Design, synthesis and docking studies of novel 4-aminophenol-1,2,4-oxadiazole hybrids as apoptosis inducers against triple negative breast cancer cells targeting MAP kinase

References

• Aamir, M., Singh, V. K., Dubey, M. K., Meena, M., Kashyap, S. P., Katari, S. K., Upadhyay, R. S., Umamaheswari, A., & Singh, S. (2018). In silico prediction, characterization, molecular docking, and dynamic studies on fungal SDRs as novel targets for searching potential fungicides against Fusarium Wilt in tomato. Frontiers in Pharmacology, 9, 1038–1038. https://doi.org/10.3389/fphar.2018.01038
   PubMed Web of Science ®Google Scholar
• Abou-Issa, H., Webb, T. E., Minton, J. P., & Moeschberger, M. (1989). Chemotherapeutic evaluation of glucarate and N-(4-hydroxyphenyl)retinamide alone and in combination in the rat mammary tumor model. Journal of the National Cancer Institute, 81(23), 1820–1823. https://doi.org/10.1093/jnci/81.23.1820
   PubMedGoogle Scholar
• Assaran Darban, R., Shareghi, B., Asoodeh, A., & Chamani, J. (2017). Multi-spectroscopic and molecular modeling studies of interaction between two different angiotensin I converting enzyme inhibitory peptides from gluten hydrolysate and human serum albumin. Journal of Biomolecular Structure & Dynamics, 35(16), 3648–3662. https://doi.org/10.1080/07391102.2016.1264892
   PubMed Web of Science ®Google Scholar
• Basappa, V. C., Kameshwar, V. H., Kumara, K., Achutha, D. K., Krishnappagowda, L. N., & Kariyappa, A. K. J. H. (2020). Design and synthesis of coumarin-triazole hybrids: Biocompatible anti-diabetic agents, in silico molecular docking and ADME screening. Heliyon, 6(10), e05290. https://doi.org/10.1016/j.heliyon.2020.e05290
   PubMed Web of Science ®Google Scholar
• Beckwith, H., & Yee, D. (2014). Insulin-like growth factors, insulin, and growth hormone signaling in breast cancer: Implications for targeted therapy. Endocrine Practice, 20(11), 1214–1221. https://doi.org/10.4158/ep14208.ra
   PubMed Web of Science ®Google Scholar
• Bonneterre, J., Peyrat, J. P., Beuscart, R., Lefebvre, J., & Demaille, A. (1987). Prognostic significance of prolactin receptors (PRL-R) in human breast cancer. Journal of Steroid Biochemistry, 28, 19. https://doi.org/10.1016/0022-4731(87)91153-8
   Google Scholar
• Carbone, M., Li, Y., Irace, C., Mollo, E., Castelluccio, F., Di Pascale, A., Cimino, G., Santamaria, R., Guo, Y.-W., & Gavagnin, M. (2011). Structure and cytotoxicity of phidianidines A and B: First finding of 1,2,4-oxadiazole system in a marine natural product. Organic Letters, 13(10), 2516–2519. https://doi.org/10.1021/ol200234r
   PubMed Web of Science ®Google Scholar
• Chimirri, A., Grasso, S., Monforte, A. M., Rao, A., & Zappala, M. (2010). ChemInform abstract: Synthesis and antitumor activity evaluation of δ2-1,2,4- oxadiazoline derivatives. ChemInform, 27(30). https://doi.org/10.1002/chin.199630165
   Google Scholar
• Clitherow, J. W., Beswick, P., Irving, W. J., Scopes, D. I. C., Barnes, J. C., Clapham, J., Brown, J. D., Evans, D. J., & Hayes, A. G. (1996). Novel 1, 2, 4-oxadiazoles as potent and selective histamine H3 receptor antagonists. Bioorganic & Medicinal Chemistry Letters, 6(7), 833–838. https://doi.org/10.1016/0960-894x(96)00122-9
   Web of Science ®Google Scholar
• Dasari, S., & Bernard Tchounwou, P. (2014). Cisplatin in cancer therapy: Molecular mechanisms of action. European Journal of Pharmacology, 740, 364–378. https://doi.org/10.1016/j.ejphar.2014.07.025
