Synthesis and antimicrobial characteristics of 4,4'-(alpha,omega-polymethylenedithio)bis(1-alkylpyridinium iodide)s

Chemical & Pharmaceutical Bulletin
K OkazakiHiroki Kourai

Abstract

Bis-quaternary ammonium compounds (bis-QACs), 4,4'-(alpha,omega-polymethylenedithio)bis(1-alkylpyridinium iodide)s (4DTBP-m,n), which have 3 to 10 carbon atoms in the connecting methylene chain (m) and 8 to 18 carbon atoms of the N-alkyl chain (n), were synthesized. 4DTBP-6,12 exhibited a wide antimicrobial spectrum against gram-positive and gram-negative bacteria and fungi. The activity was stronger than those of N-dodecylpyridinium iodide (P-12), benzyldodecyldimethylammonium chloride and 2-(4-thiazolyl)benzimidazole. The bactericidal activities of 4DTBP-m,n were scarcely affected by the lengths of the alkyl chain and methylene chain. The bis-QAC that showed the highest activity was 4DTBP-6,8 (minimum inhibitory concentration (MIC) = 1.6 microM, minimum bactericidal concentration (MBC) = 2.6 microM), and its activity was about 10 times that of N-hexadecylpyridinium iodide (P-16), which was the most active in the P-n series. In addition, 4DTBP-6,12 showed a high bactericidal activity in the ranges of pH 5 to 8.5 and 10 to 40 degrees C, in contrast to mono-QACs. The bis-QACs synthesized in this study have excellent bactericidal properties.

Citations

Dec 25, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Vildan AlptüzünErcin Erciyas
Apr 7, 2009·Biocontrol Science·Akihiro ShiraiHiroki Kourai
Apr 2, 2004·Chemical & Pharmaceutical Bulletin·Shigenobu AriharaKazuko Yoshikawa
Apr 9, 2008·Journal of Oleo Science·Marcelo C MurguíaRicardo J Grau
Jul 16, 2021·Environmental Science and Pollution Research International·Roberta Frinhani NunesAntonio Carlos Silva Costa Teixeira

❮ Previous
Next ❯

Related Concepts

Related Feeds

Anthelmintics

Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. Discover the latest research on anthelmintics here.

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.