Issue 27, 2008
From the journal:

Dalton Transactions

Nitric oxide binding and photodelivery based on ruthenium(ii) complexes of 4-arylazo-3,5-dimethylpyrazole

Mayreli Ortiz,*a   Mabel Torréns,a   José L. Mola,b   Pedro J. Ortiz,c   Alex Fragoso,d   Alicia Díaz,a   Roberto Cao,a   Pilar Prados,e   Javier de Mendoza,f   Antonio Otero,g   Antonio Antiñolog  and  Agustin Larag  

* Corresponding authors

a Laboratorio de Bioinorgánica, Facultad de Química, Universidad de La Habana, La Habana, Cuba
E-mail: mayreli@gmail.com

b Departamento de Química Orgánica, Facultad de Química, Universidad de La Habana, La Habana, Cuba

c Departamento de Química Física, Facultad de Química, Universidad de La Habana, La Habana, Cuba
E-mail: pedro@fq.uh.cu

d Departament de Enginyeria Quimica, Universitat Rovira i Virgili, Tarragona, España
E-mail: alex.fragoso@urv.cat

e Departamento de Química Orgánica, Universidad Autónoma de Madrid, Madrid, España

f Institute of Chemical Research of Catalonia, Tarragona, España

g Departamento de Química Orgánica, Inorgánica y Bioquímica, Universidad de Castilla-La Mancha, Ciudad Real, España

Abstract

Two fluorescent ligands, 3,5-dimethyl-4-(6′-sulfonylammonium-1′-azonaphthyl)pyrazole (dmpzn, 1) and 3,5-dimethyl-4-(4′-N,N′-dimethylaminoazophenyl)pyrazole (dmpza, 2) were obtained by condensation of ketoenolic derivatives with hydrazine. 1 and 2 formed the novel dinuclear complexes [(H2O)3ClRu(μ-L)2RuCl(H2O)3] (3 or 4) and [(H2O)(NO)Cl2Ru(μ-L)2RuCl2(NO)(H2O)] (6 or 7) (where L = 1 or 2, respectively) which were characterized by IR, NMR and elemental analysis. The nitrosyl complexes were prepared by bubbling purified nitric oxide through methanol solutions of the corresponding ruthenium(II) chloroderivative or by reaction of the appropriate ligands with Ru(NO)Cl3. Complexes 3 and 4 were found to bind NO, resulting in an increase in fluorescence. Ligand 1 also formed the mononuclear nitrosyl complex [Ru(NO)(bpy)2(dmpzn)]Cl2 (8) which released NO in water at physiological pH and in the solid state as revealed by fluorescence and IR measurements, respectively.

Graphical abstract: Nitric oxide binding and photodelivery based on ruthenium(ii) complexes of 4-arylazo-3,5-dimethylpyrazole

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Article information

DOI
https://doi.org/10.1039/B718645B
Article type
Paper
Submitted
03 Dec 2007
Accepted
14 Apr 2008
First published
20 May 2008

Dalton Trans., 2008, 3559-3566

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Nitric oxide binding and photodelivery based on ruthenium(II) complexes of 4-arylazo-3,5-dimethylpyrazole

M. Ortiz, M. Torréns, J. L. Mola, P. J. Ortiz, A. Fragoso, A. Díaz, R. Cao, P. Prados, J. de Mendoza, A. Otero, A. Antiñolo and A. Lara, Dalton Trans., 2008, 3559 DOI: 10.1039/B718645B

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