Spectrochimica Acta Part A 66 (2007) 1171–1174
Synthesis, spectroscopic characterization and biological analysis
of a new palladium(II) complex with methionine sulfoxide
Pedro P. Corbi
a,∗
, Fl´ avia Cagnin
a
, Lilian P.B. Sabeh
b
,
Antonio C. Massabni
a
, Claudio M. Costa-Neto
b
a
Departamento de Qu´ ımica Geral e Inorgˆ anica, Instituto de Qu´ ımica, UNESP, Rua Prof. Francisco Degni s/n,
CP 355, CEP 14801-970 Araraquara, SP, Brazil
b
Departamento de Bioqu´ ımica e Imunologia, Faculdade de Medicina de Ribeir˜ ao Preto, USP, 14049-900 Ribeir˜ ao Preto, SP, Brazil
Received 10 February 2006; received in revised form 9 June 2006; accepted 9 June 2006
Abstract
A new palladium(II) complex with methionine sulfoxide was synthesized and characterized by a set of chemical and spectroscopic techniques.
Elemental and mass spectrometry analyses of the solid complex fit to the composition [Pd(C
5
H
10
NO
3
S)
2
]·H
2
O.
13
C NMR, [
1
H–
15
N] NMR and
infrared spectra indicate coordination of the amino acid to Pd(II) through the carboxylate and amino groups in a square planar geometry. The
complex is soluble in water.
Biological activity was evaluated by cytotoxic analysis using HeLa cells. Determination of cell death was assessed using a tetrazolium salt
colorimetric assay, which reflects the cells viability. After incubation for 48 h, 20% of cell death was achieved at a concentration of 200 mol L
-1
of the complex.
© 2006 Elsevier B.V. All rights reserved.
Keywords: Palladium(II); Methionine sulfoxide; Infrared spectroscopy;
15
N NMR; Antitumor; Cytotoxicity
1. Introduction
Platinum(II) complexes and palladium(II) analogues have
been prepared and studied as anticancer drugs since Rosenberg
in 1965 discovered the antitumoral properties of cisplatin, or cis-
diammindichloroplatinum(II) [1]. Cisplatin is particularly effec-
tive in treatment of testicular tumors, with a cure rate higher than
95% [2]. It is also used for treatment of ovaries, head and neck
cancer [3]. However, cisplatin is also a highly toxic drug. The
major side effects of cisplatin are nephrotoxicity, neurotoxicity
and also ototoxicity [3]. The interest in developing new drugs
that could act as cisplatin but with reduced side effects has stim-
ulated the synthesis of many new compounds, including amino
acid complexes. Palladium(II) complexes containing S and N
donor ligands have been prepared and biological assays showed
their activities against several tumor cells (HeLa, 3T3, JURKAT,
Pam212 and Pam-ras) [4]. Platinum(II) and palladium(II) com-
plexes with phenantroline and amino acids were also described
∗
Corresponding author. Tel.: +55 16 33016630; fax: +55 16 3322 7932.
E-mail addresses: pedrocorbi@yahoo.com, pedrcorb@posgrad.iq.unesp.br
(P.P. Corbi).
and displayed cytotoxic activities on Molt-4, a human leukemia
cell line [5]. Indeed, a new palladium(II) complex with the amino
acid deoxyalliin was obtained in our laboratories and biological
studies have shown its activity against HeLa and TM5 tumori-
genic cells [6].
Methionine sulfoxide (C
5
H
11
NO
3
S, metSO) is a sulfur-
containing amino acid of vegetal origin present in many natural
products of easy access, as carrots and onions [7,8]. Ni(II),
Co(II), Cu(II) and Fe(II) complexes with metSO were obtained
in our laboratories and previously described [9–11]. Pt(II) and
Pt(IV) complexes with metSO were also described in the liter-
ature [12]. However, no biological studies were described for
such complexes. The present work is dedicated to the synthe-
sis, structural characterization and antitumor studies of a new
palladium(II) complex with metSO.
2. Experimental
2.1. Reagents and equipments
dl-methionine sulfoxide, palladium(II) chloride and
lithium(II) chloride were, respectively, Acros, Aldrich and Mall-
1386-1425/$ – see front matter © 2006 Elsevier B.V. All rights reserved.
doi:10.1016/j.saa.2006.06.003