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1 upporting Informtion Wiley-VCH Weinheim, Germny Reversibly tbilized Multifunctionl Dextrn Nnoprticles Efficiently Deliver Doxorubicin into the Nuclei of Cncer Cells** Yu-Ling Li, Li Zhu, Zhozhong Liu, Ru Cheng, Fenghu Meng,* Jing-Ho Cui, hun-jun Ji, nd Zhiyun Zhong* nie_ _sm_miscellneous_informtion.pdf
2 Mterils nd Methods 1. Mterils Dextrn (20 kd, Fluk) ws dried by zeotropic distilltion from nhydrous toluene. 1,4-dithio-D, L-threitol (DTT, 99%, Merck), lipoic cid (98%, Acros), N, N-dicyclohexylcrbodiimide (DCC, 99 %, Alf Aesr), 4-(dimethylmino)pyridine (DMAP, 99 %, Alf Aesr), nd doxorubicin hydrochloride (DX HCl, 99%, Beijing Zhonghuo Phrmceuticl Technology Development Co.,Ltd.) were used s received. Lipoic cid nhydride ws synthesized ccording to previous reports (A. downik, J. tefely,. L. Regen, J. Am. Chem. oc. 1986, 108, 7789; J. tefely, M. A. Mrkowitz,. L. Regen, J. Am. Chem. oc. 1988, 110, 7463).. 2. Chrcteriztion The 1 H NMR spectr were recorded on Unity Inov 400 spectrometer operting t 400 MHz using deuterted dimethyl sulfoxide (DM-d 6 ). The size nd zet-potentil of nnoprticles were determined using Zetsizer Nno-Z from Mlvern Instruments. The nnoprticles were prepred t polymer concentrtion of 0.2 mg/ml in PB (10 mm, ph 7.4) nd filtered through 450 nm syringe filter before mesurements. The mesurements were crried out t 25 or 37 C in PB (10 mm, ph 7.4). The fluorescence mesurements of DX were performed using n EDINBURGH FL920 spectrofluorometer. Excittion nd emission were set t 480 nd 555 nm, respectively, with bndwidths of 5 nm. 3. ynthesis of Dex-LA conjugtes To dextrn (0.25 g, 1.55 mmol AHG) solution in DM (19 ml, concentrtion of AHG is 0.08 M), were dded 4-(dimethylmino) pyridine (0.15 g, 1.21 mmol) solution in DM (2 ml) nd lipoic cid nhydride (0.48 g, 1.21 mmol) in DM (2 ml), respectively. The rection ws stirred for 48 h under nitrogen t 30 C. The product ws isolted by precipittion in cold ethnol, wshed severl times with ethnol, nd dried in vcuo. Yield: 77 %. D: H-NMR (DM-d 6 ): (m, 6 H, CH 2 CH 2 CH 2 -lipoic ring), (m, 1 H, CH 2 CH 2 CH), 2.33 (s, 2 H, CH 2 C), (m, 1 H, CH 2 CH 2 CH), (m, 2 H, CH 2 CH 2 CH), (m, dextrn glucosidic protons nd CH 2 CH 2 CH), 4.41, 4.77, 4.85, 5.12 (s, hydroxyl of dextrn), 4.68 (s, dextrn nomeric protons), (m, 1 H, dextrn glucosidic protons linked to lipoyl group). Dex-LA conjugtes with vrying degrees of substitution were obtined by using different molr rtios of lipoic cid nhydride to AHG of dextrn (rtios were 0.5, 0.8, nd 1.0). 4. Preprtion of nnoprticle nd criticl ggregtion concentrtion (CAC) Dex-LA nnoprticles were prepred by solvent exchnge method. Briefly, to 1 ml of 0.2 wt./v. % Dex-LA solution in DM, ws dded dropwise 5 ml of distilled wter under moderte stirring t 25 C. The resulting Dex-LA nnoprticle suspension ws extensively dilyzed ginst distilled wter nd 10 mm PB (PECTRA/PR, MWC 3500). 2
3 The criticl ggregtion concentrtion (CAC) ws determined using pyrene s fluorescence probe. The concentrtion of polymer ws vried from to 0.2 mg/ml nd the concentrtion of pyrene ws fixed t 0.6 M. The fluorescence spectr were recorded using FL920 fluorescence spectrometer with the excittion wvelength of 330 nm. The emission fluorescence t 372 nd 383 nm were monitored. The CAC ws estimted s the cross-point when extrpolting the intensity rtio I 372 /I 383 t low nd high concentrtion regions. 