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Merck
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SML2652

Sigma-Aldrich

Peretinoin

≥97% (HPLC)

Sinónimos:

3,7,11,15-Tetramethyl-2,4,6,10,14-hexadecapentaenoic acid, (2E,4E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,4,6,10,14-pentaenoic acid, 4,5-Didehydrogeranyl geranoic acid, ACR, Acyclic retinoid, E 5166, E-5166, E5166, K 333, K-333, K333, NIK 333, NIK-333, NIK333, Polyprenoic acid, all-trans-3,7,11,15-Tetramethyl-2,4,6,10,14-hexadecapentaenoic acid

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About This Item

Fórmula empírica (notación de Hill):
C20H30O2
Número de CAS:
81485-25-8
Peso molecular:
302.45
Número MDL:
MFCD01742209
Código UNSPSC:
12352200
NACRES:
NA.77

Análisis

≥97% (HPLC)

formulario

powder

color

white to beige

solubilidad

DMSO: 2 mg/mL, clear

temp. de almacenamiento

2-8°C

InChI

1S/C20H30O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h8-9,11,13-15H,6-7,10,12H2,1-5H3,(H,21,22)/b14-8+,17-11+,18-13+,19-15+

Clave InChI

UUBHZHZSIKRVIV-KCXSXWJSSA-N

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Acciones bioquímicas o fisiológicas

Peretinoin is an orally active synthetic acyclic retinoid (ACR) whose in vivo anti-hepatocellular carcinoma (HCC) efficacy is attributed to its upregulatory activity toward retinoid nuclear receptors (RARbeta & RXRalpha), as well as negative regulation against sphingosine kinase 1 (SPHK1) expression and, thereby, sphingosine metabolic pathway. Peretinoin inhibits the replication of hepatitis B & C viruses in cultures (HBV & HCV EC50 = 9-25 μM) and shows in vivo efficacy in rodent models of hepatocarcinogenesis among rats (10, 40, or 80 mg/kg/day p.o.) and mice (0.03% or 0.06% in diet) subjected to chronic inflammation induction by diethylnitrosamine (DEN).

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Tetsuro Sano et al.
Nutrition and cancer, 51(2), 197-206 (2005-04-30)
We investigated the preventive effects of a synthetic acyclic retinoid, NIK-333, on the early and late events of hepatocarcinogenesis in male F344 rats treated with 3'-methyl-4-dimethylaminoazobenzene (3'-MeDAB). NIK-333 was administered once a day on consecutive days at a dose of
N Nakamura et al.
Biochemical and biophysical research communications, 207(1), 382-388 (1995-02-06)
HuH-7 cells, a human hepatoma-derived cell line, underwent apoptosis in response to all-trans 3, 7, 11, 15-tetramethyl- 2, 4, 6, 10, 14-hexadecapentaenoic acid, or acyclic retinoid. The retinoid-induced apoptosis was verified by a characteristic step-wise fragmentation of genomic DNA and
Y Yamada et al.
Molecular carcinogenesis, 10(3), 151-158 (1994-07-01)
All-trans-3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid (designated "acyclic retinoid") induced upregulation of the albumin gene expression at its transcriptional level, whereas all-trans-retinoic acid (RA) induced downregulation of the expression in both PLC/PRF/5 and HuH7 human hepatoma cell lines. These up- and down regulations of
Xian-Yang Qin et al.
Cancer prevention research (Philadelphia, Pa.), 9(3), 205-214 (2016-01-09)
Acyclic retinoid (ACR) is a promising drug under clinical trials for preventing recurrence of hepatocellular carcinoma. The objective of this study was to gain insights into molecular basis of the antitumorigenic action of ACR from a metabolic point of view.
Kazuhisa Murai et al.
International journal of molecular sciences, 19(2) (2018-01-24)
Hepatocellular carcinoma (HCC) frequently develops from hepatitis C virus (HCV) and hepatitis B virus (HBV) infection. We previously reported that peretinoin, an acyclic retinoid, inhibits HCV replication. This study aimed to examine the influence of peretinoin on the HBV lifecycle.
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