Peretinoin | CAS#81485-25-8 | Acyclic retinoid

MedKoo Cat#: 205986 | Name: Peretinoin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Peretinoin, also known as NIK-333 , orally available, acyclic retinoid with potential antineoplastic and chemopreventive activities. Peretinoin binds to and activates nuclear retinoic acid receptors (RAR), which in turn recruit coactivator proteins and promote, with other transcriptional complexes, the transcription of target genes. As a result, this agent may modulate the expression of genes involved in the regulation of cell proliferation, cell differentiation, and apoptosis of both normal and tumor cells.

Chemical Structure

Peretinoin

CAS#81485-25-8

Theoretical Analysis

MedKoo Cat#: 205986

Name: Peretinoin

CAS#: 81485-25-8

Chemical Formula: C20H30O2

Exact Mass: 302.2246

Molecular Weight: 302.45

Elemental Analysis: C, 79.42; H, 10.00; O, 10.58

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00
10mg	USD 820.00

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Synonym

Peretinoin; NIK333

IUPAC/Chemical Name

(2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoic acid

InChi Key

UUBHZHZSIKRVIV-KCXSXWJSSA-N

InChi Code

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+

SMILES Code

C/C(C)=C/CC/C(C)=C/CC/C(C)=C/C=C/C(C)=C/C(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Peretinoin is an oral acyclic retinoid with a vitamin A-like structure that targets retinoid nuclear receptors such as retinoid X receptor (RXR) and retinoic acid receptor (RAR).

In vitro activity:

This study aimed to examine the influence of peretinoin on the HBV lifecycle. HBV-DNA and covalently closed circular DNA (cccDNA) were evaluated by a qPCR method in HepG2.2.15 cells. Peretinoin significantly reduced the levels of intracellular HBV-DNA, nuclear cccDNA, and HBV transcript at a concentration that did not induce cytotoxicity. Mechanistically, although peretinoin increased the expression of HBV-related transcription factors, as observed for other retinoids, peretinoin enhanced the binding of histone deacetylase 1 (HDAC1) to cccDNA in the nucleus and negatively regulated HBV transcription. Moreover, peretinoin significantly inhibited the expression of SPHK1, a potential inhibitor of HDAC activity, and might be involved in hepatic inflammation, fibrosis, and HCC. Reference: Int J Mol Sci. 2018 Jan 23;19(2):108. https://pubmed.ncbi.nlm.nih.gov/29360739/

In vivo activity:

Using two NASH-HCC mouse models, this study showed that peretinoin, an acyclic retinoid, significantly improved liver histology and reduced the incidence of liver tumors. Interestingly, this study found that peretinoin induced autophagy in the liver of mice, which was characterized by the increased co-localized expression of microtubule-associated protein light chain 3B-II and lysosome-associated membrane protein 2, and increased autophagosome formation and autophagy flux in the liver. Reference: Oncotarget. 2017 Jun 20;8(25):39978-39993. https://pubmed.ncbi.nlm.nih.gov/28591717/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	50.0	165.32

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 302.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Murai K, Shirasaki T, Honda M, Shimizu R, Shimakami T, Nakasho S, Shirasaki N, Okada H, Sakai Y, Yamashita T, Kaneko S. Peretinoin, an Acyclic Retinoid, Inhibits Hepatitis B Virus Replication by Suppressing Sphingosine Metabolic Pathway In Vitro. Int J Mol Sci. 2018 Jan 23;19(2):108. doi: 10.3390/ijms19020108. PMID: 29360739; PMCID: PMC5855541. 2. Shimakami T, Honda M, Shirasaki T, Takabatake R, Liu F, Murai K, Shiomoto T, Funaki M, Yamane D, Murakami S, Lemon SM, Kaneko S. The acyclic retinoid Peretinoin inhibits hepatitis C virus replication and infectious virus release in vitro. Sci Rep. 2014 Apr 15;4:4688. doi: 10.1038/srep04688. PMID: 24732793; PMCID: PMC3986704. 3. 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. doi: 10.1038/s41598-017-17285-2. PMID: 29208982; PMCID: PMC5717167. 4. 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. doi: 10.18632/oncotarget.18116. PMID: 28591717; PMCID: PMC5522259.

In vitro protocol:

In vivo protocol:

1. 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. doi: 10.1038/s41598-017-17285-2. PMID: 29208982; PMCID: PMC5717167. 2. 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. doi: 10.18632/oncotarget.18116. PMID: 28591717; PMCID: PMC5522259.

1: Okusaka T, Ueno H, Ikeda M, Morizane C. Phase I and pharmacokinetic clinical trial of oral administration of the acyclic retinoid NIK-333. Hepatol Res. 2011 Jun;41(6):542-52. doi: 10.1111/j.1872-034X.2011.00800.x. Epub 2011 Apr 19. PubMed PMID: 21501352. 2: Kimura M, Watanabe M, Ishibashi N, Yanagida S, Ogihara M. Acyclic retinoid NIK-333 accelerates liver regeneration and lowers serum transaminase activities in 70% partially hepatectomized rats, in vivo. Eur J Pharmacol. 2010 Sep 25;643(2-3):267-73. doi: 10.1016/j.ejphar.2010.06.037. Epub 2010 Jul 7. PubMed PMID: 20619257. 3: Tsujino T, Nagata T, Katoh F, Yamasaki H. Inhibition of Balb/c 3T3 cell transformation by synthetic acyclic retinoid NIK-333; possible involvement of enhanced gap junctional intercellular communication. Cancer Detect Prev. 2007;31(4):332-8. PubMed PMID: 17935907. 4: Okudaira T, Tomita M, Uchihara JN, Matsuda T, Ishikawa C, Kawakami H, Masuda M, Tanaka Y, Ohshiro K, Takasu N, Mori N. NIK-333 inhibits growth of human T-cell leukemia virus type I-infected T-cell lines and adult T-cell leukemia cells in association with blockade of nuclear factor-kappaB signal pathway. Mol Cancer Ther. 2006 Mar;5(3):704-12. PubMed PMID: 16546985. 5: Kagawa M, Sano T, Ishibashi N, Hashimoto M, Okuno M, Moriwaki H, Suzuki R, Kohno H, Tanaka T. An acyclic retinoid, NIK-333, inhibits N-diethylnitrosamine-induced rat hepatocarcinogenesis through suppression of TGF-alpha expression and cell proliferation. Carcinogenesis. 2004 Jun;25(6):979-85. Epub 2004 Jan 23. PubMed PMID: 14742314.