DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

  • Turgay Tunç Department of Chemistry Engineering and Process, Faculty of Engineering, University of Ahi Evran, Kırsehir
  • Nadir Demirel Department of Chemistry, Faculty of Science & Art, University of Ahi Evran, Kırsehir
  • Mahmut Emir Department of Chemistry, Faculty of Science & Art, University of Ahi Evran, Kırsehir
  • Aslıhan Günel Department of Chemistry, Faculty of Science & Art, University of Ahi Evran, Kırsehir
  • Mehmet Çolak Department of Chemistry.; Faculty of Science.; University of Dicle.; Diyarbakır
  • Nurcan Karacan Department of Chemistry.; Faculty of Science.; University of Gazi.; Ankara
Keywords: Copper (II) complexes, DFT calculations, DNA binding, DNA cleavage, Schiff base complexes.

Abstract

Abstract. Three new copper(II) complexes (1-3) with general formula [Cu(HL)CH3COO] of N-salicyl-β-amino alcohol Schiff bases containing, (S)-(+)-phenyl glycinol, (1S, 2R)-2-amino-1, 2-diphenylethanol and 1, 1, 3-triphenyl-(R)-(+)-2-amino propanol, were synthesized.  Their structures were characterized by FTIR, LCMS, magnetic moment, molar conductance and elemental analysis data. DFT calculations proposed distorted square planar geometries for the complexes. The calculated IR spectra are in good agreement with the experimental IR spectra, confirming the proposed structures. Their interactions with calf thymus DNA were investigated and their binding constants Kb were found. Gel electrophoresis reveals that all complexes display significant nuclease activity against supercoiled pentry/d-topo plasmid DNA.

 

Resumen. Tres nuevos complejos de cobre (II) (1-3) con la fórmula general [Cu (HL) CH

3COO] de N-salicil-β-amino alcohol Schiff bases que contienen, (S) - (+) - fenilglicinol, (1S, 2R). Se sintetizaron -2-amino-1, 2-difeniletanol y 1, 1, 3-trifenil- (R) - (+) - 2-amino propanol. Sus estructuras se caracterizaron por FTIR, LCMS, momento magnético, conductancia molar y datos de análisis elemental. Los cálculos de DFT propusieron geometrías planas cuadradas distorsionadas para los complejos. Los espectros de IR calculados están en buena concordancia con los espectros de IR experimentales, confirmando las estructuras propuestas. Se investigaron sus interacciones con el ADN del timo de ternera y se encontraron sus constantes de unión Kb. La electroforesis en gel revela que todos los complejos muestran una actividad nucleasa significativa contra el ADN plasmídico pentry / d-topo superenrollado.

 

References

Sharma, S.; Chauhan, M.; Jamsheera, A.; Tabassum, S.; Arjmand, F. Inorg. Chim. Acta. 2017, 458, 8-27. DOI: 10.1016/j.ica.2016.12.011

Chinnaraja, E.; Arunachalam, R.; Choudhary, M.K.; Kureshy, R.I.;d Subramanian, P.S. Appl. Organomet. Chem. 2016, 30, 95-101. DOI: 10.1002/aoc.3404

Kumari, P.; Jakhar, A.; Khan, N.H.; Tak, R; Kureshy, R.I.; Abdi, S.H.R.; Bajaj, H.C. Catal. Commun. 2015, 69, 138-142. DOI: 10.1016/j.catcom.2015.06.002

Gao, Y-G.; Chen, N.; Wu, H-J.; Li, X-S Russ. J. Org. Chem. 2007, 43,1754-1756. DOI: 10.1134/S1070428007120020.

Hsieh, S-H.; Kuo, Y-P; Gau, H-M. Dalton Trans. 2007, 97-106. DOI:10.1039/b613212j

Tak, R.; Kumar, M.; Kureshy, R.I.; Choudhary, M. K.; Khan, N.H., Abdi, S.H.R.; Bajaj, H.C. RSC Adv. 2016, 6, 7693-7700. DOI: 10.1039/C5RA23600B

Santini, C.; Pellei, M.; Gandin, V.; Porchia, M.; Tisato,F.; Marzano, C. Chem. Rev. 2014, 815-862. DOI: 10.1021/cr400135x.

