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Chemical Structure| 81485-25-8 Chemical Structure| 81485-25-8

Structure of Peretinoin
CAS No.: 81485-25-8

Chemical Structure| 81485-25-8

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Peretinoin, an acyclic retinoid, can alter lipid metabolism and inhibit HCV RNA amplification and virus release.

Synonyms: NIK333

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Product Details of Peretinoin

CAS No. :81485-25-8
Formula : C20H30O2
M.W : 302.45
SMILES Code : CC(C)=CCC/C(C)=C/CC/C(C)=C/C=C/C(C)=C/C(O)=O
Synonyms :
NIK333
MDL No. :MFCD01742209
InChI Key :UUBHZHZSIKRVIV-KCXSXWJSSA-N
Pubchem ID :6437836

Safety of Peretinoin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Human liver cells (HepG2) 1 µM 24 hours Peretinoin did not alter APOC3 mRNA or secreted APOC3 protein levels in HepG2 cells, whereas cyclic retinoids significantly elevated these levels. Arterioscler Thromb Vasc Biol. 2020 Mar;40(3):656-669
Huh-7.5 cells 10-40 µM 24-72 hours To evaluate the time-dependent effect of Peretinoin on HCV replication across different genotypes. Results showed that Peretinoin suppressed RNA replication in a time-dependent manner for all genotypes tested. Sci Rep. 2014 Apr 15;4:4688
Huh-7 cells 10, 25, 50 µM 48 hours Peretinoin significantly reduced mRNA levels, protein expression, and enzymatic activity of SPHK1. Sci Rep. 2017 Dec 5;7(1):16978
Huh7 cells 10, 20, 30 µM 5 days Peretinoin strongly repressed the levels of HBV-DNA, cccDNA, and pregenomic RNA without cytotoxicity Int J Mol Sci. 2018 Jan 23;19(2):108
HepG2.2.15 cells 5, 10, 25, 50 µM 5 days Peretinoin significantly reduced the levels of intracellular HBV-DNA, nuclear cccDNA, and HBV transcript at a concentration that did not induce cytotoxicity Int J Mol Sci. 2018 Jan 23;19(2):108
Huh-7.5 cells 5-50 µM 72 hours To assess the effect of Peretinoin on cell growth. Results showed that the cell numbers were identical under the conditions tested. Sci Rep. 2014 Apr 15;4:4688
Huh-7.5 cells 1-100 µM 72 hours To evaluate the inhibitory effect of Peretinoin on HCV RNA replication. Results showed that Peretinoin inhibited the replication of H77S.3/GLuc2A in a dose-dependent manner. Sci Rep. 2014 Apr 15;4:4688
Primary human valvular interstitial cells (VIC) 1 µM thoursee weeks Peretinoin attenuated PM-induced human VIC calcification to a similar extent as ATRA. Arterioscler Thromb Vasc Biol. 2020 Mar;40(3):656-669
Human coronary artery smooth muscle cells (SMC) 1 µM thoursee weeks Peretinoin significantly attenuated OM-induced human SMC calcification to a similar level as seen with ATRA stimulation. Arterioscler Thromb Vasc Biol. 2020 Mar;40(3):656-669

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice SPHK1 knockout mice Intraperitoneal injection 25 mg/kg Single injection, until 40 weeks of age DEN-induced hepatoma was fewer and less frequent in SPHK1 knockout mice compared to wild-type mice, indicating a crucial role of SPHK1 in hepatocarcinogenesis. Sci Rep. 2017 Dec 5;7(1):16978
Human Patients with HCV-related hepatocellular carcinoma Oral 600 mg/day or 300 mg/day Once daily for up to 2 years To evaluate the effects of Peretinoin on survival in patients with HCV-related hepatocellular carcinoma. Results showed that the 600 mg/day group had significantly longer survival than the placebo group in Child-Pugh A classified patients. J Gastroenterol. 2015 Jun;50(6):667-74

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT01640808 Hepatic Neoplasm Malignant Rec... More >>urrent Less << Phase 3 Unknown March 2017 -

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.31mL

0.66mL

0.33mL

16.53mL

3.31mL

1.65mL

33.06mL

6.61mL

3.31mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

[1]Shimakami T, Honda M, et al. The acyclic retinoid Peretinoin inhibits hepatitis C virus replication and infectious virus release in vitro. Sci Rep. 2014 Apr 15;4:4688.

[2]Honda M, Yamashita T, et al. Peretinoin, an acyclic retinoid, improves the hepatic gene signature of chronic hepatitis C following curative therapy of hepatocellular carcinoma. BMC Cancer. 2013 Apr 15;13:191.

[3]Honda M, Yamashita T, Yamashita T, Arai K, Sakai Y, Sakai A, Nakamura M, Mizukoshi E, Kaneko S. Peretinoin, an acyclic retinoid, improves the hepatic gene signature of chronic hepatitis C following curative therapy of hepatocellular carcinoma. BMC Cancer. 2013 Apr 15;13:191

[4]Funaki M, Kitabayashi J, Shimakami T, Nagata N, Sakai Y, Takegoshi K, Okada H, Murai K, Shirasaki T, Oyama T, Yamashita T, Ota T, Takuwa Y, Honda M, Kaneko S. Peretinoin, an acyclic retinoid, inhibits hepatocarcinogenesis by suppressing sphingosine kinase 1 expression in vitro and in vivo. Sci Rep. 2017 Dec 5;7(1):16978

[5]Okada H, Takabatake R, Honda M, Takegoshi K, Yamashita T, Nakamura M, Shirasaki T, Sakai Y, Shimakami T, Nagata N, Takamura T, Tanaka T, Kaneko S. Peretinoin, an acyclic retinoid, suppresses steatohepatitis and tumorigenesis by activating autophagy in mice fed an atherogenic high-fat diet. Oncotarget. 2017 Jun 20;8(25):39978-39993

[6]Okada H, Honda M, Campbell JS, Sakai Y, Yamashita T, Takebuchi Y, Hada K, Shirasaki T, Takabatake R, Nakamura M, Sunagozaka H, Tanaka T, Fausto N, Kaneko S. Acyclic retinoid targets platelet-derived growth factor signaling in the prevention of hepatic fibrosis and hepatocellular carcinoma development. Cancer Res. 2012 Sep 1;72(17):4459-71

 

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