In vitro anticancer evaluation of novel triphenyltin(IV) compounds with some N-acetyl-S-naphthoquinonylcysteine derivatives

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Nebojša Pantelić
Martina Lerbs
Katharina Wolf
Ludger Wessjohann
Goran N. Kaluđerović
https://orcid.org/0000-0001-5168-1000

Abstract

Triphenyltin(IV) compounds with naphthoquinone derivatives cont­aining N-acetylcysteine, N-acetyl-S-(3,4-dihydro-3,4-dioxo-1-naphthyl)­cys­teine (1,2-NQC), 1, and N-acetyl-S-(1,4-dihydro-1,4-dioxo-2-naphthyl)cysteine (1,4-NQC), 2, were synthe­sized and characterized by elemental microanalysis, IR, multinuclear (1H, 13C, 119Sn) NMR spectroscopy as well as HR-ESI mass spectrometry. With the aim of in vitro anticancer activity determination of lig­and precursors and novel syn­the­sized organotin(IV) compounds against human cervix adeno­car­ci­noma (HeLa), human colon carcinoma (HT-29) and mela­noma carcinoma cell line (B16F10), MTT colorimetric assay method was applied. The results indi­cate that syn­the­sized compounds exhibited remarkable antiproliferative activity toward all tested cell lines with IC50 in the range from 0.17 to 0.87 µM. Com­plex 1 showed the greatest activity against HT-29 cells, with IC50 value of 0.21±0.01 µM, 119 times better than cisplatin, while com­plex 2 demonstrated the highest activity toward HeLa cells, IC50 = 0.17±0.01 µM, which is ~26 times better than cisplatin.

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How to Cite
[1]
N. Pantelić, M. Lerbs, K. Wolf, L. Wessjohann, and G. N. Kaluđerović, “In vitro anticancer evaluation of novel triphenyltin(IV) compounds with some N-acetyl-S-naphthoquinonylcysteine derivatives”, J. Serb. Chem. Soc., vol. 84, no. 10, pp. 1119–1127, Nov. 2019.
Section
Inorganic Chemistry

References

J. Jadidi-Niaragh, G. Ghalamfarsa, M. Yousefi, M. N. Tabrizi, F. Shokri, Tumor Biol. 34 (2013) 2031 https://doi.org/10.1007/s13277-013-0832-x

G. Ghalamfarsa, A. Hadina, M. Yousefi, F. Jadidi-Niaragh, Tumor Biol. 34 (2013) 1349 https://doi.org/10.1007/s13277-013-0743-x

M. U. Haque, N. Ferdiousi, S. R. Sajon, Int. J. Pharmacogn. 32 (2016) 55 https://doi.org/10.13040/IJPSR.0975-8232.IJP.3(2).55-66

P. Anand, A. B. Kunnumakara, C. Sundaram, K. B. Harikumar, S. T. Tharakan, O. S. Lai, B. Sung, B. B. Aggarwal, Pharm. Res. 25 (2008) 2097 https://doi.org/10.1007/s11095-008-9661-9

T. H. Elizabeth, E. T. H. Fontham, CA Cancer J. Clin. 59 (2009) 5 https://doi.org/10.3322/caac.20000

B. Lippert, (ed) Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug, John Wiley & Sons, Inc., New York. 1999

B. Rosenberg, Adv. Exp. Med. Biol. 91 (1977) 129

C. A. Rabic, M. E. Dolan, Cancer Treat. Rev. 33 (2007) 9 https://doi.org/10.1016/j.ctrv.2006.09.006

Y. W. Jung, S. J. Lippard, Chem. Rev. 107 (2007) 1387 https://doi.org/10.1021/cr068207j

G. N. Kaluđerović, R. Paschke, Curr. Med. Chem. 18 (2011) 4738 https://doi.org/10.2174/092986711797535308

A. Molter, S. Kathrein, B. Kircher, F. Mohr, Dalton Trans. 47(14) (2018) 5055 https://doi.org/10.1039/C7DT04180B

L. Perdisatt, S. Moqadasi, L. O'Neill, G. Hessman, A. Ghion, M. Q. M. Warraich, A. Casey, C. O'Connor, J. Inorg. Chem. 182 (2018) 71 https://doi.org/10.1016/j.jinorgbio.2018.01.018

N. Pantelić, B. B. Zmejkovski, B. Kolundžija, M. Đorđić Crnogorac, J. M. Vujić, B. Dojčinović, S. R. Trifunović, T. P. Stanojković, T. J. Sabo, G. N. Kaluđerović, J. Inorg. Biochem. 172 (2017) 55 http://dx.doi.org/10.1016/j.jinorgbio.2017.04.001

N. Pantelić, B. B. Zmejkovski, T. P. Stanojković, T. J. Sabo, G. N. Kaluđerović, Eur. J. Med. Chem. 90 (2015) 766 http://dx.doi.org/10.1016/j.ejmech.2014.12.019

