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Targeting cancer with novel tetra-1,2,3-triazole hybrids: Synthesis, biological evaluation, and molecular dynamics.

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Title: Targeting cancer with novel tetra-1,2,3-triazole hybrids: Synthesis, biological evaluation, and molecular dynamics.
Authors: El Malah, Tamer1 (AUTHOR) tmara_nrc3000@yahoo.com, El-Rashedy, Ahmed A.2 (AUTHOR)
Source: Journal of Molecular Structure. Feb2025:Part 5, Vol. 1321, pN.PAG-N.PAG. 1p.
Subjects: Click chemistry, Molecular dynamics, Chemical synthesis, Antineoplastic agents, Colorectal cancer
Abstract: • A series of novel tetra-1,2,3-triazole hybrids were synthesized using a click chemistry approach. • Analysis of the synthesized products was conducted utilizing NMR (1H and 13C), mass spectrometry, and elemental analysis. • The cytotoxicity and in vitro anticancer activities of the newly synthesized compounds were investigated against a selection of human cancer cell lines, specifically HCT116, HePG2, and MCF-7. • Compounds 10, 14 , and 9 demonstrated the most potent inhibitory effects on colon, liver, and breast cancer cells • Validation of the anticancer activity findings was achieved using molecular dynamic simulation. This study involved the synthesis of a new category of tetra-1,2,3-triazole derivatives of types (I), (II), (III), and (IV) 7 – 14 using a Cu(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) procedure, also known as the Click reaction. The reaction between terminal alkynes ethynylbenzene 5 and 2-ethynylpyrazine 6 with substituted aryl azides 1 – 4 yielded the corresponding 1,2,3-triazole-hybrids 7 – 14. The synthesized products were analyzed using NMR (1H and 13C), mass spectrometry, and elemental analysis. The anticancer activities of the synthesized compounds were assessed in vitro against three cancer cell lines: colorectal carcinoma (HCT-116), hepatoblastoma (HePG-2), breast adenocarcinoma (MCF-7), and a normal human cell line (WI-38) through the MTT assay. Notably, compounds 10, 14 , and 9 demonstrated the most potent inhibitory effects on colon, liver, and breast cancer cells, respectively, while maintaining low toxicity towards normal cells compared to doxorubicin. Moreover, the molecular dynamics simulations revealed that compound 10 demonstrated significant interactions with essential residues of the binding site, resulting in a stable complex throughout the entire simulation run. As a result of these findings, it can be concluded that these tetra-1,2,3-Triazole hybrids may prove to be promising candidates for development as novel anticancer agents. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
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  Data: Targeting cancer with novel tetra-1,2,3-triazole hybrids: Synthesis, biological evaluation, and molecular dynamics.
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  Data: <searchLink fieldCode="AR" term="%22El+Malah%2C+Tamer%22">El Malah, Tamer</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> tmara_nrc3000@yahoo.com</i><br /><searchLink fieldCode="AR" term="%22El-Rashedy%2C+Ahmed+A%2E%22">El-Rashedy, Ahmed A.</searchLink><relatesTo>2</relatesTo> (AUTHOR)
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Structure%22">Journal of Molecular Structure</searchLink>. Feb2025:Part 5, Vol. 1321, pN.PAG-N.PAG. 1p.
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  Data: <searchLink fieldCode="DE" term="%22Click+chemistry%22">Click chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+dynamics%22">Molecular dynamics</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+synthesis%22">Chemical synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Antineoplastic+agents%22">Antineoplastic agents</searchLink><br /><searchLink fieldCode="DE" term="%22Colorectal+cancer%22">Colorectal cancer</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: • A series of novel tetra-1,2,3-triazole hybrids were synthesized using a click chemistry approach. • Analysis of the synthesized products was conducted utilizing NMR (1H and 13C), mass spectrometry, and elemental analysis. • The cytotoxicity and in vitro anticancer activities of the newly synthesized compounds were investigated against a selection of human cancer cell lines, specifically HCT116, HePG2, and MCF-7. • Compounds 10, 14 , and 9 demonstrated the most potent inhibitory effects on colon, liver, and breast cancer cells • Validation of the anticancer activity findings was achieved using molecular dynamic simulation. This study involved the synthesis of a new category of tetra-1,2,3-triazole derivatives of types (I), (II), (III), and (IV) 7 – 14 using a Cu(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) procedure, also known as the Click reaction. The reaction between terminal alkynes ethynylbenzene 5 and 2-ethynylpyrazine 6 with substituted aryl azides 1 – 4 yielded the corresponding 1,2,3-triazole-hybrids 7 – 14. The synthesized products were analyzed using NMR (1H and 13C), mass spectrometry, and elemental analysis. The anticancer activities of the synthesized compounds were assessed in vitro against three cancer cell lines: colorectal carcinoma (HCT-116), hepatoblastoma (HePG-2), breast adenocarcinoma (MCF-7), and a normal human cell line (WI-38) through the MTT assay. Notably, compounds 10, 14 , and 9 demonstrated the most potent inhibitory effects on colon, liver, and breast cancer cells, respectively, while maintaining low toxicity towards normal cells compared to doxorubicin. Moreover, the molecular dynamics simulations revealed that compound 10 demonstrated significant interactions with essential residues of the binding site, resulting in a stable complex throughout the entire simulation run. As a result of these findings, it can be concluded that these tetra-1,2,3-Triazole hybrids may prove to be promising candidates for development as novel anticancer agents. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
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  Data: <i>Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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      – Type: doi
        Value: 10.1016/j.molstruc.2024.140245
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      – Code: eng
        Text: English
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        PageCount: 1
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      – SubjectFull: Click chemistry
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      – SubjectFull: Molecular dynamics
        Type: general
      – SubjectFull: Chemical synthesis
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      – SubjectFull: Antineoplastic agents
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      – SubjectFull: Colorectal cancer
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              Text: Feb2025:Part 5
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              Y: 2025
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