   PubMed Web of Science ®Google Scholar
• Decensi, A., Bruno, S., Costantini, M., Torrisi, R., Curotto, A., Gatteschi, B., Nicolo, G., Polizzi, A., Perloff, M., Malone, W. F., & Bruzzi, P. (1994). Phase IIa study of fenretinide in superficial bladder cancer, using DNA flow cytometry as an intermediate end point. Journal of the National Cancer Institute, 86(2), 138–140. https://doi.org/10.1093/jnci/86.2.138
   PubMedGoogle Scholar
• Fernandes, F. S., Santos, H., Lima, S. R., Conti, C., Rodrigues, M. T., Zeoly, L. A., Ferreira, L. L. G., Krogh, R., Andricopulo, A. D., & Coelho, F. (2020). Discovery of highly potent and selective antiparasitic new oxadiazole and hydroxy-oxindole small molecule hybrids. European Journal of Medicinal Chemistry, 201, 112418. https://doi.org/10.1016/j.ejmech.2020.112418
   PubMed Web of Science ®Google Scholar
• Gao, X.-H., Liu, L.-B., Liu, H.-R., Tang, J.-J., Kang, L., Wu, H., Cui, P., & Yan, J. (2018). Structure-activity relationship investigation of benzamide and picolinamide derivatives containing dimethylamine side chain as acetylcholinesterase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 33(1), 110–114. https://doi.org/10.1080/14756366.2017.1399885
   PubMed Web of Science ®Google Scholar
• Girish, Y. R., Kumar, B. M. A., Kumar, K. S. S., Hamse, V. K., Prashantha, K., Sudhanva, M. S, & Shobith, R. (2022). Identification of novel benzimidazole-based small molecule targeting dual targets Tankyrase and Bcl2 to induce apoptosis in Colon cancer. Journal of Molecular Structure, 1269, 133813. https://doi.org/10.1016/j.molstruc.2022.133813
   Web of Science ®Google Scholar
• Kameshwar, V. H., Kumar, J. R., Priya, B. S., & Swamy, S. N. (2017). Synthesis, characterization and bioactivity studies of novel 1,3,4-oxadiazole small molecule that targets basic phospholipase A2 from Vipera russelli. Molecular and Cellular Biochemistry, 426(1–2), 161–175. https://doi.org/10.1007/s11010-016-2888-6
   PubMed Web of Science ®Google Scholar
• Kang, H.-S., Ahn, S. H., Mishra, S. K., Hong, K.-M., Lee, E. S., Shin, K. H., Ro, J., Lee, K. S., & Kim, M. K. (2014). Association of polymorphisms and haplotypes in the insulin-like growth factor 1 receptor (IGF1R) gene with the risk of breast cancer in Korean women. PLoS One, 9(1), e84532–e84532. https://doi.org/10.1371/journal.pone.0084532
   Web of Science ®Google Scholar
• Kumara, K., Prabhudeva, M. G., Vagish, C. B., Vivek, H. K., Lokanatha Rai, K. M., Lokanath, N. K., & Ajay Kumar, K. (2021). Design, synthesis, characterization, and antioxidant activity studies of novel thienyl-pyrazoles. Heliyon, 7(7), e07592–e07592. https://doi.org/10.1016/j.heliyon.2021.e07592
   Web of Science ®Google Scholar
• Lankau, H.-J., Unverferth, K., Grunwald, C., Hartenhauer, H., Heinecke, K., Bernöster, K., Dost, R., Egerland, U., & Rundfeldt, C. (2007). New GABA-modulating 1,2,4-oxadiazole derivatives and their anticonvulsant activity. European Journal of Medicinal Chemistry, 42(6), 873–879. https://doi.org/10.1016/j.ejmech.2006.12.022
   PubMed Web of Science ®Google Scholar
• Luthman, K., Borg, S., & Hacksell, U. (1999). Synthesis and use of pseudopeptides derived from 1,2,4-oxadiazole-, 1,3,4-oxadiazole-, and 1,2,4-triazole-based dipeptidomimetics. In W. M. Kazmierski (Ed.), Peptidomimetics protocols (pp. 1–23). Humana Press.
