97
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Synthesis of novel (R)-carvone-tagged thiazolidinone as anticancer leads: characterization, in vitro antiproliferative evaluation and in silico studies

, ORCID Icon, ORCID Icon, ORCID Icon &
Received 04 Jan 2024, Accepted 11 Mar 2024, Published online: 25 Mar 2024

References

  • Abdellatif, K. R. A., Abdelgawad, M. A., Elshemy, H. A. H., & Alsayed, S. S. R. (2016). Design, synthesis and biological screening of new 4-thiazolidinone derivatives with promising COX-2 selectivity, anti-inflammatory activity and gastric safety profile. Bioorganic Chemistry, 64, 1–12. https://doi.org/10.1016/j.bioorg.2015.11.001
  • Adachi, T., Brazard, J., Ono, R. J., Hanson, B., Traub, M. C., Wu, Z.-Q., Li, Z., Bolinger, J. C., Ganesan, V., Bielawski, C. W., Vanden Bout, D. A., & Barbara, P. F. (2011). Regioregularity and single polythiophene chain conformation. The Journal of Physical Chemistry Letters, 2(12), 1400–1404. https://doi.org/10.1021/jz200546x
  • Ahmed, M. O. (2001). Comparison of impact of the different hydrophilic carriers on the properties of piperazine-containing drug. European Journal of Pharmaceutics and Biopharmaceutics: Official Journal of Arbeitsgemeinschaft Fur Pharmazeutische Verfahrenstechnik e.V, 51(3), 221–225. https://doi.org/10.1016/s0939-6411(01)00128-x
  • Bakkali, F., Averbeck, S., Averbeck, D., & Idaomar, M. (2008). Biological effects of essential oils–a review. Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association, 46(2), 446–475. https://doi.org/10.1016/j.fct.2007.09.106
  • Darden, T., York, D., & Pedersen, L. (1993). Particle mesh Ewald: An N⋅ log (N) method for Ewald sums in large systems. The Journal of Chemical Physics, 98(12), 10089–10092. https://doi.org/10.1063/1.464397
  • Dey, S., Singh, A. K., & Kumar, S. (2022). Discovery of natural anti-apoptotic protein inhibitor using molecular docking and MM-GBSA Approach: An anticancer intervention.
  • Filippakopoulos, P., Picaud, S., Mangos, M., Keates, T., Lambert, J.-P., Barsyte-Lovejoy, D., Felletar, I., Volkmer, R., Müller, S., Pawson, T., Gingras, A.-C., Arrowsmith, C. H., & Knapp, S. (2012). Histone recognition and large-scale structural analysis of the human bromodomain family. Cell, 149(1), 214–231. https://doi.org/10.1016/j.cell.2012.02.013
  • Gomha, S. M., Riyadh, S. M., Huwaimel, B., Zayed, M. E. M., & Abdellattif, M. H. (2022). Synthesis, molecular docking study, and cytotoxic activity against MCF cells of new thiazole–thiophene scaffolds. Molecules (Basel, Switzerland), 27(14), 4639. https://doi.org/10.3390/molecules27144639
  • Gopinath, P., & Kathiravan, M. K. (2021). Docking studies and molecular dynamics simulation of triazole benzene sulfonamide derivatives with human carbonic anhydrase IX inhibition activity. RSC Advances, 11(60), 38079–38093. https://doi.org/10.1039/d1ra07377j
  • Harder, E., Damm, W., Maple, J., Wu, C., Reboul, M., Xiang, J. Y., Wang, L., Lupyan, D., Dahlgren, M. K., Knight, J. L., Kaus, J. W., Cerutti, D. S., Krilov, G., Jorgensen, W. L., Abel, R., & Friesner, R. A. (2016). OPLS3: A force field providing broad coverage of drug-like small molecules and proteins. Journal of Chemical Theory and Computation, 12(1), 281–296. https://doi.org/10.1021/acs.jctc.5b00864
  • Holohan, C., Van Schaeybroeck, S., Longley, D. B., & Johnston, P. G. (2013). Cancer drug resistance: An evolving paradigm. Nature Reviews Cancer, 13(10), 714–726. https://doi.org/10.1038/nrc3599
