Quaternization of N-aryl chitosan derivatives: synthesis, characterization, and antibacterial activity

Carbohydrate Research

Volumn 344, Issue 18, 2009, Pages 2502-2511

  Sajomsang, Warayuth ^a   Tantayanon, Supawan ^a   Tangpasuthadol, Varawut ^a   Daly, William H ^b  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

Antibacterial activity; Chitosan; N (3 Chloro 2 hydroxypropyl)trimethylammonium chloride; N Aryl chitosan derivatives; Quaternary ammonium chitosan chloride

Indexed keywords

ACIDIC CONDITIONS; AMINO GROUP; ANTI-MICROBIAL ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL STUDY; AROMATIC ALDEHYDE; ARYL SUBSTITUENTS; BIOLOGICAL ACTIVITIES; CHITOSAN DERIVATIVES; ELECTRON WITHDRAWING GROUP; ELECTRON-DONATING; ELECTRON-WITHDRAWING SUBSTITUENTS; GLUCOSAMINES; HYDROPHOBIC SUBSTITUENTS; HYDROXYL GROUPS; MINIMUM INHIBITORY CONCENTRATION; N-ARYLATIONS; N-SUBSTITUTION; NEUTRAL PH; POLYMER BACKBONES; QUATERNARY AMMONIUM; QUATERNIZATION; SCHIFF BASIS; SCHIFF-BASE; SODIUM CYANOBOROHYDRIDE; STAPHYLOCOCCUS AUREUS; WATERSOLUBLE;

ALDEHYDES; AMINATION; AMMONIUM COMPOUNDS; AROMATIC COMPOUNDS; BEARINGS (STRUCTURAL); BIOLOGICAL MATERIALS; CHEMICAL MODIFICATION; CHITIN; CHLORINE COMPOUNDS; ELECTRONS; ESCHERICHIA COLI; FLUORINE CONTAINING POLYMERS; FUNCTIONAL GROUPS; SODIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CHITOSAN;

ALDEHYDE; CHITOSAN DERIVATIVE; CHITOSAN QUAT 188; GLUCOSAMINE; HYDROXYL GROUP; N (2 METHOXYBENZYL) CHITOSAN QUAT 188; N (2 THIOPHENYLMETHYL) CHITOSAN QUAT 188; N (3 BROMOBENZYL) CHITOSAN QUAT 188; N (3 CHLORO 2 HYDROXYPROPYL) TRIMETHYLAMMONIUM CHLORIDE; N (3,4 DIMETHOXYBENZYL) CHITOSAN QUAT 188; N (4 BROMOBENZYL) CHITOSAN QUAT 188; N (4 CARBOXYBENZYL) CHITOSAN QUAT 188; N (4 CHLOROBENZYL) CHITOSAN QUAT 188; N (4 FLUOROBENZYL) CHITOSAN QUAT 188; N (4 HYDROXYBENZYL) CHITOSAN QUAT 188; N (4 METHOXYBENZYL) CHITOSAN QUAT 188; N (4 METHYLBENZYLCHITOSAN) QUAT 188; N (4 NITROBENZYL) CHITOSAN QUAT 188; N (4 PYRIDINYLMETHYL) CHITOSAN QUAT 188; N (4 TRIFLUOROBENZYL) CHITOSAN QUAT 188; N ARYL CHITOSAN DERIVATIVE; N BENZYLCHITOSAN QUAT 188; N N OCTYLCHITOSAN QUAT 188; QUATERNARY AMMONIUM DERIVATIVE; SCHIFF BASE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; ARYLATION; CONTROLLED STUDY; DRUG SYNTHESIS; ELECTRON; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR WEIGHT; NONHUMAN; PH MEASUREMENT; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS; SUBSTITUTION REACTION;

ANTI-BACTERIAL AGENTS; CHITOSAN; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; QUATERNARY AMMONIUM COMPOUNDS; SOLUBILITY; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

ESCHERICHIA COLI; STAPHYLOCOCCUS AUREUS;

EID: 71849104063     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.09.004     Document Type: Article

References (44)

