دورية أكاديمية
Dual function surfactants for pharmaceutical formulations: The case of surface active and antibacterial 1-tolyl alkyl biguanide derivatives.
| العنوان: | Dual function surfactants for pharmaceutical formulations: The case of surface active and antibacterial 1-tolyl alkyl biguanide derivatives. |
|---|---|
| المؤلفون: | Perinelli DR; Chemistry Interdisciplinary Project (CHIP), School of Pharmacy, University of Camerino, Via Madonna delle Carceri, Camerino, 62032, Italy., Del Bello F; Chemistry Interdisciplinary Project (CHIP), School of Pharmacy, University of Camerino, Via Madonna delle Carceri, Camerino, 62032, Italy., Vitali LA; Microbiology Unit, School of Pharmacy, University of Camerino, via Gentile III da Varano, Camerino, 62032, Italy., Nabissi M; Department of Experimental Medicine, School of Pharmacy, University of Camerino, Via Madonna delle Carceri 9, Camerino, 62032, Italy., Cespi M; Chemistry Interdisciplinary Project (CHIP), School of Pharmacy, University of Camerino, Via Madonna delle Carceri, Camerino, 62032, Italy., Quaglia W; Chemistry Interdisciplinary Project (CHIP), School of Pharmacy, University of Camerino, Via Madonna delle Carceri, Camerino, 62032, Italy., Aguzzi C; Department of Experimental Medicine, School of Pharmacy, University of Camerino, Via Madonna delle Carceri 9, Camerino, 62032, Italy., Lupetti V; Microbiology Unit, School of Pharmacy, University of Camerino, via Gentile III da Varano, Camerino, 62032, Italy., Giangrossi M; Department of Experimental Medicine, School of Pharmacy, University of Camerino, Via Madonna delle Carceri 9, Camerino, 62032, Italy., Bonacucina G; Chemistry Interdisciplinary Project (CHIP), School of Pharmacy, University of Camerino, Via Madonna delle Carceri, Camerino, 62032, Italy. Electronic address: giulia.bonacucina@unicam.it. |
| المصدر: | International journal of pharmaceutics [Int J Pharm] 2024 Aug 15; Vol. 661, pp. 124388. Date of Electronic Publication: 2024 Jun 24. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Elsevier/North-Holland Biomedical Press Country of Publication: Netherlands NLM ID: 7804127 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-3476 (Electronic) Linking ISSN: 03785173 NLM ISO Abbreviation: Int J Pharm Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Amsterdam, Elsevier/North-Holland Biomedical Press. |
| مواضيع طبية MeSH: | Anti-Bacterial Agents*/pharmacology , Anti-Bacterial Agents*/chemistry , Anti-Bacterial Agents*/chemical synthesis , Surface-Active Agents*/chemistry , Surface-Active Agents*/pharmacology , Surface-Active Agents*/chemical synthesis , Biguanides*/chemistry , Biguanides*/pharmacology , Microbial Sensitivity Tests* , Surface Tension*, Staphylococcus aureus/drug effects ; Pseudomonas aeruginosa/drug effects ; Micelles ; Drug Compounding ; Gram-Positive Bacteria/drug effects ; Gram-Negative Bacteria/drug effects ; Disinfectants/pharmacology ; Disinfectants/chemistry ; Chemistry, Pharmaceutical/methods |
| مستخلص: | One interesting field of research in the view of developing novel surfactants for pharmaceutical and cosmetic applications is the design of amphiphiles showing further bioactive properties in addition to those commonly displayed by surface-active compounds. We propose here the chemical synthesis, and characterization of 1-o-tolyl alkyl biguanide derivatives, having different lengths of the hydrocarbon chain (C3, C6, and C10), and showing surface active and antibacterial/disinfectant activities toward both Gram-positive and Gram-negative bacteria. Both surface active properties in terms of critical micelle concentration (CMC) and surface tension at CMC (γCMC), as well as the antimicrobial activity in terms of minimum inhibitory concentrations (MICs), were strongly dependent on the length of the hydrocarbon chain. Particularly, the C6 and C10 derivatives have a good ability to decrease surface tension (γCMC <40 mN/m) at low concentrations (CMC < 12 mM) and a satisfactory antibacterial effect (MIC values between 0.230 and 0.012 mM against S. aureus strains and between 0.910 and 0.190 against P.aeruginosa strains). Interestingly, these compounds showed a disinfectant activity at the tested concentrations that was comparable to that of the reference compound chlorhexidine digluconate. All these results support the possible use of these amphiphilic compounds as antibacterial agents and disinfectants in pharmaceutical or cosmetic formulations. Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. (Copyright © 2024. Published by Elsevier B.V.) |
| فهرسة مساهمة: | Keywords: Antibacterial; Conductivity; MTT assay; Surface tension; Surfactant; Thermal analysis |
| المشرفين على المادة: | 0 (Anti-Bacterial Agents) 0 (Surface-Active Agents) 0 (Biguanides) 0 (Micelles) 0 (Disinfectants) |
| تواريخ الأحداث: | Date Created: 20240626 Date Completed: 20240731 Latest Revision: 20240731 |
| رمز التحديث: | 20240801 |
| DOI: | 10.1016/j.ijpharm.2024.124388 |
| PMID: | 38925239 |
| قاعدة البيانات: | MEDLINE |
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