A new chitosan-thymine conjugate: Synthesis, characterization and biological activity

International Journal of Biological Macromolecules

Volumn 50, Issue 3, 2012, Pages 493-502

  Kumar, Santosh ^a   Koh, Joonseok ^a   Kim, Hyerim ^a   Gupta, M K ^a   Dutta, P K ^b  

^a Konkuk University   (South Korea)

^b MOTILAL NEHRU NATIONAL INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Acylation; Biomedical applications; Chitosan; Conjugate; Thymine 1 yl acetic acid

Indexed keywords

ACETIC ACID DERIVATIVE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; CHITOSAN THYMIDINE CONJUGATE; THYMINE 1 YL ACETIC ACID; THYMINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; ASPERGILLUS NIGER; CELL STRAIN 3T3; CELL STRAIN HEPG2; CHEMICAL REACTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; STAPHYLOCOCCUS AUREUS; THERMOGRAVIMETRY; X RAY DIFFRACTION;

ASPERGILLUS NIGER; ESCHERICHIA COLI; FUNGI; STAPHYLOCOCCUS AUREUS;

EID: 84863229826     PISSN: 01418130     EISSN: 18790003     Source Type: Journal    
DOI: 10.1016/j.ijbiomac.2012.01.015     Document Type: Article

References (44)

