Synthesis of biodegradable chiral poly(ester-imide)s derived from valine-, leucine- and tyrosine-containing monomers

Amino Acids

Volumn 41, Issue 5, 2011, Pages 1215-1222

  Mallakpour, Shadpour ^a   Asadi, Parvin ^a   Sabzalian, Mohammad R ^a  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Biodegradable polymers; Optically active material; Poly(ester imide); Polymers containing amino acid

Indexed keywords

5 AMINOISOPHTHALIC ACID; MONOMER; POLYESTERIMIDE; POLYMER; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; ASPERGILLUS; BIODEGRADABILITY; CHEMICAL ANALYSIS; CONTROLLED STUDY; CULTURE MEDIUM; ELEMENTAL ANALYSIS; ENVIRONMENTAL PROTECTION; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; FUNGUS GROWTH; HYDROGEN BOND; IN VITRO STUDY; MICROBIAL DEGRADATION; PENICILLIUM; POLLUTION CONTROL; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOIL CHANGE; SOLUBILITY; THERMOGRAVIMETRY; THERMOSTABILITY; TOXICITY TESTING; VISCOSITY;

BACTERIA; BIODEGRADATION, ENVIRONMENTAL; ESTERS; FUNGI; IMIDES; KINETICS; LEUCINE; MOLECULAR STRUCTURE; POLYMERS; TYROSINE; VALINE;

EID: 84855227064     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-010-0799-5     Document Type: Article

References (37)