5. Crosslinking nd de-crosslinking of nnoprticles The ph of bove-prepred nnoprticles solution ws djusted to 8.5 using 0.7 M borte buffer (ph = 9.0), nd the dispersion ws purged with nitrogen for 10 min. The crosslinking ws initited by dding 10 mol % DTT reltive to the mount of lipoyl units under nitrogen t room temperture. After stirring for 22 hrs, nnoprticle solution ws dilyzed ginst distilled wter for 1 dy. The de-crosslinking of crosslinked nnoprticles in response to reductive environment ws studied using DL. Under N 2 tmosphere, predetermined mount of DTT ws introduced to cuvette contining 5 ml of Dex-LA nnoprticle solution (1 µg/ml), to yield finl DTT concentrtion of 10 mm. The cuvette ws seled with septum nd thermostted t 37 C. The size of the nnoprticles ws monitored with DL t different time intervls. 6. tbility of crosslinked nd non-crosslinked nnoprticles The stbility of the crosslinked nnoprticles nd non-crosslinked nnoprticles ginst lrge volume dilution nd high slt concentrtions from 0.2 to 2 M NCl were investigted using DL. 7. Loding of DX nd drug loding efficiency (DLE) DX ws loded into nnoprticles by dropwise ddition of distilled wter to DM solution of DX nd Dex-LA (D = 34, 67, or 80; theoreticl drug loding content = 9.1 %) under stirring t room temperture, followed by dilysis ginst distilled wter for 12 h t r.t. (MWC of 3500). The dilysis medium ws chnged five times. DX-loded nnoprticles were prepred t polymer concentrtion of 200 mg/l. The bove nnoprticles solution ws djusted to ph 8.5 using borte buffer, nd the dispersion ws purged with nitrogen for 10 min, then 10 mol % DTT reltive to the mount of lipoyl units ws dded under nitrogen t room temperture. The mixture ws stirred for 22 h nd purified by dilysis ginst distilled wter nd 10 mm PB for 1 dy. The contents inside the dilysis tube were lyophilized. The whole procedure ws performed in the drk. The mount of DX ws determined using fluorescence (FL920) mesurement (excittion t 480 nm). For determintion of drug loding content, DX loded NPs were dissolved in DM nd nlyzed with fluorescence spectroscopy, wherein clibrtion curve ws obtined with DX/DM solutions with different DX concentrtions. Drug loding content (DLC) nd drug loding efficiency (DLE) were clculted ccording to the following formul: DLC (wt. %) = (weight of loded drug/totl weight of loded drug nd polymer) 100% 3
4 DLE (%) = (weight of loded drug/weight of drug in feed) 100% 8. In vitro relese of DX The relese profiles of DX from crosslinked nnoprticles s well s non-crosslinked nnoprticles (D = 80) were studied using dilysis tube (MWC 12000) under shking (200 rpm) t 37 C in two different medi, i.e. PB (10 mm, ph 7.4) with 10 mm DTT or PB (10 mm, ph 7.4). The relese studies were performed t low polymer concentrtion of 13 mg/l, which is close to its CAC (11 mg/l). Typiclly, DX-loded nnoprticles, either crosslinked or non-crosslinked, were prepred t concentrtion of 200 mg/l. The drug relese studies were performed by 15-fold dilution of nnoprticle solution nd dilysis ginst 25 ml of the sme medium. At desired time intervls, 6 ml relese medi ws tken out nd replenished with n equl volume of fresh medi. The mount of DX relesed ws determined by using fluorescence (FL920) mesurement (excittion t 480 nm). The relese experiments were conducted in triplicte nd the results presented were the verge dt. 9. Cell vibility ssy Murine RAW mcrophges or HeL cells were plted in 96-well plte ( cells/well) using Dulbecco's modified Egle medium (DMEM) or RPMI-1640 medium supplemented with 10 % fetl bovine serum, 1 % L-glutmine, ntibiotics penicillin (100IU/mL), nd streptomycin (100 g/ml). The cells were incubted with prescribed mounts of C-DNP, DX-loded C-DNP, DX-loded NC- DNP, nd free DX t 37 C nd 5 % C 2 for pre-determined time. Then, 10 L of stock solution contining 10 mg/ml of 3-(4,5-dimethylthizol-2-yl)-2,5-diphenyltetrzoliumbromide (MTT) in PB ws dded nd incubted for nother 4 h. The medium ws spirted, the MTT-formzn generted by live cells ws dissolved in 200 L of 10 % D/0.1M HCl, nd the bsorbnce t wvelength of 570 nm of ech well ws mesured using microplte reder. The reltive cell vibility (%) ws determined by compring the bsorbnce t 570 nm with control wells contining only cell culture medium. Dt re presented s verge ± D (n=6). 