Synthesis, Characterization, and Antifungal Activities of Amphiphilic Derivatives of Diethylaminoethyl Chitosan against Aspergillus flavus

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 24, 2015, Pages 5725-5731

  Gabriel, Juliana Dos Santos ^a   Tiera, Marcio José ^a   Tiera, Vera Aparecida De Oliveira ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

amphiphilic derivatives; antifungal activity; Aspergillus flavus; chitosan

Indexed keywords

CHITIN; CHITOSAN; FLUORESCENCE SPECTROSCOPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FUNGI; HYDROPHOBICITY; MULTILAYERS;

AMPHIPHILICS; ANTI-FUNGAL ACTIVITY; ASPERGILLUS FLAVUS; DEACETYLATED CHITOSANS; HIGH MOLECULAR WEIGHT; POLYMER CONCENTRATIONS; REDUCTIVE AMINATION; SYNTHESIZED DERIVATIVES;

ASPERGILLUS;

ASPERGILLUS FLAVUS;

ANTIFUNGAL AGENT; CHITOSAN;

ASPERGILLUS FLAVUS; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECTS; GROWTH, DEVELOPMENT AND AGING; MYCELIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANTIFUNGAL AGENTS; ASPERGILLUS FLAVUS; CHITOSAN; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MAGNETIC RESONANCE SPECTROSCOPY; MYCELIUM;

EID: 84933056999     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b00278     Document Type: Article

References (32)

