Chemically Tuning Resveratrol for the Effective Killing of Gram-Positive Pathogens.
Journal
Journal of natural products
ISSN: 1520-6025
Titre abrégé: J Nat Prod
Pays: United States
ID NLM: 7906882
Informations de publication
Date de publication:
24 06 2022
24 06 2022
Historique:
pubmed:
28
5
2022
medline:
28
6
2022
entrez:
27
5
2022
Statut:
ppublish
Résumé
In the era of antimicrobial resistance, the identification of new compounds with strong antimicrobial activity and the development of alternative therapies to fight drug-resistant bacteria are urgently needed. Here, we have used resveratrol, a safe and well-known plant-derived stilbene with poor antimicrobial properties, as a scaffold to design several new families of antimicrobials by adding different chemical entities at specific positions. We have characterized the mode of action of the most active compounds prepared and have examined their synergistic antibacterial activity in combination with traditional antibiotics. Some alkyl- and silyl-resveratrol derivatives show bactericidal activity against Gram-positive bacteria in the same low micromolar range of traditional antibiotics, with an original mechanism of action that combines membrane permeability activity with ionophore-related activities. No cross-resistance or antagonistic effect was observed with traditional antibiotics. Synergism was observed for some specific general-use antibiotics, such as aminoglycosides and cationic antimicrobial peptide antibiotics. No hemolytic activity was observed at the active concentrations or above, although some low toxicity against an MRC-5 cell line was noted.
Identifiants
pubmed: 35621995
doi: 10.1021/acs.jnatprod.1c01107
pmc: PMC9237828
doi:
Substances chimiques
Anti-Bacterial Agents
0
Anti-Infective Agents
0
Resveratrol
Q369O8926L
Types de publication
Journal Article
Review
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1459-1473Références
Toxicol Appl Pharmacol. 2019 Mar 15;367:23-32
pubmed: 30711533
PLoS Pathog. 2018 Feb 16;14(2):e1006876
pubmed: 29451901
Eur J Med Chem. 2021 Nov 5;223:113655
pubmed: 34175536
Sci Rep. 2020 Jul 9;10(1):11391
pubmed: 32647350
J Agric Food Chem. 2020 Feb 12;68(6):1609-1620
pubmed: 31957426
Chembiochem. 2016 Jul 15;17(14):1343-8
pubmed: 27147200
Acta Pol Pharm. 2003 Sep-Oct;60(5):401-4
pubmed: 15005425
Commun Biol. 2021 Jan 4;4(1):31
pubmed: 33398076
Carbohydr Res. 2009 Jul 27;344(11):1340-6
pubmed: 19539271
J Sci Food Agric. 2016 Oct;96(13):4531-5
pubmed: 26867522
Antimicrob Agents Chemother. 1989 Sep;33(9):1588-91
pubmed: 2554802
Food Microbiol. 2020 Apr;86:103337
pubmed: 31703870
Diagn Microbiol Infect Dis. 1993 May-Jun;16(4):343-9
pubmed: 8495592
Clin Microbiol Infect. 2000 Sep;6(9):503-8
pubmed: 11168186
NPJ Precis Oncol. 2017;1:
pubmed: 28989978
Appl Environ Microbiol. 2018 May 1;84(10):
pubmed: 29523548
Molecules. 2016 Aug 18;21(8):
pubmed: 27548123
J Nat Prod. 2020 Aug 28;83(8):2347-2356
pubmed: 32705864
Bioorg Med Chem. 2015 Oct 1;23(19):6355-63
pubmed: 26344592
