Schiff bases of tryptamine as potent inhibitors of nucleoside triphosphate diphosphohydrolases (NTPDases): Structure-activity relationship.


Journal

Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703

Informations de publication

Date de publication:
02 2019
Historique:
received: 06 08 2018
revised: 18 10 2018
accepted: 23 10 2018
pubmed: 6 11 2018
medline: 31 8 2019
entrez: 5 11 2018
Statut: ppublish

Résumé

Overexpression of NTPDases leads to a number of pathological situations such as thrombosis, and cancer. Thus, effective inhibitors are required to combat these pathological situations. Different classes of NTPDase inhibitors are reported so far including nucleotides and their derivatives, sulfonated dyes such as reactive blue 2, suramin and its derivatives, and polyoxomatalates (POMs). Suramin is a well-known and potent NTPDase inhibitor, nonetheless, a range of side effects are also associated with it. Reactive blue 2 also had non-specific side effects that become apparent at high concentrations. In addition, most of the NTPDase inhibitors are high molecular weight compounds, always required tedious chemical steps to synthesize. Hence, there is still need to explore novel, low molecular weight, easy to synthesize, and potent NTPDase inhibitors. Keeping in mind the known NTPDase inhibitors with imine functionality and nitrogen heterocycles, Schiff bases of tryptamine, 1-26, were synthesized and characterized by spectroscopic techniques such as EI-MS, HREI-MS,

Identifiants

pubmed: 30391856
pii: S0045-2068(18)30826-5
doi: 10.1016/j.bioorg.2018.10.046
pii:
doi:

Substances chimiques

Antigens, CD 0
Enzyme Inhibitors 0
Schiff Bases 0
Tryptamines 0
tryptamine 422ZU9N5TV
Adenosine Triphosphatases EC 3.6.1.-
ectoATPase EC 3.6.1.-
nucleoside triphosphate diphosphohydrolase 8, human EC 3.6.1.3
Apyrase EC 3.6.1.5
CD39 antigen EC 3.6.1.5

Types de publication

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

Langues

eng

Sous-ensembles de citation

IM

Pagination

253-266

Informations de copyright

Copyright © 2018 Elsevier Inc. All rights reserved.

Auteurs

H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.

Khalid Mohammed Khan (K)

H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia. Electronic address: khalid.khan@iccs.edu.

Uzma Salar (U)

H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.

Saira Afzal (S)

Centre for Advanced Drug Research (CADR), Department of Pharmacy COMSATS Institute of Information Technology, Abbottabad, Pakistan.

Abdul Wadood (A)

Department of Biochemistry, Computational Medicinal Chemistry Laboratory, UCSS, Abdul Wali Khan University Mardan, Pakistan.

Muhammad Taha (M)

Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 31441, Dammam, Saudi Arabia.

Shahnaz Perveen (S)

PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr. Salimuzzaman Siddiqui, Karachi 75280, Pakistan.

Huma Khan (H)

Department of Biochemistry, Computational Medicinal Chemistry Laboratory, UCSS, Abdul Wali Khan University Mardan, Pakistan.

Joanna Lecka (J)

Département de Microbiologie-infectiologie et d'immunologie, Faculté de Médecine, Université Laval, Québec, QC G1V 0A6, Canada; Centre de Recherche du CHU de Québec-Université Laval, Québec, QC G1V 4G2, Canada.

Jean Sévigny (J)

Département de Microbiologie-infectiologie et d'immunologie, Faculté de Médecine, Université Laval, Québec, QC G1V 0A6, Canada; Centre de Recherche du CHU de Québec-Université Laval, Québec, QC G1V 4G2, Canada.

Jamshed Iqbal (J)

Centre for Advanced Drug Research (CADR), Department of Pharmacy COMSATS Institute of Information Technology, Abbottabad, Pakistan. Electronic address: drjamshed@ciit.net.pk.

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Classifications MeSH