title: A new platinum complex with tryptophan: synthesis, structural characterization, DFT studies and biological assays in vitro over human tumorigenic cells.
abstract: A new platinum(II) complex with the amino acid L-tryptophan (trp), named Pt-trp, was synthesized and characterized. Elemental, thermogravimetric and ESI-QTOF mass spectrometric analyses led to the composition [Pt(C11H11N2O2)2]⋅6H2O. Infrared spectroscopic data indicate the coordination of trp to Pt(II) through the oxygen of the carboxylate group and also through the nitrogen atom of the amino group. The (13)C CP/MAS NMR spectroscopic data confirm coordination through the oxygen atom of the carboxylate group, while the (15)N CP/MAS NMR data confirm coordination of the nitrogen of the NH2 group to the metal. Density functional theory (DFT) studies were applied to evaluate the cis and trans coordination modes of trp to platinum(II). The trans isomer was shown to be energetically more stable than the cis one. The Pt-trp complex was evaluated as a cytotoxic agent against SK-Mel 103 (human melanoma) and Panc-1 (human pancreatic carcinoma) cell lines. The complex was shown to be cytotoxic over the considered cells.
authors: Bioinorganic and Medicinal Chemistry Research Laboratory, Institute of Chemistry, University of Campinas - UNICAMP, P.O. Box 6154, 13083-970 Campinas, SP, Brazil.
authors: Marcos A
authors: MA
authors: Carvalho
authors: Laboratory of Bioassays and Signal Transduction, Department of Biochemistry, Institute of Biology, University of Campinas - UNICAMP, P.O. Box 6109, 13083-970 Campinas, SP, Brazil.
authors: Silvia M
authors: SM
authors: Shishido
authors: Bioinorganic and Medicinal Chemistry Research Laboratory, Institute of Chemistry, University of Campinas - UNICAMP, P.O. Box 6154, 13083-970 Campinas, SP, Brazil.
authors: Bárbara C
authors: BC
authors: Souza
authors: Bioinorganic and Medicinal Chemistry Research Laboratory, Institute of Chemistry, University of Campinas - UNICAMP, P.O. Box 6154, 13083-970 Campinas, SP, Brazil.
authors: Raphael E F
authors: RE
authors: de Paiva
authors: Dalton Mass Spectrometry Laboratory, Organic Chemistry Department, Institute of Chemistry, University of Campinas - UNICAMP, P.O. Box 6154, 13083-970 Campinas, SP, Brazil.
authors: Alexandre F
authors: AF
authors: Gomes
authors: Dalton Mass Spectrometry Laboratory, Organic Chemistry Department, Institute of Chemistry, University of Campinas - UNICAMP, P.O. Box 6154, 13083-970 Campinas, SP, Brazil.
authors: Fábio C
authors: FC
authors: Gozzo
authors: Coordination Chemistry Laboratory, Institute of Chemistry, University of Campinas - UNICAMP, P.O. Box 6154, 13083-970 Campinas, SP, Brazil.
authors: André L B
authors: AL
authors: Formiga
authors: Bioinorganic and Medicinal Chemistry Research Laboratory, Institute of Chemistry, University of Campinas - UNICAMP, P.O. Box 6154, 13083-970 Campinas, SP, Brazil. Electronic address: ppcorbi@iqm.unicamp.br.
authors: Pedro P
authors: PP
authors: Corbi
mesh_terms: D016475:3T3 Cells; D000818:Animals; D001681:Biological Assay / Q000379:methods*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D013058:Mass Spectrometry; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D010984:Platinum / Q000737:chemistry / Q000494:pharmacology*; D011789:Quantum Theory; D013055:Spectrophotometry, Infrared; D013818:Thermogravimetry; D014364:Tryptophan / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014732:Vibration
chemical_list: D010984:Platinum; D014364:Tryptophan
keywords: Antitumoral assays; ESI-QTOF-MS; L-Tryptophan; Molecular modeling; Platinum(II)