  • Kim, S., Chen, J., Cheng, T., Gindulyte, A., He, J., He, S., Li, Q., Shoemaker, B. A., Thiessen, P. A., Yu, B., Zaslavsky, L., Zhang, J., & Bolton, E. E. (2021). PubChem in 2021: New data content and improved web interfaces. Nucleic Acids Research, 49(D1), D1388–D1395. https://doi.org/10.1093/nar/gkaa971
  • Kordali, S., Kotan, R., Mavi, A., Cakir, A., Ala, A., & Yildirim, A. (2005). Determination of the chemical composition and antioxidant activity of the essential oil of Artemisia dracunculus and of the antifungal and antibacterial activities of Turkish Artemisia absinthium, A. dracunculus, Artemisia santonicum, and Artemisia spicig. Journal of Agricultural and Food Chemistry, 53(24), 9452–9458. https://doi.org/10.1021/jf0516538
  • Kozioł, A., Stryjewska, A., Librowski, T., Sałat, K., Gaweł, M., Moniczewski, A., & Lochyński, S. (2014). An overview of the pharmacological properties and potential applications of natural monoterpenes. Mini Reviews in Medicinal Chemistry, 14(14), 1156–1168. https://doi.org/10.2174/1389557514666141127145820
  • Mahmoud, H. K., Sayed, A. R., Abdel-Aziz, M. M., & Gomha, S. M. (2022). Synthesis of new thiazole clubbed imidazo [2, 1-b] thiazole hybrid as antimycobacterial agents. Medicinal Chemistry (Shariqah (United Arab Emirates)), 18(10), 1100–1108. https://doi.org/10.2174/1573406418666220413095854
  • Marcon, V., & Raos, G. (2006). Free energies of molecular crystal surfaces by computer simulation: Application to tetrathiophene. Journal of the American Chemical Society, 128(5), 1408–1409. https://doi.org/10.1021/ja056548t
  • Martino, D., Sessa, M., Storino, R., Giuliano, M. R., Trombetti, M., Catapano, S., Bianco, R., Lo, A., Izzo, P., & Grosso, M. (2020). Transcriptional repressors of fetal globin genes as novel therapeutic targets in Beta-thalassemia. Beta Thalassemia, 1–9.
  • Moreno, M., Casalegno, M., Raos, G., Meille, S. V., & Po, R. (2010). Molecular modeling of crystalline alkylthiophene oligomers and polymers. The Journal of Physical Chemistry. B, 114(4), 1591–1602. https://doi.org/10.1021/jp9106124
  • Norberg, J., & Nilsson, L. (2000). On the truncation of long-range electrostatic interactions in DNA. Biophysical Journal, 79(3), 1537–1553. https://doi.org/10.1016/S0006-3495(00)76405-8
  • Oubella, A., Bimoussa, A., N'ait Oussidi, A., Fawzi, M., Auhmani, A., Morjani, H., Riahi, A., Esseffar, M., Parish, C., & Ait Itto, M. Y. (2022). New 1, 2, 3-triazoles from (R)-carvone: Synthesis, DFT mechanistic study and in vitro cytotoxic evaluation. Molecules (Basel, Switzerland), 27(3), 769. https://doi.org/10.3390/molecules27030769
  • Oubella, A., Byadi, S., Bimoussa, A., Fawzi, M., Auhmani, A., Podlipnik, C., Morjani, H., Riahi, A., Robert, A., & Itto, M. Y. A. (2022). Novel isoxazoline‐linked 1, 3, 4‐thiadiazole hybrids as anticancer agents: Design, synthesis, biological evaluation, molecular docking, and molecular dynamics simulation. Archiv Der Pharmazie, 355(9), e2200066. https://doi.org/10.1002/ardp.202200066
  • Oubella, A., El Mansouri, A.-E., Fawzi, M., Bimoussa, A., Laamari, Y., Auhmani, A., Morjani, H., Robert, A., Riahi, A., & Itto, M. Y. A. (2021). Thiazolidinone-linked1, 2, 3-triazoles with monoterpenic skeleton as new potential anticancer agents: Design, synthesis and molecular docking studies. Bioorganic Chemistry, 115, 105184. https://doi.org/10.1016/j.bioorg.2021.105184
  • Oubella, A., Laamari, Y., Hachim, M. E., Byadi, S., Auhmani, A., Morjani, H., Riahi, A., Podlipnik, C., Rohand, T., Van Meervelt, L., & Ait Itto, M. Y. (2022). New gem‑dichlorocyclopropane-pyrazole hybrids with monoterpenic skeleton: Synthesis, crystal structure, cytotoxic evaluation, molecular dynamics and theoretical study. Journal of Molecular Structure, 1256, 132573. https://doi.org/10.1016/j.molstruc.2022.132573