1. Amass W, Amass A, Tighe B (1998) A review of biodegradable polymers: uses, current developments in the synthesis and characterization of biodegradable polyesters, blends of biodegradable polymers and recent advances in biodegradation studies. Polym Int 47l:89-144 (Pubitemid 29126333)
2. Behniafar H, Beit-Saeed A, Hadian A (2009) Novel heat-resistant and organosoluble poly(amide-imide)s containing laterally-attached phenoxy phenylene groups. Polym Degrad Stab 94:1991-1998
3. Browna MD, Graya AI, Tetleyb L, Santovenaa A, Renea J, Schatzleinc AG, Uchegbu IF (2003) In vitro and in vivo gene transfer with poly(amino acid) vesicles. J Control Release 93:193-211 (Pubitemid 37424033)
4. Chandra R, Rustgi R (1998) Biodegradable polymers. Prog Polym Sci 23:1273-1335 (Pubitemid 128676292)
5. Chern T, Huang CM, Huang SC (1998) Synthesis and characterization of new poly(amide-imide)s containing 4,9-diamantane moieties in the main chain. Polymer 39:2929-2934
6. Eversloh TL, Nicole C, Santos S, Stephanopoulos G (2007) Perspectives of biotechnological production of L-tyrosine and its applications. Appl Microbiol Biotechnol 77:751-762 (Pubitemid 350159877)
7. Fan Y, Kobayashi M, Kise H (2001) Synthesis and specific biodegradation of novel polyesteramides containing amino acid residues. J Polym Sci Part A Polym Chem 39:1318-1328 (Pubitemid 32425401)
8. Garlick PJ (2005) The role of leucine in the regulation of protein metabolism. J Nutr 135:1553S-1556S (Pubitemid 40791669)
9. Gigante A, Chillemi C, Bevilacqua C, Greco F (2003) Effect of elastin-derived peptide on Achilles tendon healing: an experimental study. J Mater Sci Mater Med 14:717-720 (Pubitemid 36976221)
10. Guo Y, Li M, Mylonakis A, Han J, Diarmid AGM, Chen X, Lelkes PI, Wei Y (2007) Electroactive oligoaniline-containing selfassembled monolayers for tissue engineering applications. Biomacromolecules 8:3025-3034 (Pubitemid 350011621)
11. Hasegawa M, Sakamoto Y, Tanaka Y, Kobayashi Y (2010) Poly(ester imide)s possessing low coefficients of thermal expansion (CTE) and low water absorption (III). Use of bis(4-aminophenyl)terephthalate and effect of substituents. Eur Polym J 46:1510-1524
12. Higashi F, Mashimo T (1986) Direct polycondensation of hydroxybenzoic acids with thionyl chloride in pyridine. J Polym Sci Part A Polym Chem 24:1697-1701 (Pubitemid 16595062)
13. Higashi F, Ong CH, Okada Y (1999) High-molecular-weight copolyesters of dihydroxybenzophenones by 'induced' copolyesterification using TsCl/DMF/Py as a condensing agent. J PolymSci Part A Polym Chem 37:3625-3631
14. Higashi F, Watabiki M, Kim JH (2001) Promoted random orientation of the phenyl substituent of phenylhydroquinone-terephthalic acid polyesters prepared with a diphenyl chlorophosphate/ pyridine condensing agent. J Polym Sci Part A Polym Chem 39:1726-1732 (Pubitemid 32446860)
15. Huang SJ (2005) Biodegradable polymers for biomedical applications. Institute of Materials Science, University of Connecticut, Storrs, Connecticut
16. Kemnitzer J, Kohn J (1997) Degradable polymers derived from the amino acid L-tyrosine. Drug targeting and delivery. Handbook of biodegradable polymers. Harwood Academic, Amsterdam, pp 251-272
17. Layman DK, Baum JI (2004) Dietary protein impact on glycemic control during weight loss. J Nutr 134:968S-973S (Pubitemid 38456273)
18. Mallakpour S (2010) Synthesis of soluble poly(amide-ether-imideurea) s bearing amino acid moieties in the main chain under green media (ionic liquid). Amino acids (in press)
19. Mallakpour S, Asadi P (2010) Novel chiral poly(ester-imide)s with different natural amino acids in the main chain as well as in the side chain: synthesis and characterization. Colloid Polym Sci 288:1341-1349
20. Mallakpour S, Dinari M (2008) Microwave step-growth polymerization of 5-(4-methyl-2-phthalimidylpentanoylamino)isophthalic acid with different diisocyanates. Polym Adv Technol 19:1334-1342
21. Mallakpour S, Kolahdoozan M (2007) Synthesis and properties of thermally stable and optically active novel wholly aromatic polyesters containing a chiral pendent group. Eur Polym J 43:3344-3354 (Pubitemid 47175934)
22. Mallakpour S, Kolahdoozan M (2008) Synthesis and properties of novel soluble aromatic polyamides derived from 5-(2-phthalimidyl- 3-methyl butanoylamino)isophthalic acid and aromatic diamines. React Func Polym 68:91-96 (Pubitemid 350236914)
23. Mallakpour S, Mirkarimi F (2010) Synthesis and characterization of novel, optically active polyamides derived from S-valine natural amino acid and bulky anthracenic side chain. Amino acids 39:1255-1263
24. Mallakpour S, Tirgir F, Sabzalian MR (2010) Synthesis and structural characterization of novelbiologically active and thermally stable poly(ester-imide)s containing different natural amino acids linkages. J Polym Res (in press)
25. Mallakpour S, Tirgir F, Sabzalian MR (2010) Synthesis, characterization and in vitro antimicrobial and biodegradability study of pseudo-poly(amino acid)s derived from N,N0-(pyromellitoyl)- bis-L-tyrosine dimethyl ester as a chiral bioactive diphenolic monomer. Amino acids (in press)
26. Metselaar GA, Adams PJHM, Nolte RJM, Cornelissen JJLM, Rowan AE (2007) Polyisocyanides derived from tripeptides of alanine. Chem Eur J 13:950-960 (Pubitemid 46144571)
27. Pitarresi G, Palumbo FS, Cavallaro G, Fare S, Giammona G (2008) Scaffolds based on hyaluronan crosslinked with a polyaminoacid: Novel candidates for tissue engineering application. J Biomed Mater Res Part A 87:770-779
28. Shabbir S, Zulfiqar S, Ahmad Z, Sarwar MI (2010) Synthesis and characterization of hyperbranched aromatic polyester-imides with goodthermalpropertiesbasedon1,3,5-tris(30, 40-carboxyphenyl) benzene trianhydride. Polym Degrad Stab 95:1251-1259
29. Suarez N, Brocchini S, Kohn J (1998) The study of water uptake in degradable polymers by thermally stimulated depolarization currents. Biomaterials 19:2347-2356 (Pubitemid 28550402)
30. Tosi G, Costantino L, Rivasi F, Ruozi B, Leo E, Vergoni AV, Tacchi R, Bertolini A, Vandelli MA, Forni F (2007) Targeting the central nervous system: in vivo experiments with peptidederivatized nanoparticles loaded with Loperamide and Rhodamine- 123. J Control Release 122:1-9 (Pubitemid 47284547)
31. Tsitlanadzei G, Machidzei M, Kviria T, Djavakhishvili N, Chu cc, Katsarava R (2004) Biodegradation of amino-acid-based poly(ester amide)s: in vitro weight loss and preliminary in vivo studies. J Biomater Sci Polym Ed 15:1-24 (Pubitemid 38239668)
32. Wang YW, Chen WC (2010) Synthesis, properties, and anti-reflective applications of new colorless polyimide-inorganic hybrid optical materials. Compos Sci Technol 70:769-775
33. Wang CS, Leub TS (2000) Synthesis and characterization of polyimides containing naphthalene pendant group and flexible ether linkages. Polymer 41:3581-3591
34. Wathier M, Johnson SC, Kim T, Grinstaff MW (2006) Hydrogels formed by multiple peptide ligation reactions to fasten corneal transplants. Bioconjugate Chem 17:873-876 (Pubitemid 44162603)
35. Wezenberg SJ, Metselaar GA, Rowan AE, Cornelissen JJLM, Seebach D, Nolte RJM (2006) Synthesis, characterization, and folding behavior of b-amino acid derived polyisocyanides. Chem Eur J 12:2778-2786
36. Yu C, Mielewczyk SS, Breslauer KJ, Kohn J (1999) Tyrosine-PEGderived poly(ether carbonate)s as new biomaterials. Part II: study of inverse temperature transitions. Biomaterials 20:265-272 (Pubitemid 29047971)
37. Yu LMY, Kazazian K, Shoichet MS (2007) Peptide surface modification of methacrylamide chitosan for neural tissue engineering applications. J Biomed Mater Res Part A 82:243-255 (Pubitemid 46906512)