Targeted synthesis via the structure-activity relationship: Biological evaluation of new 1,2,3-triazoles monoterpene as antitumor agents

Ezaddine Irrou; Younesse Ait Elmachkouri; Soukaina El Haddad; Yassine Riadi; Ali Oubella; Aziz Auhmani; Md Tabish Rehman; Mohamed F. AlAjmi; Hamid Morjani; Nada Kheira Sebbar; Moulay Youssef Ait Itto; Mohamed Labd Taha

doi:10.1016/j.molstruc.2024.138025

Targeted synthesis via the structure-activity relationship: Biological evaluation of new 1,2,3-triazoles monoterpene as antitumor agents

Ezaddine Irrou
, Younesse Ait Elmachkouri
, Soukaina El Haddad
, Yassine Riadi
, Ali Oubella
, Aziz Auhmani
, Md Tabish Rehman
, Mohamed F. AlAjmi
, Hamid Morjani
, Nada Kheira Sebbar
, Moulay Youssef Ait Itto
, Mohamed Labd Taha

Ibn Zohr University
Mohammed V University in Rabat
Prince Sattam Bin Abdulaziz University
Cadi Ayyad University
King Saud University
Université de Reims Champagne-Ardenne

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

A novel series of thiazolidinone based 1,2,3-triazole derivatives were designed, synthesized, and evaluated for their cytotoxic activity against four human cancer cell lines, including fibrosarcoma (HT-1080), lung carcinoma (A-549), and breast carcinoma (MCF-7 and MDA-MB-231). NMR (¹H and ¹³C) and HRMS established the newly synthesized compounds' structural identification and molecular weight. Most synthesized compounds displayed moderate cytotoxic activity, with IC₅₀ values from 20 to 40 μM. Furthermore, hybrid compounds 14b and 14d showed important inhibitory activity against HT-1080 and A-549 cancer cell lines with an IC₅₀ value of 18 μM. Molecular docking analyses also confirmed a higher binding affinity of compounds 14a-e, as compared to Doxorubicin (control), towards Bcl-2 protein. In particular, compounds 14b and 14d had higher affinity for Bcl-2 as compared to other compounds.

Original language	English
Article number	138025
Journal	Journal of Molecular Structure
Volume	1308
DOIs	https://doi.org/10.1016/j.molstruc.2024.138025
State	Published - 15 Jul 2024
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

(R)-Carvone
Click chemistry
Cytotoxic activity
HRMS characterization
Molecular docking
NMR

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10.1016/j.molstruc.2024.138025

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Irrou, E., Elmachkouri, Y. A., Haddad, S. E., Riadi, Y., Oubella, A., Auhmani, A., Rehman, M. T., AlAjmi, M. F., Morjani, H., Sebbar, N. K., Itto, M. Y. A., & Taha, M. L. (2024). Targeted synthesis via the structure-activity relationship: Biological evaluation of new 1,2,3-triazoles monoterpene as antitumor agents. Journal of Molecular Structure, 1308, Article 138025. https://doi.org/10.1016/j.molstruc.2024.138025

@article{a45eb72ab88f4f679638f0c3a152364f,

title = "Targeted synthesis via the structure-activity relationship: Biological evaluation of new 1,2,3-triazoles monoterpene as antitumor agents",

abstract = "A novel series of thiazolidinone based 1,2,3-triazole derivatives were designed, synthesized, and evaluated for their cytotoxic activity against four human cancer cell lines, including fibrosarcoma (HT-1080), lung carcinoma (A-549), and breast carcinoma (MCF-7 and MDA-MB-231). NMR (1H and 13C) and HRMS established the newly synthesized compounds' structural identification and molecular weight. Most synthesized compounds displayed moderate cytotoxic activity, with IC50 values from 20 to 40 μM. Furthermore, hybrid compounds 14b and 14d showed important inhibitory activity against HT-1080 and A-549 cancer cell lines with an IC50 value of 18 μM. Molecular docking analyses also confirmed a higher binding affinity of compounds 14a-e, as compared to Doxorubicin (control), towards Bcl-2 protein. In particular, compounds 14b and 14d had higher affinity for Bcl-2 as compared to other compounds.",

keywords = "(R)-Carvone, Click chemistry, Cytotoxic activity, HRMS characterization, Molecular docking, NMR",

