Anti-lung Cancer Activity of Synthesized Substituted 1,4-Benzothiazines: An Insight from Molecular Docking and Experimental Studies

  • Authors: Amin A.1, Zubaid-Ul-Khazir 2, Ji A.3, Bhat B.4, Murtaza D.5, Hurrah A.6, Bhat I.7, Parveen S.8, Nisar S.9, Sharma P.K.10
  • Affiliations:
    1. Department of Chemistry, School of Chemical Engineering and Physical Sciences,, Lovely Professional University
    2. Transcriptomics Laboratory, Division of Plant Biotechnology, Sher-e-Kashmir University of Agricultural Sciences and Technology
    3. Transcriptomics Laboratory, Division of Plant Biotechnology, Sher-e-Kashmir University of Agricultural Sciences and Technology,
    4. Department of Bioresources, School of Biological Sciences,, University of Kashmir
    5. Transcriptomics Laboratory, Division of Plant Biotechnology,, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir
    6. Transcriptomics Laboratory, Division of Plant Biotechnology, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir
    7. Department of Endocrinology,, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir
    8. Department of Gastroenterology, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir
    9. Department of Medical Oncology, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir
    10. Department of Chemistry, School of Chemical Engineering and Physical Sciences, Lovely Professional University
  • Issue: Vol 24, No 5 (2024)
  • Pages: 358-371
  • Section: Oncology
  • URL: https://snv63.ru/1871-5206/article/view/644186
  • DOI: https://doi.org/10.2174/0118715206276737231103114924
  • ID: 644186

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Full Text

Abstract

Background:Thiazine, a 6-membered distinctive heterocyclic motif with sulfur and nitrogen atoms, is one of the heterocyclic compounds that functions as a core scaffold in a number of medicinally significant molecules. Small thiazine-based compounds may operate simultaneously on numerous therapeutic targets and by employing a variety of methods to halt the development, proliferation, and vasculature of cancer cells. We have, herein, reported a series of substituted 1,4 benzothiazines as potential anticancer agents for the treatment of lung cancer.

Methods:In order to synthesize 2,3-disubstituted-1,4 benzothiazines in good yield, a facile green approach for the oxidative cycloaddition of 2-amino benzenethiol and 1,3-dicarbonyls employing a catalytic amount of ceric ammonium nitrate has been devised. All the molecules have been characterized by spectral analysis and tested for anticancer activity against the A-549 lung cancer cell line using various functional assays. Further in silico screening of compound 3c against six crucial inflammatory molecular targets, such as Il1-α (PDB ID: 5UC6), Il1- β (PDB ID: 6Y8I), Il6 (PDB ID: 1P9M), vimentin (PDB ID: 3TRT), COX-2 (PDB ID: 5KIR), Il8 (PDB ID: 5D14), and TNF-α (PDB ID: 2AZ5), was done using AutoDock tool.

Results:Among the synthesized compounds, propyl 3-methyl-3,4-dihydro-2H-benzo[b][1,4]thiazine-2- carboxylate (3c) was found to be most active based on cell viability assays using A-549 lung cancer cell line and was found to effectively downregulate various pro-inflammatory genes, like Il1-α, Il1-β, Il6, vimentin, COX-2, Il8, and TNF-α in vitro. The ability of the molecule to effectively suppress the proliferation and migration of lung cancer cells in vitro has been further demonstrated by the colony formation unit assay and wound healing assay. Molecular docking analysis showed the maximal binding affinity (− 7.54 kcal/mol) to be exhibited by compound 3c against IL8.

Conclusion:A green unconventional route for the synthesis of 2,3-disubstituted-1,4 benzothiazines has been developed. All the molecules were screened for their activity against lung cancer and the data suggested that the presence of an additional unbranched alkyl group attached to the thiazine ring increased their activity. Also, in vitro and in silico modeling confirmed the anti-cancer efficiency of compound 3c, encouraging the exploration of such small molecules against cancer.

About the authors

Andleeb Amin

Department of Chemistry, School of Chemical Engineering and Physical Sciences,, Lovely Professional University

Email: info@benthamscience.net

Zubaid-Ul-Khazir

Transcriptomics Laboratory, Division of Plant Biotechnology, Sher-e-Kashmir University of Agricultural Sciences and Technology

Email: info@benthamscience.net

Arfa Ji

Transcriptomics Laboratory, Division of Plant Biotechnology, Sher-e-Kashmir University of Agricultural Sciences and Technology,

Email: info@benthamscience.net

Basharat Bhat

Department of Bioresources, School of Biological Sciences,, University of Kashmir

Email: info@benthamscience.net

Dar Murtaza

Transcriptomics Laboratory, Division of Plant Biotechnology,, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir

Email: info@benthamscience.net

Aaqib Hurrah

Transcriptomics Laboratory, Division of Plant Biotechnology, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir

Email: info@benthamscience.net

Imtiyaz Bhat

Department of Endocrinology,, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir

Email: info@benthamscience.net

Shaheena Parveen

Department of Gastroenterology, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir

Email: info@benthamscience.net

Syed Nisar

Department of Medical Oncology, Sher-e-Kashmir University of Agricultural Sciences and Technology of Kashmir

Email: info@benthamscience.net

Praveen Kumar Sharma

Department of Chemistry, School of Chemical Engineering and Physical Sciences, Lovely Professional University

Author for correspondence.
Email: info@benthamscience.net

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