  • Prajapati, K. S., Singh, A. K., Kushwaha, P. P., Shuaib, M., Maurya, S. K., Gupta, S., Senapati, S., Singh, S. P., Waseem, M., & Kumar, S. (2023). Withania somnifera phytochemicals possess SARS-CoV-2 RdRp and human TMPRSS2 protein binding potential. Vegetos (Bareilly, India), 36(2), 701–720. https://doi.org/10.1007/s42535-022-00404-4
  • Rana, N., Singh, A. K., Shuaib, M., Gupta, S., Habiballah, M. M., Alkhanani, M. F., Haque, S., Reshi, M. S., & Kumar, S. (2022). Drug resistance mechanism of m46i-mutation-induced saquinavir resistance in HIV-1 protease using molecular dynamics simulation and binding energy calculation. Viruses, 14(4), 697. https://doi.org/10.3390/v14040697
  • Rashid, M., Shrivastava, N., & Husain, A. (2020). Synthesis and sar strategy of thiazolidinedione: A novel approach for cancer treatment. Journal of the Chilean Chemical Society, 65(2), 4817–4832. https://doi.org/10.4067/S0717-97072020000204817
  • Samadhiya, P., Sharma, R., Srivastava, S. K., & Srivastava, S. D. (2014). Synthesis and biological evaluation of 4-thiazolidinone derivatives as antitubercular and antimicrobial agents. Arabian Journal of Chemistry, 7(5), 657–665. https://doi.org/10.1016/j.arabjc.2010.11.015
  • Seca, A. M. L., & Pinto, D. C. G. A. (2018). Plant secondary metabolites as anticancer agents: Successes in clinical trials and therapeutic application. International Journal of Molecular Sciences, 19(1), 263. https://doi.org/10.3390/ijms19010263
  • Selvarasu, S., Srinivasan, P., Mannathusamy, G., & Susai, B. M. (2021). Synthesis, characterization, in silico molecular modeling, anti-diabetic and antimicrobial screening of novel 1-aryl-N-tosyl-1H-tetrazole-5-carboxamide derivatives. Chemical Data Collections, 32, 100648. https://doi.org/10.1016/j.cdc.2021.100648
  • Shamloo, B., & Usluer, S. (2019). p21 in cancer research. Cancers, 11(8), 1178. https://doi.org/10.3390/cancers11081178
  • Siegel, R. L., Miller, K. D., & Jemal, A. (2019). Cancer statistics, 2019. CA: A Cancer Journal for Clinicians, 69(1), 7–34. https://doi.org/10.3322/caac.21551
  • Singh, A. K., Maurya, S., & Kumar, S. (2023). Repurposing FDA-approved anti-diabetic drug to target H. pylori peptidyl deformylase using computer-based drug discovery approach. Molecular Simulation, 49(1), 124–132. https://doi.org/10.1080/08927022.2022.2130377
  • Singh, A. K., Shuaib, M., Prajapati, K. S., & Kumar, S. (2022). Rutin potentially binds the gamma secretase catalytic site, down regulates the notch signaling pathway and reduces sphere formation in colonospheres. Metabolites, 12(10), 926. https://doi.org/10.3390/metabo12100926
  • Waring, M. J., Arrowsmith, J., Leach, A. R., Leeson, P. D., Mandrell, S., Owen, R. M., Pairaudeau, G., Pennie, W. D., Pickett, S. D., Wang, J., Wallace, O., & Weir, A. (2015). A comprehensive analysis of development attrition in drug candidates from four major pharmaceutical companies. Nature Reviews. Drug Discovery, 14(7), 475–486. https://doi.org/10.1038/nrd4609
  • Wang, H., Song, P., Gao, Y., Shen, L., Xu, H., Wang, J., & Cheng, M. (2021). Drug discovery targeting p21-activated kinase 4 (PAK4): A patent review. Expert Opinion on Therapeutic Patents, 31(11), 977–987. https://doi.org/10.1080/13543776.2021.1944100
  • Xu, J., Dong, X., Huang, D. C., Xu, P., Zhao, Q., & Chen, B. (2023). Current advances and future strategies for BCL-2 inhibitors: Potent weapons against cancers. Cancers, 15(20), 4957. https://doi.org/10.3390/cancers15204957

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.