Tisato, F.; Marzano, C.; Porchia, M.; Pellei, M; Santini, C. Med. Res. Rev. 2010, 30,708-749. DOI: 10.1002/med.20174

Brissos, R. F.; Torrents, E; Mariana dos Santos Mello, F.; Carvalho Pires, W.; de Paula Silveira-Lacerda, E.; Caballero,A .B.; Caubet, A.; Massera, C.; Roubeau, O.; Teat S.J. and Gamez, P. Metallomics 2014, 6, 1853-1868. DOI:10.1039/C4MT00152D.

Lian, W-J.; Wang, X-T.; Xie, C-Z.; Tian, H.; Song, X-Q.; Pan, H-T.; Qiao, X; Xu, J-Y. Dalton Trans. 2016, 45, 9073-9087. DOI: 10.1039/C6DT00461J

Shokohi-pour, Z.; Chiniforoshan, H.; Momtazi-borojeni, A.A.; Notash, B. J. Photochem. Photobiol. B Biol. 2016, 162, 34-44. DOI: 10.1016/j.jphotobiol.2016.06.022

Yu, H.; Yang, Y.; Li, Q.; Ma,T.; Xu, J.; Zhu, T.; Xie, J.; Zhu, W.; Cao, Z.; Dong, K.; Huang, J.; Jia, L. Chem Biol Drug Des 2016, 87, 398-408. DOI 10.1111/cbdd.12669

Zhang, Z.; Gou, Y.; Wang, J.; Yang, K.; Qi, J.; Zhou, Z.; Liang, S.; Liang, H.; Yang, F. Eur. J. Med. Chem. 2016, 121, 399-409. DOI: 10.1111/cbdd.12669

Arjmand, F.; Muddassir, M.; Yousuf, I. J. Photochem. Photobiol. B Biol. 2014,136, 62-71. DOI: 10.1016/j.jphotobiol.2014.04.024

da Silveira, V.C.; Luz, J.S.; Oliveira, C.C.; Graziani, I.; Ciriolo, M.R.; da Costa Ferreira, A.M. J. Inorg. Biochem. 2008, 102, 1090-1103. DOI:10.1016/j.jinorgbio.2007.12.033

Dezhahang, Z.; Poopari, M.R.; Cheramy, J.; Xu, Y. Inorg. Chem. 2015, 54, 4539-4549. DOI: 10.1021/acs.inorgchem.5b00386

Ng, C. H. ; Chan, C.W.; Lai, J.W.; Ooi, I. H.; Chong, K. V.; Maah, M. J.; Seng, H. L. J. Inorg. Biochem. 2016, 160, 1-11. DOI: 10.1016/j.jinorgbio.2016.04.003.

Zhang, W.C.; Tang, X.; Lu, X. J. Inorg. Biochem. 2016, 156, 105-112. DOI: 10.1016/j.jinorgbio.2016.01.007

Zhou, X-Q; Li, Y.; Zhang, D-Y; Nie, Y; Li, Z-J.; Gu, W.; Liu, X.; Tian, J-L.; Yan, S-P. Eur. J. Med. Chem. 2016, 114, 244-256. DOI: 10.1016/j.ejmech.2016.02.055.

Arjmand, F.; Sayeed, F.; Muddassir, M. J. Photochem. Photobiol. B Biol. 2011, 103, 166-179. DOI: 10.1016/j.jphotobiol.2011.03.001

Amjad, M.; Sumrra, S.H.; Akram, M.S.; Chohan, Z.H. J. Enzyme Inhib. Med. Chem. 2016, 31, 88-97. DOI: 10.1080/14756366.2016.1220375

Yan, H.; Yang, L.; Chang, G-L.;Li, X.; Niu, M-J. Chinese J. Struct. Chem. 2016, 35, 465-471. DOI: 10.14102/j.cnki.0254-5861.2011-0989

Niu, M.; Li, Z.; Li, H.; Li, X.; Dou, J.; Wang, S. RSC Adv. 2015, 5, 37085-37095. DOI: 10.1039/C5RA00623F.

Çolak, M.; Demirel, N. Tetrahedron: Asymm. 2008, 19, 635-639. DOI: 10.1016/j.tetasy.2008.02.005.

Frisch, M.J. Gaussian 03W (Revision B.04). Gaussian. Inc. 2003.

