COPPER(II) COMPLEXES WITH NEW N-SUBSTITUTED SULFONAMIDES – SYNTHESIS, CRYSTAL STRUCTURE AND EVALUATION OF THE NUCLEASE ACTIVITY

Authors

  • Andreea BODOKI Department of General and Inorganic Chemistry, Faculty of Pharmacy, UMF Iuliu Hatieganu, 400010 Ion Creanga, Cluj-Napoca, Romania. *Corresponding author: abota@umfcluj.ro https://orcid.org/0000-0001-7323-7293
  • Gloria ALZUET-PIÑA Department of Inorganic Chemistry, Faculty of Pharmacy, University of Valencia, 46100 Burjassot, Valencia, Spain https://orcid.org/0000-0003-0003-0413
  • Joaquín BORRÁS Department of Inorganic Chemistry, Faculty of Pharmacy, University of Valencia, 46100 Burjassot, Valencia, Spain
  • Tamara TOPALĂ Department of General and Inorganic Chemistry, Faculty of Pharmacy, UMF Iuliu Hatieganu, 400010 Ion Creanga, Cluj-Napoca, Romania https://orcid.org/0000-0001-8390-6403
  • Adriana HANGAN Department of General and Inorganic Chemistry, Faculty of Pharmacy, UMF Iuliu Hatieganu, 400010 Ion Creanga, Cluj-Napoca, Romania https://orcid.org/0000-0002-0944-3161
  • Gheorghe BORODI Department of Molecular and Biomolecular Service, National Institute for Research and Development for Isotopic and Molecular Technologies, 67-103 Donat, Cluj-Napoca, Romania https://orcid.org/0000-0003-4915-4169
  • Luminița OPREAN Department of General and Inorganic Chemistry, Faculty of Pharmacy, UMF Iuliu Hatieganu, 400010 Ion Creanga, Cluj-Napoca, Romania

DOI:

https://doi.org/10.24193/subbchem.2020.1.05

Keywords:

Cu(II) complexes, N-substituted sulfonamides, X-ray diffraction, nuclease activity

Abstract

Binary Cu(II) complexes of two new N-substituted sulfonamides, N-(pyridin-2-yl-methyl)biphenyl-4-sulfonamide (HL1) and N-bis-(pyridin-2-yl-methyl)biphenyl-4-4’-sulfonamide (H2L2), have been synthesized and characterized by X-ray diffraction, spectroscopic and electrochemical techniques. The structure of complex [Cu(L1)2] consists of a discrete monomeric Cu(II) species stabilized by π-π stacking interactions involving the pyridyl and phenyl rings of the coordinated ligands. In contrast, in the case of complex [Cu(L2)]n, each symmetrical  sulfonamide structure coordinates two Cu(II) ions, giving rise to a polymeric chain. Upon coordination, CuN4 chromophores with the N-pyrydil atoms in trans position are generated, and the coordination geometry of both complexes can be best described as highly distorted square-planar. The ability of complex [Cu(L1)2] to promote DNA cleavage with ascorbate activation was also evaluated; the complex has a moderate nuclease activity, being able to partially cleave supercoiled DNA to nicked circular and linear DNA. We herein also report the evaluation of the nuclease activity of complex Cu2(N-(pyridin-2-yl)biphenyl-4-sulfonamidate)4, previously characterized in terms of structure by our group.

