Synthesis and Structure—Activity Relationship (SAR) of Novel Perfluoroalkyl‐Containing Quaternary Ammonium Salts.

Sun, Jian-Ying; Li, Jing; Qiu, Xiao‐Long; Qing, Feng‐Ling

doi:10.1002/chin.200606067

Cited by 2 publications

(2 citation statements)

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“…On the whole, the synthesized cationic lipids exhibited lower antifungal activities than corresponding antibacterial activities. These results are in good agreement with previous results that quaternary ammonium salt-type antibacterial agents are in general less active against yeasts and fungi than against bacteria since the structure of the former is more complex than that of the latter [19][20][21][22]. The mode of action of cationic lipids and surfactants for their antifungal activity was reported by Viera and Carmona [14].…”

Section: Antibacterial Properties Of Alkyloxy Propanol Amine-based Casupporting

confidence: 92%

Chemo‐Enzymatic Synthesis and Antimicrobial Evaluation of Alkyloxy Propanol Amine‐Based Cationic Ether Lipids

Reddy

Rao

Karuna

et al. 2012

J Americ Oil Chem Soc

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The present study involved the synthesis and antimicrobial evaluation of alkyloxy propanol amine‐based cationic lipids N,N‐dimethyl‐1‐octadecylamino‐3‐alkyloxy‐2‐propanol (series A, 7a–e) and N‐methyl‐N,N‐di‐(2‐hydroxy‐3‐alkyloxy‐2 propyl) octadecylamine (series B, 9a–e) and their acetylated derivatives (8a–e and 10a–e). A simple three‐step chemo‐enzymatic approach was employed for the synthesis of 7a–e and 9a–e in 71–80 and 67–88 % yields, respectively. The first step involved the synthesis of a series of glycidyl ethers from a series of alcohols (C4, C8, C10, C12, C14) which were opened in the second step with octadecylamine to obtain 1‐octadecylamino‐3‐alkyloxy‐2 propanol (5a–e) and N,N‐di‐(2‐hydroxy‐3‐alkyloxypropyl) octadecylamine (6a–e). In the third step, alkyloxy propanolamines (5a–e, 6a–e) were quaternized using methyl iodide to yield quaternized ammonium salts. The quaternized ammonium salts were enzymatically acetylated using Candida antarctica lipase‐B based immobilized enzyme Novozym 435 to obtain their acetylated derivatives. The quaternized salts as well as their acetylated derivatives were evaluated for antibacterial and antifungal properties. The title compounds were found to possess moderate to good antibacterial activities against all the studied bacterial strains namely, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Klebsiella aerogenes compared to streptomycin and cetyl trimethyl ammonium bromide (CTAB). The title compounds exhibited relatively good antifungal activities against Candida albicans and no significant activities against other fungal strains namely, Saccharomyces cerevisiae, Rhizopus oryzae and Aspergillus niger when compared to amphotericin B and CTAB.

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Section: Antibacterial Properties Of Alkyloxy Propanol Amine-based Casupporting

confidence: 92%

Chemo‐Enzymatic Synthesis and Antimicrobial Evaluation of Alkyloxy Propanol Amine‐Based Cationic Ether Lipids

Reddy

Rao

Karuna

et al. 2012

J Americ Oil Chem Soc

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“…The major classes of synthetic antimicrobial agents for textiles include chitosan, 2–4 quaternary ammonium compounds, nanoparticles of noble, metals and metal oxides. 5–7 Silver nanoparticles (AgNPs) have been widely applied in the functional finishing of textiles due to their antibacterial activity and UV protection. In recent years, AgNPs have been synthesized by physical milling, chemical reduction, green plant leaf extraction, and sol–gel.…”

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confidence: 99%

A green in situ synthesis of silver nanoparticles on cotton fabrics using Aloe vera leaf extraction for durable ultraviolet protection and antibacterial activity

Zhou

Ren

et al. 2016

Textile Research Journal

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This study presented a simple and environmentally friendly method of in situ synthesis of silver nanoparticles (AgNPs) on cotton fabrics for durable ultraviolet (UV) protection and antibacterial activity using Aloe vera leaf extraction (AVE) as a reducing and stabilizing agent. Cotton fabrics were pretreated in water, and then immersed in AgNO3 and AVE, respectively. Cotton fabrics were characterized by small angle X-ray diffraction (XRD), scanning electron microscopy (SEM), thermogravimetric analysis, UV protection, antibacterial activity, and laundering durability. Comparing with the smooth surface of the control cotton fabric, SEM and energy dispersive X-ray spectrometry (EDX) results showed that there were a considerable number of Ag2O and AgNPs loading on the surface of the pretreated and Ag loaded cotton fabrics. The XRD pattern indicated, respectively, the existence of Ag2O and AgNPs, the structures of which were similar to JCPDS File No.65-3289 and JCPDS File No. 01-071-4613 on the pretreated and Ag loaded cotton fabrics. The pretreated and Ag loaded cotton fabrics showed excellent UV protection, antibacterial activity, and laundering durability, especially the Ag loaded cotton fabric, of which the UV protection factor value and transmission of UVA were 148 and 1.11%, respectively, after 20 washing cycles, and the clear zone width was more than 4 mm against E. coli or S. aureus. AgNPs facilitated the improvement of the thermal property of the cotton fabrics. Thus this facile in situ reduction of AgNPs with AVE may bring a promising and green strategy to produce functional textiles.

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Synthesis and Structure—Activity Relationship (SAR) of Novel Perfluoroalkyl‐Containing Quaternary Ammonium Salts.

Cited by 2 publications

References 1 publication

Chemo‐Enzymatic Synthesis and Antimicrobial Evaluation of Alkyloxy Propanol Amine‐Based Cationic Ether Lipids

Chemo‐Enzymatic Synthesis and Antimicrobial Evaluation of Alkyloxy Propanol Amine‐Based Cationic Ether Lipids

A green in situ synthesis of silver nanoparticles on cotton fabrics using Aloe vera leaf extraction for durable ultraviolet protection and antibacterial activity

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