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Year 2020, Volume: 50 Issue: 3, 176 - 180, 30.12.2020

Abstract

References

  • • Atioğlu, Z., Sevinçli, Z. Ş., Karalı, N., Akkurt, M., & Ersanlı C. C. (2017a). 2-(5-Fluoro-1-methyl-2-oxoindolin-3-ylidene)-N-[4- (methylsulfanyl)phenyl]hydrazine-1-carbothioamide. IUCrData, 2(5), x170671.
  • • Atioğlu, Z., Sevinçli, Z. Ş., Karalı, N., Akkurt, M., & Ersanlı C. C. (2017b). (2Z)-2-(5-Fluoro-1-methyl-2-oxoindolin-3-ylidene)- N-(3-fluorophenyl)hydrazine-1-carbothioamide. IUCrData, 2(6), x170900.
  • • Banerjee, D., Yogeeswari, P., Bhat, P., Thomas, A., Srividya, M., & Sriram, D. (2011). Novel isatinyl thiosemicarbazones derivatives as potential molecule to combat HIV-TB co-infection. European Journal of Medicinal Chemistry, 46(1), 106−121.
  • • Brimacombe K., Fales H. M., Gottesman M. M., Hall, M. D., & Handley, M. (2012). W.O. Patent No. 2012033601 A1.
  • • Dikmen, M., Özturk, N., & Özturk, Y. The antioxidant potency of Punica granatum L. Fruit peel reduces cell proliferation and induces apoptosis on breast cancer. Journal of Medicinal Food, 14(12), 1638−1646.
  • • Feng, L. S., Liu, M. L., Wang, B., Chai, Y., Hao, X. Q., Meng, S., & Guo, H. Y. (2010). Synthesis and in vitro antimycobacterial activity of balofloxacin ethylene isatin derivatives. European Journal of Medicinal Chemistry, 45, 3407−3412.
  • • Foongladda, S., Roengsanthia, D., Arjrattanakool, W., Chuchottaworn, C., Chaiprasert, A., & Franzblau, S. G. (2002). Rapid and simple MTT method for rifampicin and isoniazid susceptibility testing of Mycobacterium tuberculosis. The International Journal of Tuberculosis and Lung Disease, 6(12), 1118−1122.
  • • Güzel, Ö., Karalı, N., & Salman, A. (2008). Synthesis and antituberculosis activity of 5-methyl/ trifluoromethoxy-1H-indole-2,3- dione 3-thiosemicarbazone derivatives. Bioorganic & Medicinal Chemistry, 16(19), 8976−8987.
  • • Hall, M. D., Salam, N. K., Hellawell, J. L., Fales, H. M., Kensler, C. B., Ludwig, J. A. … Gottesman, M. M. (2009). Synthesis, activity, and pharmacophore development for isatin-β-thiosemicarbazones with selective activity toward multidrug-resistant cells. Journal of Medicinal Chemistry, 52(10), 3191−3204.
  • • Hall, M. D., Gottesman, M. M., Hellawell, J. L., Ludwig, J. A., Fales, H. M., Salam, N. K., & Szakács, G. (2010). U.S. Patent Application No. 12/867,206.
  • • Hall, M. D., Brimacombe, K. R., Varonka, M. S., Pluchino, K. M., Monda, J. K., Li, J. … Gottesman, M. M. (2011). Synthesis and structureactivity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing Pglycoprotein. Journal of Medicinal Chemistry, 54, 5878−5889.
  • • Karalı, N. (2002). Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives. European Journal of Medicinal Chemistry, 37(11), 909−918.
  • • Karalı, N., Gürsoy, A., Kandemirli, F., Shvets, N., Kaynak, F. B.,Özbey, S. … Dimoglo, A. (2007). Synthesis and structure–antituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorganic & Medicinal Chemistry, 15(17), 5888−5904.
  • • Karalı, N., Akdemir, A., Göktaş, F., Eraslan-Elma, P., Angeli, A., Kızılırmak, M. & Supuran, C. T. (2017). Novel sulfonamide-containing 2-indolinones that selectively inhibit tumor-associated alpha carbonic anhydrases. Bioorganic & Medicinal Chemistry, 25(14), 3714−3718.
  • • Lin, H. H., Wu, W. Y., Cao, S. L., Liao, J., Ma, L., Gao, M. ... Xu, X. (2013). Synthesis and antiproliferative evaluation of piperazine-1-carbothiohydrazide derivatives of indolin-2-one. Bioorganic & Medicinal Chemistry Letters, 23(11), 3304−3307.
  • • Matesic, L., Locke, J. M., Bremner, J. B., Pyne, S. G., Skropeta, D., & Ranson, M. (2008). N-phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents. Bioorganic & Medicinal Chemistry, 16, 3118−3124.
  • • Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65, 55−63.
  • • Pape, V. F. S., Tóth, S., Füredi, A., Szebényi, K., Lovrics, A., Szabó, P. … Szakács, G. (2016). Design, synthesis and biological evaluation of thiosemicarbazones, hydrazinobenzothiazoles and arylhydrazones as anticancer agents with a potential to overcome multidrug resistance. European Journal of Medicinal Chemistry, 117, 335−354.
  • • Pervez, H., Saira, N., Iqbal, M. S., Yaqub, M., & Khan, K. M. (2011). Synthesis and toxicity evaluation of some N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones. Molecules, 16(8), 6408−6421.
  • • Pervez, H., Saira, N., Iqbal, M. S., Yaqub, M., & Khan, K. M. (2013). Synthesis and biological evaluation of some N 4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones. Medicinal Chemistry Research, 22(12), 5878−5889.
  • • Priyanka, K. B., Manasa, C., & Sammaiah, G. (2014). Synthesis and evaluation of new isatin derivatives for cytotoxic activity. World Journal of Pharmacy and Pharmaceutical Sciences, 3, 2393−2402. •
  • Raut, U., Narang, P., Mendiratta, D. K., Narang, R., & Deotale, V. (2008). Evaluation of rapid MTT tube method for detection of drug susceptibility of Mycobacterium tuberculosis to rifampicin and isoniazid. Indian Journal of Medical Microbiology, 26, 222−227.
  • • Sabet, R., Mohammadpour, M., Sadeghi, A. & Fassihi, A. (2010). QSAR study of isatin analogues as in vitro anti-cancer agents, European Journal of Medicinal Chemistry, 45, 1113−1118.
  • • Sevinçli, Z. Ş., Duran, G., Özbil, M., & Karalı, N. (2020). Synthesis, molecular modeling and antiviral activity of novel 5-fluoro-1Hindole- 2,3-dione 3-thiosemicarbazones. Bioorganic Chemistry, In press, https://doi.org/10.1016/j.bioorg.2020.104202
  • • Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G., & Bremner, J. B. (2007). An investigation into the cytotoxicity and mode of action of some novel N-alkyl-substituted isatins. Journal of Medicinal Chemistry, 50, 5109−5117.

