journal article·2018-05

Click polymerization for the synthesis of reduction-responsive polymeric prodrug

Xiaojin Zhang, Hongquan Wang, Yu Dai

Journal of Nanoparticle Research· Volume 20· Issue 5
Publisher page

Abstract

Click polymerization is a powerful polymerization technique for the construction of new macromolecules with well-defined structures and multifaceted functionalities. Here, we synthesize reduction-responsive polymeric prodrug PEG-b-(PSS-g-MTX)-b-PEG containing disulfide bonds and pendant methotrexate (MTX) via two-step click polymerization followed by conjugating MTX to pendant hydroxyl. MTX content in polymeric prodrug is 13.5%. Polymeric prodrug is able to form polymeric micelles by self-assembly in aqueous solution. Polymeric micelles are spherical nanoparticles with tens of nanometers in size. Of note, polymeric micelles are reduction-responsive due to disulfide bonds in the backbone of PEG-b-(PSS-g-MTX)-b-PEG and could release pendant drugs in the presence of the reducing agents such as dl-dithiothreitol (DTT).
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Click Chemistry and Applications · Advanced biosensing and bioanalysis techniques · RNA Interference and Gene Delivery

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (40)

Show source-provided references
1. Ahmad Z, Shah A, Siddiq M, Kraatz HB (2014) Polymeric micelles as drug delivery vehicles. RSC Adv 4:17028–17038. https://doi.org/10.1039/c3ra47370h10.1039/C3RA47370H ↗
2. Bildstein L, Dubernet C, Couvreur P (2011) Prodrug-based intracellular delivery of anticancer agents. Adv Drug Deliv Rev 63:3–23. https://doi.org/10.1016/j.addr.2010.12.00510.1016/j.addr.2010.12.005 ↗
3. Biswas S, Kumari P, Lakhani PM, Ghosh B (2016) Recent advances in polymeric micelles for anti-cancer drug delivery. Eur J Pharm Sci 83:184–202. https://doi.org/10.1016/j.ejps.2015.12.03110.1016/j.ejps.2015.12.031 ↗
4. Cui C, Yu P, Wu M, Zhang Y, Liu L, Wu B, Wang CX, Zhuo RX, Huang SW (2015) Reduction-sensitive micelles with sheddable PEG shells self-assembled from a Y-shaped amphiphilic polymer for intracellular doxorubicine release. Colloid Surf B Biointerfaces 129:137–145. https://doi.org/10.1016/j.colsurfb.2015.03.04010.1016/j.colsurfb.2015.03.040 ↗
5. Delplace V, Couvreur P, Nicolas J (2014) Recent trends in the design of anticancer polymer prodrug nanocarriers. Polym Chem 5:1529–1544. https://doi.org/10.1039/c3py01384g10.1039/C3PY01384G ↗
6. Dong YQ, Tong YY, Dong BT, Du FS, Li ZC (2009) Preparation of tadpole-shaped amphiphilic cyclic PS-b-linear PEO via ATRP and click chemistry. Macromolecules 42:2940–2948. https://doi.org/10.1021/ma802361h10.1021/ma802361h ↗
7. Guo N, Hao TT, Shang XZ, Zhang TL, Liu H, Zhang Q, Wang J, Jiang D, Rong Y, Teng Y, Yu P (2017) Novel amphiphilic PEG-hydroxycamptothecin conjugates as glutathione-responsive prodrug nanocapsules for cancer chemotherapy. J Nanopart Res 19:205. https://doi.org/10.1007/s11051-017-3897-410.1007/s11051-017-3897-4 ↗
8. Han DH, Tong X, Zhao Y (2012) Block copolymer micelles with a dual-stimuli-responsive core for fast or slow degradation. Langmuir 28:2327–2331. https://doi.org/10.1021/la204930n10.1021/la204930n ↗
9. Hu XL, Jing XB (2009) Biodegradable amphiphilic polymer-drug conjugate micelles. Expert Opin Drug Deliv 6:1079–1090. https://doi.org/10.1517/1742524090315891710.1517/17425240903158917 ↗
10. Huang MM, Zhao KJ, Wang L, Lin SQ, Li JJ, Chen JB, Zhao CG, Ge ZS (2016) Dual stimuli-responsive polymer prodrugs quantitatively loaded by nanoparticles for enhanced cellular internalization and triggered drug release. ACS Appl Mater Interfaces 8:11226–11236. https://doi.org/10.1021/acsami.5b1222710.1021/acsami.5b12227 ↗
