Interaction of 2-formylpyridine thiosemicarbazonato copper (II) with ehrlich ascites tumor cells

Saryan, Leon A.; Mailer, Kathleen; Krishnamurti, Chitra; Antholine, William E.; Petering, David H.

doi:10.1016/0006-2952(81)90386-5

Cited by 100 publications

(53 citation statements)

References 14 publications

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“…2). Upon its addition to plasma or culture media, adduct fornation between CuL+ and Lewis bases is observed in the ESR spectrum at 77°K (7). The (Fig.…”

Section: Mr + 02mentioning

confidence: 96%

ESR of Copper and Iron Complexes with Antitumor and Cytotoxic Properties

Antholine¹,

Kalyanaraman²,

Petering³

1985

Environmental Health Perspectives

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The relatively few iron and copper metal complexes which have been examined in cells and tissues for their redox properties, radical generation properties, and antitumor activity are discussed for studies which utilized electron spin resonance spectroscopy (ESR). A common property of a number of metal complexes, which include bleomycin, adriamycin, and thiosemicarbazones described in this review, is that they are readily reduced by thiol compounds and oxidized by oxygen or reduced species of oxygen to produce radicals. Structural features ofthese reactions are identified by ESR spectroscopy in model systems and-often in cells. Furthermore, ESR spectroscopy has been most useful to probe the environment of the complexes in cells and to measure the rate of reduction of their oxidized forms. As a result of these studies, it is anticipated that more attention will be given to the exploration of redox-active metal complexes as drugs.

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“…2). Upon its addition to plasma or culture media, adduct fornation between CuL+ and Lewis bases is observed in the ESR spectrum at 77°K (7). The (Fig.…”

Section: Mr + 02mentioning

confidence: 96%

ESR of Copper and Iron Complexes with Antitumor and Cytotoxic Properties

Antholine¹,

Kalyanaraman²,

Petering³

1985

Environmental Health Perspectives

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“…7.460 (1) [a] Symmetry transformations used to generate equivalent atoms: i ϭ Ϫ x ϩ 1, Ϫy, Ϫz ϩ 1; ii ϭ Ϫ x ϩ 1, Ϫy, Ϫz. [35] The bond lengths in these complexes are quite similar to those of the free ligand.…”

Section: Crystal Structures Of the Oxadiazole Derivativesmentioning

confidence: 99%

New 1,3,4‐Oxadiazolecopper(II) Derivatives Obtained from Thiosemicarbazone Complexes

et al. 2003

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Pyridine‐2‐carbaldehyde thiosemicarbazone and pyridine‐2‐carbaldehyde 4N‐methyl thiosemicarbazone ligands (HLI and HLImm respectively) undergo an oxidative cyclization when treated with bromate or iodate, leading to 2‐amino‐5‐pyridin‐2‐yl‐1,3,4‐oxadiazole and 2‐methylamino‐5‐pyridin‐2‐yl‐1,3,4‐oxadiazole (HLII and HLIImm). This reaction occurs either with free ligands or when coordinated to copper(II). Some of the starting ([{Cu(LImm)(NO3)}2] (3), intermediate Cu(LI)(IO3)·(H2O) (1), [{Cu(LI)I}2] (2), [{Cu(LImm)Br}2] (4), and final compounds [{Cu(HLII)(H2O)3}2](SO4)2 (5), [{Cu(HLIImm)(H2O)2(SO4)}2]·2H2O (6), (HLII) (7), [HLIImm]·3H2O (8) have been isolated and characterized by elemental analyses, IR, UV‐visible, NMR, and EPR spectroscopy. The structures of 2, 3, 4, 5, 6, and 8, solved by X‐ray diffraction methods, contain dinuclear entities with either square‐pyramidal (2, 3, 4) or octahedral (5, 6) copper(II) ions. Structural and spectroscopic results suggest that ligand‐to‐metal charge transfer occurs in these compounds. The EPR spectra at 120 K exhibit rhombic (1, 3, 4), isotropic (2), and axial (5, 6) signals. Magnetic measurements show antiferromagnetic couplings for 2, 4, 5, and 6. The susceptibility data were fitted by the Bleaney−Bowers equation for copper(II) dimers. The obtained J/k values are −20.20, −8.85, −2.75, and −2.78 K for 2, 4, 5, and 6, respectively. However, ferromagnetic intradimeric interactions are present in 3 (J/k = +9.90 K) together with antiferromagnetic interdimer coupling (z′J′/k = −1.70 K). Magneto‐structural studies show the influence of the non‐thiosemicarbazone coligand in the magnetic behaviour of these complexes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…The monodentate sulfato group in 2 arises from the desulfurization of thiosemicarbazone ligands. In both cases, the crystal structures consist of dinuclear non-centrosymmetric entities where the thiosemicarbazone sulfur atoms act as bridges between copper(II) ions in distorted square-pyramidal environments.Pyridine-2-carbaldehyde thiosemicarbazone derivatives and their metal complexes exhibit relevant biological properties as cytotoxic effects against tumoral cells [1][2][3][4][5][6][7][8][9][10][11]. Comparatively, substituted related ligands have been less studied.…”

mentioning

confidence: 98%