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Hydrophobicity of Cholic Acid-Derived Amphiphiles Dictates the Antimicrobial Specificity.
- Source :
-
ACS biomaterials science & engineering [ACS Biomater Sci Eng] 2022 Nov 14; Vol. 8 (11), pp. 4996-5007. Date of Electronic Publication: 2022 Oct 26. - Publication Year :
- 2022
-
Abstract
- The unique structural components of cell membranes of Gram-positive bacteria, Gram-negative bacteria, and mycobacteria provide an excellent therapeutic target for developing highly specific antimicrobials. Here, we report the synthesis of nine cholic acid (CA)-derived amphiphiles, where three hydroxyl groups of CA were tethered to dimethylamino pyridine and the C24-carboxyl group was conjugated with different alkyl chains. Structure-activity investigations revealed that amphiphile 1 harboring a methyl group has antimicrobial activity against mycobacterial species. On the other hand, amphiphile 7 containing an octyl chain was selective against Gram-positive and Gram-negative bacilli. Biochemical assays confirmed the selective membrane permeabilization abilities of amphiphiles 1 and 7 . Importantly, we demonstrate the selective actions of amphiphiles in clearing biofilms, intracellular bacteria, and wound infections. Therefore, for the first time, we show that the unique structural features of CA-derived amphiphiles dictate selective activity against specific bacterial species.
Details
- Language :
- English
- ISSN :
- 2373-9878
- Volume :
- 8
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- ACS biomaterials science & engineering
- Publication Type :
- Academic Journal
- Accession number :
- 36288545
- Full Text :
- https://doi.org/10.1021/acsbiomaterials.2c00924