63618-91-7

Basic information

• Product Name: ATSM
• Synonyms: ATSM;Hydrazinecarbothioamide, 2,2'-(1,2-dimethyl-1,2-ethanediylidene)bis[N-methyl-;(1,1'-Butane-2,3-diylidenebishydrazine)-2,2'-diylidenebis(methylaminomethanethiol);1,1'-(Butane-2,3-diylidene)bis(4-methylthiosemicarbazide);2,3-Butanedione bis(4-methylthiosemicarbazone);2,3-Butanedione bis[mercapto(methylamino)methylenehydrazone];Biacetyl bis(4-methylthiosemicarbazone)
• CAS NO: 63618-91-7
• Molecular Formula: C₈H₁₆N₆S₂
• Molecular Weight: 260.3828
• Mol File: 63618-91-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 355.7°Cat760mmHg
• Flash Point: 168.9°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 3.07E-05mmHg at 25°C
• Refractive Index: 1.621
• PKA: 9.50±0.70(Predicted)
• CAS DataBase Reference: ATSM(CAS DataBase Reference)
• NIST Chemistry Reference: ATSM(63618-91-7)
• EPA Substance Registry System: ATSM(63618-91-7)

Safety Data

• Hazardous Substances Data: 63618-91-7(Hazardous Substances Data)

Usage

Chemical Properties

Colourless crystals

InChI:InChI=1/C8H16N6S2/c1-5(11-13-7(15)9-3)6(2)12-14-8(16)10-4/h1-4H3,(H2,9,13,15)(H2,10,14,16)

Upstream product

• 431-03-8 dimethylglyoxal 
• 6610-29-3 4-methylthiosemicarbazide 

Relevant articles and documents

Controlled axial coordination: Solid-phase synthesis and purification of metallo-radiopharmaceuticals

(Chemical Equation Presented) No sweat PET: Controlled axial coordination of pseudo-square-planar zinc(II) complexes to 4-(dimethylamino)pyridine- functionalized polystyrene resin facilitates the synthesis (by transmetalation) and purification (by selective ligation) of metallo-radiopharmaceuticals. These complexes have potential as positron emission tomography (PET) imaging agents.

Oxidative Release of Copper from Pharmacologic Copper Bis(thiosemicarbazonato) Compounds

Intracellular delivery of therapeutic or analytic copper from copper bis-thiosemicabazonato complexes is generally described in terms of mechanisms involving one-electron reduction to the Cu(I) analogue by endogenous reductants, thereby rendering the metal ion labile and less strongly coordinating to the bis-thiosemicarbazone (btsc) ligand. However, electrochemical and spectroscopic studies described herein indicate that one-electron oxidation of CuII(btsc) and ZnIIATSM (btsc = diacetyl-bis(4-methylthiosemicarbazonato)) complexes occurs within the range of physiological oxidants, leading to the likelihood that unrecognized oxidative pathways for copper release also exist. Oxidations of CuII(btsc) by H2O2 catalyzed by either myeloperoxidase or horseradish peroxidase, by HOCl and taurine chloramine (which are chlorinating agents generated primarily in activated neutrophils from MPO-catalyzed reactions), and by peroxynitrite species (ONOOH, ONOOCO2-) that can form under certain conditions of oxidative stress are demonstrated. Unlike reduction, the oxidative reactions proceed by irreversible ligand oxidation, culminating in release of Cu(II). 2-Pyridylazoresorcinol complexation was used to demonstrate that Cu(II) release by reaction with peroxynitrite species involved rate-limiting homolysis of the peroxy O-O bond to generate secondary oxidizing radicals (NO2?, ?OH, and CO3?-). Because the potentials for CuII(btsc) oxidation and reduction are ligand-dependent, varying by as much as 200 mV, it is clearly advantageous in designing therapeutic methodologies for specific treatments to identify the operative Cu-release pathway.

A novel dinuclear cobalt-bis(thiosemicarbazone) complex as a cocatalyst to enhance visible-light-driven H2 evolution on CdS nanorods and a mechanism discussion

Photocatalytic water splitting to produce hydrogen has gradually become a research hotspot in recent years, and molecular cocatalysts especially cobalt-based complexes as proton reduction cocatalysts have attracted wide attention due to their high activit

Unravelling the antitumoral potential of novel bis(thiosemicarbazonato) Zn(II) complexes: structural and cellular studies

The development of pharmacologically active compounds based on bis(thiosemicarbazones) (BTSC) and on their coordination to metal centers constitutes a promising field of research. We have recently explored this class of ligands and their Cu(II) complexes for the design of cancer theranostics agents with enhanced uptake by tumoral cells. In the present work, we expand our focus to aliphatic and aromatic BTSC Zn(II) complexes bearing piperidine/morpholine pendant arms. The new complexes ZnL1–ZnL4 were characterized by a variety of analytical techniques, which included single-crystal X-ray crystallography for ZnL2 and ZnL3. Taking advantage of the fluorescent properties of the aromatic complexes, we investigated their cellular uptake kinetics and subcellular localization. Furthermore, we tried to elucidate the mechanism of action of the cytotoxic effect observed in human cancer cell line models. The results show that the aliphatic complexes (ZnL1 and ZnL2) have a symmetrical structure, while the aromatic counterparts (ZnL3 and ZnL4) have an asymmetrical nature. The cytotoxic activity was higher for the aromatic BTSC complexes, as well as the cellular uptake, evaluated by measurement of intracellular Zn accumulation. Among the most active complexes, ZnL3 presented the fastest uptake kinetics and lysosomal localization assessed by live-cell microscopy. Detailed studies of its impact on cellular production of reactive oxygen species and impairment of lysosomal membrane integrity reinforced the influence of the pendant piperidine in the biological performance of aromatic BTSC Zn(II) complexes.