Synthesis of cleavable multi-functional mikto-arm star polymer by RAFT polymerization: Example of an anti-cancer drug 7-ethyl-10-hydroxycamptothecin (SN-38) as functional moiety

Science China Chemistry

Volumn 57, Issue 7, 2014, Pages 995-1001

  Wei, Xiaohu ^a,b   Gunatillake, Pathiraja A ^b   Moad, Graeme ^b   Rizzardo, Ezio ^b   Rosselgong, Julien ^b   Yang, Wantai ^a   Thang, San H ^b  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

^b CSIRO   (Australia)

Author keywords

cancer therapy; cleavable polymer; mikto arm star; polymer drug conjugate; RAFT; siRNA delivery

Indexed keywords

ONCOLOGY; POLYMERS; RNA;

CANCER THERAPY; FUNCTIONAL MOIETIES; NEGATIVELY CHARGED; POLYMER-DRUG CONJUGATE; RAFT; RAFT POLYMERIZATION; SIRNA DELIVERY; SMALL INTERFERING RNA (SIRNA);

LIVING POLYMERIZATION;

EID: 84903720471     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-014-5128-5     Document Type: Article

References (42)

1. Boyer S, Bulmus V. Davis TP, Ladmiral V, Liu J, Perrier S. Bioapplications of RAFT polymerization. Chem Rev, 2009, 109: 5402-5436
2. Delplace V, Couvreur P, Nicolas J. Recent trends in the design of anticancer polymer prodrug nanocarriers. Polym Chem, 2014, 5: 1529-1544
3. Kataoka K, Harada A, Nagasaki Y. Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv Drug Deliv Rev, 2001, 47: 113-131
4. Wyman I, Liu G. Self-assembly and chemical processing of block copolymers: a roadmap towards a diverse array of block copolymer nanostructures. Sci China Chem, 2013, 56: 1040-1066
5. Jenkins AD, Jones RG, Moad G. Terminology for reversible-deactivation radical polymerization previously called "controlled" radical or "living" radical polymerization. Pure Appl Chem, 2010, 82: 483-491
6. Solomon DH, Rizzardo E, Cacioli P. Polymerization process and polymers produced thereby. US Patent 4581429, 1986-04-08. (Chem Abstr, 1985, 102: 221335)
7. George MK, Veregin RPN, Kazmaier PM, Hamer GK. Narrow molecular weight resins by a free-radical polymerization process. Macromolecules, 1993, 26: 2987-2988
8. Hawker CJ, Bosman AW, Harth E. New polymer synthesis by nitroxide mediated living radical polymerizations. Chem Rev, 2001, 101: 3661-3688
9. Rizzardo E, Moad G. Alkoxyamine-initiated living radical polymerization: factors affecting alkoxyamine homolysis rates. Macromolecules, 1995, 28: 8722-8728
10. Kato M, Kamigaito M, Sawamoto M, Higashimura T. Polymerization of methyl methacrylate with the carbon tetrachloridel/dichlorotris-(triphenylphosphine) ruthedum(II)/methylaluminum bis(2,6-di-tert-butylphenoxide) initiating system: possibility of living radical polymerization. Macromolecules, 1995, 28: 1721-1723
11. nCl. Macromolecules, 1995, 28: 7970-7972
12. Wang JS, Matyjaszewski K. Controlled/"living" radical polymerization. Atom transfer radical polymerization in the presence of transition-metal complexes. J Am Chem Soc, 1995, 117: 5614-5615
13. Ouchi M, Terashima T, Sawamoto M. Transition metal-catalyzed living radical polymerization: toward perfection in catalysis and precision polymer synthesis. Chem Rev, 2009, 109: 4963-5050
14. Matyjaszewski K. Atom transfer radical polymerization (ATRP): current status and future perspectives. Macromolecules, 2012, 45: 4015-4039
15. Chiefari J, Chong YK, Ercole F, Krstina J, Jeffery J, Le TPT, Mayadunne RTA, Meijs GF, Moad CL, Moad G, Rizzardo E, Thang SH. Living free-radical polymerization by reversible addition-fragmentation chain transfer: the RAFT process. Macromolecules, 1998, 31: 5559-5562
16. Moad G, Rizzardo E, Thang SH. Living radical polymerization by the RAFT process-a third update. Aust J Chem, 2012, 65: 985-1076
17. Moad G, Rizzardo E, Thang SH. RAFT polymerization and some of its applications. Chem Asian J, 2013, 8: 1634-1644
18. Chen M, Ghiggino KP, Thang SH, Wilson GJ. Star-shaped light-harvesting polymers incorporting an energy cascade. Angew chem Int Ed, 2005, 44: 4368-4372
19. Moad G, Chen M, Häussler M, Postma, A, Rizzardo E, Thang SH. Functional polymers for optoelectronic applications by RAFT polymerization. Polym Chem, 2011, 2: 492-519
20. Isakova A, Topham PD, Sutherland AJ. Controlled RAFT polymerization and Zinc binding performance of catechol-inspired homopolymers. Macromolecules, 2014, Doi: 10.1021/ma500336u
