Preparation and antibacterial activity of Schiff bases from O-carboxymethyl chitosan and para-substituted benzaldehydes

Polymer Bulletin

Volumn 68, Issue 5, 2012, Pages 1215-1226

  Yin, Xueqiong ^a   Chen, Junhua ^a   Yuan, Wen ^a   Lin, Qiang ^a,b   Ji, Li ^a   Liu, Fang ^a  

^a HAINAN UNIVERSITY   (China)

^b HAINAN NORMAL UNIVERSITY   (China)

Author keywords

Antibacterial activity; O carboxymethyl chitosan; Schiff base; Synthesis

Indexed keywords

ACID-BASE TITRATION; ANTI-BACTERIAL ACTIVITY; CARBON-13; E. COLI; O-CARBOXYMETHYL CHITOSANS; PARA POSITION; POLARIZATION TRANSFER; S. AUREUS; SCHIFF BASE; SCHIFF BASIS; STAPHYLOCOCCUS AUREUS;

ALDEHYDES; BACTERIA; CHITOSAN; ESCHERICHIA COLI; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FUNCTIONAL GROUPS; SYNTHESIS (CHEMICAL); TITRATION;

ORGANIC POLYMERS;

EID: 84859579028     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-011-0599-4     Document Type: Article

References (38)

