title: Towards squalamine mimics: synthesis and antibacterial activities of head-to-tail dimeric sterol-polyamine conjugates.
abstract: Four dimeric sterol-polyamine conjugates have been synthesized from the homo- and hetero-connection of monomeric sterol-polyamine analogs in a head-to-tail manner. These dimeric conjugates show strong antibacterial activity against a broad spectrum of Gram-positive bacteria, whereas their corresponding activities against Gram-negative bacteria are relatively moderate. Though no significant difference was observed in the activities of these conjugates, cholic acid-containing dimeric conjugates generally exhibit higher activities than the corresponding deoxycholic acid-derived analogs. This is in contrast to the finding that a monomeric deoxycholic acid-spermine conjugate was more active than the corresponding cholic acid-derived analog.
authors.affiliation: School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, PR China. whchen@smu.edu.cn
authors.forename: Wen-Hua
authors.initials: WH
authors.lastname: Chen
authors.forename: Christine
authors.initials: C
authors.lastname: Wennersten
authors.forename: Robert C
authors.initials: RC
authors.lastname: Moellering
authors.forename: Steven L
authors.initials: SL
authors.lastname: Regen
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002777:Cholestanols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D019826:Cholic Acid / Q000737:chemistry; D003840:Deoxycholic Acid / Q000031:analogs & derivatives; D019281:Dimerization; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D011073:Polyamines / Q000737:chemistry*; D013096:Spermine / Q000737:chemistry; D013261:Sterols / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D002777:Cholestanols; D011073:Polyamines; D013261:Sterols; D003840:Deoxycholic Acid; D013096:Spermine; C079655:squalamine; D019826:Cholic Acid