References

Z. Yu; J. A. Cowan; Curr. Opin. in Chem. Biol., 2018, 43, 37-42

B. Dey; S. Thukral; S. Krishnan; M. Chakrobarty; S. Gupta; C. Manghani; V. Rani; Mol. Cell. Biochem., 2012, 365, 279-299

Z. Yang; N. E. Price; K. M. Johnson; Y. Wang; K. S. Gates; Nucleic Acids Res., 2017, 45, 6275-6283

K. Mjos; C. Orvig; Chem Rev., 2014, 114, 4540-4563

Z. Yu; J. A. Cowan; Angew. Chem. Int. Ed., 2017, 56, 2763-2766

R. Salvio; S. Volpi; R. Cacciapaglia; F. Sansone; L. Mandolini; A. Casnati; The Journal of Organic Chemistry, 2016, 81, 4728-4735

M. Soler; E. Figueras; J. Serrano-Plana; M. González-Bártulos; A. Massaguer; A. Company; M. A. Martínez; J. Malina; V. Brabec; L. Feliu; M. Planas; X. Ribas, M. Costas; Inorg. Chem., 2015, 54,10542-10558

A. M. Pisoschi; A. Pop; Eur. J. Med. Chem., 2015, 97, 55-74

C. Santini; M. Pellei; V. Gandin; M. Porchia; F. Tisato; C. Marzano; Chem Rev., 2014, 114:815-862

N. Hadjiliadis; E. Sletten; Metal Complex–DNA Interactions. John Wiley & Sons, New York, 2009

T. H. Maren; C.W. Conroy; J. Biol. Chem., 1993, 268, 26233-26239

A. K. Ghosh; L. M. Swanson; H. Cho; S. Leshchenko; K. A. Hussain; S. Kay; D. E. Walters; Y. Koh; H. Mitsuya; J. Med. Chem., 2005, 48, 3576-3585

A. Scozzafava; T. Owa; A. Mastrolorenzo; C. Supuran; Curr. Med. Chem., 2003, 10, 925-953

F. Zhong; G. Geng; B. Chen; T. Pan; Q. Li; H. Zhang; C. Bai; Org. Biomol. Chem., 2015, 13, 1792-1799

J. L. Garcia-Gimenez; J. Hernandez-Gil; A. Martinez-Ruiz; A. Castineiras; M. Liu-Gonzalez; F. V. Pallardo; J. Borras; G. Alzuet Pina; J. Inorg. Biochem., 2013, 121, 167-178

M. González-Álvarez; A. Pascual-Álvarez; L. del Castillo Agudo; A. Castiñeiras; M. Liu-González; J. Borrás; G. Alzuet-Piña; Dalton Trans., 2013, 42, 10244-10259

J. L. García-Giménez, M. González-Álvarez; M. Liu-González, B. Macías; J. Borrás, G. Alzuet; J. Inorg. Biochem., 2009, 103, 923-934

A. Bodoki; A. Hangan; L. Oprean; G. Alzuet; A. Castiñeiras; J. Borrás J; Polyhedron, 2009, 28, 2537-2544

A. Bodoki; A. Hangan; L. Oprean; A. Castiñeiras; J. Borrás; M. Bojita; Farmacia, 2008, 6, 607-614

A. Pascual-Álvarez; T. Topala; F. Estevan; F. Sanz; G. Alzuet-Piña; Eur. J. Inorg. Chem., 2016, 2016, 982-994

A. Hangan; R. Stan; A. Turza; L. Oprean, E. Pall, S. Gherorghe-Cetean; B. Sevastre; Trans. Met. Chem., 2017, 42, 153-164

A. Hangan; A. Turza; R. Stan; B. Sevastre, E. Pall; S. Cetean; L. Oprean; J. Chem. Sci., 2016, 128, 815-824

T. Topala; A. Pascual–Álvarez; M.A. Moldes–Tolosa; A. Bodoki A; A. Castiñeiras; J. Torres; C. del Pozo, J. Borrás; G. Alzuet–Piña; J. Inorg. Biochem., 2020, 202, 110823. doi:https://doi.org/10.1016/j.jinorgbio.2019.110823

A. Bodoki; G. Alzuet, A. Hangan; L. Oprean; F. Estevan, A. Castiñeiras; J. Borrás; Inorg. Chim. Acta, 2010, 363, 3139-3144

