Design of Coibamide A Mimetics with Improved Cellular Bioactivity.


Journal

ACS medicinal chemistry letters
ISSN: 1948-5875
Titre abrégé: ACS Med Chem Lett
Pays: United States
ID NLM: 101521073

Informations de publication

Date de publication:
13 Jan 2022
Historique:
received: 26 10 2021
accepted: 06 12 2021
entrez: 21 1 2022
pubmed: 22 1 2022
medline: 22 1 2022
Statut: epublish

Résumé

Coibamide A, a cyclic depsipeptide isolated from a Panamanian marine cyanobacterium, shows potent cytotoxic activity via the inhibition of the Sec61 translocon. We designed a coibamide A mimetic in which the ester linkage between MeThr and d-MeAla in coibamide A was replaced with an alkyl linker to provide a stable macrocyclic scaffold possessing a MeLys(Me) residue. Taking advantage of a facile solid-phase synthetic approach, an structure-activity relationship (SAR) study of the newly designed macrocyclic structure was performed, with a focus on altering the pattern of

Identifiants

pubmed: 35059129
doi: 10.1021/acsmedchemlett.1c00591
pmc: PMC8762706
doi:

Types de publication

Journal Article

Langues

eng

Pagination

105-110

Informations de copyright

© 2021 The Authors. Published by American Chemical Society.

Déclaration de conflit d'intérêts

The authors declare no competing financial interest.

Références

Cell Chem Biol. 2019 Apr 18;26(4):571-583.e6
pubmed: 30799222
J Pept Sci. 2006 Mar;12(3):213-9
pubmed: 16189816
J Am Chem Soc. 2002 May 15;124(19):5431-40
pubmed: 11996584
J Exp Med. 2016 Dec 12;213(13):2885-2896
pubmed: 27821549
J Am Chem Soc. 2015 Oct 28;137(42):13488-91
pubmed: 26469305
J Med Chem. 2017 Aug 10;60(15):6751-6765
pubmed: 28682609
J Med Chem. 2021 Jan 28;64(2):991-1000
pubmed: 33417771
J Am Chem Soc. 2021 Jan 20;143(2):705-714
pubmed: 33381960
Cell Chem Biol. 2016 May 19;23(5):561-566
pubmed: 27203376
J Cell Sci. 2015 Mar 15;128(6):1217-29
pubmed: 25616894
Invest New Drugs. 2016 Feb;34(1):24-40
pubmed: 26563191
Nature. 2005 Jul 14;436(7048):290-3
pubmed: 16015337
ACS Chem Biol. 2020 Aug 21;15(8):2125-2136
pubmed: 32608972
Biochem Biophys Res Commun. 2021 Apr 2;547:52-58
pubmed: 33592379
ACS Med Chem Lett. 2011 Nov 10;2(11):861-865
pubmed: 22081789
J Am Chem Soc. 2007 Nov 28;129(47):14560-1
pubmed: 17983236
Mar Drugs. 2018 Mar 01;16(3):
pubmed: 29494533
J Med Chem. 2018 Oct 11;61(19):8908-8916
pubmed: 30247036
Signal Transduct Target Ther. 2017 Apr 28;2:17002
pubmed: 29263911
J Cell Sci. 2009 Dec 1;122(Pt 23):4393-400
pubmed: 19903691
Front Physiol. 2017 Nov 01;8:887
pubmed: 29163222
Bioorg Med Chem Lett. 2015 Jan 15;25(2):302-6
pubmed: 25488840
Mol Cancer Ther. 2016 Jun;15(6):1208-16
pubmed: 27196783
Cell Mol Life Sci. 2018 May;75(9):1541-1558
pubmed: 29305616
Org Lett. 2019 Aug 2;21(15):5853-5857
pubmed: 31295000
Nat Prod Rep. 2020 May 1;37(5):717-736
pubmed: 32067014
J Org Chem. 2020 Dec 18;85(24):16226-16235
pubmed: 33264019
PLoS One. 2013 Jun 06;8(6):e65250
pubmed: 23762328
J Am Chem Soc. 2008 May 21;130(20):6324-5
pubmed: 18444611
J Cell Sci. 2021 Feb 19;134(4):
pubmed: 33468620
Nature. 2005 Jul 14;436(7048):285-9
pubmed: 16015336
Biochem Pharmacol. 2021 Jan;183:114317
pubmed: 33152346
J Am Chem Soc. 2019 May 29;141(21):8450-8461
pubmed: 31059257
Cells. 2021 Apr 27;10(5):
pubmed: 33925740
Bioorg Med Chem Lett. 2016 Nov 1;26(21):5177-5181
pubmed: 27729187

Auteurs

Takashi Kitamura (T)

Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.

Rikito Suzuki (R)

Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan.

Shinsuke Inuki (S)

Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.

Hiroaki Ohno (H)

Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.

Kerry L McPhail (KL)

Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, United States.

Shinya Oishi (S)

Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan.

Classifications MeSH