, 10 μm),

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Content Synthesis of compounds 2a, 2b in Scheme

More information

A novel smart polymer responsive to CO 2

A novel smart polymer responsive to CO 2 A novel smart polymer responsive to CO 2 Zanru Guo, a,b Yujun Feng,* a Yu Wang, a Jiyu Wang, a,b Yufeng Wu, a,b and Yongmin Zhang a,b a Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences,

More information

Organized polymeric submicron particles via selfassembly. and crosslinking of double hydrophilic. poly(ethylene oxide)-b-poly(n-vinylpyrrolidone) in

Organized polymeric submicron particles via selfassembly. and crosslinking of double hydrophilic. poly(ethylene oxide)-b-poly(n-vinylpyrrolidone) in Supporting Information Organized polymeric submicron particles via selfassembly and crosslinking of double hydrophilic poly(ethylene oxide)-b-poly(n-vinylpyrrolidone) in aqueous solution Jochen Willersinn,

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION doi:10.1038/nature16966 Supplementary Synthetic Protocols General Solvents and chemicals were of analytical grade and were purchased from Sigma- Aldrich. Inorganic pyrophosphatase from baker's yeast and

More information

In-situ polymerization of a novel surfactant on graphene surface for the

In-situ polymerization of a novel surfactant on graphene surface for the Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information In-situ polymerization of a novel surfactant on graphene

More information

Supporting Information

Supporting Information Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,

More information

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and

More information

Chemically recyclable alternating copolymers with low polydispersity from

Chemically recyclable alternating copolymers with low polydispersity from Electronic Supplementary Information Chemically recyclable alternating copolymers with low polydispersity from conjugated/aromatic aldehydes with vinyl ethers: selective degradation to another monomer

More information

Facile Synthesis and Optical Properties of Colloidal Silica Microspheres Encapsulating Quantum Dots-Layer

Facile Synthesis and Optical Properties of Colloidal Silica Microspheres Encapsulating Quantum Dots-Layer Electronic Supplementary Information for: Facile Synthesis and Optical Properties of Colloidal Silica Microspheres Encapsulating Quantum Dots-Layer Myungje Cho, Kipil Lim, Kyoungja Woo* Nano-Materials

More information