   Google Scholar
• Ly, J. D., Grubb, D. R., & Lawen, A. (2003). The mitochondrial membrane potential (deltapsi(m)) in apoptosis; an update. Apoptosis, 8(2), 115–128. https://doi.org/10.1023/a:1022945107762
   PubMed Web of Science ®Google Scholar
• Lyne, P. D., Lamb, M. L., & Saeh, J. C. (2006). Accurate prediction of the relative potencies of members of a series of kinase inhibitors using molecular docking and MM-GBSA scoring. Journal of Medicinal Chemistry, 49(16), 4805–4808. https://doi.org/10.1021/jm060522a
   PubMed Web of Science ®Google Scholar
• Malek-Esfandiari, Z., Rezvani-Noghani, A., Sohrabi, T., Mokaberi, P., Amiri-Tehranizadeh, Z., & Chamani, J. (2023). Molecular dynamics and multi-spectroscopic of the interaction behavior between bladder cancer cells and calf thymus DNA with rebeccamycin: Apoptosis through the down regulation of PI3K/AKT signaling pathway. Journal of Fluorescence, 33(4), 1537–1557. https://doi.org/10.1007/s10895-023-03169-4
   PubMed Web of Science ®Google Scholar
• Matsumoto, J., Takahashi, T., Agata, M., Toyofuku, H., & Sasada, N. (1994). A study of the biological pharmacology of IFO, a new selective and reversible monoamine oxidase-B inhibitor. Japanese Journal of Pharmacology, 65(1), 51–57. https://doi.org/10.1016/s0021-5198(19)35793-2
   PubMedGoogle Scholar
• Meyskens, F. L., Alberts, D. S., & Salmon, S. E. (1983). Effect of 13-cis-retinoic acid and 4-hydroxyphenyl-all-trans-retinamide on human tumor colony formation in soft agar. International Journal of Cancer, 32(3), 295–299. https://doi.org/10.1002/ijc.2910320306
   PubMed Web of Science ®Google Scholar
• Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. https://doi.org/10.1002/jcc.21256
   PubMed Web of Science ®Google Scholar
• Nicolaides, D. N., Fylaktakidou, K. C., Litinas, K. E., & Hadjipavlou-Litina, D. (1998). Synthesis and biological evaluation of several coumarin-4-carboxamidoxime and 3-(coumarin-4-yl)-1,2,4-oxadiazole derivatives. European Journal of Medicinal Chemistry, 33(9), 715–724. https://doi.org/10.1016/s0223-5234(98)80030-5
   Web of Science ®Google Scholar
• Orlek, B. S., Blaney, F. E., Brown, F., Clark, M. S. G., Hadley, M. S., Hatcher, J., Riley, G. J., Rosenberg, H. E., Wadsworth, H. J., & Wyman, P. (1991). Comparison of azabicyclic esters and oxadiazoles as ligands for the muscarinic receptor. Journal of Medicinal Chemistry, 34(9), 2726–2735. https://doi.org/10.1021/jm00113a009
   PubMed Web of Science ®Google Scholar
• Pallavi, H., Al-Ostoot, F. H., Vivek, H. K., & Khanum, S. A. (2022a). Design, docking, synthesis, and characterization of novel N'(2-phenoxyacetyl) nicotinohydrazide and N'(2-phenoxyacetyl) isonicotinohydrazide derivatives as anti-inflammatory and analgesic agents. Journal of Molecular Structure, 1247, 131404. https://doi.org/10.1016/j.molstruc.2021.131404
   Web of Science ®Google Scholar
