Copper complexes of imidazole-2-, pyrrole-2- and indol-3-carbaldehyde thiosemicarbazones: Inhibitory activity against fungi and bacteria

Rodrı́guez-Argüelles, Marı́a C.; López-Silva, Estefania C.; Sanmartı́n, Jesús; Pelagatti, Paolo; Zani, Franca

doi:10.1016/j.jinorgbio.2005.07.018

Cited by 145 publications

(66 citation statements)

References 21 publications

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“…Research in recent years has demonstrated the ability of thiosemicarbazones and their complexes to be antifungal, antibacterial, antiviral, anti-inflammatory and chemotherapeutic agents, potentially useful for inhibiting the activities of cancer cells [7][8][9][10][11][12][13][14][15][16][17]. The cytotoxicity of these ligands is enhanced by coordination to metal ions such as copper, zinc, platinum and palladium.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel Cu(II), Pd(II) and Pt(II) Complexes with 8-Ethyl-2-hydroxytricyclo(7.3.1.02,7)tridecan-13-one-thiosemicarbazone: Antimicrobial and in Vitro Antiproliferative Activity

et al. 2016

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New Cu(II), Pd(II) and Pt(II) complexes, (Cu(L)(H 2 O) 2 (OAc)) ( 1 ), (Cu(HL)(H 2 O) 2 (SO 4 )) ( 2 ), (Cu(L)(H 2 O) 2 (NO 3 )) ( 3 ), (Cu(L)(H 2 O) 2 (ClO 4 )) ( 4 ), (Cu(L) 2 (H 2 O) 2 ) ( 5 ), (Pd(L)(OAc))H 2 O ( 6 ), and (Pt(L) 2 ) ( 7 ) were synthesized from 8-ethyl-2-hydroxytricyclo(7.3.1.0 2,7 )tridecan-13-one thiosemicarbazone ( HL ). The ligand and its metal complexes were characterized by IR, 1 H-NMR, 13 C-NMR, UV-Vis, FAB, EPR, mass spectroscopy, elemental and thermal analysis, magnetic susceptibility measurements and molar electric conductivity. The free ligand and the metal complexes have been tested for their antimicrobial activity against E. coli , S. enteritidis , S. aureus , E. faecalis, C. albicans and cytotoxicity against the NCI-H1573 lung adenocarcinoma, SKBR-3 human breast, MCF-7 human breast, A375 human melanoma and HL-60 human promyelocytic leukemia cell lines. Copper complex 2 exhibited the best antiproliferative activities against MCF-7 human breast cancer cells. A significant inhibition of malignant HL-60 cell growth was observed for copper complex 2 , palladium complex 6 and platinum complex 7 , with IC 50 values of 1.6 µM, 6.5 µM and 6.4 µM, respectively.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Novel Cu(II), Pd(II) and Pt(II) Complexes with 8-Ethyl-2-hydroxytricyclo(7.3.1.02,7)tridecan-13-one-thiosemicarbazone: Antimicrobial and in Vitro Antiproliferative Activity

et al. 2016

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“…2 Specific feature of TSCs and their metal complexes is their broad spectrum of biological properties including antiviral, antibacterial, antimalarial, antifungal and anticancer activity. 3,4,5,6 α-Nheterocyclic TSCs (HCTs) are known for their anticancer activity since the 1950s when 2-formylpyridine thiosemicarbazone was discovered to possess in vivo antileukemic activity in a mice model. 7 The best studied HCT to date is 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP), also referred to as Triapine, which has already been examined in several clinical phase I and II trials.…”

