Maytansinol Derivatives: Side Reactions as a Chance for New Tubulin Binders.
maytansine binding site
maytansinol
microtubules
tubulin
tubulin binders
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
10 Jan 2022
10 Jan 2022
Historique:
received:
28
09
2021
pubmed:
18
11
2021
medline:
15
1
2022
entrez:
17
11
2021
Statut:
ppublish
Résumé
Maytansinol is a valuable precursor for the preparation of maytansine derivatives (known as maytansinoids). Inspired by the intriguing structure of the macrocycle and the success in targeted cancer therapy of the derivatives, we explored the maytansinol acylation reaction. As a result, we were able to obtain a series of derivatives with novel modifications of the maytansine scaffold. We characterized these molecules by docking studies, by a comprehensive biochemical evaluation, and by determination of their crystal structures in complex with tubulin. The results shed further light on the intriguing chemical behavior of maytansinoids and confirm the relevance of this peculiar scaffold in the scenario of tubulin binders.
Identifiants
pubmed: 34788896
doi: 10.1002/chem.202103520
pmc: PMC9299702
doi:
Substances chimiques
Tubulin
0
Tubulin Modulators
0
maytansinol
0
Maytansine
14083FR882
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202103520Subventions
Organisme : Horizon 2020 Framework Programme
ID : 860070 TUBINTRAIN
Organisme : Ministerio de Ciencia e Innovación
ID : PID2019-104545RB-I00
Informations de copyright
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
Trends Cancer. 2020 Feb;6(2):130-146
pubmed: 32061303
J Med Chem. 2006 Jul 13;49(14):4392-408
pubmed: 16821799
J Cell Biol. 2013 Feb 4;200(3):259-70
pubmed: 23358242
Theranostics. 2017 Jul 23;7(13):3306-3318
pubmed: 28900511
J Am Chem Soc. 1972 Feb 23;94(4):1354-6
pubmed: 5062169
Proc Natl Acad Sci U S A. 2014 Sep 23;111(38):13817-21
pubmed: 25114240
Nat Commun. 2018 May 29;9(1):2106
pubmed: 29844393
Science. 2013 Feb 1;339(6119):587-90
pubmed: 23287720
J Org Chem. 1977 Jul 8;42(14):2349-57
pubmed: 874612
Chem Biol. 2008 Jun;15(6):573-85
pubmed: 18559268
Chemistry. 2022 Jan 10;28(2):e202103520
pubmed: 34788896
Chempluschem. 2019 Jan;84(1):98-102
pubmed: 31950734
Bioorg Med Chem Lett. 2020 Dec 15;30(24):127634
pubmed: 33148516
Chem Pharm Bull (Tokyo). 2004 Jan;52(1):1-26
pubmed: 14709862
Acta Pharm Sin B. 2020 Sep;10(9):1589-1600
pubmed: 33088681
Chem Pharm Bull (Tokyo). 1984 Sep;32(9):3341-51
pubmed: 6441645
Clin Cancer Res. 2014 Sep 1;20(17):4436-41
pubmed: 24879797
Mol Cancer Ther. 2010 Oct;9(10):2689-99
pubmed: 20937594
ACS Med Chem Lett. 2019 Sep 27;10(10):1393-1399
pubmed: 31620224
Biochem Pharmacol. 1981 Sep 1;30(17):2421-5
pubmed: 21043240
Bioorg Med Chem. 2018 May 15;26(9):2271-2279
pubmed: 29605304
Cancer. 2020 Dec 15;126(24):5303-5310
pubmed: 32914879
Curr Pharm Des. 2017;23(5):784-808
pubmed: 27981911
Drug Discov Today. 2021 Feb;26(2):604-615
pubmed: 33279455
Biochem Biophys Res Commun. 2021 Aug 20;566:197-203
pubmed: 34144258
Cancer Treat Rev. 1978 Dec;5(4):199-207
pubmed: 367597
Bioconjug Chem. 2019 Mar 20;30(3):703-713
pubmed: 30582799
Clin Cancer Res. 2020 Aug 15;26(16):4180-4185
pubmed: 32217612
J Med Chem. 2019 Mar 14;62(5):2708-2719
pubmed: 30735385
Science. 1975 Sep 19;189(4207):1002-5
pubmed: 1241159
Bioconjug Chem. 2015 Nov 18;26(11):2261-78
pubmed: 26355774