• Pallavi, H., Al-Ostoot, F. H., Vivek, H. K., & Khanum, S. A. (2022b). Synthesis, characterization, DFT, docking studies and molecular dynamics of some 3-phenyl-5-furan isoxazole derivatives as anti-inflammatory and anti-ulcer agents. Journal of Molecular Structure, 1250, 131812. https://doi.org/10.1016/j.molstruc.2021.131812
   Web of Science ®Google Scholar
• Pattar, S. V., Adhoni, S. A., Kamanavalli, C. M., & Kumbar, S. S. (2020). In silico molecular docking studies and MM/GBSA analysis of coumarin-carbonodithioate hybrid derivatives divulge the anticancer potential against breast cancer. Beni-Suef University Journal of Basic and Applied Sciences, 9(1), 1-10. https://doi.org/10.1186/s43088-020-00059-7
   Google Scholar
• Pharoah, P. D. P., Dunning, A. M., Ponder, B. A. J., & Easton, D. F. (2004). Association studies for finding cancer-susceptibility genetic variants. Nature Reviews. Cancer, 4(11), 850–860. https://doi.org/10.1038/nrc1476
   PubMed Web of Science ®Google Scholar
• Pienta, K. J., & Lehr, J. E. (1993). A common set of nuclear matrix proteins in prostate cancer cells. The Prostate, 23(1), 61–67. https://doi.org/10.1002/pros.2990230106
   PubMed Web of Science ®Google Scholar
• Pollak, M. (2008). Insulin and insulin-like growth factor signalling in neoplasia. Nature Reviews. Cancer, 8(12), 915–928. https://doi.org/10.1038/nrc2536
   PubMed Web of Science ®Google Scholar
• Raghavendra, K. R., Renuka, N., Kameshwar, V. H., Srinivasan, B., Ajay Kumar, K., & Shashikanth, S. (2016). Synthesis of lignan conjugates via cyclopropanation: Antimicrobial and antioxidant studies. Bioorganic & Medicinal Chemistry Letters, 26(15), 3621–3625. https://doi.org/10.1016/j.bmcl.2016.06.005
   PubMed Web of Science ®Google Scholar
• Reynolds, C. P. (2000). Differentiating agents in pediatric malignancies: Retinoids in neuroblastoma. Current Oncology Reports, 2(6), 511–518. https://doi.org/10.1007/s11912-000-0104-y
   PubMedGoogle Scholar
• Rotmensz, N., De Palo, G., Formelli, F., Costa, A., Marubini, E., Campa, T., Crippa, A., Danesini, G. M., Delle Grottaglie, M., Di Mauro, M. G., Filiberti, A., Gallazzi, M., Guzzon, A., Magni, A., Malone, W., Mariani, L., Palvarini, M., Perloff, M., Pizzichetta, M., & Veronesi, U. (1991). Long-term tolerability of fenretinide (4-HPR) in breast cancer patients. European Journal of Cancer (Oxford, England: 1990), 27(9), 1127–1131. https://doi.org/10.1016/0277-5379(91)90309-2
   PubMed Web of Science ®Google Scholar
• Sakamoto, T., Cullen, M. D., Hartman, T. L., Watson, K. M., Buckheit, R. W., Pannecouque, C., De Clercq, E., & Cushman, M. (2007). Synthesis and anti-HIV activity of new metabolically stable alkenyldiarylmethane non-nucleoside reverse transcriptase inhibitors incorporating N-methoxy imidoyl halide and 1,2,4-oxadiazole systems. Journal of Medicinal Chemistry, 50(14), 3314–3321. https://doi.org/10.1021/jm070236e
   PubMed Web of Science ®Google Scholar
• Shabbits, J. A., Hu, Y., & Mayer, L. D. (2003). Tumor chemosensitization strategies based on apoptosis manipulations. Molecular Cancer Therapeutics, 2(8), 805–813.