N. Pantelić, B. B. Zmejkovski, J. Trifunović-Macedoljan, A. Savić, D. Stanković, A. Damjanović, Z. Juranić, G. N. Kaluđerović, T. J. Sabo, J. Inorg. Biochem. 128 (2013) 146 http://dx.doi.org/10.1016/j.jinorgbio.2013.08.002

S. Gómez-Ruiz, T. P. Stanojkovic, G. N. Kaluđerović, Appl. Organomet. Chem. 26 (2012) 383 https://doi.org/10.1002/aoc.2878

N. Muhammad, Z. U. Rehman, S. Shujah, S. Ali, A. Shah, A. Meetsma, J. Coord. Chem. 67 (2014) 1110 https://doi.org/10.1080/00958972.2014.898755

H. M. Wahba, M. J. Stevenson, A. Mansour, J. Sygusch, D. E. Wilcox, J. G. Omichinski, J. Am. Chem. Soc. 139 (2017) 910 https://doi.org/10.1021/jacs.6b11327

T. S. B. Baul, P. Kehie, A .Duthie, N. Guchhait, N. Raviprakash, R. B. Mokhamatam, S. K. Manna, N. Armata, M. Scopelliti, R. Wang, U. Englert, J. Inorg. Biochem. 168 (2017) 76 https://doi.org/10.1016/j.jinorgbio.2016.12.001

X. Han, M. Tian, X. Xiao, J. Liang, D. Zhu, J. Iran. Chem. Soc. 15 (2018) 513 https://doi.org/10.1007/s13738-017-1251-5

M. Yousefi, M. Safari, M. B. Torbati, V. M. Kazemiha, H. Sanati, Appl. Organometal. Chem. 26 (2012) 438 https://doi.org/10.1002/aoc.2885

G. Gasser, I. Otto, N. Metzler-Nolte, J. Med. Chem. 54 (2011) 3 https://doi.org/10.1021/jm100020w

M. Z. Bulatović, D. Maksimović-Ivanić, C. Bensing, S. Gomez-Ruiz, D. Steinborn, H. Schmidt. M. Mojić, A. Korać, I. Golić, D. Perez-Quintanilla, M. Momčilović, S. Mijatović, G. N. Kaluđerović, Angew. Chem. Int. Ed. 53 (2014) 5982 https://doi.org/10.1002/anie.201400763

M. Sirajuddin, S. Ali, V. McKee, M. Sohail, H. Pasha, Eur. J. Med. Chem. 84 (2014) 343 https://doi.org/10.1016/j.ejmech.2014.07.028

F. Javed, S. Ali, S. Shahzadi, S. K. Sharma, K. Qanungo, M. N. Tahir, N. A. Shah, M. R. Khan, N. Khalid, J. Inorg. Organomet. Polym. 26 (2016) 48 https://doi.org/10.1007/s10904-015-0303-5

Y. G. Yang, M. Hong, L. D. Xu, J. C. Cui, G. L. Chang, D. C. Li, C. Z. Li, J. Organometal. Chem. 804 (2016) 48 https://doi.org/10.1016/j.jorganchem.2015.12.041

T. Mosmann, J. Immunol. Methods 65 (1983) 55 https://doi.org/10.1016/0022-1759(83)90303-4

M. Ohno, T. Abe, J. Immunol. Methods 145 (1991) 199 https://doi.org/10.1016/0022-1759(91)90327-C

G. B. Deacon, R. J. Philips, Coord. Chem. Rev. 33 (1980) 227 https://doi.org/10.1016/S0010-8545(00)80455-5

G. N. Kaluđerović, H. Kommera, E. Hey-Hawkins, R. Paschke, S. Gómez-Ruiz, Metallomics 2 (2010) 419 https://doi.org/10.1039/C0MT00007H

S. Gómez-Ruiz, S. Prashar, T. Walther, M. Fajardo, D. Steinborn, R. Paschke, G. N. Kaluđerović, Polyhedron 29 (2010) 16 https://doi.org/10.1016/j.poly.2009.05.056

S. Gómez -Ruiz, G. N. Kaluđerović, S. Prashar, E. Hey-Hawkins, A. Erić, Ž. Žižak, Z. D. Juranić, Inorg. Biochem. 102 (2008) 2087 https://doi:10.1016/j.jinorgbio.2008.07.009

G. N. Kaluđerović, R. Paschke, S. Prashar, S. Gómez –Ruiz, J. Organomet. Chem. 695 (2010) 1883 https://doi:10.1016/j.jorganchem.2010.04.029

A. Molter, G. N. Kaluđerović, H. Kommera, R. Paschke, T. Langer, R. Pöttgen, F. Mohr, J. Organomet. Chem. 701 (2012) 80 https://doi:10.1016/j.jorganchem.2011.12.027

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