Tadpole-shaped β-cyclodextrin-tagged poly(N-vinylpyrrolidone): Synthesis, characterization and studies of its complexation with phenolphthalein and anti tumor activities

RSC Advances

Volumn 5, Issue 20, 2015, Pages 15547-15558

  Vishwakarma, Niraj Kumar ^a   Patel, Vijay Kumar ^a   Hira, Sumit Kumar ^a   Ramesh, K ^a,b   Srivastava, Prateek ^a   Mitra, Kheyanath ^a   Singh, Shikha ^a   Chattopadhyay, Dipankar ^c   Maiti, Pralay ^b   Misra, Nira ^b   Manna, Partha Pratim ^a   Ray, Biswajit ^a  

^a BANARAS HINDU UNIVERSITY   (India)

^b BANARAS HINDU UNIVERSITY   (India)

^c UNIVERSITY OF CALCUTTA   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CELL DEATH; CYCLODEXTRINS; SYNTHESIS (CHEMICAL);

ANTI-TUMOR ACTIVITIES; BETA-CYCLODEXTRIN; CLICK REACTION; COMPLEXING ABILITY; DOXORUBICIN; FUNCTIONALIZED; N VINYLPYRROLIDONE; TUMOR CELL LINES;

TUMORS;

EID: 84922559812     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra15359f     Document Type: Article

References (33)

