Gemini Alkyldeoxy-D-Glucitolammonium Salts as Modern Surfactants and Microbiocides: Synthesis, Antimicrobial and Surface Activity, Biodegradation

被引:26
作者
Brycki, Bogumil [1 ]
Szulc, Adrianna [1 ]
机构
[1] Adam Mickiewicz Univ, Fac Chem, Lab Microbiocides Chem, PL-60780 Poznan, Poland
关键词
TO-MICELLE TRANSITION; CATIONIC SURFACTANTS; ANTIFUNGAL ACTIVITY; PH; GLUCAMINES; BEHAVIOR;
D O I
10.1371/journal.pone.0084936
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Dimeric quaternary alkylammonium salts possess a favourable surface and antimicrobial activity. In this paper we describe synthesis, spectroscopic analysis, surface and antimicrobial activity as well as biodegradability of polymethylene-alpha, omega-bis(N,N-dialkyl-N-deoxy-D-glucitolammonium iodides), a new group of dimeric quaternary ammonium salts. This new group of gemini surfactants can be produced from chemicals which come from renewable sources. The structure of products has been determined by the FTIR and H-1 and C-13 NMR spectroscopy. The biodegradability, surface activity and antimicrobial efficacy against Escherichia coli, Staphylococcus aureus, Candida albicans, Aspergillus niger and Penicillium chrysogenum were determined. The influence of the number of alkyl chains and their lengths on surface and antimicrobial properties has been shown. In general, dimeric quaternary alkyldeoxy-D-glucitolammonium salts with long alkyl substituents show favourable surface properties and an excellent antimicrobial activity.
引用
收藏
页数:7
相关论文
共 38 条
[1]  
[Anonymous], 1992, OECD GUIDELINE TESTI
[2]   Creation of Novel Green and Sustainable Gemini-Type Cationics Containing Carbonate Linkages [J].
Banno, Taisuke ;
Kawada, Kazuo ;
Matsumura, Shuichi .
JOURNAL OF SURFACTANTS AND DETERGENTS, 2010, 13 (04) :387-398
[3]   Synthesis and Properties of Gemini-type Cationic Surfactants Containing Carbonate Linkages in the Linker Moiety Directed Toward Green and Sustainable Chemistry [J].
Banno, Taisuke ;
Toshima, Kazunobu ;
Kawada, Kazuo ;
Matsumura, Shuichi .
JOURNAL OF SURFACTANTS AND DETERGENTS, 2009, 12 (03) :249-259
[4]   Transfection mediated by gemini surfactants: Engineered escape from the endosomal compartment [J].
Bell, PC ;
Bergsma, M ;
Dolbnya, IP ;
Bras, W ;
Stuart, MCA ;
Rowan, AE ;
Feiters, MC ;
Engberts, JBFN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) :1551-1558
[5]   CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].
BORCH, RF ;
BERNSTEIN, MD ;
DURST, HD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+
[6]   Polyamines - V: The structure of tetramethylene-1,4-bis(N-deoxyglucitolammonium chloride) studied by X-ray diffraction, DFT calculations, NMR and FTIR spectroscopy [J].
Brycki, Bogumil ;
Szulc, Adrianna ;
Kowalczyk, Iwona ;
Borowiak, Teresa ;
Dutkiewicz, Grzegorz .
JOURNAL OF MOLECULAR STRUCTURE, 2012, 1020 :41-47
[7]   Gemini Alkylammonium Salts as Biodeterioration Inhibitors [J].
Brycki, Bogumil .
POLISH JOURNAL OF MICROBIOLOGY, 2010, 59 (04) :227-231
[8]   Synthesis, Molecular Structure, Spectral Properties and Antifungal Activity of Polymethylene-α,ω-bis(N,N-dimethyl-N-dodecyloammonium bromides) [J].
Brycki, Bogumil ;
Kowalczyk, Iwona ;
Kozirog, Anna .
MOLECULES, 2011, 16 (01) :319-335
[9]   SYNTHESIS, SURFACE-ACTIVE PROPERTIES AND ANTIMICROBIAL ACTIVITY OF NEW BIS QUATERNARY AMMONIUM-COMPOUNDS [J].
DIZ, M ;
MANRESA, A ;
PINAZO, A ;
ERRA, P ;
INFANTE, MR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (08) :1871-1876
[10]   Sugar-based tertiary amino gemini surfactants with a vesicle-to-micelle transition in the endosomal pH range mediate efficient transfection in vitro [J].
Fielden, ML ;
Perrin, C ;
Kremer, A ;
Bergsma, M ;
Stuart, MC ;
Camilleri, P ;
Engberts, JBFN .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 2001, 268 (05) :1269-1279