1. Tumir L.M., Grabar M., Tomic S., Piantanida I. The interactions of bis-phenanthridinium-nucleobase conjugates with nucleotides: adenine-conjugate recognizes UMP in aqueous medium. Tetrahedron 2010, 66:2501-2513.
2. Pike A.R., Ryder L.C., Horrocks B.R., Clegg W., Elsegood M.R.J., Connolly B.A., Houlton A. Metallocene-DNA: synthesis, molecular and electronic structure and DNA incorporation of C5-Ferrocenylthymidine derivatives. Chem. A: Eur. J. 2002, 8:2891-2899.
3. Boncel S., Maczka M., Koziol K.K.K., Motyka R., Walczakv K.Z. Symmetrical and unsymmetrical alpha,omega-nucleobase amide-conjugated systems. Beilstein J. Org. Chem. 2010, 6. 10.3762/bjoc.6.34.
4. Ihara T., Uemura A., Futamura A., Shimizu M., Baba N., Nishizawa S., Teramae N., Jyo A. Cooperative DNA probing using a β-cyclodextrin-DNA conjugate and a nucleobase specific fluorescent ligand. J. Am. Chem. Soc. 2009, 131:1386-1387.
5. Kraatz H.B. Ferrocene-conjugates of amino acids, peptides and nucleic acids. J. Inorg. Organomet. Polym. Mater. 2005, 15:83-106.
6. Wlassoff W.A., King G.C. Ferrocene conjugates of dUTP for enzymatic redox labeling of DNA. Nucleic Acids Res. 2002, 30:1-7.
7. Xu Y., Jin H., Yang Z., Zhang L., Zhang L. Synthesis and biological evaluation of novel neamine-nucleoside conjugates potentially targeting to RNAs. Tetrahedron 2009, 65:5228-5239.
8. Kubo T., Rumiana B., Ohba H., Fujii M. Antisense effects of DNA-peptide conjugate. Nucleic Acids Res. Suppl. 2003, 3:179-180.
9. Roviello G.N., Benedetti E., Pedone C., Bucci E.M. Nucleobase-containing peptides: an overview of their characteristic features and applications. Amino Acids 2010, 39:45-57.
10. Gross A., Neukamm M., Metzler-Nolte N. Synthesis and cytotoxicity of a bimetallic ruthenocene dicobalt-hexacarbonyl alkyne peptide biconjugate. Dalton Trans 2011, 40:1382-1386.
11. Kumar S., Dutta J., Dutta P.K. Preparation and characterisation of N-heterocyclic chitosan derivative based gels for biomedical applications. Int. J. Biol. Macromol. 2009, 45:330-337.
12. Kumar S., Nigam N., Ghosh T., Dutta P.K., Singh S.P., Datta P.K., An L., Shi T.F. Preparation, characterisation and optical properties of novel azo-based chitosan biopolymer. Mater. Chem. Phys. 2010, 120:361-370.
13. Kumar S., Dutta P.K., Sen P. Preparation and characterisation of optical property of crosslinkable film of chitosan with 2-thiophenecarboxaldehyde. Carbohyd. Polym. 2010, 80:564-570.
14. Kumar S., Koh J., Tiwari D.K., Dutta P.K. Optical study of chitosan-ofloxacin complex for biomedical applications. J. Macromol. Sci. A 2011, 48:789-795.
15. Muzzarelli R.A.A. Human enzymatic activities related to the therapeutic administration of chitin derivatives. Cell. Mol. Life Sci. 1997, 53:131-140.
16. Jayakumar R., Chennazhi K.P., Muzzarelli R.A., Tamura H., Nair S.V., Selvamurugan S. Chitosan conjugated DNA nanoparticles in gene therapy. Carbohyd. Polym. 2010, 79:1-8.
17. Jayakumar R., Nwe N., Tokura S., Tamura H. Sulfated chitin and chitosan as novel biomaterials. Int. J. Biol. Macromol. 2007, 40:175-181.
18. Jaykumar R., Prabaharan M., Nair S.V., Tamura H. Novel chitin and chitosan nanofibers in biomedical applications. Biotechnol. Adv. 2010, 28:142-150.
19. Batista M.K.S., Pinto L.F., Gomes C.A.R., Gomes P. Novel highly soluble peptide-chitosan polymers: chemical synthesis and spectral characterization. Carbohydr. Polym. 2006, 64:299-305.
20. Alves N.M., Mano J.F. Chitosan derivatives obtained by chemical modifications for biomedical and environmental applications. Int. J. Biol. Macromol. 2008, 43:401-414.
21. Mourya V.K., Inamdar N.N. Chitosan-modification and applications: opportunities galore. React. Funct. Polym. 2008, 68:1013-1051.
22. Manna U., Bharani S., Patil S. Layer-by-layer self-assembly of modified hyaluronic acid/chitosan based on hydrogen bonding. Biomacromolecules 2009, 10:2632-2639.
23. Jayakumar R., Prabaharan M., Reis R.L., Mano J.F. Graft copolymerized chitosan present status and applications. Carbohyd. Polym. 2005, 62:142-158.
24. Jayakumar R., Nagahama H., Furuike T., Tamura H. Synthesis of phosphorylated chitosan by novel method and its characterization. Int. J. Biol. Macromol. 2008, 42:335-339.
25. Jayakumar R., Tamura H., Synthesis characterization and thermal properties of chitin-g-poly(e{open}-caprolactone) copolymers by using chitin hydrogel. Int. J. Biol. Macromol. 2008, 43:32-36.
26. Jayakumar R., Prabaharan M., Kumar P.T.S., Nair S.V., Tamura H. Biomaterials based on chitin and chitosan in wound dressing applications. Biotechnol. Adv. 2011, 29:322-337.
27. Rejinold N.S., Chennazhi K.P., Nair S.V., Tamura H., Jayakumar R. Biodegradable and thermo-sensitive chitosan-g-poly(N-vinyl-caprolactam) nanoparticles as a 5-fluorouracil carrier. Carbohyd. Polym. 2011, 83:776-786.
28. Kumar S., Dutta P.K., Koh J. A physico-chemical and biological study of novel chitosan-chloroquinoline derivative for biomedical applications. Int. J. Biol. Macromol. 2011, 49:356-361.
29. Borg N., Zhou X.X., Johansson N.G., Oberg B., Stahle L. Distribution to the brain and protein binding of 3' and 5-substituted 2',3'-dideoxyuridine derivatives studied by microdialysis. Antiviral Chem. Chemother. 1997, 8:47-53.
30. Liu X.-J., Chen R.-Y. Synthesis of novel phosphonotripeptides containing uracil or thymine group. Phosphorus, Sulfur Silicon 2001, 176:19-28.
31. Tanaka H., Takashima H., Ubasawa M., Sekiya K., Inouye N., Shigeta S., Walker R.T., De Clercq, Miyasaka E.T. Synthesis and antiviral activity of 6-benzyl analogs of 1-[2-Hydroxyethoxy] methyl]-5-(phenylthio) thymine (HEPT) as potent and selective anti-HIV-1 agents. J. Med. Chem. 1995, 38:2860-2865.
32. Roviello G.N., Gaetano S.D., Capasso D., Franco S., Crescenzo C., Bucci E.M., Pedone C. RNA-binding and viral reverse transciptase inhibitory activity of a novel cationic diamino acid based peptide. J. Med. Chem. 2011, 10.1021/jm1012769.
33. Nelson D.L., Cox M.M. DNA replication. Lehninger Principles of Biochemistry 2005, pp. 950-966. 4th ed.
34. Hanahan D., Weinberg R.A. Hallmarks of cancer: the next generation. Cell 2011, 144:646-674.
35. Katritzky A.R., Narindoshvili T. Chiral peptide nucleic acid monomers (PNAM) with modified backbones. Org. Biomol. Chem. 2008, 6:3171-3176.
36. Clark C.L., Jacobs M.R.J., Appelbaum P.C. Antipneumococcal activities of levofloxacin and clarithromycin as determined by agar dilution, microdilution, E-test, and disk diffusion methodologies. J. Clin. Microbiol. 1998, 36:3579-3584.
37. Das Z.C., Gupta M.K., Uhm S.J., Lee H.T. Increasing histone acetylation of cloned embryos, but not donor cells, by sodium butyrate improves their in vitro development in pigs. Cell Reprogram. 2010, 12:95-104.
38. Jung Y.H., Gupta M.K., Oh S.H., Uhm S.J., Lee H.T. Glial cell line derived neurotrophic factor alters the growth characteristics and genomic imprinting of mouse multipotent adult germline stem cells. Exp. Cell Res. 2010, 316:747-761.
39. Peniche C., San Roman Arguelles-Monal W. A kinetic study of the thermal degradation of chitosan and a mercaptan derivative of chitosan. Polym. Degrad. Stab. 1993, 39:21-28.
40. Goosen M.F.A. Applications of Chitin and Chitosan 2001, Technomic Publishing Inc, Lancaster, p. 131.
41. Zheng L.Y., Zhu J.F. Study on antimicrobial activity of chitosan with different molecular weights. Carbohyd. Polym. 2003, 54:527.
42. Baguley B.C. Multiple drug resistance mechanisms in cancer. Mol. Biotechnol. 2010, 46:308-316.
43. The intensity of diffracted X-rays 1998, Oxford Science Publication, p. 21. W. Clegg (Ed.).
44. Ungár T. Characterization of nanocrystalline materials by X-ray line profile analysis. J. Mater. Sci. 2007, 42:1584-1593.