Adarotene | ST1926 | CAS#496868-77-0 | Anti-tumour agent

MedKoo Cat#: 402120 | Name: Adarotene

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Description:

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

Adarotene, also known as ST1926, is an atypical retinoid and a promising anti-tumour agent with selective apoptotic activity on the leukaemic blast. The anti-tumour activity of the compound has been associated with its capacity to induce DNA double stranded breaks. (source: Eur J Cancer. 2012 Dec 11. pii: S0959-8049(12)00909-4.).

Chemical Structure

Adarotene

CAS#496868-77-0

Theoretical Analysis

MedKoo Cat#: 402120

Name: Adarotene

CAS#: 496868-77-0

Chemical Formula: C25H26O3

Exact Mass: 374.1882

Molecular Weight: 374.47

Elemental Analysis: C, 80.18; H, 7.00; O, 12.82

Price and Availability

Size	Price	Availability
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks
50mg	USD 1,050.00	2 Weeks

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Related CAS #

No Data

Synonym

ST1926; ST 1926; ST-1926; Adarotene.

IUPAC/Chemical Name

(E)-3-(3'-((3r,5r,7r)-adamantan-1-yl)-4'-hydroxy-[1,1'-biphenyl]-4-yl)acrylic acid

InChi Key

QAWBIEIZDDIEMW-RXJOCBMKSA-N

InChi Code

InChI=1S/C25H26O3/c26-23-7-6-21(20-4-1-16(2-5-20)3-8-24(27)28)12-22(23)25-13-17-9-18(14-25)11-19(10-17)15-25/h1-8,12,17-19,26H,9-11,13-15H2,(H,27,28)/b8-3+/t17-,18+,19-,25?

SMILES Code

O=C(O)/C=C/C1=CC=C(C2=CC=C(O)C(C34C[C@H]5C[C@@H](C4)C[C@H](C5)C3)=C2)C=C1

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, not in water

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:

Adarotene is an effective apoptosis inducer, which produces DNA damage and exhibits a potent antiproliferative activity on a large panel of human tumor cells.

In vitro activity:

The growth of human PCa cells, DU145 and PC3, and mouse PCa cells, PLum-AD and PLum-AI, was not altered even in the presence of suprapharmacological ATRA concentrations (10 µmol/L) (Figure 1B). However, a significant decrease in PCa cell proliferation of all tested cells was detected at pharmacologically achievable µmol/L concentrations of ST1926 (Figure 1A). The antiproliferative effect of ST1926 on mouse PLum-AD and PLum-AI PCa cells, which represent primary and advanced PCa cells, respectively, and on human PC3 and DU145 cells representing androgen-independent PCa, showed potent reduction in the proliferation rate in the presence of sub-µmol/L ST1926 concentrations (Figure 1A). Reference: Biosci Rep. 2020 Oct 30;40(10):BSR20200050. https://pubmed.ncbi.nlm.nih.gov/30883933/

In vivo activity:

As shown in Fig. 8A, ST1926 treatment markedly reduced the tumor growth. Also, the significantly reduced tumor volume and weight was detected in ST1926-treated mice (Fig. 8B and C). No significant difference was monitored in the change of body weight of mice (Fig. 8D). Then, IHC assays showed that ST1926 markedly reduced KI-67 expression in tumor sections, indicating the suppressed proliferation of glioma. In contrast, obvious apoptosis was observed in tumor samples, as evidenced by the markedly increased expression levels of TUNEL and cleaved Caspase-3 (Fig. 8E and F). Finally, the toxicity of ST1926 was assessed. As displayed in Fig. 9A, H&E staining showed that there was no obvious histological changes in the major organ samples (kidney, spleen, heart and liver) between the Con and ST1926 groups of mice. In addition, the activities or levels of GOT, GPT, ALP, BUN, CRE, TP and ALB were not markedly different between the Con and ST1926-treated groups (Fig. 9B). The in vivo findings indicated that ST1926 exhibited effective anti-glioma activities with few side effects. Reference: Biomed Pharmacother. 2020 Aug;128:110291. https://pubmed.ncbi.nlm.nih.gov/32526455/

	Solvent	mg/mL	mM
Solubility
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.88
	DMF	5.0	13.35
	Ethanol	1.0	2.67

