Synthesis, modeling, and biological evaluation of anti-tubulin indole-substituted furanones.


Journal

Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377

Informations de publication

Date de publication:
15 06 2023
Historique:
received: 18 04 2023
revised: 12 05 2023
accepted: 19 05 2023
medline: 9 6 2023
pubmed: 27 5 2023
entrez: 26 5 2023
Statut: ppublish

Résumé

Due to the central role of tubulin in various cellular functions, it is a validated target for anti-cancer therapeutics. However, many of the current tubulin inhibitors are derived from complex natural products and suffer from multidrug resistance, low solubility, toxicity issues, and/or the lack of multi-cancer efficacy. As such, there is a continued need for the discovery and development of new anti-tubulin drugs to enter the pipeline. Herein we report on a group of indole-substituted furanones that were prepared and tested for anti-cancer activity. Molecular docking studies showed positive correlations between favorable binding in the colchicine binding site (CBS) of tubulin and anti-proliferative activity, and the most potent compound was found to inhibit tubulin polymerization. These compounds represent a promising new structural motif in the search for small heterocyclic CBS cancer inhibitors.

Identifiants

pubmed: 37236376
pii: S0960-894X(23)00225-1
doi: 10.1016/j.bmcl.2023.129347
pii:
doi:

Substances chimiques

Tubulin 0
Antineoplastic Agents 0
Tubulin Modulators 0
Colchicine SML2Y3J35T
Indoles 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.

Langues

eng

Sous-ensembles de citation

IM

Pagination

129347

Informations de copyright

Copyright © 2023 Elsevier Ltd. All rights reserved.

Déclaration de conflit d'intérêts

Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Auteurs

Brianna Hurysz (B)

Department of Biology, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Blake A Evans (BA)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Reuben N Laryea (RN)

Department of Molecular Biology and Chemistry, Christopher Newport University, Newport News, VA 23606, USA.

Brooke E Boyer (BE)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Taylor E Coburn (TE)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Molly S Dexter (MS)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA; Department of Biology, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Marissa A Edwards (MA)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Grace V Faulkner (GV)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Rebecca L Huss (RL)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Megan M Lafferty (MM)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Maegan Manning (M)

Department of Biology, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Matthew McNulty (M)

Department of Biology, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Sophia J Melvin (SJ)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Christina M Mitrow (CM)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Roslyn R Patel (RR)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Kelsey Pierce (K)

Department of Biology, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Jack Russo (J)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Allie M Seminer (AM)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Kaitlynn A Sockett (KA)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Nathan R Webster (NR)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA.

Kathryn E Cole (KE)

Department of Molecular Biology and Chemistry, Christopher Newport University, Newport News, VA 23606, USA. Electronic address: kathryn.cole@cnu.edu.

Patricia Mowery (P)

Department of Biology, Hobart and William Smith Colleges, Geneva, NY 14456, USA. Electronic address: mowery@hws.edu.

Erin T Pelkey (ET)

Department of Chemistry, Hobart and William Smith Colleges, Geneva, NY 14456, USA. Electronic address: pelkey@hws.edu.

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Classifications MeSH