Facile regioselective synthesis of a novel chitosan-pexiganan conjugate with potential interest for the treatment of infected skin lesions

Synthetic Communications

Volumn 39, Issue 7, 2009, Pages 1228-1240

  Batista, Mary K S ^a   Gallemí, Marçal ^a   Adeva, Alberto ^b   Gomes, Carlos A R ^a   Gomes, Paula ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Antimicrobials; Biopolymers; Chitosan; Diabetes; Drug delivery; Peptides; Pexiganan

Indexed keywords

CHITOSAN; PEXIGANAN ACETATE;

AMINO ACID ANALYSIS; AMINO ACID COMPOSITION; ARTICLE; CATALYSIS; COVALENT BOND; DRUG CONJUGATION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; PEPTIDE SYNTHESIS; SKIN DEFECT;

EID: 61949271021     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802517855     Document Type: Article

References (43)

1. Ge, Y.; McDonald, D. L.; Holroyd, K. J.; Thornsberry, C.; Wexler, H.; Zasloff, M. In vitro antibacterial properties of Pexiganan, an analog of Magainin. Antimicrob. Agents Chemother. 1999, 43, 782-788.
2. Jenssen, H.; Hamill, P.; Hancock, R. E. W. Peptide antimicrobial agents. Clin. Microbiol. Rev. 2006, 19, 491-511.
3. Giuliani, A.; Pirri, G.; Nicoletto, S. F. Antimicrobial peptides: An overview of a promising class of therapeutics. Central Eur. J. Biol. 2007, 2, 1-33.
4. Lamb, H. M.; Wiseman, L. R. Pexiganan acetate. Drugs 1998, 56, 1047-1052.
5. Moore, A. The big and small of drug discovery: Biotech versus pharma: Advantages and drawbacks in drug development. EMBO Rep. 2003, 4, 114-117.
6. BIOTECH Patent News. Accessed 27 February 2008. http://www.entrepreneur. com/tradejournals/article/168795681.html
7. MacroChem Corp. Accessed 17 March 2008. http://www.bio-medicine.org/ medicine-technology-1/MacroChem-Announces-Presentation-of-Pexiganan-Phase-3- Study-Results-for-Topical-Treatment-of-Diabetic-Foot-Infection-1515-1/
8. Abrunhosa, F.; Faria, S.; Gomes, P.; Thomaz, I.; Pessoa, J. C.; Andreu, D.; Bastos, M. Interaction and lipid-induced conformation of two cecropin-melittin hybrid peptides depends on peptide and membrane composition. J. Phys. Chem. B 2005, 109, 17311-17319.
9. Bastos, M.; Bai, G.; Gomes, P.; Andreu, D.; Goormaghtigh, E.; Prieto, M. Energetics and partition of two cecropin-melittin hybrid peptides to model membranes of different composition. Biophys. J. 2008, 94, 2128-2141.
10. Adão, R.; Seixas, R.; Gomes, P.; Pessoa, J. C.; Bastos, M. Membrane structure and interactions of a short Lycotoxin I analogue. J. Pept. Sci. 2008, 14, 528-534.
11. Kogan, G.; Skorik, Y. A.; Žitňanova, I.; Križková, L.; Ďuračková, Z.; Gomes, C. A. R.; Yatluk, Y. G.; Krajčovič, J. Antioxidant and antimutagenic activity of N-(2-carboxyethyl)chitosan. Toxicol. Appl. Pharm. 2004, 201, 303-310.
12. Batista, M. K. S.; Pinto, L. F.; Gomes, C. A. R.; Gomes, P. Novel highly-soluble peptide-chitosan polymers: Synthesis and spectral characterization. Carbohydr. Polym. 2006, 64, 699-305.
13. Gomes, P.; Gomes, C. A. R.; Batista, M. K. S.; Pinto, L. F.; Silva, P. Synthesis, structural characterization, and properties of water-soluble N-(γ-propanoyl-amino acid)-chitosans. Carbohydr. Polym. 2008, 71, 54-65.
