ChemInform Abstract: 2‐ACETYLPYRIDINE THIOSEMICARBAZONES. 3. SELENIUM ANALOGS AS POTENTIAL ANTIMALARIAL AGENTS

Klayman, Daniel L.; Scovill, John P.; Bartosevich, J. F.; Mason, C.

doi:10.1002/chin.198147263

Cited by 4 publications

(10 citation statements)

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“…2-Acetylpyridine 4,4-dimethyl-3-selenosemicarbazone (Ap44mSe) was prepared by S -methylation of Ap44mT with methyl iodide in the presence of a base . This was followed by substitution of the S -methyl group by selenium using sodium hydrogen selenide under argon . The Cu II complexes were prepared following methods employed previously for Ap44mT and its complexes .…”

Section: Results and Discussionmentioning

confidence: 99%

“…38 This was followed by substitution of the S-methyl group by selenium using sodium hydrogen selenide under argon. 38 The Cu II complexes were prepared following methods employed previously for Ap44mT and its complexes. 18 Using cupric acetate provides both a coordinating coligand and a base to deprotonate the NH group of the selenosemicarbazone, which coordinates in its imino-selenolate anionic form.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Selenosemicarbazones have gained considerable attention due to their activity as antibacterial, antiparasitic, antiviral, and anticancer agents. − Significantly, selenosemicarbazones and their metal complexes have been observed to exhibit potent anticancer activity both in vitro − and in vivo with high tolerability. , Despite extensive investigations on the biological activity of selenosemicarbazones, further studies were required to elucidate their cellular targets and mechanisms of action. In this investigation, we compared the selectivity and mechanisms of action of the selenosemicarbazone, Ap44mSe, in comparison to its well characterized thiosemicarbazone counterparts, Ap44mT and Dp44mT.…”

Section: Discussionmentioning

confidence: 99%

“…2-Acetylpyridine 4,4-dimethyl-3-selenosemicarbazone (Ap44mSe). The ligand was synthesized following a published protocol, 38 with slight modifications. A suspension of 2-acetylpyridine 4,4-dimethyl-3-thiosemicarbazone (1 g, 4.5 mmol) in 10 mL of H 2 O was treated with 5 mL of 50% w/w aqueous NaOH.…”

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

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Novel Mechanism of Cytotoxicity for the Selective Selenosemicarbazone, 2-Acetylpyridine 4,4-Dimethyl-3-selenosemicarbazone (Ap44mSe): Lysosomal Membrane Permeabilization

et al. 2015

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Selenosemicarbazones show marked antitumor activity. However, their mechanism of action remains unknown. We examined the medicinal chemistry of the selenosemicarbazone, 2-acetylpyridine 4,4-dimethyl-3-selenosemicarbazone (Ap44mSe), and its iron and copper complexes to elucidate its mechanisms of action. Ap44mSe demonstrated a pronounced improvement in selectivity toward neoplastic relative to normal cells compared to its parent thiosemicarbazone. It also effectively depleted cellular Fe, resulting in transferrin receptor-1 up-regulation, ferritin down-regulation, and increased expression of the potent metastasis suppressor, N-myc downstream regulated gene-1. Significantly, Ap44mSe limited deleterious methemoglobin formation, highlighting its usefulness in overcoming toxicities of clinically relevant thiosemicarbazones. Furthermore, Cu-Ap44mSe mediated intracellular reactive oxygen species generation, which was attenuated by the antioxidant, N-acetyl-L-cysteine, or Cu sequestration. Notably, Ap44mSe forms redox active Cu complexes that target the lysosome to induce lysosomal membrane permeabilization. This investigation highlights novel structure-activity relationships for future chemotherapeutic design and underlines the potential of Ap44mSe as a selective anticancer/antimetastatic agent.

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Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Novel Mechanism of Cytotoxicity for the Selective Selenosemicarbazone, 2-Acetylpyridine 4,4-Dimethyl-3-selenosemicarbazone (Ap44mSe): Lysosomal Membrane Permeabilization

et al. 2015

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“…Biochemical and pharmacological properties of schiff bases have been extensively investigated owing to their potential applications such as antibacterial (1-2), antiviral (3)(4), anti-inflammatory (5)(6), anti-tubercular (7)(8), antileprosy (9), antileukemia (10) activities.…”

Section: Introductionmentioning

confidence: 99%

Antineoplastic Activities of Acetone Thiosemicarbazone against Ehrlich Ascites Carcinoma Cells Bearing Mice

Ali¹,

Jesmin²,

Islam³

et al. 2013

MJIWAS

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A schiff base acetone semicarbazone has been synthesized and characterized. Its anticancer activities have been studied against Ehrlich Ascites Carcinoma (EAC) cells in swiss albino mice by monitoring the parameters like tumour cell growth inhibition, tumour weight, survival time, peritoneal cells and haematological parameters. It was found that this compound significantly reduces tumour cell growth rate, decreases tumour weight and increases life span in comparison to those of EAC bearing mice. The test compound restored the depleted haematological parameters of EAC bearing mice towards normal. The compound also enhanced number of macrophages in normal mice. The results obtained were compared with those obtained with the standard drug bleomycin.

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Thiosemicarbazones from the Old to New: Iron Chelators That Are More Than Just Ribonucleotide Reductase Inhibitors

et al. 2009

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ChemInform Abstract: 2‐ACETYLPYRIDINE THIOSEMICARBAZONES. 3. SELENIUM ANALOGS AS POTENTIAL ANTIMALARIAL AGENTS

Abstract: S‐Methylierung der Acetylpyridinthiosemicarbazone (I) führt zu den Derivaten (II), die mit NaSeH unter Argon zu den Selenosemicarbazonen (III) reagieren; (IIIc) wird alternativ durch Umsetzen von Acetylpyridinhydrazon (IV) mit Phenylisoselenocyanat synthetisiert.

Cited by 4 publications

References 0 publications

Novel Mechanism of Cytotoxicity for the Selective Selenosemicarbazone, 2-Acetylpyridine 4,4-Dimethyl-3-selenosemicarbazone (Ap44mSe): Lysosomal Membrane Permeabilization

Novel Mechanism of Cytotoxicity for the Selective Selenosemicarbazone, 2-Acetylpyridine 4,4-Dimethyl-3-selenosemicarbazone (Ap44mSe): Lysosomal Membrane Permeabilization

Antineoplastic Activities of Acetone Thiosemicarbazone against Ehrlich Ascites Carcinoma Cells Bearing Mice

Thiosemicarbazones from the Old to New: Iron Chelators That Are More Than Just Ribonucleotide Reductase Inhibitors

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