1. A. S. Wood, Kirk-Othmer Encyclopedia of Chemical Technology, ed., J. J. McKetta, D. F. Othmer, and, A. Standen, 2nd edn, Interscience, New York, 1970, p. 427
2. F. Haaf A. Sanner F. Straub Polymers of N-Vinylpyrrolidone: Synthesis, Characterization and Uses Polym. J. 1985 17 143 152
3. J. Chiefari, R. T. A. Mayadunne, G. Moad, E. Rizzardo and S. H. Thang, 1999, PCT IntAppl W099/31144
4. V. Coessens T. Pintaver K. Matyzaszewski Functional polymers by atom transfer radical polymerization Prog. Polym. Sci. 2001 26 337 377
5. D. Wan K. Satoh M. Kamigaito Y. Okamoto Xanthate-mediated radical polymerization of N-vinylpyrrolidone in fluoroalcohols for simultaneous control of molecular weight and tacticity Macromolecules 2005 38 10397 10405
6. R. Devasia R. L. Bindu N. Mougia Y. Gnanou Controlled radical polymerization of N-vinylpyrrolidone by reversible addition-fragmentation Macromol. Symp. 2005 229 8 17
7. P. Bilalis M. Pitsikalis N. Hadjichristidis Controlled nitroxide-mediated and reversible addition-fragmentation chain transfer polymerization of N-vinylpyrrolidone: synthesis of block copolymers with styrene and 2-vinylpyridine J. Polym. Sci., Part A: Polym. Chem. 2006 44 659 665
8. S. Yamago B. Ray K. Iida J. I. Yoshida T. Tada K. Yoshizawa Y. Kwak A. Goto T. Fukuda Highly versatile organostibine mediators for living radical polymerization J. Am. Chem. Soc. 2004 126 13908 13909
9. B. Ray M. Kotani S. Yamago Highly controlled synthesis of poly(N-vinylpyrrolidone) and its block copolymers by organostibine-mediated living radical polymerization Macromolecules 2006 39 5259 5265
10. S. I. Yusa S. Yamago M. Sugahara S. Morikawa T. Yamamoto Y. Morishima Thermoresponsivediblock copolymers of poly(N-isopropylacrylamide) and poly(N-vinyl-2-pyrroridone) synthesized via organotellurium-mediated controlled radical polymerization (TERP) Macromolecules 2007 40 5907 5915
11. S. Yamago E. Kayahara M. Kotani B. Ray Y. Kwak A. Goto T. Fukuda Highly controlled living radical polymerization through dual activation of organobismuthines Angew. Chem., Int. Ed. 2007 46 1304 1306
12. X. Lu S. Gong L. Meng C. Li S. Yang L. Zhang Controllable synthesis of poly(N-vinylpyrrolidone) and its block copolymers by atom transfer radical polymerization Polymer 2007 48 2835 2842
13. G. Pound Z. Eksteen R. Pfukwa J. M. McKenzie R. F. M. Lange B. Klumperman Unexpected reactions associated with the xanthate-mediated polymerization of N-vinylpyrrolidone J. Polym. Sci., Part A: Polym. Chem. 2008 46 6575 6593
14. G. Pound F. Aguesse J. B. McLeary R. F. M. Lange B. Klumperman Xanthate-mediated copolymerization of vinyl monomers for amphiphilic and double-hydrophilic block copolymers with poly(ethylene glycol) Macromolecules 2007 40 8861 8871
15. V. K. Patel A. K. Mishra N. K. Vishwakarma C. S. Biswas B. Ray (S)-2-(Ethyl propionate)-(O-ethyl xanthate) and (S)-2-(Ethyl isobutyrate)-(O-ethyl xanthate)-mediated RAFT polymerization of N-vinylpyrrolidone Polym. Bull. 2010 65 97 101
16. V. K. Patel A. K. Mishra N. K. Vishwakarma C. S. Biswas P. Maiti B. Ray Synthesis of Alkyne-Terminated Xanthate RAFT Agents and Their Uses for the Controlled Radical Polymerization of N-Vinylpyrrolidone and the Synthesis of Its Block Copolymer Using Click Chemistry J. Appl. Polym. Sci. 2013 127 4305 4317
17. K. Uekama F. Hirayama T. Irie Cyclodextrin Drug Carrier Systems Chem. Rev. 1998 98 2045 2076
18. X. Ma Y. Zhao Biomedical Applications of Supramolecular Systems Based on Host-Guest Interactions Chem. Rev. 2015 10.1021/cr500392w
19. J. Xin Z. Guo X. Chen W. Jing J. Li Studies of branched cationic β-cyclodextrin polymer/Iodomethacin complex and its release profile from alginate hydrogel Int. J. Pharm. 2010 386 221 228
20. Q. He W. Wu K. Xiu Q. Zhang F. Xu J. Li Controlled drug release system based on cyclodextrin-conjugated poly(lactic acid)-b-poly(ethylene glycol) micelles Int. J. Pharm. 2013 443 110 119
21. A. L. Nielsen K. Steffensen K. L. Larsen Self-assembling microparticles with controllable disruption properties based on cyclodextrin interactions Colloids Surf., B 2009 73 267 275
22. S. Ren D. Chen M. Jiang Noncovalently Connected Micelles Based on a β-Cyclodextrin-Containing Polymer and Adamantane End-Capped Poly(ε-caprolactone) via Host-Guest Interactions J. Polym. Sci., Part A: Polym. Chem. 2009 47 4267 4278
23. T. Trellenkamp H. Ritter Poly(N-vinylpyrrolidone) Bearing Covalently Attached Cyclodextrin via Click-Chemistry: Synthesis, Characterization, and Complexation Behavior with Phenolphthalein Macromolecules 2010 43 5538 5543
24. W. Zhang B. Fang A. Walther A. H. E. Müller Synthesis via RAFT Polymerization of tadpole-shaped organic/inorganic hybrid poly(acrylic acid) containing polyhedral oligomeric silsesquioxane (POSS) and their self-assembly in water Macromolecules 2009 42 2563 2569
25. J. Y. Kim W. I. Choi Y. H. Kim G. Tae S. Y. Lee K. Kim I. C. Kwon In-vivo tumor targeting of pluronic-based nano-carriers J. Controlled Release 2010 147 109 117
26. X. P. Duan Y. P. Li Physicochemical characteristics of nanoparticles affect circulation, biodistribution, cellular internalization and trafficking Small 2013 9 1521 1532
27. W. Wu Q. Zhang J. Wang M. Chen S. Li Z. Lin J. Li Tumor-targeted aggregation of pH-sensitive nanocarriers for enhanced retention and rapid intracellular drug release Polym. Chem. 2014 5 5668 5679
28. A. K. Mishra V. K. Patel N. K. Vishwakarma C. S. Biswas M. Raula A. Mishra T. K. Mandal B. Ray Synthesis of Well-Defined Amphiphilic Poly(ε-caprolactone)-b-poly-(N-vinylpyrrolidone) Block Copolymers via the Combination of ROP and Xanthate-Mediated RAFT Polymerization Macromolecules 2011 44 2465 2473
29. T. P. Thomas I. J. Majoros A. Kotlyar J. F. Kukowska-Latallo A. Bielinska A. Mycand J. R. Baker Targeting and Inhibition of Cell Growth by an Engineered Dendritic Nanodevice J. Med. Chem. 2005 48 3729 3735
30. P. P. Manna S. K. Hira A. A. Das S. Bandyopadhyay K. K. Gupta IL-15 activated human peripheral blood dendritic cell kill allogeneic and xenogeneic endothelial cells via apoptosis Cytokine 2013 61 118 126
31. S. K. Hira A. K. Mishra B. Ray P. P. Manna Targeted Delivery of Doxorubicin-Loaded Poly(ε-caprolactone)-b-Poly(N-vinylpyrrolidone) Micelles Enhances Antitumor Effect in Lymphoma PLoS One 2014 9 4 e94309
32. K. Ramesh A. K. Mishra V. K. Patel N. K. Vishwakarma C. S. Biswas T. K. Paira T. K. Mandal P. Maiti N. Misra B. Ray Synthesis of well-defined amphiphilic poly(d,l-lactide)-b-poly(N-vinylpyrrolidone) block copolymers using ROP and xanthate-mediated RAFT polymerization Polymer 2012 53 5743 5753
33. F. Trotta M. Zanetti G. Camino Thermal degradation of cyclodextrins Polym. Degrad. Stab. 2000 69 373 379