1. Satpathy, G.; Tyagi, Y. K.; Gupta, R. K. A novel optimized and validated method for analysis of multi-residues of pesticides in fruits and vegetables by microwave-assisted extraction (MAE)-dispersive solid-phase extraction (d-SPE)-retention time locked (RTL)-gas chromatography-mass spectrometry with deconvolution reporting software (DRS) Food Chem. 2011, 127 (3) 1300-1308 10.1016/j.foodchem.2011.01.087
2. Ymele-Leki, P.; Cao, S.; Sharp, J.; Lambert, K. G.; McAdam, A. J.; Husson, R. N.; Tamayo, G.; Clardy, J.; Watnick, P. I. A high-throughput screen Identifies a new natural product with broad-spectrum antibacterial activity PLoS One 2012, 7 (2 e31307 10.1371/journal.pone.0031307
3. Tian, J.; Huang, B.; Luo, X.; Zeng, H.; Ban, X.; He, J.; Wang, Y. The control of Aspergillus flavus with Cinnamomum jensenianum Hand.-Mazz essential oil and its potential use as a food preservative Food Chem. 2012, 130 (3) 520-527 10.1016/j.foodchem.2011.07.061
4. Kong, M.; Chen, X. G.; Xing, K.; Park, H. J. Antimicrobial properties of chitosan and mode of action: a state of the art review Int. J. Food Microbiol. 2010, 144 (1) 51-63 10.1016/j.ijfoodmicro.2010.09.012
5. Zhang, H. Y.; Li, R. P.; Liu, W. M. Effects of chitin and its derivative chitosan on postharvest decay of fruits: a review Int. J. Mol. Sci. 2011, 12 (2) 917-934 10.3390/ijms12020917
6. Jayakumar, R.; Prabaharan, M.; Sudheesh Kumar, P. T.; Nair, S. V.; Tamura, H. Biomaterials based on chitin and chitosan in wound dressing applications Biotechnol. Adv. 2011, 29 (3) 322-337 10.1016/j.biotechadv.2011.01.005
7. Alburquenque, C.; Bucarey, S. A.; Neira-Carrillo, A.; Urzúa, B.; Hermosilla, G.; Tapia, C. V. Antifungal activity of low molecular weight chitosan against clinical isolates of Candida spp Med. Mycol. 2010, 48 (8) 1018-1023 10.3109/13693786.2010.486412
8. Liu, X.; Xia, W.; Jiang, Q.; Xu, Y.; Yu, P. Synthesis, characterization, and antimicrobial activity of kojio acid grafted chitosan oligossaccharide J. Agric. Food Chem. 2014, 62, 297-303 10.1021/jf404026f
9. Rabea, E. A.; Badawy, M. E. T.; Stevens, C. V.; Smagghe, G.; Steurbaut, W. Chitosan as antimicrobial agent: applications and mode of action Biomacromolecules 2003, 4, 1457-1465 10.1021/bm034130m
10. El Ghaouth, A.; Aru, l. J.; Asselin, A.; Benhamou, N. Antifungal activity of chitosan on post-harvest pathogens: induction of morphological and cytological alterations in Rhizopus stolonifer Mycol. Res. 1992, 96 (9) 769-779 10.1016/S0953-7562(09)80447-4
11. Li, M. Q.; Chen, X. G.; Liu, J. M.; Zhang, W. F.; Tang, X. X. Molecular weight-dependent antifungal activity and action mode of chitosan against Fulvia fulva (Cooke) Ciffrri J. Appl. Polym. Sci. 2011, 119 (6) 3127-3135 10.1002/app.31831
12. Geisberger, G.; Gyenge, E. B.; Hinger, D.; Kach, A.; Maake, C.; Patzke, G. R. Chitosan-thioglycolic acid as a versatile antimicrobial agent Biomacromolecules 2013, 14, 1010-1017 10.1021/bm3018593
13. Kulikov, S. N.; Lisovskaya, S. A.; Zelenikin, P. V.; Bezrodnykh, E. A.; Shakirova, D. R.; Blagodatskikh, I. V.; Tikhonov, V. E. Antifungal activity of oligochitosans (short chain chitosans) against some Candida species and clinical isolates of Candida albicans: molecular weight-activity relationship Eur. J. Med. Chem. 2014, 74, 169-178 10.1016/j.ejmech.2013.12.017
14. Mohamed, N. A.; Mohamed, R. R.; Seoudi, R. S. Synthesis and characterization of some novel antimicrobial thiosemicarbazone O -carboxymethyl chitosan derivatives Int. J. Biol. Macromol. 2014, 63, 163-169 10.1016/j.ijbiomac.2013.10.044
15. Rúnarsson, Ö. V.; Holappa, J.; Malainer, C.; Steinsson, H.; Hjálmarsdóttir, M.; Nevalainen, T.; Másson, M. Antibacterial activity of N-quaternary chitosan derivatives: synthesis, characterization and structure activity relationship (SAR) investigations Eur. Polym. J. 2010, 46, 1251-1267 10.1016/j.eurpolymj.2010.03.001
16. Pedro, R. O.; Takaki, M.; Gorayeb, T. C. C.; Del Bianchi, V. L.; Thomeo, J. C.; Tiera, M. J.; Tiera, V. A. O. Synthesis, characterization and antifungal activity of quaternary derivatives of chitosan on Aspergillus flavus Microbiol. Res. 2013, 168, 50-55 10.1016/j.micres.2012.06.006
