Cargando…
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-...
Autores principales: | , , , , , , , , |
---|---|
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 |
_version_ | 1783564622900494336 |
---|---|
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. |
format | Online Article Text |
id | pubmed-7391369 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT anandkrishnan greensynthesisexperimentalandtheoreticalstudiestodiscovernovelbindersofexosomaltetraspanincd81protein AT khanfaezi greensynthesisexperimentalandtheoreticalstudiestodiscovernovelbindersofexosomaltetraspanincd81protein AT singhthishana greensynthesisexperimentalandtheoreticalstudiestodiscovernovelbindersofexosomaltetraspanincd81protein AT elumalaipalani greensynthesisexperimentalandtheoreticalstudiestodiscovernovelbindersofexosomaltetraspanincd81protein AT balakumarchandrasekaran greensynthesisexperimentalandtheoreticalstudiestodiscovernovelbindersofexosomaltetraspanincd81protein AT premnathdhanaraj greensynthesisexperimentalandtheoreticalstudiestodiscovernovelbindersofexosomaltetraspanincd81protein AT laidakun greensynthesisexperimentalandtheoreticalstudiestodiscovernovelbindersofexosomaltetraspanincd81protein AT chuturgoonanila greensynthesisexperimentalandtheoreticalstudiestodiscovernovelbindersofexosomaltetraspanincd81protein AT saravananmuthupandian greensynthesisexperimentalandtheoreticalstudiestodiscovernovelbindersofexosomaltetraspanincd81protein |