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Volume 21, Issue 16
  • ISSN: 1570-1808
  • E-ISSN: 1875-628X

Abstract

Background

Mcl-1 is a kind of antiapoptotic protein and its overexpression is closely related to the occurrence of cancer. Aryl sulfonamide derivatives are expected to become new anticancer agents due to their high inhibitory activity on the Mcl-1 protein.

Objective

The study aimed to establish the QSAR model with good prediction ability and elaborate the influence of structure and chirality on the inhibitory activity.

Methods

Multiple QSAR models were built with different types of descriptors and modeling methods. The molecular docking was performed on compounds , , , , and . The MCCV method was used to perform rigorous validations with up to 216 = 65,536 samplings for MLR, SVM, LSSVM, RF, and GP methods based on the model of 2D and 3D combined descriptors.

Results

The models based on 2D and 3D combined descriptors demonstrated non-linear LSSVM and GP methods to provide better results (2>0.94, > 0.86). The predictive performances of MCCV tests have been basically coincident with the single test set’s results. The hydrogen bond acceptor at the appropriate position of the substituent on the chiral center could form the hydrogen bond interaction with residue ASN260, resulting in stronger interaction and higher inhibitory activity. The interaction differences between and configurations could be mainly attributed to two residues, HIS224 and ASN260. Furthermore, the steric effect of the substituent on chiral carbon atoms was crucial. A high steric effect could prevent the binding of the substituent and protein, resulting in low inhibitory activity.

Conclusion

The study may provide theoretical guidance on the design and synthesis of novel aryl sulfonamide derivatives with high inhibitory activity.

© 2024 Bentham Science Publishers
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QSAR Analysis and Molecular Docking Studies of Aryl Sulfonamide Derivatives as Mcl-1 Inhibitors and the Influence of Structure and Chirality on the Inhibitory Activity
Letters in Drug Design & Discovery 21, 3465 (2024); https://doi.org/10.2174/0115701808278918240109053316
/content/journals/lddd/10.2174/0115701808278918240109053316
/content/journals/lddd/10.2174/0115701808278918240109053316
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  • Article Type:     Research Article
Keyword(s): aryl sulfonamide; chirality; molecular docking; Monte Carlo cross-validation; Myeloid cell leukemia-1; quantitative structure-activity relationship

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