Syntheses and Glycosidase Inhibitory Activities, and in Silico Docking Studies of Pericosine E Analogs Methoxy-Substituted at C6.
C6-methoxy analogue
anti-diabetes drug
docking simulation
marine natural product
pericosine E
α-glucosidase inhibitor
Journal
Marine drugs
ISSN: 1660-3397
Titre abrégé: Mar Drugs
Pays: Switzerland
ID NLM: 101213729
Informations de publication
Date de publication:
20 Apr 2020
20 Apr 2020
Historique:
received:
15
02
2020
revised:
15
04
2020
accepted:
17
04
2020
entrez:
25
4
2020
pubmed:
25
4
2020
medline:
17
2
2021
Statut:
epublish
Résumé
Inspired by the significant -glucosidase inhibitory activities of (+)- and (-)-pericosine E, we herein designed and synthesized 16 analogs of these marine natural products bearing a methoxy group instead of a chlorine atom at C6. Four of these compounds exhibited moderate -glucosidase inhibitory activities, which were weaker than those of the corresponding chlorine-containing species. The four compounds could be prepared by coupling reactions utilizing the (-)-pericosine B moiety. An additional in silico docking simulation suggested that the reason of reduced activity of the C6-methoxylated analogs might be an absence of hydrogen bonding between a methoxy group with the surrounding amino acid residues in the active site in -glucosidase.
Identifiants
pubmed: 32326065
pii: md18040221
doi: 10.3390/md18040221
pmc: PMC7230162
pii:
doi:
Substances chimiques
Glycoside Hydrolase Inhibitors
0
Ligands
0
pericosine E
0
Shikimic Acid
29MS2WI2NU
alpha-Glucosidases
EC 3.2.1.20
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Déclaration de conflit d'intérêts
The authors declare no conflict of interest.
Références
J Pharm Anal. 2019 Apr;9(2):91-99
pubmed: 31011465
Molecules. 2018 Sep 19;23(9):
pubmed: 30235889
Org Biomol Chem. 2007 Dec 21;5(24):3979-86
pubmed: 18043803
ACS Omega. 2018 May 28;3(5):5704-5714
pubmed: 31458770
Proteins. 2009 Apr;75(1):187-205
pubmed: 18814299
Org Lett. 2018 Oct 5;20(19):6225-6228
pubmed: 30221525
Org Lett. 2014 Jul 18;16(14):3760-3
pubmed: 24991702
J Org Chem. 2013 Aug 2;78(15):7406-13
pubmed: 23806010
ChemMedChem. 2016 Jan 5;11(1):133-41
pubmed: 26644389
Phytochemistry. 2013 Oct;94:198-205
pubmed: 23809634
Carbohydr Res. 2014 Mar 31;388:130-7
pubmed: 24637047
Org Biomol Chem. 2009 Jan 21;7(2):315-8
pubmed: 19109676
J Comput Aided Mol Des. 2012 Jun;26(6):775-86
pubmed: 22566074
Org Biomol Chem. 2011 Nov 7;9(21):7306-8
pubmed: 21915422
Org Lett. 2010 May 21;12(10):2206-9
pubmed: 20411952
Org Lett. 2009 Jun 18;11(12):2699-701
pubmed: 19514797
PLoS One. 2010 Sep 16;5(9):e12713
pubmed: 20877634
FEBS J. 2010 Oct;277(20):4205-14
pubmed: 20812985
Mar Drugs. 2017 Jan 23;15(1):
pubmed: 28124983
Mini Rev Med Chem. 2007 Jul;7(7):679-91
pubmed: 17627580
J Sci Food Agric. 2019 Mar 30;99(5):2521-2529
pubmed: 30393852