Synthesis, spectroscopic characterization and radiosensitizing properties of acetato-bridged copper(II) complexes with 5-nitroimidazole drugs

Ana Cecilia Valderrama-Negrón; Wendel A. Alves; Áurea S. Cruz; Sizue O. Rogero; Denise De Oliveira Silva

doi:10.1016/j.ica.2010.12.006

Synthesis, spectroscopic characterization and radiosensitizing properties of acetato-bridged copper(II) complexes with 5-nitroimidazole drugs

Ana Cecilia Valderrama-Negrón
, Wendel A. Alves
, Áurea S. Cruz
, Sizue O. Rogero
, Denise De Oliveira Silva

Research output: Contribution to journal › Article (Contribution to Journal) › peer-review

29 Scopus citations

Abstract

Three novel acetato-bridged dinuclear copper(II) complexes with 5-nitroimidazoles (CuAcNtrim) and the known copper-acetato-metronidazole have been prepared by an environment-friendly route and spectroscopically characterized. The CuAcNtrim compounds of formula [Cu₂(μ-O ₂CCH₃)₄Ntrim₂], where Ntrim = metronidazole (1), secnidazole (2), tinidazole (3) or nimorazole (4), exhibit dimeric copper-acetato paddle-wheel structures with Ntrim axial ligands coordinated to copper(II) ions through the N₃ atoms of the imidazole rings. EPR data indicate antiferromagnetic behavior for this novel series of copper complexes. The constant coupling has been found to decrease along with the increasing of basicity of the Ntrim axial ligand. The CuAcNtrim complexes and the correspondent Ntrim parent drugs have shown radiosensitizer properties for Hep2 (human larynx cancer) cell line in vitro. The best enhancement of radiosensitizer activity upon coordination of the Ntrim drug to copper(II) has been found for the nimorazole compound which has the strongest Cu-Ntrim bond and exhibits the highest lipophilicity within the series of CuAcNtrim complexes.

Translated title of the contribution	Síntesis, caracterización espectroscópica y propiedades radiosensibilizantes de complejos de cobre (II) con puentes de acetato con fármacos 5-nitroimidazol
Original language	English
Pages (from-to)	85-92
Number of pages	8
Journal	Inorganica Chimica Acta
Volume	367
Issue number	1
DOIs	https://doi.org/10.1016/j.ica.2010.12.006
State	Published - 28 Feb 2011
Externally published	Yes

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This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

5-Nitroimidazoles
Copper acetato
Gamma irradiation
Hep2 cells
Magnetic properties
Radiosensitizer properties

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10.1016/j.ica.2010.12.006

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@article{d46fc2ed1b084459b88d0fb5fe23fee3,

title = "Synthesis, spectroscopic characterization and radiosensitizing properties of acetato-bridged copper(II) complexes with 5-nitroimidazole drugs",

abstract = "Three novel acetato-bridged dinuclear copper(II) complexes with 5-nitroimidazoles (CuAcNtrim) and the known copper-acetato-metronidazole have been prepared by an environment-friendly route and spectroscopically characterized. The CuAcNtrim compounds of formula [Cu2(μ-O 2CCH3)4Ntrim2], where Ntrim = metronidazole (1), secnidazole (2), tinidazole (3) or nimorazole (4), exhibit dimeric copper-acetato paddle-wheel structures with Ntrim axial ligands coordinated to copper(II) ions through the N3 atoms of the imidazole rings. EPR data indicate antiferromagnetic behavior for this novel series of copper complexes. The constant coupling has been found to decrease along with the increasing of basicity of the Ntrim axial ligand. The CuAcNtrim complexes and the correspondent Ntrim parent drugs have shown radiosensitizer properties for Hep2 (human larynx cancer) cell line in vitro. The best enhancement of radiosensitizer activity upon coordination of the Ntrim drug to copper(II) has been found for the nimorazole compound which has the strongest Cu-Ntrim bond and exhibits the highest lipophilicity within the series of CuAcNtrim complexes.",

keywords = "5-Nitroimidazoles, Copper acetato, Gamma irradiation, Hep2 cells, Magnetic properties, Radiosensitizer properties, Copper acetato, 5-Nitroimidazoles, Magnetic properties, Radiosensitizer properties, Gamma irradiation, Hep2 cells",

author = "Valderrama-Negr{\'o}n, \{Ana Cecilia\} and Alves, \{Wendel A.\} and Cruz, \{{\'A}urea S.\} and Rogero, \{Sizue O.\} and \{De Oliveira Silva\}, Denise",

note = "Funding Information: The authors gratefully acknowledge the financial support from Brazilian agency Funda{\c c}{\~a}o de Amparo {\`a} Pesquisa do Estado de S{\~a}o Paulo (FAPESP) and the Ph.D. fellowship for A.C. Valderrama-Negron from Conselho Nacional de Desenvolvimento Cient{\'i}fico e Tecnol{\'o}gico (CNPq) . The authors are also thankful to E. Somessari and C. G. Silveira from CTR-IPEN for irradiation processes; A. Paduan-Filho, A.M.D.C. Ferreira and H. Toma from S{\~a}o Paulo University, for allowing the use of magnetometer, EPR and Guide-wave equipments, respectively.",

