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SML2652

Sigma-Aldrich

Peretinoin

≥97% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):
C20H30O2
CAS-Nummer:
81485-25-8
Molekulargewicht:
302.45
MDL-Nummer:
MFCD01742209
UNSPSC-Code:
12352200
NACRES:
NA.77

Assay

≥97% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 2 mg/mL, clear

Lagertemp.

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+

InChIKey

UUBHZHZSIKRVIV-KCXSXWJSSA-N

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Biochem./physiol. Wirkung

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).

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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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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