14. Ping, H.; Daves, S. S.; Illum, S. In vitro evaluation of the mucoadhesive properties of chitosan microspheres. Int. J. Pharm. 1998, 166, 75-88.
15. Gupta, K. C.; Ravikumar, M. N. V. Drug release behavior of beads and microgranules of chitosan. Biomaterials 2000, 21, 1115-1119.
16. Bernkop-Schnürch, A. Chitosan and its derivatives: Potential excipients for peroral peptide delivery systems. Int. J. Pharm. 2000, 194, 1-13.
17. Bernkop-Schnürch, A.; Kast, C. E. Chemically modified chitosans as enzyme inhibitors. Adv. Drug Deliv. Rev. 2001, 52, 127-137.
18. Berger, J.; Reist, M.; Mayer, J. M.; Felt, O.; Gurny, R. Structure and interactions in chitosan hydrogels formed by complexation or aggregation for biomedical applications. Eur. J. Pharm. Biopharm. 2004, 57, 35-52.
19. Berger, J.; Reist, M.; Mayer, J. M.; Felt, O.; Peppas, N. A.; Gurny, R. Structure and interactions in covalently and ionically crosslinked chitosan hydrogels for biomedical applications. Eur. J. Pharm. Biopharm. 2004, 57, 19-34.
20. Iwasaki, N.; Yamane, S.-T.; Majima, T.; Kasahara, Y.; Minami, A.; Harada, K.; Nonaka, S.; Maekawa, N.; Tamura, H.; Tokura, S.; Shiono, M.; Monde, K.; Nishimura, S.-I. Feasibility of polysaccharide hybrid materials for scaffolds in cartilage tissue engineering: Evaluation of chondrocyte adhesion to polyion complex fibres prepared from alginate and chitosan. Biomacromolecules 2004, 5, 828-833.
21. Amaral, I. F.; Lamghari, M.; Sousa, S. R.; Sampaio, P.; Barbosa, M. A. Rat bone marrow stromal cell osteogenic differentiation and fibronectin adsorption on chitosan membranes: The effect of the degree of acetylation. J. Biomed. Mat. Res. 2005, 75A, 387-397.
22. Amaral, I. F.; Sampaio, P.; Barbosa, M. A. Three-dimensional culture of human osteoblastic cells in chitosan sponges: The effect of the degree of acetylation. J. Biomed. Mat. Res. 2005, 76A, 335-346.
23. Krauland, H.; Guggi, D.; Bernkop-Schnürch, A. Thiolated chitosan microparticles: A vehicle for nasal peptide drug delivery. Int. J. Pharm. 2006, 307, 270-277.
24. Martien, R.; Loretz, B.; Bernkop-Schnürch, A. Oral gene delivery: Design of polymeric carrier systems shielding toward intestinal enzymatic attack. Biopolymers 2006, 83, 327-336.
25. Kotzé, A. F.; Lueben, H. L.; Thanou, M. M.; Verhoef, J. C.; de Boer, A. G.; Junginger, H. E.; Lehr, C.-M. Chitosan and chitosan derivatives as absorption enhancers for peptide drugs across mucosal epithelia. In: Bioadhesive Drug Delivery Systems: Fundamentals, Novel Approaches, and Development; E. Mathiowitz, D. E. Chickering, C.-M. Lehr (Eds.); Marcel Dekker: New York, 1999, pp. 341-387.
26. Gopinath, D.; Kumar, M. S.; Selvaraj, D.; Jayakumar, R. Pexiganan-incorporated collagen matrices for infected wound-healing processes in rat. J. Biomed. Mat. Res. 2005, 73A, 320-331.
27. Xiao, S.-J.; Wieland, M.; Brunner, S. Reactions of surface amines with heterobifunctional cross-linkers bearing both succinimidyl ester. J. Coll. Interface Sci. 2005, 290, 172-183.