10. Confocl Lser cnning Microscopy (CLM) observtion K562 cells or HeL cells were plted on microscope slides in 6-well plte ( cells/well) using RPMI-1640 medium supplemented with 10 % fetl bovine serum, 1 % L-glutmine, ntibiotics penicillin (100IU/mL), nd streptomycin (100 g/ml). The cells were incubted with prescribed mounts of DXloded C-DNP or free DX t 37 C nd 5 % C 2. After incubtion for 0.5 nd 2 hrs, the culture medium ws removed nd the cells on microscope pltes were wshed three times with PB. The cells were fixed nd the cell nuclei were stined with 4,6-dimidino-2-phenylindole (DAPI, blue). Fluorescence imges of cells were obtined using confocl microscope (TC P2). 4
5 Tble 1. Chrcteristics of non-crosslinked nd crosslinked dextrn nnoprticles. entry LA/AHG [mol/mol] [] non-crosslinked nnoprticles crosslinked nnoprticles ize PDI [c] Zet CAC ize PDI [c] Zet DLE [nm] [c] [mv] [c] [mg/l] [d] [nm] [c] [mv] [c] [%] [e] 1 0.5: D [b] 2 0.8: : [] Molr feed rtio of LA to AHG of Dextrn. [b] The degree of substitution (D), defined s the number of substituents per 100 AHG of dextrn, ws determined by 1 H NMR. [c] Determined using Zetsizer Nno-Z (Mlvern Instruments) t Dex-LA nnoprticle concentrtion of 0.2 mg/ml in PB (10 mm, ph 7.4) t 25 C. [d] Determined using pyrene s fluorescence probe. [e] DLE (%) = (weight of loded drug/weight of drug in feed) 100%. DLE ws determined by fluorescence mesurements (theoreticl drug loding content = 9.1 wt.%). 5
6 ) Lipoic cid H DCC Lipoic cid nhydride b) H H H Dextrn p (1) Lipoic cid nhydride (2) DMAP, 2d, 30 H H m Dex-LA H H H p-m cheme 1. ynthesis of Dex-LA. 6
7 j k i h g f e i k j+e j f+h H 2 g k H H j i h g e f c m d H H d H d b p-m H 2 DM c d b d +i k j e j f+h g Figure 1. 1 H NMR spectr (400 MHz) of the lipoic cid nhydride in CDCl 3 nd Dex-LA (D 34) in DM-d 6. 7
8 ) b) Figure 2. TEM imges of the nnoprticles (D 80). ) NC-DNP, b) C-DNP. 8
9 2.0 non-xlinked NPs Xlinked NPs 1.5 Absorbnce Wvelength /nm Figure 3. UV spectrl chnges of NC-DNP nd C-DNP (D 67) in DM. 9
10 ) Volume / % non-xlinked Xlinked Xlinked, 0.2 M NCl Xlinked, 2.0 M NCl non-xlinked, 0.2 M NCl d / nm b) non-xlinked Xlinked Xlinked,1000 times non-xlinked,1000 times Volume /% d /nm Figure 4. tbility of C-DNP (D 80) in solutions with different slt concentrtions () nd t different concentrtions in wter (b). 10
11 volume (%) dy 8 dy 15 dy d / nm Figure 5. Time-dependent chnge of prticle size of C-DNP (D 80) in 20 mm PB. 11
12 k H H j i h g e f c m d H H d H d b p-m H 2 DM 0 dy c d b d +i k e j j f+h g ppm 8 dy ppm 15 dy ppm Figure 6. 1 HNMR spectr (400 MHz, DM-d 6 ) of C-DNP (D 80) before nd fter degrdtion in PB (20 mm, ph 7.4) for 8 nd 15 dys. 12
13 ) b ) Figure 7. CLM imges of HeL cells fter 6 h incubtion with DX-loded C-DNP nd free DX (25µg/mL). For ech pnel, imges from left to right show DX fluorescence in cells (red), cell nuclei stined by DAPI (blue), nd overlys of two imges. cle brs correspond to 40 µm in ll the imges. ) DX-loded C-DNP; b) free DX. 13
14 ) b)) c)) Figure 8. CLM imges of HeL cells incubted with DX-loded NC-DNP. For ech pnel, imges from left to right show DX fluorescence in cells (red), cell nuclei stined by DAPI (blue), nd overlys of two imges. cle brs correspond to 40 µm in ll the imges. ) DX-loded NC-DNP, 0.5 h incubtion; b) DX-loded NC-DNP, 2 h incubtion; c) DX-loded NC-DNP, 6 h incubtion. 14
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