17. Souza, R. H. F. V.; Takaki, M.; Pedro, R. O.; Gabriel, J. S.; Tiera, M. J.; Tiera, V. A. O. Hydrophobic effect of amphiphilic derivatives of chitosan on the antifungal activity against Aspergillus flavus and Aspergillus parasiticus Molecules 2013, 18 (4) 4437-4450 10.3390/molecules18044437
18. Jiang, X. Z.; Ge, Z. Z.; Xu, J.; Liu, H.; Liu, S. Y. Fabrication of multiresponsive shell cross-linked micelles possessing pH-controllable core swellability and thermo-tunable corona permeability Biomacromolecules 2007, 8, 3184-3192 10.1021/bm700743h
19. Syntor Fine Chemicals home page, http://www.syntor.co.uk/diethylaminoethyl-chloride-hydrochloride (accessed April 2, 2015).
20. Tiera, M. J.; Qiu, X. P.; Bechaouch, S.; Shi, Q.; Fernandes, J. C.; Winnik, F. M. Synthesis and characterization of phosphorylcholine-substituted chitosans soluble in physiological pH conditions Biomacromolecules 2006, 7 (11) 3151-3156 10.1021/bm060381u
21. Oliveira, F. P. P.; Picola, I. P. D.; Fernandes, J.; Tiera, V. A. O.; SHI, Q.; Barbosa, H. F. G.; Tiera, M. J. Synthesis and evaluation of diethylethylamine-chitosan for gene delivery Nanotechnology 2013, 24, 055101-055106 10.1088/0957-4484/24/5/055101
22. Vieira, N. A. B.; Moscardini, M. S.; Tiera, V. A. D. O.; Tiera, M. J. Aggregation behavior of hydrophobically modified dextran in aqueous solution: a fluorescence probe study Carbohydr. Polym. 2003, 53, 137-143 10.1016/S0144-8617(03)00048-1
23. Guo, Z. Y.; Chen, R.; Xing, R.; Liu, S.; Yu, H.; Wang, P.; Li, C.; Li, P. Novel derivatives of chitosan and their antifungal activities in vitro Carbohydr. Res. 2006, 341 (3) 351-354 10.1016/j.carres.2005.11.002
24. Desbrieres, J.; Martinez, C.; Rinaudo, M. Hydrophobic derivatives of chitosan: Characterization and rheological behaviour Int. J. Biol. Macromol. 1996, 19, 21-28 10.1016/0141-8130(96)01095-1
25. Philippova, O. E.; Volkov, E. V.; Sitnikova, N. L.; Khokhlov, A. R.; Desbrieres, J.; Rinaudo, M.. Two types of hydrophobic aggregates in aqueous solutions of chitosan and its hydrophobic derivative Biomacromolecules 2001, 2, 483-490 10.1021/bm005649a
26. Fukushima, K.; Liu, S.; Wu, H.; Engler, A. C.; Coady, D. J.; Maune, H.; Pitera, J.; Nelson, A.; Wiradharma, N.; Venkataraman, S.; Huang, Y.; Fan, W.; Ying, J. Y.; Yang, Y. Y.; Hedrick, J. L. Supramolecular high-aspect ratio assemblies with strong antifungal activity Nat. Commun. 2013, 4, 2861 10.1038/ncomms3861
27. Younes, I.; Sellimi, S.; Rinaudo, M.; Jellouli, K.; Nasri, M. Influence of acetylation degree and molecular weight of homogeneous chitosans on antibacterial and antifungal activities Int. J. Food Microbiol. 2014, 185 (18) 57-63 10.1016/j.ijfoodmicro.2014.04.029
28. Seyfarth, F.; Schliemann, S.; Elsner, P.; Hipler, U.-C. Antifungal effect of high- and low-molecular-weight chitosan hydrochloride, carboxymethyl chitosan, chitosan oligosaccharide and N-acetyl-D-glucosamine against Candida albicans, Candida krusei and Candida glabrata Int. J. Pharm. 2008, 353, 139-148 10.1016/j.ijpharm.2007.11.029
29. Cota-Arriola, O.; Cortez-Rocha, M. O.; Rosas-Burgos, E. C.; Burgos-Hernández, A.; López-Franco, Y. L.; Plascencia-Jatomea, M. Antifungal effect of chitosan on the growth of Aspergillus parasiticus and production of aflatoxin B1 Polym. Int. 2011, 60, 937-944 10.1002/pi.3054
30. Jagadish, R. S.; Divyashree, K. N.; Viswanath, P.; Srinivas, P.; Raj, B. Preparation of N -vanillyl chitosan and 4-hydroxybenzyl chitosan and their physico-mechanical, optical, barrier, and antimicrobial properties Carbohydr. Polym. 2012, 87, 110-116 10.1016/j.carbpol.2011.07.024
31. Sajomsang, W.; Gonil, P.; Saesoo, S.; Ovatlarnporn, C. Antifungal property of quaternized chitosan and its derivatives Int. J. Biol. Macromol. 2012, 50, 263-269 10.1016/j.ijbiomac.2011.11.004
32. Sajomsang, W.; Tantayanon, S.; Tangpasuthadol, V.; Daly, W. H. Quaternization of N -aryl chitosan derivatives: synthesis, characterization and antibacterial activity Carbohydr. Res. 2009, 344, 2502-2511 10.1016/j.carres.2009.09.004