Nat Chem Biol. 2011 Jun;7(6):348-50
pubmed: 21516114
Antimicrob Agents Chemother. 2014 Jul;58(7):3599-609
pubmed: 24709265
Eur J Med Chem. 2009 Feb;44(2):701-7
pubmed: 18586355
Elife. 2020 Aug 04;9:
pubmed: 32748785
PLoS One. 2013;8(3):e60328
pubmed: 23544135
Int J Antimicrob Agents. 2018 Feb;51(2):255-259
pubmed: 29107093
J Lipid Res. 2015 Apr;56(4):909-19
pubmed: 25681964
Nat Rev Microbiol. 2019 Mar;17(3):141-155
pubmed: 30683887
Molecules. 2017 Mar 17;22(3):
pubmed: 28304328
Antimicrob Agents Chemother. 2018 Mar 27;62(4):
pubmed: 29339386
Antibiotics (Basel). 2020 Mar 02;9(3):
pubmed: 32131427
Biochem Biophys Res Commun. 2017 Jul 22;489(2):228-234
pubmed: 28552524
J Antibiot (Tokyo). 2020 Jun;73(6):329-364
pubmed: 32152527
BMC Chem. 2020 Mar 30;14(1):24
pubmed: 32259136
Front Microbiol. 2017 Jun 13;8:1103
pubmed: 28659908
Nat Rev Drug Discov. 2006 Jun;5(6):493-506
pubmed: 16732220
Food Sci Nutr. 2019 May 29;7(7):2312-2318
pubmed: 31367359
J Med Chem. 2010 Oct 28;53(20):7365-76
pubmed: 20866032
J Agric Food Chem. 2012 Aug 1;60(30):7367-74
pubmed: 22762450
PLoS One. 2011;6(10):e25421
pubmed: 22022392
Acta Microbiol Immunol Hung. 2018 Dec 1;65(4):467-476
pubmed: 30203690
BMC Microbiol. 2020 Oct 12;20(1):306
pubmed: 33045992
Molecules. 2014 Jun 10;19(6):7679-88
pubmed: 24918540
J Glob Antimicrob Resist. 2020 Jun;21:445-451
pubmed: 31830536
Sci Rep. 2015 May 05;5:10029
pubmed: 25942564
Int J Food Microbiol. 2013 Feb 15;161(3):209-13
pubmed: 23334100
Sci Rep. 2017 Oct 16;7(1):12860
pubmed: 29038519
Front Pharmacol. 2018 Feb 19;9:102
pubmed: 29515440
Cold Spring Harb Perspect Med. 2016 Jun 01;6(6):
pubmed: 27252397
mBio. 2020 Sep 22;11(5):
pubmed: 32963002
Fitoterapia. 2005 Mar;76(2):258-60
pubmed: 15752644
Cold Spring Harb Perspect Med. 2016 Oct 3;6(10):
pubmed: 27503996
Sci Rep. 2019 Dec 20;9(1):19525
pubmed: 31862939
Nat Rev Drug Discov. 2011 Mar;10(3):221-37
pubmed: 21358741
Phytomedicine. 2017 Dec 15;37:27-48
pubmed: 29174958
Arch Pathol Lab Med. 2005 Oct;129(10):1295-8
pubmed: 16196519
Nat Rev Drug Discov. 2016 Apr;15(4):249-74
pubmed: 26794269
Eur J Med Chem. 2018 Oct 5;158:91-105
pubmed: 30205261
Int J Antimicrob Agents. 2018 Sep;52(3):390-396
pubmed: 29906565
J Antibiot (Tokyo). 2021 Jan;74(1):24-41
pubmed: 32647212
J Med Chem. 2010 Jul 8;53(13):5033-43
pubmed: 20527891
Eur J Med Chem. 2018 Feb 25;146:123-138
pubmed: 29407944
Clin Infect Dis. 2015 Jun 1;60(11):1726-8
pubmed: 25697741
J Nat Prod. 2004 Mar;67(3):421-6
pubmed: 15043422
Nature. 2001 Jun 14;411(6839):843-7
pubmed: 11459067
Nat Rev Microbiol. 2020 May;18(5):286-298
pubmed: 32152509
Bioorg Med Chem. 2009 Apr 1;17(7):2886-93
pubmed: 19269184
Front Cell Dev Biol. 2016 Apr 13;4:29
pubmed: 27148531
J Nat Med. 2017 Oct;71(4):665-682
pubmed: 28600778
Int J Antimicrob Agents. 2019 Jun;53(6):716-723
pubmed: 30825504
Nat Rev Microbiol. 2020 May;18(5):275-285
pubmed: 31745331
ChemMedChem. 2012 Sep;7(9):1541-5
pubmed: 22847956
mBio. 2017 Sep 5;8(5):
pubmed: 28874470
Med Res Rev. 2020 Nov;40(6):2605-2649
pubmed: 32779240