Synthesis, crystal structure and in vitro anticancer studies of two bis(8-quinolinolato-N,O)-platinum(II) complexes

Hong Chen; Mingguo Liu

doi:10.5155/eurjchem.10.1.37-44.1814

PDF

Published: Mar 31, 2019

DOI: https://doi.org/10.5155/eurjchem.10.1.37-44.1814

Keywords:

DFT calculations, Crystal structure, Anticancer activity, 8-Hydroxyquinoline, Platinum(II) complexes, 8-Hydroxy-2-methylquinoline

Section

Research Article

Issue

Vol. 10 No. 1 (2019): March 2019

Dates

Received 2018-11-06
Accepted 2018-12-18
Published 2019-03-31

Hong Chen

Key Laboratory of Radiation Physics and Technology of Ministry of Education, Institute of Nuclear Science and Technology, Sichuan University, Chengdu 610064, P. R. China

http://orcid.org/0000-0002-8415-7333

Mingguo Liu

Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. China

http://orcid.org/0000-0003-2686-3034

Abstract

Two bis(8-quinolinolato-N,O)-platinum(II) complexes, C₁₈H₁₂N₂O₂Pt (1) and C₂₀H₁₆N₂O₂Pt (2), were synthesized and characterized by FT-IR, elementary analysis and X-ray single crystal diffraction. Complex 1 crystallizes in monoclinic, space group P2₁/c with a = 9.3413(7), b = 10.3893(9), c = 14.8495(12) Å, β = 100.574(7)°, V = 1416.7(2) Å³. Complex 2 crystallizes in monoclinic, space group P2₁/n with a = 9.5115(11), b = 15.5692(18), c = 16.720(2) Å, β = 94.544(2)°, V = 2468.3(5) Å³. Intermolecular C-H···O hydrogen bonding interactions, as well as Pt···Pt and π-π stacking interactions, help to stabilize the crystal structures. The preliminary in vitro anticancer activity of complexes 1 and 2 and the corresponding ligands (L1 and L2) were investigated using human cervical (Hela) and hepatocellular carcinoma (Hep-G2) cancer cell lines. The platinum(II) complexes can greatly inhibit the cell proliferation and show stronger cytotoxic activities against the tested cancer cell lines than both ligands.

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Chen, H.; Liu, M. Synthesis, Crystal Structure and in Vitro Anticancer Studies of Two bis(8-Quinolinolato-N,O)-platinum(II) Complexes. Eur. J. Chem. 2019, 10, 37-44.

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References

[1]. Shi, X. C.; Chen, Z. Y.; Wang, Y. J.; Guo, Z. J.; Wang, X. Y. Dalton Trans. 2018, 47, 5049-5054.
https://doi.org/10.1039/C8DT00794B

[2]. Hannon, M. J. Chem. Soc. Rev. 2007, 36, 280-295.
https://doi.org/10.1039/B606046N

[3]. Dyson, P. J.; Sava, G. Dalton Trans. 2006, 1929-1933.
https://doi.org/10.1039/b601840h

[4]. Guo, Z. J.; Sadler, P. J. Adv. Inorg. Chem. 2000, 49, 183-306.
https://doi.org/10.1016/S0898-8838(08)60271-8

[5]. Zhang, S. R.; Yuan, H.; Guo, Y.; Wang, K.; Wang, X. Y.; Guo, Z. J. Chem. Commun. 2018, 54, 11717-11720.
https://doi.org/10.1039/C8CC06576D

[6]. Kelland, L. Nat. Rev. Cancer 2007, 7, 573-584.
https://doi.org/10.1038/nrc2167

[7]. Hannon M. J. Pure Appl. Chem. 2007, 79, 2243-2261.
https://doi.org/10.1351/pac200779122243

[8]. Fricker, S. P. Dalton Trans. 2007, 4903-4917.
https://doi.org/10.1039/b705551j

[9]. Reedijk, J. Chem. Commun. 1996, 801-813.