11. Huo M, Yuan J, Tao L, Wei Y (2014) Redox-responsive polymers for drug delivery: from molecular design to applications. Polym Chem 5:1519–1528. https://doi.org/10.1039/c3py01192e10.1039/C3PY01192E ↗
12. Irby D, Du CG, Li F (2017) Lipid-drug conjugate for enhancing drug delivery. Mol Pharm 14:1325–1338. https://doi.org/10.1021/acs.molpharmaceut.6b0102710.1021/acs.molpharmaceut.6b01027 ↗
13. Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Edit 40:2004–2021. https://doi.org/10.1002/1521-3773(20010601)40:11<2004::aid-anie2004>3.0.co;2-510.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 ↗
14. Lee YS, Kim SW (2014) Bioreducible polymers for therapeutic gene delivery. J Control Release 190:424–439. https://doi.org/10.1016/j.jconrel.2014.04.01210.1016/j.jconrel.2014.04.012 ↗
15. Li HY, Aneja R, Chaiken I (2013) Click chemistry in peptide-based drug design. Molecules 18:9797–9817. https://doi.org/10.3390/molecules1808979710.3390/molecules18089797 ↗
16. Li D, Lu B, Zhang H, Huang ZJ, Xu PH, Zheng H, Yin YH, Xu HX, Liu X, Lou YC, Zhang XQ, Xiong FL (2014) Synthesis and in vitro evaluation of methotrexate conjugated O,N-carboxymethyl chitosan via peptidyl spacers. J Nanopart Res 16:2609. https://doi.org/10.1007/s11051-014-2609-610.1007/s11051-014-2609-6 ↗
17. Liu ZS, Ou JJ, Zou HF (2016) Click polymerization for preparation of monolithic columns for liquid chromatography. TrAC Trends Anal Chem 82:89–99. https://doi.org/10.1016/j.trac.2016.05.01610.1016/j.trac.2016.05.016 ↗
18. Luo P, Luo Y, Huang J, Lu W, Luo DJ, Yu JH, Liu SY (2013) Incorporation of camptothecin into reduction-degradable supramolecular micelles for enhancing its stability. Colloid Surf B Biointerfaces 109:167–175. https://doi.org/10.1016/j.colsurfb.2013.03.04810.1016/j.colsurfb.2013.03.048 ↗
19. Luo C, Sun J, Liu D, Sun BJ, Miao L, Musetti S, Li J, Han XP, Du YQ, Li L, Huang L, He ZG (2016) Self-assembled redox dual-responsive prodrug-nanosystem formed by single thioether-bridged paclitaxel-fatty acid conjugate for cancer chemotherapy. Nano Lett 16:5401–5408. https://doi.org/10.1021/acs.nanolett.6b0163210.1021/acs.nanolett.6b01632 ↗
20. Mandal B, Basu B (2014) Recent advances in S-S bond formation. RSC Adv 4:13854–13881. https://doi.org/10.1039/c3ra45997g10.1039/c3ra45997g ↗
21. Marrocchi A, Facchetti A, Lanari D, Santoro S, Vaccaro L (2016) Click-chemistry approaches to pi-conjugated polymers for organic electronics applications. Chem Sci 7:6298–6308. https://doi.org/10.1039/c6sc01832g10.1039/C6SC01832G ↗
22. McKay CS, Finn MG (2014) Click chemistry in complex mixtures: bioorthogonal bioconjugation. Chem Biol 21:1075–1101. https://doi.org/10.1016/j.chembiol.2014.09.00210.1016/j.chembiol.2014.09.002 ↗
23. Meng FH, Hennink WE, Zhong Z (2009) Reduction-sensitive polymers and bioconjugates for biomedical applications. Biomaterials 30:2180–2198. https://doi.org/10.1016/j.biomaterials.2009.01.02610.1016/j.biomaterials.2009.01.026 ↗
24. Postma TM, Albericio F (2014) Disulfide formation strategies in peptide synthesis. Eur J Org Chem 2014:3519–3530. https://doi.org/10.1002/ejoc.20140214910.1002/ejoc.201402149 ↗
25. Qin AJ, Lam JWY, Tang BZ (2010) Click polymerization. Chem Soc Rev 39:2522–2544. https://doi.org/10.1039/b909064a10.1039/b909064a ↗
26. Qiu FY, Zhang M, Ji R, Du FS, Li ZC (2015) Oxidation-responsive polymer-drug conjugates with a phenylboronic ester linker. Macromol Rapid Commun 36:2012–2018. https://doi.org/10.1002/marc.20150034910.1002/marc.201500349 ↗
