Structure guided design and synthesis of furyl thiazolidinedione derivatives as inhibitors of GLUT 1 and GLUT 4, and evaluation of their anti-leukemic potential.

Animals Antineoplastic Agents / chemical synthesis Apoptosis / drug effects Cell Cycle / drug effects Cell Line, Tumor Cell Proliferation / drug effects Dose-Response Relationship, Drug Drug Design Drug Screening Assays, Antitumor Glucose Transporter Type 1 / antagonists & inhibitors Glucose Transporter Type 4 / antagonists & inhibitors Humans Mice Mice, SCID Models, Molecular Molecular Structure Neoplasms, Experimental / drug therapy Structure-Activity Relationship Thiazolidinediones / chemical synthesis
Antiproliferative Cytotoxicity Furan GLUT1 GLUT4 GLUT5 Inhibitor specificity Leukemia Thiazolidinedione (TZD)

Journal

European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510

Informations de publication

Date de publication:
15 Sep 2020
Historique:
received: 06 05 2020
revised: 14 06 2020
accepted: 18 06 2020
pubmed: 8 7 2020
medline: 2 4 2021
entrez: 8 7 2020
Statut: ppublish

Résumé

Cancer cells increase their glucose uptake and glycolytic activity to meet the high energy requirements of proliferation. Glucose transporters (GLUTs), which facilitate the transport of glucose and related hexoses across the cell membrane, play a vital role in tumor cell survival and are overexpressed in various cancers. GLUT1, the most overexpressed GLUT in many cancers, is emerging as a promising anti-cancer target. To develop GLUT1 inhibitors, we rationally designed, synthesized, structurally characterized, and biologically evaluated in-vitro and in-vivo a novel series of furyl-2-methylene thiazolidinediones (TZDs). Among 25 TZDs tested, F18 and F19 inhibited GLUT1 most potently (IC

Identifiants

DOI: 10.1016/j.ejmech.2020.112603 PMID: 32634629 PMC: PMC7451030
pubmed: 32634629
pii: S0223-5234(20)30575-4
doi: 10.1016/j.ejmech.2020.112603
pmc: PMC7451030
mid: NIHMS1608647
pii:
doi:

Substances chimiques

Antineoplastic Agents 0
Glucose Transporter Type 1 0
Glucose Transporter Type 4 0
SLC2A1 protein, human 0
SLC2A4 protein, human 0
Thiazolidinediones 0
2,4-thiazolidinedione AA68LXK93C

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

112603

Subventions

Organisme : NIGMS NIH HHS
ID : R01 GM123103
Pays : United States
Organisme : NIMHD NIH HHS
ID : U54 MD007592
Pays : United States

Informations de copyright

Copyright © 2020 Elsevier Masson SAS. 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.

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Auteurs

Kalpana Tilekar (K)

Department of Pharmaceutical Chemistry, Bharati Vidyapeeth's College of Pharmacy, Navi Mumbai, Maharashtra, India.

Neha Upadhyay (N)

Department of Pharmaceutical Chemistry, Bharati Vidyapeeth's College of Pharmacy, Navi Mumbai, Maharashtra, India.

Jessica D Hess (JD)

The Cytometry, Screening and Imaging Core Facility & Border Biomedical Research Center & Department of Biological Sciences, The University of Texas at El Paso, El Paso, TX, USA.

Lucasantiago Henze Macias (LH)

The Cytometry, Screening and Imaging Core Facility & Border Biomedical Research Center & Department of Biological Sciences, The University of Texas at El Paso, El Paso, TX, USA.

Piotr Mrowka (P)

Department of Biophysics and Human Physiology, Medical University of Warsaw, Chalubinskiego, Warsaw, Poland.

Renato J Aguilera (RJ)

The Cytometry, Screening and Imaging Core Facility & Border Biomedical Research Center & Department of Biological Sciences, The University of Texas at El Paso, El Paso, TX, USA.

Franz-Josef Meyer-Almes (FJ)

Department of Chemical Engineering and Biotechnology, University of Applied Sciences, Darmstadt, Germany.

Cristina V Iancu (CV)

East Carolina Diabetes and Obesity Institute, Department of Chemistry, East Carolina University, Greenville, NC, USA.

Jun-Yong Choe (JY)

East Carolina Diabetes and Obesity Institute, Department of Chemistry, East Carolina University, Greenville, NC, USA; Department of Biochemistry and Molecular Biology, The Chicago Medical School, Rosalind Franklin University of Medicine and Science, North Chicago, IL, USA. Electronic address: choej18@ecu.edu.

C S Ramaa (CS)

Department of Pharmaceutical Chemistry, Bharati Vidyapeeth's College of Pharmacy, Navi Mumbai, Maharashtra, India. Electronic address: sinharamaa@yahoo.in.

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Classifications MeSH

questionsmedicales.fr › Eucaryotes › Animaux › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Antinéoplasiques › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Phénomènes physiologiques cellulaires › Mort cellulaire › Mort cellulaire régulée › Apoptose › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Phénomènes physiologiques cellulaires › Cycle cellulaire › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Cellules › Cellules cultivées › Cellules cancéreuses en culture › Lignée cellulaire tumorale › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Phénomènes physiologiques › Croissance et développement › Croissance › Processus de croissance cellulaire › Prolifération cellulaire › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes toxicologiques › Relation dose-effet des médicaments › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Techniques d'investigation › Développement de médicament › Découverte de médicament › Conception de médicament › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Techniques d'investigation › Évaluation préclinique de médicament › Tests de criblage d'agents antitumoraux › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines membranaires › Protéines de transport membranaire › Protéines transporteurs de solutés › Transporteurs de glucose par diffusion facilitée › Transporteur de glucose de type 1 › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines membranaires › Protéines de transport membranaire › Protéines transporteurs de solutés › Transporteurs de glucose par diffusion facilitée › Transporteur de glucose de type 4 › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Rodentia › Muridae › Murinae › Souris › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Rodentia › Muridae › Murinae › Souris › Souches mutantes de souris › Souris SCID › Structure guided design and synthesis of furyl...
questionsmedicales.fr › Techniques d'investigation › Modèles théoriques › Modèles moléculaires › Structure guided design and synthesis of furyl...
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questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Azoles › Thiazoles › Thiazolidinediones › Structure guided design and synthesis of furyl...