year = "2011",

month = feb,

day = "28",

doi = "10.1016/j.ica.2010.12.006",

language = "Ingl{\'e}s",

volume = "367",

pages = "85--92",

journal = "Inorganica Chimica Acta",

issn = "0020-1693",

publisher = "Elsevier B.V.",

number = "1",

}

Synthesis, spectroscopic characterization and radiosensitizing properties of acetato-bridged copper(II) complexes with 5-nitroimidazole drugs. / Valderrama-Negrón, Ana Cecilia; Alves, Wendel A.; Cruz, Áurea S. et al.
In: Inorganica Chimica Acta, Vol. 367, No. 1, 28.02.2011, p. 85-92.

Research output: Contribution to journal › Article (Contribution to Journal) › peer-review

TY - JOUR

T1 - Synthesis, spectroscopic characterization and radiosensitizing properties of acetato-bridged copper(II) complexes with 5-nitroimidazole drugs

AU - Valderrama-Negrón, Ana Cecilia

AU - Alves, Wendel A.

AU - Cruz, Áurea S.

AU - Rogero, Sizue O.

AU - De Oliveira Silva, Denise

N1 - Funding Information: The authors gratefully acknowledge the financial support from Brazilian agency Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) and the Ph.D. fellowship for A.C. Valderrama-Negron from Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) . The authors are also thankful to E. Somessari and C. G. Silveira from CTR-IPEN for irradiation processes; A. Paduan-Filho, A.M.D.C. Ferreira and H. Toma from São Paulo University, for allowing the use of magnetometer, EPR and Guide-wave equipments, respectively.

PY - 2011/2/28

Y1 - 2011/2/28

N2 - Three novel acetato-bridged dinuclear copper(II) complexes with 5-nitroimidazoles (CuAcNtrim) and the known copper-acetato-metronidazole have been prepared by an environment-friendly route and spectroscopically characterized. The CuAcNtrim compounds of formula [Cu2(μ-O 2CCH3)4Ntrim2], where Ntrim = metronidazole (1), secnidazole (2), tinidazole (3) or nimorazole (4), exhibit dimeric copper-acetato paddle-wheel structures with Ntrim axial ligands coordinated to copper(II) ions through the N3 atoms of the imidazole rings. EPR data indicate antiferromagnetic behavior for this novel series of copper complexes. The constant coupling has been found to decrease along with the increasing of basicity of the Ntrim axial ligand. The CuAcNtrim complexes and the correspondent Ntrim parent drugs have shown radiosensitizer properties for Hep2 (human larynx cancer) cell line in vitro. The best enhancement of radiosensitizer activity upon coordination of the Ntrim drug to copper(II) has been found for the nimorazole compound which has the strongest Cu-Ntrim bond and exhibits the highest lipophilicity within the series of CuAcNtrim complexes.

AB - Three novel acetato-bridged dinuclear copper(II) complexes with 5-nitroimidazoles (CuAcNtrim) and the known copper-acetato-metronidazole have been prepared by an environment-friendly route and spectroscopically characterized. The CuAcNtrim compounds of formula [Cu2(μ-O 2CCH3)4Ntrim2], where Ntrim = metronidazole (1), secnidazole (2), tinidazole (3) or nimorazole (4), exhibit dimeric copper-acetato paddle-wheel structures with Ntrim axial ligands coordinated to copper(II) ions through the N3 atoms of the imidazole rings. EPR data indicate antiferromagnetic behavior for this novel series of copper complexes. The constant coupling has been found to decrease along with the increasing of basicity of the Ntrim axial ligand. The CuAcNtrim complexes and the correspondent Ntrim parent drugs have shown radiosensitizer properties for Hep2 (human larynx cancer) cell line in vitro. The best enhancement of radiosensitizer activity upon coordination of the Ntrim drug to copper(II) has been found for the nimorazole compound which has the strongest Cu-Ntrim bond and exhibits the highest lipophilicity within the series of CuAcNtrim complexes.

KW - 5-Nitroimidazoles

KW - Copper acetato

KW - Gamma irradiation

KW - Hep2 cells

KW - Magnetic properties

KW - Radiosensitizer properties

KW - Copper acetato

KW - 5-Nitroimidazoles

KW - Magnetic properties

KW - Radiosensitizer properties

KW - Gamma irradiation

KW - Hep2 cells

UR - https://www.scopus.com/pages/publications/79551685895

U2 - 10.1016/j.ica.2010.12.006

DO - 10.1016/j.ica.2010.12.006

M3 - Artículo (Contribución a Revista)

AN - SCOPUS:79551685895

SN - 0020-1693

VL - 367

SP - 85

EP - 92

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

IS - 1

ER -

Synthesis, spectroscopic characterization and radiosensitizing properties of acetato-bridged copper(II) complexes with 5-nitroimidazole drugs

Abstract

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Keywords

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