1477-57-2 Usage
Description
N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE), also known as Win 18446, is a white crystalline powder that is a carboxamide derivative of 1,8-diaminooctane. Each amino group in the molecule has a dichloroacetyl group attached, making it a potent inhibitor of aldehyde dehydrogenase 1a2 (ALDH1a2). N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE) has been found to inhibit the biosynthesis of retinoic acid from retinol in neonatal and adult murine testis and embryonic murine gonads. Additionally, it has been observed to down-regulate sex-related genes in zebrafish.
Uses
Used in Biochemical Research:
N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE) is used as a research compound for studying the inhibition of aldehyde dehydrogenase 1a2 (ALDH1a2) and its effects on the biosynthesis of retinoic acid from retinol in various biological systems.
Used in Pharmaceutical Industry:
N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE) is used as a potential therapeutic agent for targeting ALDH1a2, which may have implications in the treatment of various diseases and conditions related to the enzyme's activity.
Used in Toxicology and Environmental Studies:
N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE) is used as a tool in toxicology and environmental studies to investigate the effects of this compound on gene regulation, particularly in relation to sex-related genes in zebrafish and other model organisms.
Used in Drug Development:
N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE) is used as a lead compound in the development of new drugs targeting ALDH1a2, with potential applications in the treatment of diseases associated with the enzyme's dysregulation.
Biological Activity
win 18446 is a bis-(dichloroacetyl)-diamine which inhibits aldehyde dehydrogenase 1a2 (aldh1a2), with ic50 value of 300 nm [1].aldh1a2, expressed almost exclusively in the testes, localizes to developing germ cells within the seminiferous tubules and strongly binds retinol, but does not recognize acetaldehyde as a substrate, suggesting that aldh1a2 functions in testicular retinoic acid biosynthesis [1].in whole testes or germ cells isolated from mice at 2 days postpartum, win 18,446 alone (1 μm) or in combination with retinol significantly reduced the expression of stra8, a marker for retinoic acid activity [2].in male rabbits, oral administration of win 18446 at 200 mg/kg for 16 weeks substantially reduced intratesticular concentrations of retinoic acid, significantly impaired spermatogenesis, and resulted in infertility. reduced concentrations of intratesticular retinoic acid became obvious after only 4 weeks of treatment and preceded the decrease in sperm counts and the loss of mature germ cells in tissue samples. sperm counts and fertility recovered after treatment was discontinued [1].[1]. amory j k, muller c h, shimshoni j a, et al. suppression of spermatogenesis by bisdichloroacetyldiamines is mediated by inhibition of testicular retinoic acid biosynthesis. journal of andrology, 2011, 32(1): 111-119.[2]. hogarth c a, evanoff r, snyder e, et al. suppression of stra8 expression in the mouse gonad by win 18,446. biology of reproduction, 2011, 84(5): 957-965.
Safety Profile
Poison by intraperitoneal route.Human systemic effects by ingestion: nausea andvomiting. Human reproductive effects by ingestion:changes in spermatogenesis. An experimental teratogen.Other experimental reproductive effects. Human mutationdata reporte
Check Digit Verification of cas no
The CAS Registry Mumber 1477-57-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,7 and 7 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1477-57:
(6*1)+(5*4)+(4*7)+(3*7)+(2*5)+(1*7)=92
92 % 10 = 2
So 1477-57-2 is a valid CAS Registry Number.
