Synthesis, Characterisation, Invitro anticancer activity of Diazo Derivatives of 1,3,4-oxadiazole
Abstract
This study delves into the comprehensive evaluation of newly synthesized Diazo Derivatives of 1,3,4-oxadiazole compounds, including Aniline, Ortho nitro aniline, Meta nitro aniline, Ortho anisidine, Meta anisidine, 3-chloro aniline, 2,6-dimethyl aniline, 2,5- dicloro aniline, and 3,5- dichloro aniline, aiming to unravel their potential as antioxidants and anticancer agents. The assessment of antioxidant potential involved the utilization of the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay. The cytotoxic activity of these compounds was assessed against MCF-7 breast cancer cells using the MTT assay. Morphological assessments using acridine orange/ethidium bromide (AO/EB) staining. Results were expressed as IC50 values, with 2,5-dichloro aniline and 3-chloro aniline demonstrating remarkable antioxidant activity, each with an IC50 value of 62.5 µg/mL. Several other compounds also exhibited significant antioxidant properties, albeit with slightly higher IC50 values. Notably, Ortho anisidine and Ortho nitro aniline displayed no substantial inhibitory activity against oxidative stress. The cytotoxic activity of these compounds was assessed against MCF-7 breast cancer cells using the MTT assay, with IC50 values ranging from 62.5 to 1000 µg/mL. 2,5-dichloro aniline and 3-chloro aniline emerged as potent inhibitors, both achieving an IC50 value of 62.5 µg/mL. Aniline, Meta nitro aniline, Meta anisidine, 2,6-dimethyl aniline, and 3,5-dichloro aniline exhibited intermediate inhibitory activity, while Ortho anisidine and Ortho nitro aniline showed no significant inhibition. Morphological assessments using acridine orange/ethidium bromide (AO/EB) staining revealed diverse cellular responses induced by 2,5-dichloro aniline and 3-chloro aniline treatment. These changes align with well-established apoptotic processes observed in therapeutically treated cell lines. This research contributes valuable insights into the antioxidant and anticancer potential of Diazo Derivatives of 1,3,4-oxadiazole compounds, with 2,5-dichloro aniline and 3-chloro aniline emerging as promising candidates for further exploration in combatting oxidative stress and breast cancer. These findings underscore the importance of antioxidants in cancer prevention and the potential therapeutic applications of these compounds.
Keywords: Diazo Derivatives of 1,3,4-oxadiazole, 2,5-dichloro aniline, 3-chloro aniline, DPPH, MTT assay, MCF-7
Keywords:
Diazo Derivatives of 1,3,4-oxadiazole, 2,5-dichloro aniline, 3-chloro aniline, DPPH, MTT assay, MCF-7DOI
https://doi.org/10.22270/jddt.v13i10.5984References
Cooper GM. The Cell: A Molecular Approach. 2nd edition. Sunderland (MA): Sinauer Associates; 2000. The Development and Causes of Cancer. Available from: https://www.ncbi.nlm.nih.gov/books/NBK9963/.
Benz EJ Jr. The Jeremiah Metzger Lecture Cancer in the Twenty-First Century: An Inside View from an Outsider. Trans Am Clin Climatol Assoc. 2017; 128:275-297.