L. P. Battaglia; A. B. Corradi; G. Marcotrigiano; L. Menabue; G. C. Pellacani; Inorg. Chem., 1979, 18, 148-152

L Yang; D. Powell; R. Houser; Dalton Trans., 2007, 9, 955-964

B. Macias; M. V. Villa; M. Salgado; J. Borras; M. Gonzalez-Alvarez; F. Sanz; Inorg. Chim. Acta, 2006, 359, 1465-1472

M. Barquín; M. J. González Garmendia; L. Larrínaga; E. Pinilla; M.R. Torres; Inorg. Chim. Acta, 2009, 362, 2334-2340

L. Gutierrez; G Alzuet; J. Borrás; M. Liu-González; F. Sanz; A. Castiñeiras; Polyhedron 2001, 20, 703-709

J. Casanova; G. Alzuet; J. Latorre; J. Borras; Inorg. Chem., 1997, 36, 2052-2058

J. Casanova; G. Alzuet; S. Ferrer; J. Latorre, J. A. Ramirez; J. Borras; Inorg. Chim. Acta, 2000, 304,170-177

S. T. Frey; H. H. J. Sun; N. N. Murthy; K. D. Karlin; Inorg. Chim. Acta, 1996, 242, 329-338

J. L. García-Giménez; G. Alzuet; M. González-Álvarez; A. Castiñeiras; M. Liu-González; J. Borrás; Inorg. Chem., 2007, 46, 7178-7188

G. Alzuet, J. A. Real; J. Borrás’ R. Santiago-García; S. García-Granda; Inorg. Chem., 2001, 40, 2420-2423

C. Janiak; J. Chem. Soc., Dalton Trans., 2000, 21, 3885-3896

B. Macias, M. Villa; M. Salgado; J. Borras; M. Gonzalez-Alvarez; F. Sanz; Inorg. Chim. Acta, 2006, 359, 1465-1472

WINEPR Simfonia 1.25, Bruker Analytik GmbH, Karlsruhe, FRG, 1994

M. F. El-Shazly; A. El-Dissowky; T. Salem; M. Osman; Inorg. Chim. Acta, 1980, 40, 1-6

Y. Zhao; J. Zhu; W. He; Z. Yang; Y. Zhu; Y. Li; J. Zhang; Z. Guo; Chem.: Eur. J., 2006, 12, 6621-6629

K. J. Humphreys; K. D. Karlin; S. E. Rokita; J. Am. Chem. Soc., 2002, 124, 8055-8066

A. Eskandari; J. N. Boodram; P. B. Cressey; C. Lu; P. M. Bruno; M. T. Hemann; K. Suntharalingam; Dalton Trans., 2016, 45, 17867-17873

O. Dolomanov; L. Bourhis; R. Gildea; J. Howard; H. Puschmann; J. Appl. Crystallogr., 2009, 42, 339-341

G. Sheldrick; Acta Crystallogr., 2008, A64, 112-122

G. Sheldrick; Acta Crystallogr., 2015, C71, 3-8

C. F. Macrae; I. J. Bruno; J. A. Chisholm; P. R. Edgington; P. McCabe, E.Pidcock; L. Rodriguez-Monge, R.Taylor; J. van de Streek; P. A. Wood; J. Appl. Crystallogr., 2008, 41, 466-470

Downloads

Published

2020-03-20

How to Cite

BODOKI, A., ALZUET-PIÑA, G., BORRÁS, J., TOPALĂ, T., HANGAN, A., BORODI, G., & OPREAN, L. (2020). COPPER(II) COMPLEXES WITH NEW N-SUBSTITUTED SULFONAMIDES – SYNTHESIS, CRYSTAL STRUCTURE AND EVALUATION OF THE NUCLEASE ACTIVITY. Studia Universitatis Babeș-Bolyai Chemia, 65(1), 55–69. https://doi.org/10.24193/subbchem.2020.1.05

Issue

Section

Articles

Most read articles by the same author(s)

Similar Articles

<< < 19 20 21 22 23 24 25 > >> 

You may also start an advanced similarity search for this article.