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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
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