[10]. Florea, A. M.; Büsselberg, D. Cancers 2011, 3, 1351-1371.
https://doi.org/10.3390/cancers3011351

[11]. Wang, X. Y.; Guo, Z. J. Dalton Trans. 2008, 1521-1532.
https://doi.org/10.1039/B715903J

[12]. Roberts, J. D.; Peroutka, J.; Farrell, N. J. Inorg. Biochem. 1999, 77, 51-57.
https://doi.org/10.1016/S0162-0134(99)00147-6

[13]. Farrer, N. J.; Woods, J. A.; Salassa, L.; Zhao, Y.; Robinson, K. S.; Clarkson, G.; Mackay, F. S.; Sadler, P. J. Angew. Chem. Int. Ed. 2010, 49, 8905-8908.
https://doi.org/10.1002/anie.201003399

[14]. Miodragovic, D. U.; Quentzel, J. A.; Kurutz, J. W.; Stern, C. L.; Ahn, R. W.; Kandela, I.; Mazar, A.; O'Halloran, T. V. Angew. Chem. Int. Ed. 2013, 52, 10749-10752.
https://doi.org/10.1002/anie.201303251

[15]. Rosenberg, B.; VanCamp. L.; Trosko, J. E.; Mansour, V. H. Nature 1969, 222, 385-386.
https://doi.org/10.1038/222385a0

[16]. Reedijk, J. Eur. J. Inorg. Chem. 2009, 2009, 1303-1312.

[17]. Wheate, N. J.; Walker, S.; Craig, G. E.; Oun, R. Dalton Trans. 2010, 39, 8113-8127.
https://doi.org/10.1039/c0dt00292e

[18]. Wang, X. Y.; Guo, Z. J. Chem. Soc. Rev. 2013, 42, 202-224.
https://doi.org/10.1039/C2CS35259A

[19]. Zhu, Z. Z.; Wang, X. Y.; Li, T. J.; Aime, S.; Sadler, P. J.; Guo, Z. J. Angew. Chem. Int. Ed. 2014, 53, 13225-13228.
https://doi.org/10.1002/anie.201407406

[20]. Wang, J. Z.; Wang, X. Y.; Song, Y. J.; Wang, J.; Zhang, C. L.; Chang, C. J.; Yan, J.; Qiu, L.; Wu, M. M.; Guo, Z. J. Chem. Sci. 2013, 4, 2605-2612.
https://doi.org/10.1039/c3sc50554e

[21]. Varbanov, H. P.; Jakupec, M. A.; Roller, A.; Jensen, F.; Galanski, M.; Keppler, B. K. J. Med. Chem. 2013, 56, 330-344.
https://doi.org/10.1021/jm3016427

[22]. Pichler, V.; Heffeter, P.; Valiahdi, S. M.; Kowol, C. R.; Egger, A.; Berger, W.; Jakupec, M. A.; Galanski, M.; Keppler, B. K. J. Med. Chem. 2012, 55, 11052-11061.
https://doi.org/10.1021/jm301645g

[23]. Liu, Z. P.; He, W. J.; Guo, Z. J. Chem. Soc. Rev. 2013, 42, 1568-1600.
https://doi.org/10.1039/c2cs35363f

[24]. Tu, C.; Lin, J.; Shao, Y.; Guo, Z. J. Inorg.Chem. 2003, 42, 5795-5797.
https://doi.org/10.1021/ic034604q

[25]. Proetto, M.; Liu, W. K.; Hagenbach, A.; Abram, U.; Gust, R. Eur. J. Med. Chem. 2012, 53, 168-175.
https://doi.org/10.1016/j.ejmech.2012.03.053

[26]. Zhang, Q. Y.; Huang, N. Y.; Wang, J. Z.; Luo, H. J.; He, H. B.; Ding, M. R.; Deng, W. Q.; Zou, K. Fitoterapia 2013, 89, 210-217.
https://doi.org/10.1016/j.fitote.2013.05.021

[27]. Fang, H. B.; Jin, L.; Huang, N. Y.; Wang, J. Z.; Zou, K.; Luo, Z. G. Chin. J. Chem. 2013, 31, 831-836.
https://doi.org/10.1002/cjoc.201300119

[28]. Huang, N. Y.; Chen, L.; Liao, Z. J.; Fang, H. B.; Wang, J. Z.; Zou, K. Chin. J. Chem. 2012, 30, 71-76.
https://doi.org/10.1002/cjoc.201100051

[29]. Ballardini, R.; Varani, G.; Indelli, M. T.; Scandola, F. Inorg. Chem. 1986, 25, 3858-3865.
https://doi.org/10.1021/ic00242a006

[30]. Ballardinia, R.; Indelli, M. T.; Varani, G.; Bignozzi, C. A.; Scandola, F. Inorg. Chim. Acta 1978, 31, L423-L424.
https://doi.org/10.1016/S0020-1693(00)94946-6

[31]. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J, Howard, J. A. K. & Puschmann, H. J. Appl. Cryst. 2009, 42, 339-341.
https://doi.org/10.1107/S0021889808042726

