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Green Synthesis, Experimental and Theoretical Studies to Discover Novel Binders of Exosomal Tetraspanin CD81 Protein

[Image: see text] A new class of benzothiazole-appended quinoline derivatives (6–8) was synthesized via one-pot TPGS micellar-mediated acid-catalyzed nucleophilic addition, followed by aerobic oxidative cyclization of 3-formylquinoline-2-one (2), 3-formylquinoline-2-thione (3), and 2-azidoquinoline-...

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Autores principales: Anand, Krishnan, Khan, Faez I., Singh, Thishana, Elumalai, Palani, Balakumar, Chandrasekaran, Premnath, Dhanaraj, Lai, Dakun, Chuturgoon, Anil A., Saravanan, Muthupandian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7391369/
https://www.ncbi.nlm.nih.gov/pubmed/32743170
http://dx.doi.org/10.1021/acsomega.0c01166
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author Anand, Krishnan
Khan, Faez I.
Singh, Thishana
Elumalai, Palani
Balakumar, Chandrasekaran
Premnath, Dhanaraj
Lai, Dakun
Chuturgoon, Anil A.
Saravanan, Muthupandian
author_facet Anand, Krishnan
Khan, Faez I.
Singh, Thishana
Elumalai, Palani
Balakumar, Chandrasekaran
Premnath, Dhanaraj
Lai, Dakun
Chuturgoon, Anil A.
Saravanan, Muthupandian
author_sort Anand, Krishnan
collection PubMed
description [Image: see text] A new class of benzothiazole-appended quinoline derivatives (6–8) was synthesized via one-pot TPGS micellar-mediated acid-catalyzed nucleophilic addition, followed by aerobic oxidative cyclization of 3-formylquinoline-2-one (2), 3-formylquinoline-2-thione (3), and 2-azidoquinoline-3-carbaldehyde (4) individually with 2-amino thiophenol (5). The structures of the prepared compounds were confirmed using suitable spectroscopic methods complemented with single-crystal X-ray diffraction analysis. Time-dependent density functional theory-based optimization of molecular structures, bond lengths, bond angles, HOMO–LUMO energy gaps, and molecular electrostatic potential maps was theoretically computed at the B3LYP/6-311++g(d) level. The molecular docking studies recommended that 6–8 bound to the active site cavity of CD81 effectively with the binding energies of −6.9, −6.3, and −6.5 kcal mol(–1), respectively. Further, MD simulation studies of compound 6 suggested that the binding resulted in the stabilization of the CD81 molecule. Thus, all theoretical predictions associated with the experimental verifications motivated to discover novel approaches for cancer therapy.
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spelling pubmed-73913692020-07-31 Green Synthesis, Experimental and Theoretical Studies to Discover Novel Binders of Exosomal Tetraspanin CD81 Protein Anand, Krishnan Khan, Faez I. Singh, Thishana Elumalai, Palani Balakumar, Chandrasekaran Premnath, Dhanaraj Lai, Dakun Chuturgoon, Anil A. Saravanan, Muthupandian ACS Omega [Image: see text] A new class of benzothiazole-appended quinoline derivatives (6–8) was synthesized via one-pot TPGS micellar-mediated acid-catalyzed nucleophilic addition, followed by aerobic oxidative cyclization of 3-formylquinoline-2-one (2), 3-formylquinoline-2-thione (3), and 2-azidoquinoline-3-carbaldehyde (4) individually with 2-amino thiophenol (5). The structures of the prepared compounds were confirmed using suitable spectroscopic methods complemented with single-crystal X-ray diffraction analysis. Time-dependent density functional theory-based optimization of molecular structures, bond lengths, bond angles, HOMO–LUMO energy gaps, and molecular electrostatic potential maps was theoretically computed at the B3LYP/6-311++g(d) level. The molecular docking studies recommended that 6–8 bound to the active site cavity of CD81 effectively with the binding energies of −6.9, −6.3, and −6.5 kcal mol(–1), respectively. Further, MD simulation studies of compound 6 suggested that the binding resulted in the stabilization of the CD81 molecule. Thus, all theoretical predictions associated with the experimental verifications motivated to discover novel approaches for cancer therapy. American Chemical Society 2020-07-16 /pmc/articles/PMC7391369/ /pubmed/32743170 http://dx.doi.org/10.1021/acsomega.0c01166 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Anand, Krishnan
Khan, Faez I.
Singh, Thishana
Elumalai, Palani
Balakumar, Chandrasekaran
Premnath, Dhanaraj
Lai, Dakun
Chuturgoon, Anil A.
Saravanan, Muthupandian
Green Synthesis, Experimental and Theoretical Studies to Discover Novel Binders of Exosomal Tetraspanin CD81 Protein
title Green Synthesis, Experimental and Theoretical Studies to Discover Novel Binders of Exosomal Tetraspanin CD81 Protein
title_full Green Synthesis, Experimental and Theoretical Studies to Discover Novel Binders of Exosomal Tetraspanin CD81 Protein
title_fullStr Green Synthesis, Experimental and Theoretical Studies to Discover Novel Binders of Exosomal Tetraspanin CD81 Protein
title_full_unstemmed Green Synthesis, Experimental and Theoretical Studies to Discover Novel Binders of Exosomal Tetraspanin CD81 Protein
title_short Green Synthesis, Experimental and Theoretical Studies to Discover Novel Binders of Exosomal Tetraspanin CD81 Protein
title_sort green synthesis, experimental and theoretical studies to discover novel binders of exosomal tetraspanin cd81 protein
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7391369/
https://www.ncbi.nlm.nih.gov/pubmed/32743170
http://dx.doi.org/10.1021/acsomega.0c01166
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