500579-04-4

Basic information

• Product Name: 2,2'-[[Dihydro-2-(4-pyridinyl)-1,3(2H,4H)-pyrimidinediyl]bis(methylene)]bis[N,N-dimethylbenzenamine
• Synonyms: 2,2'-[[Dihydro-2-(4-pyridinyl)-1,3(2H,4H)-pyrimidinediyl]bis(methylene)]bis[N,N-dimethylbenzenamine;GANT 61;NSC 136476;Benzenamine, 2,2'-[[dihydro-2-(4-pyridinyl)-1,3(2H,4H)-pyrimidinediyl]bis(methylene)]bis[N,N-dimethyl-;2,2'-[[Dihydro-2-(4-pyridinyl)-1,3(2H,4H)-pyrimidinediyl]bis(methylene)]bis[N,N-dimethylbenzenamine] GANT61;GNT61;GANT61, >=98%;GANT-61,NSC 136476
• CAS NO: 500579-04-4
• Molecular Formula: C27H35N5
• Molecular Weight: 429.61
• Product Categories: Inhibitors
• Mol File: 500579-04-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 548.999 °C at 760 mmHg
• Flash Point: 285.825 °C
• Appearance: white to off-white/
• Density: 1.135 g/cm³
• Storage Temp.: Store at -20°C
• Solubility: DMSO: >2mg/mL
• PKA: 5.97±0.10(Predicted)
• CAS DataBase Reference: 2,2'-[[Dihydro-2-(4-pyridinyl)-1,3(2H,4H)-pyrimidinediyl]bis(methylene)]bis[N,N-dimethylbenzenamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-[[Dihydro-2-(4-pyridinyl)-1,3(2H,4H)-pyrimidinediyl]bis(methylene)]bis[N,N-dimethylbenzenamine(500579-04-4)
• EPA Substance Registry System: 2,2'-[[Dihydro-2-(4-pyridinyl)-1,3(2H,4H)-pyrimidinediyl]bis(methylene)]bis[N,N-dimethylbenzenamine(500579-04-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 500579-04-4(Hazardous Substances Data)

Usage

Uses

GANT61 is an inhibitor for GLI1 as well as GLI2-induced transcription, inhibits hedgehog, displays selectivity over other pathways, such as TNF and glucocorticoid receptor gene transactivation.

Biochem/physiol Actions

GANT61 blocks hedgehog pathway signaling by inhibiting the transcripional activity of Gli1 (IC50 = 5 μM). GANT 61 led to a regression of 22Rv1 human prostate tumor cell xenografts in nude mice.

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 

Relevant articles and documents

Chemical, computational and functional insights into the chemical stability of the Hedgehog pathway inhibitor GANT61

This work aims at elucidating the mechanism and kinetics of hydrolysis of GANT61, the first and most-widely used inhibitor of the Hedgehog (Hh) signalling pathway that targets Glioma-associated oncogene homologue (Gli) proteins, and at confirming the chemical nature of its bioactive form. GANT61 is poorly stable under physiological conditions and rapidly hydrolyses into an aldehyde species (GANT61-A), which is devoid of the biological activity against Hh signalling, and a diamine derivative (GANT61-D), which has shown inhibition of Gli-mediated transcription. Here, we combined chemical synthesis, NMR spectroscopy, analytical studies, molecular modelling and functional cell assays to characterise the GANT61 hydrolysis pathway. Our results show that GANT61-D is the bioactive form of GANT61 in NIH3T3 Shh-Light II cells and SuFu?/? mouse embryonic fibroblasts, and clarify the structural requirements for GANT61-D binding to Gli1. This study paves the way to the design of GANT61 derivatives with improved potency and chemical stability.