author = "Ezaddine Irrou and Elmachkouri, \{Younesse Ait\} and Haddad, \{Soukaina El\} and Yassine Riadi and Ali Oubella and Aziz Auhmani and Rehman, \{Md Tabish\} and AlAjmi, \{Mohamed F.\} and Hamid Morjani and Sebbar, \{Nada Kheira\} and Itto, \{Moulay Youssef Ait\} and Taha, \{Mohamed Labd\}",

note = "Publisher Copyright: {\textcopyright} 2024 Elsevier B.V.",

year = "2024",

month = jul,

day = "15",

doi = "10.1016/j.molstruc.2024.138025",

language = "English",

volume = "1308",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier B.V.",

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Irrou, E, Elmachkouri, YA, Haddad, SE, Riadi, Y, Oubella, A, Auhmani, A, Rehman, MT, AlAjmi, MF, Morjani, H, Sebbar, NK, Itto, MYA & Taha, ML 2024, 'Targeted synthesis via the structure-activity relationship: Biological evaluation of new 1,2,3-triazoles monoterpene as antitumor agents', Journal of Molecular Structure, vol. 1308, 138025. https://doi.org/10.1016/j.molstruc.2024.138025

TY - JOUR

T1 - Targeted synthesis via the structure-activity relationship

T2 - Biological evaluation of new 1,2,3-triazoles monoterpene as antitumor agents

AU - Irrou, Ezaddine

AU - Elmachkouri, Younesse Ait

AU - Haddad, Soukaina El

AU - Riadi, Yassine

AU - Oubella, Ali

AU - Auhmani, Aziz

AU - Rehman, Md Tabish

AU - AlAjmi, Mohamed F.

AU - Morjani, Hamid

AU - Sebbar, Nada Kheira

AU - Itto, Moulay Youssef Ait

AU - Taha, Mohamed Labd

PY - 2024/7/15

Y1 - 2024/7/15

N2 - A novel series of thiazolidinone based 1,2,3-triazole derivatives were designed, synthesized, and evaluated for their cytotoxic activity against four human cancer cell lines, including fibrosarcoma (HT-1080), lung carcinoma (A-549), and breast carcinoma (MCF-7 and MDA-MB-231). NMR (1H and 13C) and HRMS established the newly synthesized compounds' structural identification and molecular weight. Most synthesized compounds displayed moderate cytotoxic activity, with IC50 values from 20 to 40 μM. Furthermore, hybrid compounds 14b and 14d showed important inhibitory activity against HT-1080 and A-549 cancer cell lines with an IC50 value of 18 μM. Molecular docking analyses also confirmed a higher binding affinity of compounds 14a-e, as compared to Doxorubicin (control), towards Bcl-2 protein. In particular, compounds 14b and 14d had higher affinity for Bcl-2 as compared to other compounds.

AB - A novel series of thiazolidinone based 1,2,3-triazole derivatives were designed, synthesized, and evaluated for their cytotoxic activity against four human cancer cell lines, including fibrosarcoma (HT-1080), lung carcinoma (A-549), and breast carcinoma (MCF-7 and MDA-MB-231). NMR (1H and 13C) and HRMS established the newly synthesized compounds' structural identification and molecular weight. Most synthesized compounds displayed moderate cytotoxic activity, with IC50 values from 20 to 40 μM. Furthermore, hybrid compounds 14b and 14d showed important inhibitory activity against HT-1080 and A-549 cancer cell lines with an IC50 value of 18 μM. Molecular docking analyses also confirmed a higher binding affinity of compounds 14a-e, as compared to Doxorubicin (control), towards Bcl-2 protein. In particular, compounds 14b and 14d had higher affinity for Bcl-2 as compared to other compounds.

KW - (R)-Carvone

KW - Click chemistry

KW - Cytotoxic activity

KW - HRMS characterization

KW - Molecular docking

KW - NMR

UR - https://www.scopus.com/pages/publications/85188992161

U2 - 10.1016/j.molstruc.2024.138025

DO - 10.1016/j.molstruc.2024.138025

M3 - Article

AN - SCOPUS:85188992161

SN - 0022-2860

VL - 1308

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

M1 - 138025

ER -

Targeted synthesis via the structure-activity relationship: Biological evaluation of new 1,2,3-triazoles monoterpene as antitumor agents

Abstract

UN SDGs

Keywords

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