Synthesis and antimicrobial activity testing of quaternary ammonium silane compounds

被引:0
作者
Kuruca, Tugce [1 ]
Akarsu, Esin [1 ]
机构
[1] Akdeniz Univ, Sci Fac, TR-07058 Antalya, Turkiye
关键词
Antimicrobial agents; Antimicrobial activity; Aspergillus brasiliensis; Candida albicans; Quaternary ammonium compounds; DISINFECTANTS; DURABILITY; COVID-19; SURFACES; FABRICS;
D O I
10.1016/j.bioorg.2024.107614
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
With increasing health awareness of the pathogenic effects of disease-causing microorganisms, interest in and use (of medical textiles, disinfectants in medical devices, etc.) of antimicrobial substances have increased in various applications, such as medical textiles and disinfectants (alcohol-based and nonalcoholic), in medical devices There are several concerns with alcohol-based disinfectants, such as surface deformation of medical devices due to high alcohol content and damage to skin tissue caused by lipid and protein denaturation of cell membranes. Quaternary ammonium compounds (quats) were preferred because they have the potential to prepare waterbased disinfectants. In this study, novel (3-chloropropyl)triethoxysilane (CPTMO) and (3-chloropropyl)triethoxysilane (CPTEO) based quaternary ammonium silane compounds (silane-quats) were developed using quats with carbon chain lengths of C12, C14, C16 and C18. Titration (ASTM D2074) was used to calculate the yield of the synthesis and the structures of the products were characterised by Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy ( 13 C NMR, 1 H NMR) and gas chromatography-mass spectrometry (GC -MS).The in vitro antimicrobial activity of the synthesized samples was evaluated against Grampositive ( Staphylococcus aureus (S. aureus) , Enterococcus hirae (E. hirae)) and Gram-negative ( Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa)) bacteria and fungi (Candida albicans (C. albicans), Aspergillus brasiliensis (A. brasiliensis)) using the minimum inhibitory concentration (MIC) test. According to MIC tests, the silane-quats with the highest antimicrobial effects were dimethylhexadecyl[3-( trimethoxysilyl ) propyl ]ammonium chloride (SQ3), which had an MIC of < 16 mu g/ml (ppm) against E. coli, S. aureus, E. hirae, C. albicans, and A. brasiliensis and 32 mu g/ml against P. aeruginosa . The MIC test results also showed antimicrobial activity at least 2 times greater than that of the commercially available disinfectant benzalkonium chloride (BAC). Findings suggest that SQ3 (C16) holds promise as an effective medical disinfectant, presenting a novel approach to combating microbial infections in healthcare settings.
引用
收藏
页数:8
相关论文
共 50 条
[41]   Reproductive & developmental toxicity of quaternary ammonium compounds [J].
Bobic, Leyla ;
Harbolic, Allison ;
Warner, Genoa R. .
BIOLOGY OF REPRODUCTION, 2024, 111 (04) :742-756
[42]   QUATERNARY AMMONIUM COMPOUNDS - NEW OCCUPATIONAL HAZARDS [J].
Lipinska-Ojrzanowska, Agnieszka ;
Walusiak-Skorupa, Jolanta .
MEDYCYNA PRACY, 2014, 65 (05) :675-682
[43]   Quaternary Ammonium Polyethyleneimine: Antibacterial Activity [J].
Yudovin-Farber, Ira ;
Golenser, Jacob ;
Beyth, Nurit ;
Weiss, Ervin I. ;
Domb, Abraham J. .
JOURNAL OF NANOMATERIALS, 2010, 2010
[44]   Quaternary ammonium compounds in the Capparaceae [J].
McLean, WFH ;
Blunden, G ;
Jewers, K .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1996, 24 (05) :427-434
[45]   Synthesis, characterization, and evaluation of quaternary ammonium-based polymerizable antimicrobial monomers for prosthodontic applications [J].
Rao, Sowmya ;
Nandish, B. T. ;
Preman, Namitha K. ;
Johnson, Renjith P. ;
Ginjupalli, Kishore ;
Preethishree, P. ;
Prabhu, Ashwini ;
Das, Ranajit ;
Jayaprakash, K. ;
Pai, Vidya .
HELIYON, 2022, 8 (08)
[46]   Design, synthesis, antibacterial activity and toxicity of novel quaternary ammonium compounds based on pyridoxine and fatty acids [J].
Sapozhnikov, Sergey, V ;
Sabirova, Alina E. ;
Shtyrlin, Nikita, V ;
Druk, Anastasia Y. ;
Agafonova, Mariya N. ;
Chirkova, Milana N. ;
Kazakova, Renata R. ;
Grishaev, Denis Y. ;
Nikishova, Tatyana, V ;
Krylova, Elena S. ;
Nikitina, Elena, V ;
Kayumov, Airat R. ;
Shtyrlin, Yurii G. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2021, 211
[47]   Discovery of novel quaternary ammonium compounds based on quinuclidine-3-ol as new potential antimicrobial candidates [J].
Bazina, Linda ;
Maravic, Ana ;
Krce, Lucija ;
Soldo, Barbara ;
Odzak, Renata ;
Popovic, Viljemka Butevic ;
Aviani, Ivica ;
Primozic, Ines ;
Sprung, Matilda .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 163 :626-635
[48]   Synthesis and antimicrobial activity of quaternary salts of the alkaloid glaucine [J].
A. Zh. Turmukhambetov ;
G. K. Mukusheva ;
R. B. Seidakhmetova ;
E. E. Shults ;
M. M. Shakirov ;
I. Yu. Bagryanskaya ;
Yu. V. Gatilov ;
S. M. Adekenov .
Pharmaceutical Chemistry Journal, 2009, 43 :255-257
[49]   Synthesis and antimicrobial activity of quaternary salts of the alkaloid glaucine [J].
Turmukhambetov, A. Zh. ;
Mukusheva, G. K. ;
Seidakhmetova, R. B. ;
Shults, E. E. ;
Shakirov, M. M. ;
Bagryanskaya, I. Yu. ;
Gatilov, Yu. V. ;
Adekenov, S. M. .
PHARMACEUTICAL CHEMISTRY JOURNAL, 2009, 43 (05) :255-257
[50]   Antimicrobial Properties of a Biocide Based on Quaternary Ammonium Compounds plus Polyhexamethylene Guanidine and Possible Methods for Its Deactivation [J].
Yu. V. Litti ;
D. V. Serdyukov ;
O. V. Kanunnikov ;
V. A. Akselrod ;
N. G. Loiko .
Applied Biochemistry and Microbiology, 2021, 57 :962-972