Synthesis, characterization, crystal structure and in vitro antiproliferative assays of the 2-thiouracilato(triphenylphosphine) gold(I) complex

Author(s)

Bormio Nunes, Julia H. ^[1] ; Simoni, Deborah A. ^[1] ; Braga, Lucia E. O. ^{[2, 3]} ; Ruiz, Ana Lucia T. G. ^{[4, 3]} ; de Carvalho, joao Ernesto ^[4] ; Corbi, Pedro P. ^[1]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, POB 6154, BR-13083970 Campinas, SP - Brazil

^[2] Univ Estadual Campinas, Piracicaba Dent Sch, Dept Physiol Sci, BR-13414903 Piracicaba, SP - Brazil

^[3] Univ Estadual Campinas, Chem Biol & Agr Pluridisciplinary Res Ctr CPQBA, BR-13148218 Paulinia, SP - Brazil

^[4] Univ Estadual Campinas, Fac Pharmaceut Sci, BR-13081970 Campinas, SP - Brazil

• Document type: Journal article
• Source: Journal of Molecular Structure; v. 1178, p. 169-178, FEB 15 2019.
• Web of Science Citations: 0

Abstract

A gold(I) complex with triphenylphosphine and 2-thiouracil, named 2-thiouracilato(triphenylphosphine) gold(I) (Ph3P-Au-tuH), was synthesized and characterized by a set of chemical and spectroscopic techniques. By elemental and mass spectrometric (ESI-QTOF-MS) analyses, the molecular formula AuC22H18N2OSP was proposed, corresponding to a 1:1 metal/ligand composition. Spectroscopic studies based on the infrared (IR) and nuclear magnetic resonance (NMR) of H-1, C-13 and P-31 evidenced the conversion of the chlorido(triphenylphosphine)gold(I) into the 2-thiouracilato(triphenylphosphine) gold(I), with substitution of Cl- by thiouracil. The crystal structure of the Ph3P-Au-tuH complex was determined by single crystal X-ray diffraction and shows the coordination of 2-thiouracil to gold(I) by the thiol group. Further, the in vitro antiproliferative assays of the 2-thiouracilato(triphenylphosphine)gold(I) complex showed its high activity when compared to the chlorido(triphenylphosphine)gold(I) one against lung (NCI-H460) and colon (HT29) tumor cell lines, with total growth inhibition (TGI) values of 26.7 and 28.5 mu g mL(-1), respectively, and also high selectivity towards tumor cells when compared to the normal cell line (HaCat). In addition, the Ph3P-Au-tuH complex showed a TGI value lower than 0.25 mu g mL(-1) for the leukemia cell line (K-562) with a selectivity index (SI) of 24.4, exhibiting a better in vitro cytotoxicity and selectivity than doxorubicin against this specific cell. (C) 2018 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 15/25114-4 - Synthesis of New Ag(I), Cu(II), Pd(II) and Pt(II) complexes based on sulfonamides and derivatives: antibacterial activities and application prospects on skin critically colonized wounds.
• Grantee: Pedro Paulo Corbi
• Support Opportunities: Regular Research Grants