28. Mochizuki, M.; Yamagata, N.; Philp, D.; Hozumi, K.; Watanabe, T.; Kikkawa, Y.; Kadoya, Y.; Kleinman, H. K.; Nomizu, M. Integrin-dependent cell behaviour on ecm peptide-conjugated chitosan membranes. Biopolymers 2007, 88, 122-130.
29. Chen, T. H.; Embree, H. D.; Payne, G. F. In vitro protein-polysaccharide conjugation: tyrosinase-catalyzed conjugation of gelatin and chitosan. Biopolymers 2002, 64, 292-302.
30. Masuko, T.; Minami, A.; Iwasaki, N.; Majima, T.; Nishimura, S.-I.; Lee, Y. C. Thiolation of chitosan: Attachment of proteins via thioether formation. Biomacromolecules 2005, 6, 880-884.
31. Shanmugam, G.; Polavarapu, P. L.; Gopinath, D.; Jayakumar, R. The structure of antimicrobial pexiganan peptide in solution probed by FT-IR absorption, vibrational circular dichroism, and electronic circular dichroism spectroscopy. Biopolymers 2005, 80, 636-642.
32. Kaiden, K.; Matsui, T.; Tanaka, S. A study of the amide III band by FTIR spectrometry of albumin, myoglobin, and γ-globulin. Appl. Spectrosc. 1987, 41, 180-184.
33. Cai, S.; Singh, B. R. Identification of β-turn and random coil amide III infrared bands for secondary structure estimation of proteins. Biophys. Chem. 1999, 80, 7-20.
34. Sheehan, C.; Preston, J.; Cruishank, P. A. A rapid synthesis of oligopeptide derivatives without isolation of intermediates. J. Am. Chem. Soc. 1965, 87, 2492-2493.
35. Bodnar, M. J.; Hartman, F.; Borbely, J. Synthesis and study of cross-linked chitosan-N-poly(ethyleneglycol) nanoparticles. Biomacromolecules 2006, 7, 3030-3036.
36. Lee, Y.; Jo, W. H. Physicochemical characteristics of self-aggregates of hydrophobically modified chitosans. Langmuir 1998, 14, 2329-2332.
37. Damink, H. H. O.; Dijkstra, P. J.; van Luyn, M. J. A.; van Wachem, P. B.; Nieuwenhuis, P.; Feijen, J. Cross-linking of dermal sheep collagen using a water-soluble carbodiimide. Biomaterials 1996, 17, 765-773.
38. Hojo, K.; Maeda, M.; Mu, Y.; Kamada, H.; Tsutsumi, Y.; Nishiyama, Y.; Yoshikawa, T.; Kurita, K.; Block, L. H.; Mayumi, T.; Kawasaki, K. Preparation of a chitosan hybrid of an antimetastatic laminin-related peptide. Pharm. Pharmacol. Commun. 1999, 5, 277-280.
39. Bray, L. Large-scale manufacture of peptide therapeutics by chemical synthesis. Nature Rev. Drug Discov. 2003, 2, 587-593.
40. Kurita, K.; Ikeda, H.; Yoshida, Y.; Shimojoh, M.; Harata, M. Chemoselective protection of the amino groups of chitosan by controlled phthaloylation: Facile preparation of a precursor useful for chemical modifications. Biomacromolecules 2002, 3, 1-4.
41. Kurita, K.; Hayakawa, M.; Nishiyama, Y.; Harata, M. Polymeric asymmetric reducing agents: Preparation and reducing performance of chitosan/ dihydronicotinamide conjugates having D- and L-phenylalanine spacer arms. Carbohydr. Polym. 2002, 47, 7-14.
42. Holappa, J.; Nevalainen, T.; Soininen, P.; Elomaa, M.; Safin, R.; Másson, M.; Järvinen, T. N-chloroacyl-6-O-triphenylmethylchitosans: Useful intermediates for synthetic modifications of chitosan. Biomacromolecules 2005, 6, 858-863.
43. Holappa, J.; Nevalainen, T.; Soininen, P.; Másson, M.; Järvinen, T. Synthesis of novel quaternary chitosan derivatives via N-chloroacyl-6-O-triphenylmethylchitosans. Biomacromolecules 2006, 7, 407-410.