Anticancer and antituberculosis effects of 5-fluoro- 1H-indole-2,3-dione 3-thiosemicarbazones

Year 2020, Volume: 50 Issue: 3, 176 - 180, 30.12.2020

Abstract

Background and Aims: The aim of this study was to screen the in vitro anticancer/antituberculosis activities of 5-fluoro- 1-methyl/ethyl-1H-indole-2,3-dione 3-thiosemicarbazones. Methods: A549/U-87MG cell lines were used for the anticancer activity of the compounds, while CCD-19Lu cell line was used to determine their cytotoxic effects. In antituberculosis activity studies using MTB H37Rv cell line, BJ cell line was used to determine the cytotoxic effects. MTT assay was used to obtain IC50 values. Results: 6a, 6b, 6g, 6h, 6l, 6n, 7c, 7k and 7l were found to be highly effective against A549 cell line compared to cisplatin whereas 6d, 6h, 6l, 6n, 7d and 7f were found to be effective against U-87MG cell line compared to cisplatin. It was also determined that 6a, 6b and 7l did not show cytotoxic effects on CCD-19Lu cell line. The antituberculosis effects of the compounds were investigated against MTB H37Rv cell groups using rifampicin as standard. It was determined that 6b, 6c, 6g-k, 6n, 7b, 7j and 7l have near-standard activity and 6b, 7b and 7l were not cytotoxic on BJ cell line. Conclusion: While determining effective compounds in anticancer studies, it was concluded that active compounds can be reached by modifications in compounds in antituberculosis studies.

