Antimicrobial and mutagenic properties of organotin(IV) complexes with isatin and N-alkylisatin bisthiocarbonohydrazones.
A new series of ligands is synthesised starting from thiocarbonohydrazide and isatin (H(2)itc) or N-alkylisatin (methyl, H(2)mtc; butyl, H(2)btc; pentyl, H(2)ptc); the X-ray structure of H(2)mtc is discussed. The bis imine ligands are reacted with diorganotin(IV) compounds, obtaining monometallic complexes. In order to establish unequivocally their coordination geometry, the X-ray structures of (C(2)H(5))(2)Sn(Hmtc)Cl.THF (THF, tetrahydrofuran) and (C(6)H(5))Sn(Hptc)Cl(2) are determined. In (C(2)H(5))(2)Sn(Hmtc)Cl.THF, the ligand results monodeprotonated and, essentially, monodentate through the sulphur atom, while in (C(6)H(5))Sn(Hptc)Cl(2) the ligand is still monodeprotonated but SNO tridentate. The organotin(IV) complexes of isatin and N-methylisatin exhibit good antibacterial activity, better than that of the corresponding N-butyl and N-pentylisatin derivatives. Gram positive bacteria are the most sensitive microorganisms. No growth inhibition of fungi is detected up to the concentration of 100 microg/ml. H(2)mtc shows mutagenic activity with and without metabolic activation, whereas no mutagenicity is found for its organotin complexes and for the other compounds.
Bacchi
A
A
Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Università di Parma, Parco Area delle Scienze, 17A, 43100 Parma, Italy.
Carcelli
M
M
Pelagatti
P
P
Pelizzi
G
G
Rodriguez-Arguelles
M C
MC
Rogolino
D
D
Solinas
C
C
Zani
F
F
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007510:Isatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009152:Mutagenicity Tests; D009153:Mutagens / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009947:Organotin Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D006835:Hydrazones; D009153:Mutagens; D009947:Organotin Compounds; D007510:Isatin