21. Wei Z, Hao X, Kambouris PA, Gan Z, Hughes TC. One-pot synthesis of hyperbranched polymers using small molecule and macro RAFT inimers. Polymer, 2012, 53: 1429-1436
22. Yang J, Luo K, Pan H, Kopeckova P, Kopecek J. Synthesis of biodegradable multiblock copolymers by click coupling of RAFT-generated heterotelechelic PolyHPMA conjugates. React Funct Polym, 2011, 71: 294-302
23. Blencowe A, Tan JF, Goh TK, Qiao GG. Core cross-linked star polymers via controlled radical polymerisation. Polymer, 2009, 50: 5-32
24. Gao H, Matyjaszewski K. Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: from stars to gels. Prog Polym Sci, 2009, 34: 317-350
25. Rosselgong J, Williams EG, Le TP, Grusche F, Hinton TM, Tizard M, Gunatillake P, Thang SH. Core degradable star RAFT polymers: synthesis, polymerization, and degradation Studies. Macromolecules, 2013, 46: 9181-9188
26. Altintas O, Hizal G, Tunca U. ABC-type hetero-arm star terpolymers through "Click" chemistry. J Polym Sci, Part A: Polym Chem, 2006, 44: 5699-5707
27. Gao H, Matyjaszewski K. Synthesis of star polymers by a combination of ATRP and the "Click" coupling method. Macromolecules, 2006, 39: 4960-4965
28. Chan JW, Yu B, Hoyle CE, Lowe AB. Convergent synthesis of 3-arm star polymers from RAFT-prepared poly(N, N-diethylacrylamide) via a thiol-ene click reaction. Chem Commun, 2008, 4959-4961
29. Gao H, Matyjaszewski K. Arm-first method as a simple and general method for synthesis of miktoarm star copolymers. J Am Chem Soc, 2007, 129: 11828-11834
30. Cheng F, Bonder EM, Doshi A, Jäkle F. Organoboron star polymers via arm-first RAFT polymerization: synthesis, luminescent behavior, and aqueous self-assembly. Polym Chem, 2012, 3: 596-600
31. Shi X, Zhou W, Qiu Q, An Z. Amphiphilic heteroarm star polymer synthesized by RAFT dispersion polymerization in water/ethanol solution. Chem Commun, 2012, 48: 7389-7391
32. Ferreira J, Syrett J, Whittaker M, Haddleton D, Davis TP, Boyer C. Optimizing the generation of narrow polydispersity 'arm-first'star polymers made using RAFT polymerization. Polym Chem, 2011, 2:1671-1677
33. Wei X, Moad G, Muir BW, Rizzardo E, Rosselgong J, Yang W, Thang SH. An arm-first approach to cleavable mikto-arm star polymers by RAFT polymerization. Macromol Rapid Commun, 2014, 35: 840-845
34. Rosselgong J, Armes SP, Barton W, Price D. Synthesis of highly branched methacrylic copolymers: observation of near-ideal behavior using RAFT polymerization. Macromolecules, 2009, 42: 5919-5924
35. Peng CL, Lai PS, Lin FH. Yueh-Hsiu Wu S, Shieh MJ. Dual chemotherapy and photodynamic therapy in an HT-29 human colon cancer xenograft model using SN-38-loaded chlorin-core star block copolymer micelles. Biomaterials, 2009, 30: 3614-3625
36. Caiolfa VR, Zamai M, Fiorino A, Frigerio E, Pellizzoni C, d'Argy R, Ghiglieri A, Castelli MG, Farao M, Pesenti E, Gigli M, Angelucci F, Suarato A. Polymer-bound camptothecin: initial biodistribution and antitumour activity studies. J Control Rel, 2000, 65: 105-119
37. Hamaguchi T, Doi T, Eguchi-Nakajima T, Kato K, Yamada Y, Shimada Y, Fuse N, Ohtsu A, Matsumoto S, Takanashi M, Matsumura Y. Phase I study of NK012, a novel SN-38-incorporating micellar nanoparticle, in adult patients with solid tumors. Clin Cancer Res, 2010, 16: 5058-5066
38. Matsumura Y. Preclinical and clinical studies of NK012, an SN-38-incorporating polymeric micelles, which is designed based on EPR effect. Adv Drug Deliv Rev, 2011, 63: 184-192
39. Hu X, Hu J, Tian J, Ge Z, Zhang G, Luo K, Liu S. Polyprodrug amphiphiles: hierarchical assemblies for shape-regulated cellular internalization, trafficking, and drug delivery. J Am Chem Soc, 2013, 135: 17617-17629
40. Hu X, Tian J, Liu T, Zhang G, Liu S. Photo-triggered release of caged camptothecin prodrugs from dually responsive shell cross-linked micelles. Macromolecules, 2013, 46: 6243-6256.
41. Williams CC, Thang SH, Hantke T, Vogel U, Seeberger PH, Tsanaktsidis J, Lepenies B. RAFT-derived polymer-drug conjugates: poly(hydroxypropyl methacrylamide) (HPMA)-7-ethyl-10-hydroxycamptothecin (SN-38) conjugates. ChemMedChem, 2012, 7: 281-291
42. Moad G, Chong YK, Rizzardo E, Postma A, Thang SH. Advances in RAFT polymerization: the synthesis of polymers with defined end-groups. Polymer, 2005, 46: 8458-8468