References

  • • Atioğlu, Z., Sevinçli, Z. Ş., Karalı, N., Akkurt, M., & Ersanlı C. C. (2017a). 2-(5-Fluoro-1-methyl-2-oxoindolin-3-ylidene)-N-[4- (methylsulfanyl)phenyl]hydrazine-1-carbothioamide. IUCrData, 2(5), x170671.
  • • Atioğlu, Z., Sevinçli, Z. Ş., Karalı, N., Akkurt, M., & Ersanlı C. C. (2017b). (2Z)-2-(5-Fluoro-1-methyl-2-oxoindolin-3-ylidene)- N-(3-fluorophenyl)hydrazine-1-carbothioamide. IUCrData, 2(6), x170900.
  • • Banerjee, D., Yogeeswari, P., Bhat, P., Thomas, A., Srividya, M., & Sriram, D. (2011). Novel isatinyl thiosemicarbazones derivatives as potential molecule to combat HIV-TB co-infection. European Journal of Medicinal Chemistry, 46(1), 106−121.
  • • Brimacombe K., Fales H. M., Gottesman M. M., Hall, M. D., & Handley, M. (2012). W.O. Patent No. 2012033601 A1.
  • • Dikmen, M., Özturk, N., & Özturk, Y. The antioxidant potency of Punica granatum L. Fruit peel reduces cell proliferation and induces apoptosis on breast cancer. Journal of Medicinal Food, 14(12), 1638−1646.
  • • Feng, L. S., Liu, M. L., Wang, B., Chai, Y., Hao, X. Q., Meng, S., & Guo, H. Y. (2010). Synthesis and in vitro antimycobacterial activity of balofloxacin ethylene isatin derivatives. European Journal of Medicinal Chemistry, 45, 3407−3412.
  • • Foongladda, S., Roengsanthia, D., Arjrattanakool, W., Chuchottaworn, C., Chaiprasert, A., & Franzblau, S. G. (2002). Rapid and simple MTT method for rifampicin and isoniazid susceptibility testing of Mycobacterium tuberculosis. The International Journal of Tuberculosis and Lung Disease, 6(12), 1118−1122.
  • • Güzel, Ö., Karalı, N., & Salman, A. (2008). Synthesis and antituberculosis activity of 5-methyl/ trifluoromethoxy-1H-indole-2,3- dione 3-thiosemicarbazone derivatives. Bioorganic & Medicinal Chemistry, 16(19), 8976−8987.
  • • Hall, M. D., Salam, N. K., Hellawell, J. L., Fales, H. M., Kensler, C. B., Ludwig, J. A. … Gottesman, M. M. (2009). Synthesis, activity, and pharmacophore development for isatin-β-thiosemicarbazones with selective activity toward multidrug-resistant cells. Journal of Medicinal Chemistry, 52(10), 3191−3204.
  • • Hall, M. D., Gottesman, M. M., Hellawell, J. L., Ludwig, J. A., Fales, H. M., Salam, N. K., & Szakács, G. (2010). U.S. Patent Application No. 12/867,206.
  • • Hall, M. D., Brimacombe, K. R., Varonka, M. S., Pluchino, K. M., Monda, J. K., Li, J. … Gottesman, M. M. (2011). Synthesis and structureactivity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing Pglycoprotein. Journal of Medicinal Chemistry, 54, 5878−5889.
  • • Karalı, N. (2002). Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives. European Journal of Medicinal Chemistry, 37(11), 909−918.
  • • Karalı, N., Gürsoy, A., Kandemirli, F., Shvets, N., Kaynak, F. B.,Özbey, S. … Dimoglo, A. (2007). Synthesis and structure–antituberculosis activity relationship of 1H-indole-2,3-dione derivatives. Bioorganic & Medicinal Chemistry, 15(17), 5888−5904.
  • • Karalı, N., Akdemir, A., Göktaş, F., Eraslan-Elma, P., Angeli, A., Kızılırmak, M. & Supuran, C. T. (2017). Novel sulfonamide-containing 2-indolinones that selectively inhibit tumor-associated alpha carbonic anhydrases. Bioorganic & Medicinal Chemistry, 25(14), 3714−3718.
  • • Lin, H. H., Wu, W. Y., Cao, S. L., Liao, J., Ma, L., Gao, M. ... Xu, X. (2013). Synthesis and antiproliferative evaluation of piperazine-1-carbothiohydrazide derivatives of indolin-2-one. Bioorganic & Medicinal Chemistry Letters, 23(11), 3304−3307.
  • • Matesic, L., Locke, J. M., Bremner, J. B., Pyne, S. G., Skropeta, D., & Ranson, M. (2008). N-phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents. Bioorganic & Medicinal Chemistry, 16, 3118−3124.
  • • Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65, 55−63.
  • • Pape, V. F. S., Tóth, S., Füredi, A., Szebényi, K., Lovrics, A., Szabó, P. … Szakács, G. (2016). Design, synthesis and biological evaluation of thiosemicarbazones, hydrazinobenzothiazoles and arylhydrazones as anticancer agents with a potential to overcome multidrug resistance. European Journal of Medicinal Chemistry, 117, 335−354.
  • • Pervez, H., Saira, N., Iqbal, M. S., Yaqub, M., & Khan, K. M. (2011). Synthesis and toxicity evaluation of some N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones. Molecules, 16(8), 6408−6421.
  • • Pervez, H., Saira, N., Iqbal, M. S., Yaqub, M., & Khan, K. M. (2013). Synthesis and biological evaluation of some N 4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones. Medicinal Chemistry Research, 22(12), 5878−5889.
  • • Priyanka, K. B., Manasa, C., & Sammaiah, G. (2014). Synthesis and evaluation of new isatin derivatives for cytotoxic activity. World Journal of Pharmacy and Pharmaceutical Sciences, 3, 2393−2402. •
  • Raut, U., Narang, P., Mendiratta, D. K., Narang, R., & Deotale, V. (2008). Evaluation of rapid MTT tube method for detection of drug susceptibility of Mycobacterium tuberculosis to rifampicin and isoniazid. Indian Journal of Medical Microbiology, 26, 222−227.
  • • Sabet, R., Mohammadpour, M., Sadeghi, A. & Fassihi, A. (2010). QSAR study of isatin analogues as in vitro anti-cancer agents, European Journal of Medicinal Chemistry, 45, 1113−1118.
  • • Sevinçli, Z. Ş., Duran, G., Özbil, M., & Karalı, N. (2020). Synthesis, molecular modeling and antiviral activity of novel 5-fluoro-1Hindole- 2,3-dione 3-thiosemicarbazones. Bioorganic Chemistry, In press, https://doi.org/10.1016/j.bioorg.2020.104202
  • • Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G., & Bremner, J. B. (2007). An investigation into the cytotoxicity and mode of action of some novel N-alkyl-substituted isatins. Journal of Medicinal Chemistry, 50, 5109−5117.
There are 25 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences, Health Care Administration
Journal Section Original Article
Authors