1. Liu X.F., Guan Y.L., Yang D.Z., Li Z., and Yao K.D. J. Appl. Polym. Sci. 79 (2001) 1324-1335
2. Rabea E.I., Badawy M.E.T., Stevens C.V., Smagghe G., and Steurbaut W. Biomacromolecules 4 (2003) 1457-1465
3. Muzzarelli R., Tarsi R., Filippini O., Giovanetti E., Biagini G., and Varaldo P.E. Antimicrob. Agents Chemother. 34 (1990) 2019-2023
4. Helander I.M., Nurmiabo-Lassila E.L., Ahvenainen R., Rhoades J., and Roller S. Int. J. Food Microbiol. 71 (2001) 235-244
5. Liu H., Du Y., Wang X., and Sun L. Int. J. Food Microbiol. 95 (2004) 147-155
6. Je J.Y., and Kim S.K. J. Agric. Food Chem. 54 (2006) 5529-6633
7. Jia Z., Shen D., and Xu W. Carbohydr. Res. 333 (2001) 1-6
8. Avadi M.R., Sadeghi A.M.M., Tahzibi A., Bayati K., Pouladzadeh M., Zohuriaan-Mehr M.J., and Rafiee-Tehrani M. Eur. Polym. J. 40 (2004) 1355-1361
9. Rúnarsson O.V., Holappa J., Nevalainen T., Hjálmarsdóttir M., Järvinen T., Loftsson T., Einarsson J.M., Jónsdóttir S., Valdimarsdóttir M., and Másson M. Eur. Polym. J. 43 (2007) 2660-2671
10. Sajomsang W., Tantayanon S., Tangpasuthadol V., and Daly W.H. Carbohydr. Polym. 7 (2008) 740-750
11. Daly W.H., and Manuszak-Guerrini M.A. Polym. Mater. Sci. Eng. 79 (1998) 220-221
12. Domard A., Rinaudo M., and Terrassin C. Int. J. Biol. Macromol. 8 (1986) 105-107
13. Dung P.L., Milas M., Rinaudo M., and Desbrieres J. Carbohydr. Polym. 24 (1994) 209-214
14. Kotz A.F., Luessen H.L., De Leeuw B.J., De Boer A.G., Verhoef J.C., and Junginger H.E. Pharm. Res. 14 (1997) 1197-1202
15. Hamman J.H., and Kotze A.F. Drug Dev. Ind. Pharm. 27 (2001) 373-380
16. Elisabete C., Douglas D.B., and Sergio P.C.F. Macromol. Biosci. 3 (2003) 571-576
17. Polnok A., Borchard G., Verhoef J.C., Sarisuta N., and Junginger H.E. Eur. J. Pharm. Biopharm. 57 (2004) 77-83
18. Thanou M.M., Verhoef J.C., Romeijn S.G., Nagelkerke J.F., Merkus F., and Junginger H.E. Int. J. Pharm. 185 (1999) 73-82
19. Kean T., Roth S., and Thoanou M. J. Controlled Release 103 (2005) 643-653
20. Cafaggi S., Russo E., Stefani R., Leardi R., Caviglioli G., Parodi B., Bignardi G., De Totero D., Aiello C., and Viale M. J. Controlled Release 121 (2007) 110-123
21. Fu C., Zhi-Rong Z., Fang Y., Xuan Q., Minting W., and Yuan H. Int. J. Pharm. 349 (2008) 226-233
22. Britto D., and Assis O.B.G. Int. J. Bio. Macromol. 41 (2007) 198-203
23. Daly, W. H.; Manuszak-Guerrini, M. A. U.S. Patent 6,306,835, October 23, 2001.
24. Heinze T., Haack V., and Rensing S. Starch/Staerke 56 (2004) 288-296
25. Hashem M., Hauser P., and Smith B. Textile Res. J. 73 (2003) 1017-1023
26. Lavertu M., Xia Z., Serreqi A.N., Berrada M., Rodrigues A., Wang D., Buschmann M.D., and Gupta A.A. J. Pharm. Biomed. Anal. 32 (2003) 1149-1158
27. Crini G., Torri G., Guerrini M., Morcellet M., Weltrowski M., and Martel B. Carbohydr. Polym. 33 (1997) 145-151
28. Sieval A.B., Thanou M., Kotze A.F., Verhoef J.C., Brussee J., and Junginger H.E. Carbohydr. Polym. 36 (1998) 157-165
29. Sajomsang W., Tantayanon S., Tangpasuthadol V., Thatte M., and Daly W.H. Int. J. Biol. Macromol. 43 (2008) 79-87
30. Yu H., Huang Y., Ying H., and Xiao C. Carbohydr. Polym. 69 (2007) 29-40
31. Geresh S., Dawadi R.P., and Arad S.M. Carbohydr. Polym. 63 (2000) 75-80
32. Song Y., Sun Y., Zhang X., Zhou J., and Zhang L. Biomacromolecules 9 (2008) 2259-2264
33. Loubaki E., Ourevitch M., and Sicsic S. Eur. Polym. J. 27 (1991) 311-317
34. Num C.W., Kim Y.H., and Ko S.W. J. Appl. Polym. Sci. 74 (1999) 2258-2265
35. Lim S.H., and Hudson S.M. Carbohydr. Res. 339 (2004) 313-319
36. No K.H., Park N.Y., Lee S.H., and Meyers S.P. Int. J. Food Microbiol. 74 (2002) 65-72
37. Jeon Y.J., and Kim S.K. Carbohydr. Polym. 41 (2000) 133-144
38. Holappa J., Hjálmarsdóttir M., Másson M., Rúnarsson O., Asplund T., Soininen P., Nevalainen T., and Järvinen T. Carbohydr. Polym. 41 (2006) 114-118
39. Stockmayer W.H., and Schmidt M. Pure Appl. Chem. 54 (1982) 407-414
40. Huber K., Burchard W., and Fetters L.J. Macromolecules 17 (1984) 541-548
41. Burchard W. Adv. Polym. Sci. 143 (1999) 113-194
42. Hu Y., Du Y., Yang J., Kennedy J.F., Wang X., and Wang L. Carbohydr. Polym. 67 (2007) 66-72
43. Kim C.H., Choi J.W., Chun H.J., and Choi K.S. Polym. Bull. 38 (1997) 387-393
44. Kenawy E.-R., Abdel-Hay F.I., El-Shanshoury A.E.-R.R., and El-Newehy M.H. J. Controlled Release 50 (1998) 145-152