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  • Product Name: Triapine
  • Price: $550.0/100mg $950.0/250mg $1600.0/1g
  • Purity: 98.0%
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Related CAS#:
200933-27-3 143621-35-6
236392-56-6

143621-35-6

143621-35-6 structure
143621-35-6 structure
Name 2-((3-Aminopyridin-2-yl)methylene)hydrazinecarbothioamide
Synonyms 2-[(3-Amino-2-pyridinyl)methylene]hydrazinecarbothioamide
2-[(3-Aminopyridin-2-yl)methylene]hydrazinecarbothioamide
3-Aminopyridine-2-carboxaldehyde thiosemicarbazone 3-AP PAN-811
(2E)-2-[(3-Amino-2-pyridinyl)methylene]hydrazinecarbothioamide
Hydrazinecarbothioamide, 2-[(3-amino-2-pyridinyl)methylene]-
Description Triapine is a novel inhibitor of the M2 subunit of ribonucleotide reductase (RR), and is a potent radiosensitizer.
Related Catalog
Target

Ribonucleotide reductase (RR)[1]
In Vitro Triapine is a potent derivative of α-heterocyclic carboxaldehyde thiosemicarbazone (HCT) that inhibits hRRM2 and p53R2 isoforms of the M2 subunit[1]. Triapine is thought to inhibit ribonucleotide reductase through its preformed iron chelate, rather than directly by removing iron from the active site. In cells containing less topoisomerase IIα fewer DNA strand breaks will be produced, and thus topoisomerase II poisons will be less inhibitory in the K/VP.5 cell line. The IC50s for Dp44mT growth inhibition are 48±9 nM and 60±12 nM, for K562 and K/VP.5 cells, respectively. The IC50s for Triapine growth inhibition are 476±39 nM and 661±69 nM for K562 and K/VP.5 cells, respectively[2]. PKIH and DpT Fe chelators show high antiproliferative activity against a range of tumor cell lines. Dp44mT shows the greatest antitumor efficacy with an IC50 that ranged from 0.005 to 0.4 μM. The average IC50 of Dp44mT over 28 cell types is 0.03±0.01 μM, which is significantly lower than that of Triapine (average IC50: 1.41±0.37 μM)[3].
In Vivo Triapine causes a significant increase (1.7-fold) in splenic weight when expressed as a percentage of total body weight (1.02±0.06%; n=25) compared with control mice (0.6±0.03%; n=27). In the long-term group, a significant increase in heart weight is observed after Dp44mT (0.4 mg/kg per day) (0.8±0.06%; n=4) compared with control mice (0.5±0.01%; n=6). A significant decrease in the expression of Ndrg1, TfR1, and VEGF1 in the liver is noted for Dp44mT- and Triapine (12 mg/kg per day)-treated animals. The decreased expression could be related to the increased liver Fe in both Dp44mT- and Triapine-treated mice[3].
Cell Assay An MTT assay is used to determine cell growth inhibition of CHO cells. Human leukemia K562 cells and K/VP.5 cells (a 26-fold etoposide-resistant K562-derived sub-line with decreased levels of topoisomerase IIα mRNA and protein) are maintained as suspension cultures in "MEM (Minimal Essential Medium Alpha, Invitrogen) containing 10% fetal calf serum (FCS). For growth inhibition assays, K562 and K/VP.5 cells are plated at a concentration of 1.5×105 cell/mL, and incubated 5 d with various concentrations of Dp44mT, Triapine or vehicle (DMSO) for 48 h, after which cells are counted on a model ZBF Coulter counter. The IC50 growth inhibitory concentration for each cell line is calculated from a non-linear least-squares fit to a 2-parameter logistic equation[2].
Animal Admin Mice[3] Female BALB/c nu/nu mice are used at 8-10 weeks of age. Tumor cells in culture are harvested, and 107 cells are suspended in Matrigel and injected s.c. into the right flanks of mice. After engraftment, tumor size is measured by Vernier calipers. Tumor volumes (in cubic millimeters) are calculated. When tumor volumes reached 120 mm3, i.v. treatment began (day 0). Chelators (e.g., Triapine) are dissolved in 15% propylene glycol in 0.9% saline and injected i.v. over 5 consecutive days per week for up to 7 weeks. Control mice are treated with vehicle alone.
References

[1]. Martin LK, et al. A dose escalation and pharmacodynamic study of Triapine and radiation in patients with locally advanced pancreas cancer. Int J Radiat Oncol Biol Phys. 2012 Nov 15;84(4):e475-81.

[2]. Yalowich JC, et al. The anticancer thiosemicarbazones Dp44mT and Triapine lack inhibitory effects as catalytic inhibitors or poisons of DNA topoisomerase IIα. Biochem Pharmacol. 2012 Jul 1;84(1):52-8.

[3]. Whitnall M, et al. A class of iron chelators with a wide spectrum of potent antitumor activity that overcomes resistance to chemotherapeutics. Proc Natl Acad Sci U S A. 2006 Oct 3;103(40):14901-6.
Density 1.5±0.1 g/cm3
Boiling Point 436.0±55.0 °C at 760 mmHg
Melting Point 234°C(lit.)
Molecular Formula C7H9N5S
Molecular Weight 195.245
Flash Point 217.5±31.5 °C
Exact Mass 195.057861
PSA 125.95000
LogP 0.98
Appearance white to light brown
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.720
Storage condition 2-8°C
Water Solubility DMSO: soluble10Meq/mL, clear
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301-H315-H319-H335
Precautionary Statements P261-P301 + P310-P305 + P351 + P338
Hazard Codes Xn
Risk Phrases 22-36/37/38
Safety Phrases 26
RIDADR UN 2811 6.1 / PGIII
HS Code 2933990090
HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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