1. Kang YM, Lee BN, Ko JH, Kim GH, Kang KN, Kim DY, Kim JH, Park YH, Chun HJ, Kim CH, Kim MS (2010) In vivo biocompatibility study of electrospun chitosan microfiber for tissue engineering. Int J Mol Sci 10:4140-4148
2. VandeVord PJ, Matthew HW, DeSilva SP, Mayton L, Wu B, Wooley PH (2002) Evaluation of the biocompatibility of a chitosan scaffold in mice. J Biomed Mater Res 59:585-590 (Pubitemid 34037503)
3. Ratajska M, Strobin G, Wisniewska-Wrona M, Ciechanska D, Struszczyk H, Boryniec S, Binias D, Binias W (2003) Studies on the biodegradation of chitosan in an aqueous medium. Fibres Text East Eur 11:75-79 (Pubitemid 38341979)
4. Qin CQ, Du YM, Xiao L, Liu Y, Yu HG (2002) Moisture retention and antibacterial activity of modified chitosan by hydrogen peroxide. J Appl Polym Sci 86:1724-1730
5. Vargas M, González-Martínez C (2002) Recent patents on food applications of chitosan. Recent Pat Food Nutr Agric 2:121-128
6. Campos M, Cordi LV, Dura N, Mei L (2006) Antibacterial activity of chitosan solutions for wound dressing. Macromol Symp 245-246:515-518 (Pubitemid 46396363)
7. Fabris R, Chow CW, Drikas M (2010) Evaluation of chitosan as a natural coagulant for drinking water treatment. Water Sci Technol 61:2119-2128
8. Rabea EI, Badawy ME, Stevens CV, Smagghe Guy, Steurbaut W (2003) Chitosan as antimicrobial agent: applications and mode of action. Biomacromolecules 6:1457-1465 (Pubitemid 37455555)
9. Chung YC, Chen CY (2007) Antibacterial characteristics and activity of acid-soluble chitosan. Biores Technol 99:2806-2814
10. Chuang YC, Su YP, Chen CC, Jia G, Wang HL, Wu JC, Lin JG (2004) Relationship between antibacterial activity of chitosan and surface characteristics of cell wall. Acta Pharmacol Sin 25: 932-936 (Pubitemid 38915453)
11. Li Zh, Liu XF, Zhuang XP, Guan YL, Yao KD (2002) Manufacture and properties of chitosan/ N, O-carboxymethylated chitosan/viscose rayon antibacterial fibers. J Appl Polym Sci 84:2049-2059
12. Wang JT, Wang HD (2011) Preparation of soluble p-aminobenzoyl chitosan ester by Schiff's base and Antibacterial activity of the derivatives. Int J Biol Macromol 48:523-529
13. Liu N, Chen XG, Park HJ, Liu CG, Liu CS, Yu LJ, Meng XH (2006) Effect of MW and concentration of chitosan on antibacterial activity of Escherichia coli. Carbohydr Polym 64:60-66
14. Kim CH, Jang WC, Heung JC, Kyu SC (1997) Synthesis of chitosan derivatives with quaternary ammonium salt and their antibacterial activity. Polym Bull 38:387-393 (Pubitemid 127484927)
15. Liu XF, Guan YL, Yang DZ, Li Z, Yao KD (2001) Antibacterial action of chitosan and carboxymethylated chitosan. J Appl Polym Sci 79:1324-1335 (Pubitemid 32138450)
16. Xie WM, Xu PX, Wang W, Liu Q (2002) Preparation of water-soluble chitosan derivatives and their antibacterial activity. J Appl Polym Sci 85:1357-1361 (Pubitemid 34691242)
17. Wang XH, Du YM, Fan LH, Liu H, Hu Y (2005) Chitosan-metal complexes as antimicrobial agent: synthesis, characterization and structure-activity study. Polym Bull 55:105-113 (Pubitemid 41042638)
18. Gu CJ, Sun B, Wu WH, Wang FC, Zhu MF (2007) Synthesis, characterization of copper-loaded carboxymethyl-chitosan nanoparticles with effective antibacterial activity. Macromol Symp 254: 160-166 (Pubitemid 47366319)
19. Slavica BI, Konstantinovic SS, Savic DS, Veljkovic VB, Gojgic-Cvijov G (2010) The impact of Schiff bases on antibiotic production by Streptomyces hygroscopicus. Med Chem Res 19:690-697
20. Rehman W, Baloch MK, Muhammad B, Badshah A, Khan KM (2004) Characteristic spectral studies and in vitra anti fungal activity of some Schiff bases and their organotin(IV) complexes. Chin Sci Bull 2:119-122 (Pubitemid 44552964)
21. Varghese S, Muraleedharan Nair MK (2010) Antibacterial and antialgal studies of some lanthanide Schiff base complexes. Int J Appl Bio Pharm Tech 2:608-614
22. Jin X, Wang JT, Bai J (2009) Synthesis and antibacterial activity of Schiff base from chitosan and citral. Chem Ind Eng Proc 28:2014-2017
23. Xiao-xia J, Wang JT, Bai J (2010) Synthesis of Schiff base from chitosan and cinnamaldehyde and its antimicrobial activity. J Chem Eng Chinese Univ 24:645-650
24. Guo ZY, Chen R, Xing R, Liu S, Yu HH, Wang PB, Li CP, Li PC (2006) Novel derivatives of chitosan and their antifungal activities in vitro. Carbohydr Res 341:351-354 (Pubitemid 43098773)
25. Fu XR, Shen Y, Jiang X, Huang D, Yan YQ (2011) Chitosan derivatives with dual-antibacterial functional groups for antimicrobial finishing of cotton fabrics. Carbohydr Polym 85:221-227
26. Ding CM, Yin PC, Song QP, Li N, Qiao YB (2005) Preparation and characterization of complete deacetylized chitosan. J East China Univ Sci Technol (Nat Sci Ed) 31(3):296-299
27. Chen XG, Park HJ (2003) Chemical characteristics of O-carboxymethyl chitosans related to the preparation conditions. Carbohydr Polym 53:355-359
28. Sun T, Xie WM, Xu PX (2004) Superoxide anion scavenging activity of graft chitosan derivatives. Carbohydr Polym 58:379-382
29. Park JW, Park DM, Park KK (1986) Characterization and metal ion binding properties of carboxymethylchitosan. Polymer (Korea) 10:641-645
30. Abreu FR, Campana-filho SP (2005) Preparation and characterization of carboxymethylchitosan. Polímeros [online] 2: 79-83
31. Chen LY, Du YM, Wu HQ, Xiao L (2002) Relationship between molecular structure and moistureretention ability of carboxymethyl chitin and chitosan. J Appl Polym Sci 83:1233-1241 (Pubitemid 34043789)
32. Liu P, Jia L, Tong QS, Meng XH, Feng YF, Shi JC (2008) Chiral ligands derived from carbohydrates crystal structure of methyl-4, 6-O-benzylidene-3- deoxy-3-(salicylideneamino)-a-D-altropyranoside. Chinese J Struct Chem 9:1119-1122
33. Young DH, Kauss H (1983) Release of calcium from suspension-cultured Glycine max cells by chitosan, other polycations, and polyamines in relation to effects on membrane permeability. Plant Physiol 73:698-702
34. Liu XF, Song L, Li L, Li SY, Yao KD (2007) Antibacterial effects of chitosan and its water-soluble derivatives on E. coli, Plasmids DNA, and mRNA. J Appl Polym Sci 103:3521-3528 (Pubitemid 46347176)
35. Qi LF, Xu ZR, Jiang X, Hu CH, Zou XF (2004) Preparation and antibacterial activity of chitosan nanoparticles. Carbohydr Res 339:2693-2700 (Pubitemid 39425140)
36. Hammett LP (1937) The effect of structure upon the reactions of organic compounds benzene derivatives. J Am Chem Soc 59:96
37. Meneses L, Araya A, Pilaquinga F, Fuentealba P (2008) Relationship between the electrophilicity and rp Hammett constant in Baeyer-Villiger reaction. Chem Phys Lett 460:27-30
38. Hou HN, Zhu JC, Qi ZD, Zhou B, LiI MY, Liu Y (2010) Antibacterial activity and structure-activity relationships of Schiff bases on Staphylococcus aureus by microcalorimetry. J Wuhan Univ Nat Sci 15:71-77