Dennington, R. GaussView.W (Rev 2.1). Gaussian. Inc. 2000.

Chumakov, Y.M.; Antosyak, B.Y.; Tsapkov, V.I.; Bocelli, G.; Gulya, A.P. Russ. J. Coord. Chem. 2004, 30, 486-490.

Dey, M.; Rao, C.P.; Saarenketo P.; Rissanen, K.; Kolehmainen, E. Eur. J. Inorg. Chem. 2002 2207-2215.

Marmur, J. J. Mol. Biol.1961, 3, 208-218. DOI: 10.1016/S0022-2836(61)80047-8

Reichmann, M.E.; Rice, S.A.; Thomas, C.A.; Doty, P. J. Am. Chem. Soc., 1954, 76, 3047-3053. DOI: 10.1021/ja01640a067

Chen, F-J.; Xu, M.; Xi, P-X.;Liu, H-Y.; Zeng, Z-Z. Spectrochim. Acta - Part A Mol. Biomol. Spectrosc. 2011, 81, 21-27. DOI: 10.1016/j.saa.2011.05.020

Keller, B.O.; Sui, J.; Young, A.B.; Whittal, R.M. Anal. Chim. Acta, 2008, 627, 71-81. DOI: 10.1016/j.aca.2008.04.043

Kozlyuk, N.; Lopez, T.; Roth, P.; Acquaye, H. Inorg. Chim. Acta. 2015, 428, 176-184. DOI: 10.1016/j.ica.2014.12.034

Poyraz, M.; Sarı, M. Acta Crystallogr. Sect. E Crystallogr. Commun. 2017, 73, 209-212. DOI: 10.1107/S2056989017000780

Maloth, S.; Pal, S. Polyhedron. 2010, 29, 3257-3261. DOI: 10.1016/j.poly.2010.09.003.

Mansour, A.M. Inorg. Chim. Acta. 2013, 408, 186-192. DOI: 10.1016/j.ica.2014.12.034

Vafazadeh, R.; Hayeri, V.; Willis, A.C. Polyhedron, 2010, 29, 1810-1814. DOI: 10.1016/j.poly.2010.02.030.

Bytheway, I.; Wong, M.W. Chem. Phys. Lett. 1998, 282, 219-226. DOI: 10.1016/S0009-2614(97)01281-5

Socrates, G. Infrared and Raman characteristic group frequencies, John Wiley & Sons,Chichester, 2004.

40. Deacon, G.B.; Phillips, R.J. Coord.Chem.Rev. 2008, 33, 227-250.

Maslejova, A.; Boca, R.; Dlhhan, L; Papankova, B.; Svoboda, I.; Fuess, H. Chem.Phys.Lett. 2001, 347, 397-402.

Faniran, J.A; Patel, K.S., Baliar, J. Inorg. Nucl. Chem. 1974, 36, 1547-1551. DOI:10.1016/0022-1902(74)80621-4.

P.E. Aranha, M.P. dos Santos, S. Romera, E.R. Dockal, Polyhedron 26 (2007) 1373.

Rehman, S.U.; Sarwar, T.; Husain, M.A.; Ishqi, H.M.; Tabish, M. Arch. Biochem. Biophys. 2015, 576, 49-60. DOI: 10.1016/j.abb.2015.03.024

Sirajuddin, M.; Ali, S.; Badshah, A. J. Photochem. Photobiol. B Biol. 2013, 124, 1-19. DOI: 10.1016/j.jphotobiol.2013.03.013

Nakamoto, K.; Tsuboi, M.; Strahan, G.D. Drug-DNA Interactions, John Wiley & Sons, Hoboken, New Jersey,2008.

Brissos, R.F.; Torrents, E.; dos Santos Mello, F.M.; Pires, W.C.; de Paula Silveira-Lacerda, E.; Metallomics 2014, 1853-1868.

Inclan, M.; Albelda, M. T.; Frias, J. C.; Blasco, S.; Verdejo, B.; Serena, C.; Canela-Salat, C.; Diaz, M. D.; Garcia-Espana, A.; Garcia-Espana, E., J. Am. Chem. Soc. 2012, 134, 9644−9656

Norden, B.; Tjerneld , F.; Palm, E.; Biophys. Chem.1978, 8,1–15.

Published
04-22-2019