[32]. Sheldrick, G. M. A short history of SHELX. Acta Cryst. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[33]. Shapira, A.; Davidson, I.; Avni, N.; Assaraf, Y. G.; Livney, Y. D. Eur. J. Pharm. Biopharm. 2012, 80, 298-305.
https://doi.org/10.1016/j.ejpb.2011.10.022

[34]. Etaiw, S. E. D. H.; Sultan, A. S.; El-Bendary, M. M. J. Organomet. Chem. 2011, 696, 1668-1676.
https://doi.org/10.1016/j.jorganchem.2011.02.003

[35]. Creaven, B. S.; Duff, B.; Egan, D. A.; Kavanagh, K.; Rosair, G.; Thangella, V. R.; Walsh, M. Inorg. Chim. Acta 2010, 363, 4048-4058.
https://doi.org/10.1016/j.ica.2010.08.009

[36]. Chan, M. H. E.; Crouse, K. A.; Tahir, M. I. M.; Rosli, R.; Umar-Tsafe, N.; Cowley, A. R. Polyhedron 2008, 27, 1141-1149.
https://doi.org/10.1016/j.poly.2007.11.035

[37]. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63.
https://doi.org/10.1016/0022-1759(83)90303-4

[38]. Wu, H. L.; Yuan, J. K.; Pan, G. L.; Zhang, Y. H.; Wang, X. L.; Shi, F. R.; Fan, X. Y. J. Photoch. Photobio. B 2013, 122, 37-44.
https://doi.org/10.1016/j.jphotobiol.2013.03.004

[39]. Kaniskan, N.; Ogretir, C. J. Mol. Struct. 2002, 584, 45-52.
https://doi.org/10.1016/S0166-1280(02)00018-0

[40]. Cumming, G.; Fidler, F.; Vaux, D. L. J. Cell Biol. 2007, 177, 7-11.
https://doi.org/10.1083/jcb.200611141

[41]. West, B. T. Eval. Health Prof. 2009, 32, 207-228.
https://doi.org/10.1177/0163278709338554

[42]. Kresse, G.; Hafner, J. Phys. Rev. B 1993, 47, 558-561.
https://doi.org/10.1103/PhysRevB.47.558

[43]. Kresse, G.; Hafner, J. Phys. Rev. B 1994, 49, 14251-14269.
https://doi.org/10.1103/PhysRevB.49.14251

[44]. Kresse, G.; Furthmuller, J. Phys. Rev. B 1996, 54, 11169-11186.
https://doi.org/10.1103/PhysRevB.54.11169

[45]. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865-3868.
https://doi.org/10.1103/PhysRevLett.77.3865

[46]. Kresse, G.; Joubert, D. Phys. Rev. B 1999, 59, 1758-1775.
https://doi.org/10.1103/PhysRevB.59.1758

[47]. Dudarev, S. L.; Botton, G. A.; Savrasov, S.Y.; Humphreys, C.J.; Sutton, A. P. Phys. Rev. B 1998, 57, 1505-1509.
https://doi.org/10.1103/PhysRevB.57.1505

[48]. Kato, M.; Ogawa, Y.; Kozakai, M.; Sugimoto, Y. Acta Crystallogr. C. 2002, 58, m147-m149.
https://doi.org/10.1107/S0108270102000045

[49]. Low, K. H.; Xu, Z. X.; Xiang, H. F.; Chui, S. S. Y.; Roy, V. A. L.; Che, C. M. Chem. Asian J. 2011, 6, 3223-3229.
https://doi.org/10.1002/asia.201100450

[50]. Janiak, C. J. Chem. Soc., Dalton Trans. 2000, 3885-3896.
https://doi.org/10.1039/b003010o

[51]. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc. Dalton Trans. II 1989, S1-S83.
https://doi.org/10.1039/dt98900000s1

[52]. Wong, E.; Giandomenico, C. M. Chem. Rev. 1999, 99, 2451-2466.
https://doi.org/10.1021/cr980420v

[53]. Jamieson, E. R.; Lippard, S. J. Chem. Rev. 1999, 99, 2467-2498.
https://doi.org/10.1021/cr980421n

[54]. Qin, Q. P.; Chen, Z. F.; Qin, J. L.; He, X. J.; Li, Y. L.; Liu, Y. C.; Huang, K. B.; Liang, H. Eur. J. Med. Chem., 2015, 92, 302-313.
https://doi.org/10.1016/j.ejmech.2014.12.052

Supporting Agencies

Analytical & Testing Center of China Three Gorges University, Yichang 443002, P. R. China.

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