Lipophilic gold(I) complexes with 1,3,4-oxadiazol-2-thione or 1,3-thiazolidine-2-thione moieties: synthesis and their cytotoxic and antimicrobial activities

• Published in: Biometals 2017-12, Vol.30 (6), p.841-857
• Main Authors: de Almeida, Angelina Maria, de Oliveira, Bruno Assis, de Castro, Pedro Pôssa, de Mendonça, Camille Carvalho, Furtado, Ricardo Andrade, Nicolella, Heloiza Diniz, da Silva, Vânia Lúcia, Diniz, Cláudio Galuppo, Tavares, Denise Crispim, Silva, Heveline, de Almeida, Mauro Vieira
• Format: Article
• Language: English
• Subjects: Adenocarcinoma; Animals; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Bacteria; Biochemistry; Biomedical and Life Sciences; Cell Biology; Cell Line, Tumor; Cervical cancer; Cervical carcinoma; Cervix; Chemistry Techniques, Synthetic; Chloramphenicol; Cisplatin; Colon; Colon cancer; Cricetinae; Cytotoxicity; Drug Evaluation, Preclinical; E coli; Escherichia coli; Escherichia coli - drug effects; Fibroblasts; Glioblastoma; Gold; Gram-negative bacteria; Gram-positive bacteria; Humans; Life Sciences; Ligands; Lipophilic; Lungs; Magnetic Resonance Spectroscopy; Mass spectrometry; Mass spectroscopy; Medicine/Public Health; Melanoma; Metastases; Mice; Microbial Sensitivity Tests; Microbiology; Minimum inhibitory concentration; NMR; Nuclear magnetic resonance; Organogold Compounds - chemical synthesis; Organogold Compounds - chemistry; Organogold Compounds - pharmacology; Pharmacology/Toxicology; Plant Physiology; Pseudomonas aeruginosa; Pseudomonas aeruginosa - drug effects; Skin; Staphylococcus aureus - drug effects; Structure-Activity Relationship; Thiones - chemistry; Toxicity; Tumor cell lines
• ISSN: 0966-0844; 1572-8773
• DOI: 10.1007/s10534-017-0046-6

Novel lipophilic gold(I) complexes containing 1,3,4-oxadiazol-2-thione or 1,3-thiazolidine-2-thione derivatives were synthesized and characterized by IR, high resolution mass spectrometry, and 1 H, 13 C 31 P NMR. The cytotoxicity of the compounds was evaluated considering cisplatin and/or auranofin as reference in different tumor cell lines: colon cancer (CT26WT), metastatic skin melanoma (B16F10), breast adenocarcinoma (MCF-7), cervical carcinoma (HeLa), glioblastoma (M059 J). Normal human lung fibroblasts (GM07492-A) and kidney normal cell (BHK-21) were also evaluated. The gold(I) complexes were more active than their respective free ligands and cisplatin. Furthermore, antibacterial activity was evaluated against Gram-positive bacteria Staphylococcus aureus ATCC 25213, Staphylococcus epidermidis ATCC 12228 and Gram-negative bacteria Escherichia coli ATCC 11229 and Pseudomonas aeruginosa ATCC 27853 and expressed as the minimum inhibitory concentration (MIC). The complexes exhibited lower MIC values when compared to the ligands and chloramphenicol against Gram-positive bacteria and Gram-negative bacteria. Escherichia coli was sensitive one to the action of gold(I) complexes.