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SML2652

Sigma-Aldrich

Peretinoin

≥97% (HPLC)

Synonyme(s) :

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

Formule empirique (notation de Hill):
C20H30O2
Numéro CAS:
81485-25-8
Poids moléculaire :
302.45
Numéro MDL:
MFCD01742209
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥97% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

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+

Clé InChI

UUBHZHZSIKRVIV-KCXSXWJSSA-N

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Actions biochimiques/physiologiques

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).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Masaya Funaki et al.
Scientific reports, 7(1), 16978-16978 (2017-12-07)
Sphingosine-1-phospate is a potent bioactive lipid metabolite that regulates cancer progression. Because sphingosine kinase 1 and sphingosine kinase 2 (SPHK 1/2) are both essential for sphingosine-1-phospate production, they could be a therapeutic target in various cancers. Peretinoin, an acyclic retinoid
Xian-Yang Qin et al.
Proceedings of the National Academy of Sciences of the United States of America, 115(19), 4969-4974 (2018-04-25)
Hepatocellular carcinoma (HCC) is a highly lethal cancer that has a high rate of recurrence, in part because of cancer stem cell (CSC)-dependent field cancerization. Acyclic retinoid (ACR) is a synthetic vitamin A-like compound capable of preventing the recurrence of
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
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
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
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