Synthesis of genistein-containing star-shaped homo- and copolyesters by the ring-opening polymerization

Polymer Bulletin

Volumn 70, Issue 9, 2013, Pages 2587-2597

  Oledzka, Ewa ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Biodegradable polymers; Drug delivery systems; Genistein; Natural initiator; Star shaped polymers

Indexed keywords

DIRECT SYNTHESIS; DRUG DELIVERY SYSTEM; FUNCTIONALIZED POLYMERS; GENISTEIN; NATURALLY OCCURRING; PHARMACEUTICAL APPLICATIONS; POLY (L-LACTIDE); STAR-SHAPED POLYMER;

BIOCOMPATIBILITY; BIODEGRADABLE POLYMERS; DRUG DELIVERY; FUNCTIONAL POLYMERS; HOMOPOLYMERIZATION; NATURAL POLYMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

FLAVONOIDS;

EID: 84881162383     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-013-0973-5     Document Type: Article

References (27)

1. Albertsson AC, Varma IK (2003) Recent developments in ring opening polymerization of lactones for biomedical applications. Biomacromolecules 4(6):1466-1486
2. Hu Z, Fan X, Wang H, Wang J (2009) Synthesis and characterization of biodegradable and biocompatible amphiphilic block copolymers bearing pendant amino acid residues. Polymer 50(17):4175-4181
3. Oh JK (2011) Polylactide (PLA)-based amphiphilic block copolymers: synthesis, self-assembly, and biomedical applications. Soft Matter 7(11):5096-5108
4. He Ch, Kim SW, Lee DS (2007) In situ gelling stimuli-sensitive block copolymer hydrogels for drug delivery. J Control Release 127(3):189-207
5. Broström J, Boss A, Chronakis IS (2004) Biodegradable films of partly branched poly(l-lactide)-co-poly(ε-caprolactone) copolymer: modulation of phase morphology, plasticization properties and thermal depolymerization. Biomacromolecules 5(3):1124-1134
6. Wang F, Bronich TK, Kabanov AV, Rauh RD, Roovers J (2005) Synthesis and evaluation of a star amphiphilic block copolymer from poly(ε-caprolactone) and poly(ethylene glycol) as a potential drug delivery carrier. Bioconjugate Chem 16(2):397-405
7. Kikkawa Y, Abe H, Iwata T, Inoue Y, Doi Y (2002) Crystallization, stability, and enzymatic degradation of poly(l-lactide) thin film. Biomacromolecules 3(2):350-356
8. Persenaire O, Alexandre M, Degée P, Dubois P (2001) Mechanisms and kinetics of thermal degradation of poly(ε-caprolactone). Biomacromolecules 2(1):288-294
9. Meneghetti SP, Lutz PJ, Rein D (1999) Star-shaped polymers via anionic polymerization methods. In: Mishra MK, Kobayashi S (eds) Star and hyperbranched polymers, Marcel Dekker, New York, pp. 27-57
10. Cameron DJA, Shaver MP (2011) Aliphatic polyester polymer stars: synthesis, properties and applications in biomedicine and nanotechnology. Chem Soc Rev 40:1761-1776
11. Oledzka E, Sobczak M (2012) Polymers in the pharmaceutical applications - natural and bioactive initiators and catalysts in the synthesis of biodegradable and bioresorbable polyesters and polycarbonates. In: Agbo EC (ed) Innovations in biotechnology, InTech, Croatia, pp. 139-160
12. Oledzka E, Sokolowski K, Sobczak M, Kołodziejski WL (2011) α-Amino acids as initiators of ε-caprolactone and L, l-lactide polymerization. Polym Int 60(5):787-793
13. Wang J-L, Wang L, Dong Ch-M (2005) Synthesis, crystallization and morphology of star-shaped poly(ε-caprolactone). J Polym Sci A Polym Chem 43:5449-5457
14. Dai X-H, Dong Ch-M, Fa H-B, Yan D, Wei Y (2006) Supramolecular polypseudorotaxanes composed of star-shaped porphyrin-cored poly(ε- caprolactone) and α-cyclodextrin. Biomacromolecules 7:3527-3533
15. Hua Ch, Peng S-M, Dong Ch-M (2008) Synthesis and characterization of linear-dendron-like poly(ε-caprolactone)-b-poly(ethylene oxide) copolymers via the combination of ring-opening polymerization and click chemistry. Macromolecules 41:6686-6695
16. An SG, Cho GCh (2004) Synthesis and characterization of amphiphilic poly(ε-caprolactone) star block copolymers. Macromol Rapid Comm 25(5):618-622
17. Cui Y, Tang X, Huang X, Chen Y (2003) Synthesis of the star-shaped copolymer of ε-caprolactone and l-lactide from a cyclotriphosphazene core. Biomacromolecules 4(6):1491-1494
18. Oledzka E, Kaliszewska D, Sobczak M, Raczak A, Nikel P, Kołodziejski W (2012) Synthesis and properties of a star-shaped poly(ε-caprolactone)-ibuprofen conjugate. J Biomat Sci Polym E 23(16):2039-2054
19. Doerge DR, Chang HC, Churchwell MI, Holder CL (2000) Analysis of soy isoflavone conjugation in vitro and in human blood using liquid chromatography-mass spectrometry. Drug Metab Dispos 28:298-307
20. Lamartiniere CA (2000) Protection against breast cancer with genistein: a compound of soy. Am J Clin Nutr 71(6):1705-1707
21. 13C CP/MAS NMR study of a genistein/piperazine complex. Chem Phys Lett 328:263-269
22. Chang KY, Lee YD (2009) Ring-opening polymerization of ε-caprolactone initiated by the antitumor agent doxifluridine. Acta Biomater 5:1075-1081
23. Kricheldorf HR, Boettcher C, Tönnes KU (1992) Polylactones: 23. Polymerization of racemic and meso-d, Llactide with various organotin catalysts: stereochemical aspects. Polymer 33(13):2817-2824
24. Spassky N, Simic V, Montaudo MS, Hubert-Pfalzgraf LG (2000) Inter- and intramolecular ester exchange reactions in the ring-opening polymerization of (d, l-lactide using lanthanide alkoxide initiators. Macromol Chem Phys 201:2432-2440
25. Sobczak M, Kolodziejski W (2009) Polymerization of cyclic esters initiated by carnitine and tin (II) octoate. Molecules 14:621-632
26. Morrison RT, Boyd RK (1976)Organic Chemistry. In: Baes CF, Mesmer RE (eds) The hydrolysis of cations. 6th edns. Wiley, New York, pp 112-123
27. Kricheldorf HR, Eggerstedt S (1999) Macrocycles, 6. MALDI-TOF mass spectrometry of tin-initiated macrocyclic polylactones in comparison to classical mass-spectroscopic methods. Macromol. Chem Phys 200(6):1284-1291