Structural and spectral studies of copper(II) and nickel(II) complexes of pyruvaldehyde mixed bis{N(4)-substituted thiosemicarbazones}

Ackerman, Lily J.; Fanwick, Phillip E.; Green, Mark; John, Elizabeth; Running, William E.; Swearingen, John K.; Webb, James W.; West, Douglas X.

doi:10.1016/s0277-5387(99)00173-4

Cited by 65 publications

(42 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The scope of this route has been expanded to include a range of alkyl and alicyclic groups at N (4) . [35] Use of non-symmetrical dicarbonyls: West et al used the standard conditions, with H 2 SO 4 added, to prepare N (4) -methyl-and N (4) -ethyl-substituted bis(thiosemicarbazones) from 1-phenyl-1,2-propanedione [36] and phenylglyoxal. [17,[37][38][39] Pyruvaldehyde [40] and various alkyl-substituted glyoxals [41,42] have been prepared, along with a series of compounds derived from branched chain diketones.…”

Section: Route C-formation Of the C=n (1) Bondmentioning

confidence: 99%

Ligands for Molecular Imaging: The Synthesis of Bis(thiosemicarbazone) Ligands

Christlieb

Dilworth

2006

Chemistry A European J

View full text Add to dashboard Cite

Bis(thiosemicarbazones) have been of interest to chemists for over fifty years; they display antitumour, antibiotic and antiviral properties. Recently it has become apparent that they may also provide a convenient way of labelling biologically active molecules by using metallic radionuclides and/or fluorescence. Although apparently simple, the synthesis of bis(thiosemicarbazone) ligands can be problematic. This article provides a summary of the published literature, based on the synthetic strategies used and indicates some of the difficulties that may arise.

show abstract

Section: Route C-formation Of the C=n (1) Bondmentioning

confidence: 99%

Ligands for Molecular Imaging: The Synthesis of Bis(thiosemicarbazone) Ligands

Christlieb

Dilworth

2006

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…[7] It is, however, their use as delivery agents for radioactive copper in new copper-based radiopharmaceuticals and the hypoxic selectivity of certain copper bis(thiosemicarbazonate) complexes that has created much recent interest. [8][9][10][11][12][13][14][15][16][17][18][19][20] The biological characteristics of copper bis(thiosemicarbazonate) complexes derived from 1,2-diones are dependent on the nature of the "backbone" substituents in the ligand. The most detailed studies of these structureactivity relationship have been carried out in connection with hypoxia imaging.…”

Section: Introductionmentioning

confidence: 99%

Structural Trends in Divalent Benzil Bis(thiosemicarbazone) Complexes

et al. 2005

View full text Add to dashboard Cite

Redox-related changes in the biological properties of copper bis(thiosemicarbazones) are induced by the backbone of the ligand. To get information about how these changes depend on the structural parameters, three X-ray structures of complexes with different behaviour of the benzil bis(thiosemicarbazone) ligand have been determined. These include two almost planar copper(II) complexes with different grades of deprotonation in the ligand and a Zn II complex in which the ligand acts as a monoanion and a nitrate group is bonded to

show abstract

“…All test compounds were previously synthesized and their spectral characterization and representative structures of both the uncomplexed bis(thiosemicarbazones) and their complexes have been reported [8][9][10][11][12][13][14][15][16][17][18].…”

Section: Source Of Compoundsmentioning

confidence: 99%

The Cytotoxicity of Symmetrical and Unsymmetrical Bis(thiosemicarbazones) and Their Metal Complexes in Murine and Human Tumor Cells

Hall

Lackey

Kistler

et al. 2000

Arch. Pharm. Pharm. Med. Chem.

Self Cite

View full text Add to dashboard Cite

A number of thiosemicarbazones have been tested previously and herein are included three bis(thiosemicarbazones) for comparison to the previous derivatives. In general the uncomplexed thiosemicarbazones were more potent in the cytotoxic screens than the bis(thiosemicarbazone) except in the murine L1210 and the human colon SW480 screens. Mode of action studies have only demonstrated slight differences in the effects of the two types of compounds on nucleic acid metabolism. The symmetrical and unsymmetrical bis(thiosemicarbazones) complexes of copper, nickel, zinc, and cadmium have been examined to compare them to the heterocyclic N(4)‐substituted thiosemicarbazones metal complexes. These new derivatives demonstrated excellent activity against the growth of suspended lymphomas and leukemias although it should be pointed out that generally they were not as active as the copper complexes of N(4)‐substituted thiosemicarbazones. Nevertheless, selected bis(thiosemicarbazones) complexes were active against the growth of human lung MB9812, KB nasopharynx, epidermoid A431, glioma UM‐86, colon SW480, ovary 1‐A9, breast MCK‐7, and osteosarcoma Saos‐2. In human HL‐60 promyelocytic leukemia cells the complexes preferentially inhibited DNA and purine syntheses over 60 min. The regulatory enzyme of the de novo purine pathway, IMP dehydrogenase, appeared to be a major target of the complexes. However, minor inhibition of the activities of DNA polymerase α, PRPP‐amido transferase, ribonucleotide reductase, and nucleoside kinases occurred over the same time period. No doubt these effects of the complexes on nucleic acid metabolism were additive since the d[NTP] pool levels were reduced after 60 min as was DNA synthesis. The symmetrical and unsymmetrical bis(thiosemicarbazones) and their metal complexes did not cause as severe DNA fragmentation as the heterocyclic N(4)‐substituted thiosemicarbazone metal complexes; furthermore, their metabolic effects in the tumor cell were more focused on a single synthetic pathway.

show abstract

Structural and spectral studies of copper(II) and nickel(II) complexes of pyruvaldehyde mixed bis{N(4)-substituted thiosemicarbazones}

Cited by 65 publications

References 19 publications

Ligands for Molecular Imaging: The Synthesis of Bis(thiosemicarbazone) Ligands

Ligands for Molecular Imaging: The Synthesis of Bis(thiosemicarbazone) Ligands

Structural Trends in Divalent Benzil Bis(thiosemicarbazone) Complexes

The Cytotoxicity of Symmetrical and Unsymmetrical Bis(thiosemicarbazones) and Their Metal Complexes in Murine and Human Tumor Cells

Contact Info

Product

Resources

About