Spiroindoline-Capped Selective HDAC6 Inhibitors: Design, Synthesis, Structural Analysis, and Biological Evaluation.


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:
12 Nov 2020
Historique:
received: 17 07 2020
accepted: 29 09 2020
entrez: 20 11 2020
pubmed: 21 11 2020
medline: 21 11 2020
Statut: epublish

Résumé

Histone deacetylase inhibitors (HDACi) have emerged as promising therapeutics for the treatment of neurodegeneration, cancer, and rare disorders. Herein, we report the development of a series of spiroindoline-based HDAC6 isoform-selective inhibitors based on the X-ray crystal studies of the hit

Identifiants

pubmed: 33214839
doi: 10.1021/acsmedchemlett.0c00395
pmc: PMC7667836
doi:

Types de publication

Journal Article

Langues

eng

Pagination

2268-2276

Subventions

Organisme : NIGMS NIH HHS
ID : P30 GM124165
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01 GM049758
Pays : United States
Organisme : NCRR NIH HHS
ID : S10 RR029205
Pays : United States

Déclaration de conflit d'intérêts

The authors declare no competing financial interest.

Références

Int J Cancer. 2019 Aug 1;145(3):735-747
pubmed: 30694564
ChemMedChem. 2016 Jan 5;11(1):15-21
pubmed: 26603496
J Biomed Biotechnol. 2011;2011:875824
pubmed: 21076528
Nat Chem Biol. 2016 Sep;12(9):741-7
pubmed: 27454933
Cell Death Dis. 2018 Jul 26;9(8):817
pubmed: 30050135
Leuk Res. 1999 Feb;23(2):127-36
pubmed: 10071128
Int J Oncol. 2006 Jul;29(1):117-24
pubmed: 16773191
Expert Opin Ther Pat. 2020 Feb;30(2):121-136
pubmed: 31865813
ACS Infect Dis. 2020 Jan 10;6(1):100-113
pubmed: 31661956
J Med Chem. 2018 Sep 13;61(17):8054-8060
pubmed: 30118224
Org Lett. 2018 Jun 1;20(11):3255-3258
pubmed: 29790770
Cancer Chemother Pharmacol. 2019 Feb;83(2):255-264
pubmed: 30430228
J Med Chem. 2018 Nov 21;61(22):10299-10309
pubmed: 30365892
Future Med Chem. 2012 Mar;4(4):505-24
pubmed: 22416777
Eur J Med Chem. 2018 Sep 5;157:127-138
pubmed: 30092367
Future Med Chem. 2016 Sep;8(13):1573-87
pubmed: 27556815
Sci Transl Med. 2019 Sep 11;11(509):
pubmed: 31511426
Immunity. 1999 Jan;10(1):105-15
pubmed: 10023775
Nat Commun. 2017 May 18;8:15368
pubmed: 28516954
J Med Chem. 2020 Jan 9;63(1):295-308
pubmed: 31793776
Cancer Res. 1980 Dec;40(12):4704-8
pubmed: 7002295
ACS Chem Biol. 2020 Aug 21;15(8):2154-2163
pubmed: 32659072
Exp Cell Res. 2018 Jul 15;368(2):225-235
pubmed: 29730163
Curr Opin Chem Biol. 1997 Oct;1(3):300-8
pubmed: 9667866
J Med Chem. 2020 Jan 9;63(1):23-39
pubmed: 31415174

Auteurs

A Prasanth Saraswati (AP)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Nicola Relitti (N)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Margherita Brindisi (M)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Jeremy D Osko (JD)

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.

Giulia Chemi (G)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Stefano Federico (S)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Alessandro Grillo (A)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Simone Brogi (S)

Department of Pharmacy, University of Pisa, via Bonanno 6, 56126, Pisa, Italy.

Niamh H McCabe (NH)

Centre for Cancer Research and Cell Biology, Queens University Belfast, Belfast, U.K.

Richard C Turkington (RC)

Centre for Cancer Research and Cell Biology, Queens University Belfast, Belfast, U.K.

Ola Ibrahim (O)

School of Dental Science, Trinity College Dublin, Lincoln Place, Dublin 2, Ireland.

Jeffrey O'Sullivan (J)

School of Dental Science, Trinity College Dublin, Lincoln Place, Dublin 2, Ireland.

Stefania Lamponi (S)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Magda Ghanim (M)

School of Biochemistry and Immunology, Trinity Biomedical Science Institute, Trinity College, 152-160, Pearse Street, Dublin 2, Ireland.

Vincent P Kelly (VP)

School of Biochemistry and Immunology, Trinity Biomedical Science Institute, Trinity College, 152-160, Pearse Street, Dublin 2, Ireland.

Daniela Zisterer (D)

School of Biochemistry and Immunology, Trinity Biomedical Science Institute, Trinity College, 152-160, Pearse Street, Dublin 2, Ireland.

Rebecca Amet (R)

School of Biochemistry and Immunology, Trinity Biomedical Science Institute, Trinity College, 152-160, Pearse Street, Dublin 2, Ireland.

Patricia Hannon Barroeta (P)

School of Biochemistry and Immunology, Trinity Biomedical Science Institute, Trinity College, 152-160, Pearse Street, Dublin 2, Ireland.

Francesca Vanni (F)

Department of Life Sciences, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Cristina Ulivieri (C)

Department of Life Sciences, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Daniel Herp (D)

Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Albertstraße 25, 79104, Freiburg, Germany.

Federica Sarno (F)

Department of Precision Medicine, University of Campania "Luigi Vanvitelli″, 80138 Naples, Italy.

Antonella Di Costanzo (A)

Department of Precision Medicine, University of Campania "Luigi Vanvitelli″, 80138 Naples, Italy.

Fulvio Saccoccia (F)

Institute of Biochemistry and Cell Biology (IBBC), National Research Council (CNR), via E. Ramarini 32, 00015 Monterotondo, Rome, Italy.

Giovina Ruberti (G)

Institute of Biochemistry and Cell Biology (IBBC), National Research Council (CNR), via E. Ramarini 32, 00015 Monterotondo, Rome, Italy.

Manfred Jung (M)

Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Albertstraße 25, 79104, Freiburg, Germany.

Lucia Altucci (L)

Department of Precision Medicine, University of Campania "Luigi Vanvitelli″, 80138 Naples, Italy.

Sandra Gemma (S)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Stefania Butini (S)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

David W Christianson (DW)

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.

Giuseppe Campiani (G)

Department of Biotechnology, Chemistry and Pharmacy, DoE Department of Excellence 2018-2022, University of Siena, via Aldo Moro 2, I-53100 Siena, Italy.

Classifications MeSH