Synthesis of poly(cystine bisamide)-PEG block copolymers grafted with 1-(3-aminopropyl)imidazole and their phase transition behaviors

Polymers for Advanced Technologies

Volumn 19, Issue 11, 2008, Pages 1558-1565

  Jin, Byung Suk ^a   Kang, Han Chang ^b   Kim, Dongin ^b   Lee, Kwang Hee ^c   Bae, You Han ^b  

^a Dongduk Women's University   (South Korea)

^b UNIVERSITY OF UTAH   (United States)

^c Inha University   (South Korea)

Author keywords

Aggregation; Critical aggregation concentration; Imidazole ring; pH sensitive copolymer

Indexed keywords

AGGREGATES; AMINES; BIODEGRADABLE POLYMERS; BLOCK COPOLYMERS; COPOLYMERIZATION; COPOLYMERS; EMISSION SPECTROSCOPY; GRAFTING (CHEMICAL); HYDROPHOBICITY; PHASE TRANSITIONS; PLASTIC PRODUCTS; POLYCONDENSATION; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES; POLYMERS; POTENTIOMETRIC SENSORS; PROTONATION; SYNTHESIS (CHEMICAL); THEOREM PROVING;

ACIDIC CONDITIONS; AGGREGATION; AMINOPROPYL; BACKBONE POLYMERS; BASIC CONDITIONS; BUFFERING CAPACITIES; CONDENSATION POLYMERIZATIONS; COPOLYMER AGGREGATES; CRITICAL AGGREGATION CONCENTRATION; CRITICAL AGGREGATIONS; EMISSION SPECTRUMS; HEXATRIENE; HYDROPHOBIC DOMAINS; HYDROPHOBIC INTERACTIONS; IMIDAZOLE RING; INTENSITY RATIOS; MICRO VISCOSITIES; POLYMER CHAINS; TERTIARY AMINES; TRANSITION BEHAVIORS;

AGGLOMERATION;

BLOCK COPOLYMER; CONDENSATION; COPOLYMER; GRAFTING; POLYMERIZATION; SYNTHESIS;

EID: 58049127527     PISSN: 10427147     EISSN: 10991581     Source Type: Journal    
DOI: 10.1002/pat.1169     Document Type: Article

References (35)