   PubMed Web of Science ®Google Scholar
• Shwetha, B., Sudhanva, M. S., Jagadeesha, G. S., Thimmegowda, N. R., Hamse, V. K., Sridhar, B. T., Thimmaiah, K. N., Ananda Kumar, C. S., Shobith, R., & Rangappa, K. S. (2021). Furan-2-carboxamide derivative, a novel microtubule stabilizing agent induces mitotic arrest and potentiates apoptosis in cancer cells. Bioorganic Chemistry, 108, 104586. https://doi.org/10.1016/j.bioorg.2020.104586
   PubMed Web of Science ®Google Scholar
• Siegel, R. L., Miller, K. D., Wagle, N. S., & Jemal, A. (2023). Cancer statistics. CA: A Cancer Journal for Clinicians, 73(1), 17–48. https://doi.org/10.3322/caac.21763
   PubMed Web of Science ®Google Scholar
• Singh, A. K., Novak, J., Kumar, A., Singh, H., Thareja, S., Pathak, P., Grishina, M., Verma, A., Yadav, J. P., Khalilullah, H., Pathania, V., Nandanwar, H., Jaremko, M., Emwas, A.-H., & Kumar, P. (2022). Gaussian field-based 3D-QSAR and molecular simulation studies to design potent pyrimidine–sulfonamide hybrids as selective BRAFV600E inhibitors. RSC Advances, 12(46), 30181–30200. https://doi.org/10.1039/D2RA05751D
   PubMed Web of Science ®Google Scholar
• Singh, Y., Sanjay, K. S., Kumar, P., Singh, S., & Thareja, S. (2023). Molecular dynamics and 3D-QSAR studies on indazole derivatives as HIF-1α inhibitors. Journal of Biomolecular Structure & Dynamics, 41(8), 3524–3541. https://doi.org/10.1080/07391102.2022.2051745
   PubMed Web of Science ®Google Scholar
• Sreenatha, V., Srinivasa, S. M., & Rajendra Prasad, K. J. (2022). Design, synthesis, bioevaluation, DFT, docking, and molecular dynamic simulation for selected novel 1,3,4-Oxadiazole - indole derivatives hybrid against estrogen receptor alpha. Journal of Molecular Structure, 1269, 133789. https://doi.org/10.1016/j.molstruc.2022.133789
   Google Scholar
• Suryakoppa, K. S., Kameshwar, V. H., Appadurai, R., Eranna, S., & Khan, M. M. (2022). Enantiomeric separation of indole-3-propanamide derivatives by using supercritical fluid chromatography on a polysaccharide-based chiral stationary phase. Journal of Chromatographic Science, 60(7), 692–704. https://doi.org/10.1093/chromsci/bmab102
   PubMed Web of Science ®Google Scholar
• Taimi, M., & Breitman, T. R. (1997). N-4-hydroxyphenylretinamide enhances retinoic acid-induced differentiation and retinoylation of proteins in the human acute promyelocytic leukemia cell line, NB4, by a mechanism that may involve inhibition of retinoic acid catabolism. Biochemical and Biophysical Research Communications, 232(2), 432–436. https://doi.org/10.1006/bbrc.1997.6309
   PubMed Web of Science ®Google Scholar
• Takahashi, N. (2000). Antioxidant properties of N-(4-hydroxyphenyl)retinamide (fenretinide). Biological & Pharmaceutical Bulletin, 23(2), 222–225. https://doi.org/10.1248/bpb.23.222
   PubMed Web of Science ®Google Scholar
• Uttarkar, A., Kishore, A. P., Srinivas, S. M., Rangappa, S., Kusanur, R., & Niranjan, V. (2023). Coumarin derivative as a potent drug candidate against triple negative breast cancer targeting the frizzled receptor of wingless-related integration site signaling pathway. Journal of Biomolecular Structure & Dynamics, 41(5), 1561–1573. https://doi.org/10.1080/07391102.2021.2022536
   PubMed Web of Science ®Google Scholar
• Vu, C. B., Corpuz, E. G., Merry, T. J., Pradeepan, S. G., Bartlett, C., Bohacek, R. S., Botfield, M. C., Eyermann, C. J., Lynch, B. A., MacNeil, I. A., Ram, M. K., van Schravendijk, M. R., Violette, S., & Sawyer, T. K. (1999). Discovery of potent and selective SH2 inhibitors of the tyrosine kinase ZAP-70. Journal of Medicinal Chemistry, 42(20), 4088–4098. https://doi.org/10.1021/jm990229t
   PubMed Web of Science ®Google Scholar