27. Saha B, Haldar U, De P (2016) Polymer-chlorambucil drug conjugates: a dynamic platform of anticancer drug delivery. Macromol Rapid Commun 37:1015–1020. https://doi.org/10.1002/marc.20160014610.1002/marc.201600146 ↗
28. Senevirathne SA, Washington KE, Biewer MC, Stefan MC (2016) PEG based anti-cancer drug conjugated prodrug micelles for the delivery of anti-cancer agents. J Mater Chem B 4:360–370. https://doi.org/10.1039/c5tb02053k10.1039/C5TB02053K ↗
29. Su YG, Hu YW, Du YZ, Huang X, He JB, You J, Yuan H, Hu FQ (2015) Redox-responsive polymer drug conjugates based on doxorubicin and chitosan oligosaccharide-g-stearic acid for cancer therapy. Mol Pharm 12:1193–1202. https://doi.org/10.1021/mp500710x10.1021/mp500710x ↗
30. Such GK, Johnston APR, Liang K, Caruso F (2012) Synthesis and functionalization of nanoengineered materials using click chemistry. Prog Polym Sci 37:985–1003. https://doi.org/10.1016/j.progpolymsci.2011.12.00210.1016/j.progpolymsci.2011.12.002 ↗
31. Sun HL, Guo BN, Li XQ, Cheng R, Meng FH, Liu HY, Zhong ZY (2010) Shell-sheddable micelles based on dextran-SS-poly(ε-caprolactone) diblock copolymer for efficient intracellular release of doxorubicin. Biomacromolecules 11:848–854. https://doi.org/10.1021/bm100106910.1021/bm1001069 ↗
32. Sun HL, Meng FH, Cheng R, Deng C, Zhong ZY (2013) Reduction-sensitive degradable micellar nanoparticles as smart and intuitive delivery systems for cancer chemotherapy. Expert Opin Drug Deliv 10:1109–1122. https://doi.org/10.1517/17425247.2013.78300910.1517/17425247.2013.783009 ↗
33. Sun HL, Meng FH, Cheng R, Deng C, Zhong ZY (2014) Reduction-responsive polymeric micelles and vesicles for triggered intracellular drug release. Antioxid Redox Signal 21:755–767. https://doi.org/10.1089/ars.2013.573310.1089/ars.2013.5733 ↗
34. Sun JJ, Liu YH, Chen YC, Zhao WC, Zhai QY, Rathod S, Huang YX, Tang SQ, Kwon YT, Fernandez C, Venkataramanan R, Li S (2017) Doxorubicin delivered by a redox-responsive dasatinib-containing polymeric prodrug carrier for combination therapy. J Control Release 258:43–55. https://doi.org/10.1016/j.jconrel.2017.05.00610.1016/j.jconrel.2017.05.006 ↗
35. Thirumurugan P, Matosiuk D, Jozwiak K (2013) Click chemistry for drug development and diverse chemical-biology applications. Chem Rev 113:4905–4979. https://doi.org/10.1021/cr200409f10.1021/cr200409f ↗
36. Wang XS, Huang BS, Liu XY, Zhan P (2016) Discovery of bioactive molecules from CuAAC click-chemistry-based combinatorial libraries. Drug Discov Today 21:118–132. https://doi.org/10.1016/j.drudis.2015.08.00410.1016/j.drudis.2015.08.004 ↗
37. Yao BC, Sun JZ, Qin AJ, Tang BZ (2013) Thiol-yne click polymerization. Chin Sci Bull 58:2711–2718. https://doi.org/10.1007/s11434-013-5892-110.1007/s11434-013-5892-1 ↗
38. Yoon HY, Koo H, Kim K, Kwon IC (2017) Molecular imaging based on metabolic glycoengineering and bioorthogonal click chemistry. Biomaterials 132:28–36. https://doi.org/10.1016/j.biomaterials.2017.04.00310.1016/j.biomaterials.2017.04.003 ↗
39. Zhang XJ, Zhong ZL, Zhuo RX (2011) Preparation of azido polycarbonates and their functionalization via click chemistry. Macromolecules 44:1755–1759. https://doi.org/10.1021/ma200137a10.1021/ma200137a ↗
40. Zhang WJ, Hong CY, Pan CY (2016) Fabrication of reductive-responsive prodrug nanoparticles with superior structural stability by polymerization-induced self-assembly and functional nanoscopic platform for drug delivery. Biomacromolecules 17:2992–2999. https://doi.org/10.1021/acs.biomac.6b0081910.1021/acs.biomac.6b00819 ↗