Zekiye Şeyma Sevinçli This is me 0000-0001-7821-6854

Zerrin Cantürk This is me 0000-0001-7709-4285

Miriş Dikmen This is me 0000-0002-9856-3148

Nilgün Karalı This is me 0000-0002-6916-122X

Publication Date December 30, 2020
Submission Date September 8, 2020
Published in Issue Year 2020 Volume: 50 Issue: 3

Cite

APA Sevinçli, Z. Ş., Cantürk, Z., Dikmen, M., Karalı, N. (2020). Anticancer and antituberculosis effects of 5-fluoro- 1H-indole-2,3-dione 3-thiosemicarbazones. İstanbul Journal of Pharmacy, 50(3), 176-180.
AMA Sevinçli ZŞ, Cantürk Z, Dikmen M, Karalı N. Anticancer and antituberculosis effects of 5-fluoro- 1H-indole-2,3-dione 3-thiosemicarbazones. iujp. December 2020;50(3):176-180.
Chicago Sevinçli, Zekiye Şeyma, Zerrin Cantürk, Miriş Dikmen, and Nilgün Karalı. “Anticancer and Antituberculosis Effects of 5-Fluoro- 1H-Indole-2,3-Dione 3-Thiosemicarbazones”. İstanbul Journal of Pharmacy 50, no. 3 (December 2020): 176-80.
EndNote Sevinçli ZŞ, Cantürk Z, Dikmen M, Karalı N (December 1, 2020) Anticancer and antituberculosis effects of 5-fluoro- 1H-indole-2,3-dione 3-thiosemicarbazones. İstanbul Journal of Pharmacy 50 3 176–180.
IEEE Z. Ş. Sevinçli, Z. Cantürk, M. Dikmen, and N. Karalı, “Anticancer and antituberculosis effects of 5-fluoro- 1H-indole-2,3-dione 3-thiosemicarbazones”, iujp, vol. 50, no. 3, pp. 176–180, 2020.
ISNAD Sevinçli, Zekiye Şeyma et al. “Anticancer and Antituberculosis Effects of 5-Fluoro- 1H-Indole-2,3-Dione 3-Thiosemicarbazones”. İstanbul Journal of Pharmacy 50/3 (December 2020), 176-180.
JAMA Sevinçli ZŞ, Cantürk Z, Dikmen M, Karalı N. Anticancer and antituberculosis effects of 5-fluoro- 1H-indole-2,3-dione 3-thiosemicarbazones. iujp. 2020;50:176–180.
MLA Sevinçli, Zekiye Şeyma et al. “Anticancer and Antituberculosis Effects of 5-Fluoro- 1H-Indole-2,3-Dione 3-Thiosemicarbazones”. İstanbul Journal of Pharmacy, vol. 50, no. 3, 2020, pp. 176-80.
Vancouver Sevinçli ZŞ, Cantürk Z, Dikmen M, Karalı N. Anticancer and antituberculosis effects of 5-fluoro- 1H-indole-2,3-dione 3-thiosemicarbazones. iujp. 2020;50(3):176-80.