Coventry BJ, Henneberg M. The Immune System and Responses to Cancer: Coordinated Evolution. F1000Res.2015; 4:552. https://doi.org/10.12688/f1000research.6718.3 PMid:33365125 PMCid:PMC7735224
Liu YP, Zheng CC, Huang YN, He ML, Xu WW, Li B. Molecular mechanisms of chemo- and radiotherapy resistance and the potential implications for cancer treatment. MedComm (2020). 2021;2(3):315-340. https://doi.org/10.1002/mco2.55 PMid:34766149 PMCid:PMC8554658
Stein KD, Syrjala KL, Andrykowski MA. Physical and psychological long-term and late effects of cancer. Cancer. 2008;112(11 Suppl):2577-2592. https://doi.org/10.1002/cncr.23448 PMid:18428205 PMCid:PMC7047657
Glomb T, Szymankiewicz K, Świątek P. Anti-Cancer Activity of Derivatives of 1,3,4-Oxadiazole. Molecules. 2018;23(12):3361. https://doi.org/10.3390/molecules23123361 PMid:30567416 PMCid:PMC6320996
Biernacki K, Daśko M, Ciupak O, Kubiński K, Rachon J, Demkowicz S. Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery. Pharmaceuticals (Basel). 2020;13(6):111. Published 2020 May 29. https://doi.org/10.3390/ph13060111 PMid:32485996 PMCid:PMC7345688
Glomb T, Szymankiewicz K, Świątek P. Anti-Cancer Activity of Derivatives of 1,3,4-Oxadiazole. Molecules. 2018;23(12):3361. https://doi.org/10.3390/molecules23123361 PMid:30567416 PMCid:PMC6320996
Benassi A, Doria F, Pirota V. Groundbreaking Anticancer Activity of Highly Diversified Oxadiazole Scaffolds. Int J Mol Sci. 2020;21(22):8692. Published 2020 Nov 18. https://doi.org/10.3390/ijms21228692 PMid:33217987 PMCid:PMC7698752
Muddukrishnaiah K, Sumita S. Antimicrobial, synergistic activity and antioxidant studies on multidrug resistance human pathogen using crude extract of Azadirachta indica leaf and Withania somnifera rhizome. Journal of Plant Pathology and Microbiology. 2015;6(Special Issue 3). https://doi.org/10.4172/2157-7471.1000S3-009
Elmorsy MR, Abdel-Latif E, Gaffer HE, Mahmoud SE, Fadda AA. Anticancer evaluation and molecular docking of new pyridopyrazolo-triazine and pyridopyrazolo-triazole derivatives. Sci Rep. 2023;13(1):2782. https://doi.org/10.1038/s41598-023-29908-y PMid:36797448 PMCid:PMC9935538
Bala S, Kamboj S, Kajal A, Saini V, Prasad DN. 1,3,4-oxadiazole derivatives: synthesis, characterization, antimicrobial potential, and computational studies. Biomed Res Int. 2014; 2014:172791. https://doi.org/10.1155/2014/172791 PMid:25147788 PMCid:PMC4131560
Kedare SB, Singh RP. Genesis and development of DPPH method of antioxidant assay. J Food Sci Technol. 2011;48(4):412-422. https://doi.org/10.1007/s13197-011-0251-1 PMid:23572765 PMCid:PMC3551182
Lobo V, Patil A, Phatak A, Chandra N. Free radicals, antioxidants and functional foods: Impact on human health. Pharmacogn Rev. 2010;4(8):118-126. https://doi.org/10.4103/0973-7847.70902 PMid:22228951 PMCid:PMC3249911
Reuter S, Gupta SC, Chaturvedi MM, Aggarwal BB. Oxidative stress, inflammation, and cancer: how are they linked. Free Radic Biol Med. 2010;49(11):1603-1616. https://doi.org/10.1016/j.freeradbiomed.2010.09.006 PMid:20840865 PMCid:PMC2990475
Slaga TJ. Inhibition of skin tumor initiation, promotion, and progression by antioxidants and related compounds. Crit Rev Food Sci Nutr. 1995;35(1-2):51-57. https://doi.org/10.1080/10408399509527686 PMid:7748479
Lobo V, Patil A, Phatak A, Chandra N. Free radicals, antioxidants, and functional foods: Impact on human health. Pharmacogn Rev. 2010;4(8):118-126. https://doi.org/10.4103/0973-7847.70902 PMid:22228951 PMCid:PMC3249911
Buranrat B, Prawan A, Senggunprai L, Kukongviriyapan V. Inhibition of growth and migration of cholangiocarcinoma cells by pamidronate. Exp Ther Med. 2019;18(5):3977-3983. https://doi.org/10.3892/etm.2019.8041 PMid:31611937 PMCid:PMC6781803
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