Structure-antibacterial Activity Research Articles

PEGylated Bis-Quaternary Triphenyl-Phosphonium Tosylate Allows for Balanced Antibacterial Activity and Cytotoxicity.

Quaternary triphenylphosphonium compounds (TPP+) have been widely recognized as an important antimicrobial because of their fast antimicrobial speed and broad antimicrobial spectrum. However, small-molecule TPP+ compounds have the defects of toxicity, which is the key factor that limits their practical applications. Here, two mono- and one bis-quaternary phosphonium tosylate compounds with different lengths of oligo(ethylene glycol) (OEG) chains and TPP+ as the active moiety were synthesized. Bis-TPP+ have a short OEG chain coupling two TPP+ at both ends, while mono-TPP+ attaches the OEG chain at one end in one molecule. In vitro antibacterial activities were evaluated against both Gram-positive as well as Gram-negative bacteria in terms of the inhibition zone (ZOI) and minimum inhibitory concentration (MIC). To investigate the antibacterial mechanism, β-galactosidase activity was monitored for measuring the degree of membrane permeability correlated to the abilities to disrupt the membranes of bacteria. Moreover, their structure-antibacterial activity and structure-cytotoxicity relationships were further analyzed. The results indicated that bis-TPP+ synthesized can reach the sterilization rate 90% or more against Escherichia coli and Staphylococcus aureus at MICs of 3.1 and 1.5 mg/mL, respectively, and meanwhile, the cell proliferation can reach more than 80%. This paper represents an excellent approach for development of bis-TPP+ bactericidal molecules that would achieve an optimal balance between antimicrobial activity and cytotoxicity.

Structure-antibacterial activity and cytotoxicity relationships of thiazolo and thiazetoquinolone derivatives.

In the course of our search for derivatives with potent antibacterial activity and low cytotoxicity, we have studied the relationships among the structure, antibacterial activity and cytotoxicity of thiazoloquinolone and thiazetoquinolone derivatives (the term quinolone as used in this paper includes the quinolone, 1,8-naphthyridine and pyridopyrimidine nuclei). The antibacterial activities and cytotoxicity of these derivatives were compared with those of norfloxacin, ofloxacin, enoxacin and ciprofloxacin. The antibacterial activities of the thiazoloquinolone derivatives were more potent than those of the dihyrothiazoloquinolone derivatives, and comparable to that of ciprofloxacin. All of the thiazoloquinolone derivatives were highly cytotoxic against mammalian cells, but some of the dihyrothiazoloquinolone derivatives were less cytotoxic, being comparable in cytotoxicity to the reference drugs. The thiazetoquinolone derivatives were less cytotoxic than the thiazoloquinolone derivatives, and one of them, 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a] quinoline-3-carboxylic acid, showed the most potent antibacterial activity of all compounds tested in this study, as well as a very low cytotoxicity. The antibacterial activity and cytotoxicity of this compound were similar to that of ciprofloxacin.

ChemInform Abstract: STUDIES ON β‐LACTAM ANTIBIOTICS FOR MEDICINAL PURPOSE. VIII. SYNTHESIS OF 7‐(D(‐)‐α‐(4‐ALKYL‐2,3‐DIOXO‐1‐PIPERAZINECARBOXAMIDO)PHENYLACETAMIDO)‐CEP# HALOSPORANIC ACIDS AND STRUCTURE‐ANTIBACTERIAL ACTIVITY

Chemischer InformationsdienstVolume 11, Issue 10 Natural Products ChemInform Abstract: STUDIES ON β-LACTAM ANTIBIOTICS FOR MEDICINAL PURPOSE. VIII. SYNTHESIS OF 7-(D(-)-α-(4-ALKYL-2,3-DIOXO-1-PIPERAZINECARBOXAMIDO)PHENYLACETAMIDO)-CEP# HALOSPORANIC ACIDS AND STRUCTURE-ANTIBACTERIAL ACTIVITY I. SAIKAWA, Search for more papers by this authorS. TAKANO, Search for more papers by this authorK. MOMONOI, Search for more papers by this authorI. TAKAKURA, Search for more papers by this authorC. KUTANI, Search for more papers by this authorH. OCHIAI, Search for more papers by this authorC. YOSHIDA, Search for more papers by this authorT. YASUDA, Search for more papers by this authorH. TAKI, Search for more papers by this author I. SAIKAWA, Search for more papers by this authorS. TAKANO, Search for more papers by this authorK. MOMONOI, Search for more papers by this authorI. TAKAKURA, Search for more papers by this authorC. KUTANI, Search for more papers by this authorH. OCHIAI, Search for more papers by this authorC. YOSHIDA, Search for more papers by this authorT. YASUDA, Search for more papers by this authorH. TAKI, Search for more papers by this author First published: March 11, 1980 https://doi.org/10.1002/chin.198010378Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume11, Issue10March 11, 1980 RelatedInformation

3(5)-〔2-(5-Nitro-2-furyl)vinyl〕-5(3)-(5-nitro-2-furyl)pyrazole誘導体の合成ならびに構造-抗菌活性ニトロフラン系化合物の薬学的研究(第19報)

3(5)-〔2-(5-Nitro-2-furyl)vinyl〕-5(3)-(5-nitro-2-furyl)pyrazole誘導体の合成ならびに構造-抗菌活性ニトロフラン系化合物の薬学的研究(第19報)