1 Chiral Platinum(II) Complexes Featuring Phosphine and Chloroquine Ligands as Cytotoxic and Monofunctional DNA-Binding Agents Wilmer Villarreal, *,† Legna Colina-Vegas, † Clayton Rodrigues de Oliveira, † Juan C. Tenorio, ‡ Javier Ellena, ‡ Fábio C. Gozzo, ∴ Marcia Regina Cominetti, ǁ Antonio G. Ferreira, † Marco Antonio Barbosa Ferreira, † Maribel Navarro, § Alzir A. Batista *,† † Departamento de Química, Universidade Federal de São Carlos - UFSCar, CEP. 13565-905; São Carlos - SP, Brazil. ‡ Instituto de Física de São Carlos, Universidade de São Paulo, CEP. 13560-970; São Carlos - SP, Brazil. ∴ Instituto de Química, Universidade Estadual de Campinas – UNICAMP, CEP. 13083-862; Campinas – SP, Brazil. ǁ Departamento de Gerontologia, Universidade Federal de São Carlos - UFSCar, CEP. 13565- 905; São Carlos - SP, Brazil. § Instituto Nacional de Metrologia, Qualidade e Tecnologia, INMETRO, CEP. 25250-020 Rio de Janeiro - RJ, Brazil Supporting Information Materials for synthesis Instrumentation Characterization of complexes 1-8. Fig. S1: IR spectrum of complexes 1 and 5 in KBr. Fig. S2-S9: 1 H- 1 H COSY, 1 H- 15 N HMBC, 1 H- 13 C HSQC and 1 H- 13 C HMBC NMR spectra of 5-8 in CD 2 Cl 2 at 298 K. Fig. S10: 31 P{ 1 H} NMR spectra of phosphine platinum(II) complexes (1-8) in CD 2 Cl 2 . Fig. S11: 195 Pt{ 1 H} NMR spectra of phosphine platinum(II) complexes (1,4-8) in CD 2 Cl 2 . Fig. S12-S14: MS and MS-MS spectrum of cis-[PtCl(CQ)(PPh 3 ) 2 ]PF 6 (5) in Acetone. Fig. S15-S17: MS spectrum of compounds 6-8 in Acetone. Fig. S18: Cyclic voltammograms of the complexes 5-8 in acetonitrile. Fig. S19: Spectrophotometric titration spectra of compounds with CT-DNA. Fig. S20: Effects of the concentration of complexes 5-8, CQ and CDDP on the conformation of pBR322 plasmid DNA. The Ri values of the complex:DNA ratio are 0.5 (A), 1.0 (B), 2.0 (C) and 4.0 (D). Molecular weight marker (MWM) and DNA in DMSO (10%). Fig. S21: (A) 1 H NMR spectrum of guanosine in DMSO; (B) spectrum of a mixture of (5) and an excess of guanosine (1:1.2) immediately after sample preparation, only resonances of free (X f ) and bound (X b ) guanosine are assigned; (C) the 1 H NMR spectra of (5) in DMSO.