Section: Introductionmentioning

confidence: 99%

Effects of Terminal Dimethylation and Metal Coordination of Proline-2-formylpyridine Thiosemicarbazone Hybrids on Lipophilicity, Antiproliferative Activity, and hR2 RNR Inhibition

et al. 2014

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The nickel(II), copper(II) and zinc(II) complexes of the proline-thiosemicarbazone hybrids 3-methyl-(S)-pyrrolidine-2-carboxylate-2-formylpyridine thiosemicarbazone (L-Pro-FTSC or (S)-H 2 L 1 ) and 3-methyl-(R)-pyrrolidine-2-carboxylate-2-formylpyridine thiosemicarbazonehave been synthesized and characterized by elemental analysis, one-and two-dimensional 1 H and 13 C NMR spectroscopy, CD, UV−vis and ESI mass spectrometry. Compounds 13, 6 and 7 have been also studied by single crystal X-ray diffraction. Magnetic properties and solid state high-field EPR spectra of 2 over the range 50420 GHz were investigated. The complex formation processes of L-Pro-FTSC with nickel(II) and zinc(II) have been studied in aqueous solution due to the excellent water solubility of the complexes via pH-potentiometry, UV−vis and 1 H NMR spectroscopy. The results of the antiproliferative activity in vitro showed that dimethylation improves the cytotoxicity and hR2 RNR inhibition. Therefore introduction of more lipophilic groups into thiosemicarbazone-proline backbone becomes an option for the synthesis of more efficient cytotoxic agents of this family of compounds.3

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“…[14][15][16] It has already been shown, for example, that Pd-thiosemicarbazone complexes possess interesting antiproliferative effects on human breast cancer, including tumor cell lines resistant to cisplatin [17][18][19][20] and have also presented good antimycobacterial effects. 21 The presence of phosphine ligands in potential anti-cancer complexes is supposed to provide better cytotoxicity by enhancing lipophilicity -and consequently permeability through the cell membrane.…”

Section: Introductionmentioning

confidence: 99%

Palladium(II) complexes with thiosemicarbazones: syntheses, characterization and cytotoxicity against breast cancer cells and Anti-Mycobacterium tuberculosis activity

Maia¹,

Graminha²,

Pavan³

et al. 2010

J. Braz. Chem. Soc.

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= triphenylphosphine; Haptsc = 2-acetylpyridine-thiosemicarbazone; Hapmtsc = 2-acetylpyridine-N(4)-methyl-thiosemicarbazone and Happtsc = 2-acetylpyridine-N(4)-phenylthiosemicarbazone. All complexes were characterized by elemental analysis, IR, UV-Vis, 1 H and 31 P{ 1 H} NMR spectroscopies, and had their crystalline structures determined by X-ray diffractometry from single crystals. The monoanionic thiosemicarbazonate ligands act in a tridentate mode, binding to the metal through the pyridine nitrogen, the azomethine nitrogen and the sulfur atoms. The cytotoxic activity against the breast cancer cell line MDA-MB231 and the anti-Mycobacterium tuberculosis H 37 Rv ATCC 27294 activity were evaluated for the compounds. All Pd II complexes were highly active against the studied cell line, presenting similar values of IC 50 , around 5 μmol L -1 , while the clinically applied antitumor agent cisplatin was inactive. The compounds show remarkable anti-M. tuberculosis activities, presenting MIC values comparable or better than some commercial anti-M tuberculosis drugs.

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Copper complexes of imidazole-2-, pyrrole-2- and indol-3-carbaldehyde thiosemicarbazones: Inhibitory activity against fungi and bacteria

Cited by 145 publications

References 21 publications

Synthesis and Characterization of Novel Cu(II), Pd(II) and Pt(II) Complexes with 8-Ethyl-2-hydroxytricyclo(7.3.1.02,7)tridecan-13-one-thiosemicarbazone: Antimicrobial and in Vitro Antiproliferative Activity

Synthesis and Characterization of Novel Cu(II), Pd(II) and Pt(II) Complexes with 8-Ethyl-2-hydroxytricyclo(7.3.1.02,7)tridecan-13-one-thiosemicarbazone: Antimicrobial and in Vitro Antiproliferative Activity

Effects of Terminal Dimethylation and Metal Coordination of Proline-2-formylpyridine Thiosemicarbazone Hybrids on Lipophilicity, Antiproliferative Activity, and hR2 RNR Inhibition

Palladium(II) complexes with thiosemicarbazones: syntheses, characterization and cytotoxicity against breast cancer cells and Anti-Mycobacterium tuberculosis activity

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