1. Allen C, Maysinger D, Eisenberg A. Nano-engineering block copolymer aggregates for drug delivery. Colloids Surf. B Biointerfaces 1999; 16: 3-27.
2. Wei H, Zhang XZ, Cheng H, Chen WQ, Cheng SX, Zhuo RX. Self-assembled thermo- and pH responsive micelles of poly(10-undecenoic acid-b-N-isopropylacrylamide) for drug delivery. J. Control Release 2006; 116: 266-274.
3. Schmaljohann D. Thermo- and pH-responsive polymers in drug delivery. Adv. Drug Deliv. Rev. 2006; 58: 1655-1670.
4. Gil ES, Hudson SM. Stimuli-responsive polymers and their bioconjugates. Prog. Polym. Sci. 2004; 29: 1173-1222.
5. Gupta P, Vermani K, Garg S. Hydrogels: from controlled release to pH-responsive drug delivery. Drug Discov. Today 2002; 7: 569-579.
6. Jeong B, Gutowska A. Lessons from nature: stimuli-responsive polymers and their biomedical applications. Trends Biotechnol. 2002; 20: 305-311.
7. Galaev IY, Mattiasson B. 'Smart' polymers and what they could do in biotechnology and medicine. Trends Biotechnol. 1999; 17: 335-340.
8. Sharma S, Kaur P, Jain A, Rajeswari MR, Gupta MN. A smart bioconjugate of chymotrypsin. Biomacromolecules 2003; 4: 330-336.
9. Soppimath KS, Tan DCW, Yang YY. pH-triggered thermally responsive polymer core-shell nanoparticles for drug delivery. Adv. Mater. 2005; 17: 318-320.
10. Yoo HS, Lee EA, Park TG. Doxorubicin-conjugated biodegradable polymeric micelles having acid-cleavable linkages. J. Control Release 2002; 82: 17-27.
11. Bae Y, Nishiyama N, Fukushima S, Koyama H, Yasuhiro M, Kataoka K. Preparation and biological characterization of polymeric micelle drug carriers with intracellular pH-triggered drug release property: tumor permeability, controlled subcellular drug distribution, and enhanced in vivo antitumor efficacy. Bioconjug. Chem. 2005; 16: 122-130.
12. Gillies ER, Frechet JM. pH-responsive copolymer assemblies for controlled release of doxorubicin. Bioconjug. Chem. 2005; 16: 361-368.
13. Tang Y, Liu SY, Armes SP, Billingham NC. Solubilization and controlled release of a hydrophobic drug using novel micelle-forming ABC triblock copolymers. Biomacromolecules 2003; 4: 1636-1645.
14. Lee ES, Na K, Bae YH. Doxorubicin loaded pH-sensitive polymeric micelles for reversal of resistant MCF-7 tumor. J. Control Release 2005; 103: 405-418.
15. Lee ES, Na K, Bae YH. Super pH-sensitive multifunctional polymeric micelle. Nano Lett. 2005; 5: 325-329.
16. Lee ES, Na K, Bae YH. Polymeric micelle for tumor pH and folate-mediated targeting. J. Control Release 2003; 91: 103-113.
17. Na K, Bae YH. Self-assembled hydrogel nanoparticles responsive to tumor extracellular pH from pullulan derivative/sulfonamide conjugate: characterization, aggregation, and adriamycin release in vitro. Pharm. Res. 2002; 19: 681-688.
18. Na K, Lee ES, Bae YH. Adriamycin loaded pullulan acetate/sulfonamide conjugate nanoparticles responding to tumor pH: pH-dependent cell interaction, internalization and cytotoxicity in vitro. J. Control Release 2003; 87: 3-13.
19. Han SK, Na K, Bae YH. Sulfonamide based pH-sensitive polymeric micelles: physicochemical characteristics and pH-dependent aggregation. Colloid Surf. A Physicochem. Eng. Asp. 2003; 214: 49-59.
20. Sethuraman VA, Na K, Bae YH. pH-responsive sulfonamide/PEI system for tumor specific gene delivery: in vitro study. Biomacromolecules 2006; 7: 64-70.
21. Lee ES, Shin HJ, Na K, Bae YH. Poly(L-histidine)-PEG block copolymer micelles and pH-induced destabilization. J. Control Release 2003; 90: 363-374.
22. Midoux P, Monsigny M. Efficient gene transfer by histidylated polylysine/ pDNA complexes. Bioconjug. Chem. 1999; 10: 406-411.
23. Benns JM, Choi JS, Mahato RI, Park JS, Kim SW. pH-sensitive cationic polymer gene delivery vehicle: N-Ac-poly(L- histidine)- graft-poly(L-lysine) comb shaped polymer. Bioconjug. Chem. 2000; 11: 637-645.
24. a shifts in polypentapeptides. The lysine residue. Chem. Phys. Lett. 1994; 225: 97-103.
25. Yang SR, Lee HJ, Kim JD. Histidine-conjugated poly(amino acid) derivatives for the novel endosomolytic delivery carrier of doxorubicin. J. Control Release 2006; 114: 60-68.
26. Yue Z, Eccleston ME, Slater NK. Modulation of the pH-responsive properties of poly(L-lysine iso-phthalamide) grafted with a poly(ethylene glycol) analogue. Biomaterials 2005; 26: 6357-6366.
27. Kaneshiro TL, Ke T, Jeong EK, Parker DL, Lu ZR. Gd-DTPA L-cystine bisamide copolymers as novel biodegradable macromolecular contrast agents for MR blood pool imaging. Pharm. Res. 2006; 23: 1285-1294.
28. Mohs AM, Wang X, Goodrich KC, Zong Y, Parker DL, Lu ZR. PEG-g-poly(GdDTPA-co-L-cystine): a biodegradable macromolecular blood pool contrast agent for MR imaging. Bioconjug. Chem. 2004; 15: 1424-1430.
29. Zalipsky S, Barany G. Facile synthesis of α-hydroxy-ω-carboxymethylpolyethylene oxide. J. Bioact. Compat. Polym. 1990; 5: 227-231.
30. Seo K, Kim D. Phase transition behavior of novel pH-sensitive polyaspartamide derivatives grafted with 1-(3-aminopropyl) imidazole. Macromol. Biosci. 2006; 6: 758-766.
31. Chen W-Y, Alexandridis P, Su C-K, Patrickios CS, Hertler WR, Hatton TA. Effect of block size and sequence on the micellization of ABC triblock methacrylic polyampholytes. Macromolecules 1995; 28: 8604-8611.
32. Holappa S, Kantonen L, Winnik FM, Tenhu H. Self-complexation of poly(ethylene oxide)-block-poly(methacrylic acid) studied by fluorescence spectroscopy. Macromolecules 2004; 37: 7008-7018.
33. Hu YQ, Kim MS, Kim BS, Lee DS. Synthesis and pH-dependent micellization of 2-(diisopropylamino)ethyl methacrylate based amphiphilic diblock copolymers via RAFT polymerization. Polymer 2007; 48: 3437-3443.
34. Na K, Lee DH, Hwang DJ, Park HS, Lee KH, Bae YH. pH-Sensitivity and pH-dependent structural change in polymeric nanoparticles of poly(vinyl sulfadimethoxine)- deoxycholic acid conjugate. Eur. Polym. J. 2006; 42: 2581-2588.
35. Kim C, Lee SC, Kang SW, Kwon IC, Kim YH, Jeong SY. Synthesis and the micellar characteristics of poly(ethylene oxide)-deoxycholic acid conjugates. Langmuir 2000; 16: 4792-4797.