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Geographic variability and anti-staphylococcal activity of the chrysophaentins and their synthetic fragments

Keffer, JL and Hammill, JT and Lloyd, JR and Plaza, A and Wipf, P and Bewley, CA (2012) Geographic variability and anti-staphylococcal activity of the chrysophaentins and their synthetic fragments. Marine Drugs, 10 (5). 1103 - 1125.

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Drug-resistant Staphylococcus aureus is a continuing public health concern, both in the hospital and community settings. Antibacterial compounds that possess novel structural scaffolds and are effective against multiple S. aureus strains, including current drug-resistant ones, are needed. Previously, we have described the chrysophaentins, a family of bisdiarylbutene macrocycles from the chrysophyte alga Chrysophaeum taylori that inhibit the growth of S. aureus and methicillin-resistant S. aureus (MRSA). In this study we have analyzed the geographic variability of chrysophaentin production in C. taylori located at different sites on the island of St. John, U.S. Virgin Islands, and identified two new linear chrysophaentin analogs, E2 and E3. In addition, we have expanded the structure activity relationship through synthesis of fragments comprising conserved portions of the chrysophaentins, and determined the antimicrobial activity of natural chrysophaentins and their synthetic analogs against five diverse S. aureus strains. We find that the chrysophaentins show similar activity against all S. aureus strains, regardless of their drug sensitivity profiles. The synthetic chrysophaentin fragments indeed mimic the natural compounds in their spectrum of antibacterial activity, and therefore represent logical starting points for future medicinal chemistry studies of the natural products and their analogs. © 2012 by the authors.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Keffer, JL
Hammill, JT
Lloyd, JR
Plaza, A
Wipf, Ppwipf@pitt.eduPWIPF
Bewley, CA
Date: 1 January 2012
Date Type: Publication
Journal or Publication Title: Marine Drugs
Volume: 10
Number: 5
Page Range: 1103 - 1125
DOI or Unique Handle: 10.3390/md10051103
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
MeSH Headings: Anti-Bacterial Agents--chemical synthesis; Anti-Bacterial Agents--chemistry; Anti-Bacterial Agents--pharmacology; Chrysophyta--chemistry; Geography; Macrocyclic Compounds--chemical synthesis; Macrocyclic Compounds--chemistry; Macrocyclic Compounds--pharmacology; Methicillin-Resistant Staphylococcus aureus--chemistry; Microbial Sensitivity Tests--methods; United States Virgin Islands
Other ID: NLM PMC3397459
PubMed Central ID: PMC3397459
PubMed ID: 22822360
Date Deposited: 31 Jul 2014 20:50
Last Modified: 22 Dec 2020 16:55


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