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 374.47 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. Ghandour B, Pisano C, Darwiche N, Dbaibo G. Restoration of ceramide de novo synthesis by the synthetic retinoid ST1926 as it induces adult T-cell leukemia cell death. Biosci Rep. 2020 Oct 30;40(10):BSR20200050. doi: 10.1042/BSR20200050. PMID: 33048123; PMCID: PMC7593536. 2. Bahmad HF, Samman H, Monzer A, Hadadeh O, Cheaito K, Abdel-Samad R, Hayar B, Pisano C, Msheik H, Liu YN, Darwiche N, Abou-Kheir W. The synthetic retinoid ST1926 attenuates prostate cancer growth and potentially targets prostate cancer stem-like cells. Mol Carcinog. 2019 Jul;58(7):1208-1220. doi: 10.1002/mc.23004. Epub 2019 Mar 18. PMID: 30883933. 3. De L, Yuan T, Yong Z. ST1926 inhibits glioma progression through regulating mitochondrial complex II. Biomed Pharmacother. 2020 Aug;128:110291. doi: 10.1016/j.biopha.2020.110291. Epub 2020 Jun 8. PMID: 32526455. 4. Dong Z, Yuan Y. Accelerated inflammation and oxidative stress induced by LPS in acute lung injury: Ιnhibition by ST1926. Int J Mol Med. 2018 Jun;41(6):3405-3421. doi: 10.3892/ijmm.2018.3574. Epub 2018 Mar 19. PMID: 29568857; PMCID: PMC5881729.

In vitro protocol:

In vivo protocol:

1. De L, Yuan T, Yong Z. ST1926 inhibits glioma progression through regulating mitochondrial complex II. Biomed Pharmacother. 2020 Aug;128:110291. doi: 10.1016/j.biopha.2020.110291. Epub 2020 Jun 8. PMID: 32526455. 2. Dong Z, Yuan Y. Accelerated inflammation and oxidative stress induced by LPS in acute lung injury: Ιnhibition by ST1926. Int J Mol Med. 2018 Jun;41(6):3405-3421. doi: 10.3892/ijmm.2018.3574. Epub 2018 Mar 19. PMID: 29568857; PMCID: PMC5881729.

1: Fratelli M, Fisher JN, Paroni G, Di Francesco AM, Pierri F, Pisano C, Godl K, Marx S, Tebbe A, Valli C, Gianni M, Stravalaci M, Gobbi M, Terao M, Garattini E. New insights into the molecular mechanisms underlying sensitivity/resistance to the atypical retinoid ST1926 in acute myeloid leukaemia cells: The role of histone H2A.Z, cAMP-dependent protein kinase A and the proteasome. Eur J Cancer. 2012 Dec 11. doi:pii: S0959-8049(12)00909-4. 10.1016/j.ejca.2012.11.013. [Epub ahead of print] PubMed PMID: 23245330. 2: Di Francesco AM, Ubezio P, Torella AR, Meco D, Pierri F, Barone G, Cusano G, Pisano C, D'Incalci M, Riccardi R. Enhanced cell cycle perturbation and apoptosis mediate the synergistic effects of ST1926 and ATRA in neuroblastoma preclinical models. Invest New Drugs. 2012 Aug;30(4):1319-30. doi: 10.1007/s10637-011-9689-2. Epub 2011 Jun 3. PubMed PMID: 21633925. 3: Sala F, Zucchetti M, Bagnati R, D'Incalci M, Pace S, Capocasa F, Marangon E. Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of ST1926, a novel oral antitumor agent, adamantyl retinoid derivative, in plasma of patients in a Phase I study. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Oct 1;877(27):3118-26. doi: 10.1016/j.jchromb.2009.08.001. Epub 2009 Aug 7. PubMed PMID: 19695967. 4: Zuco V, Benedetti V, De Cesare M, Zunino F. Sensitization of ovarian carcinoma cells to the atypical retinoid ST1926 by the histone deacetylase inhibitor, RC307: enhanced DNA damage response. Int J Cancer. 2010 Mar 1;126(5):1246-55. doi: 10.1002/ijc.24819. PubMed PMID: 19676051. 5: Valli C, Paroni G, Di Francesco AM, Riccardi R, Tavecchio M, Erba E, Boldetti A, Gianni' M, Fratelli M, Pisano C, Merlini L, Antoccia A, Cenciarelli C, Terao M, Garattini E. Atypical retinoids ST1926 and CD437 are S-phase-specific agents causing DNA double-strand breaks: significance for the cytotoxic and antiproliferative activity. Mol Cancer Ther. 2008 Sep;7(9):2941-54. doi: 10.1158/1535-7163.MCT-08-0419. PubMed PMID: 18790775. 6: Pisano C, Vesci L, FoderÃ R, Ferrara FF, Rossi C, De Cesare M, Zuco V, Pratesi G, Supino R, Zunino F. Antitumor activity of the combination of synthetic retinoid ST1926 and cisplatin in ovarian carcinoma models. Ann Oncol. 2007 Sep;18(9):1500-5. Epub 2007 Aug 13. PubMed PMID: 17698835. 7: Di Francesco AM, Meco D, Torella AR, Barone G, D'Incalci M, Pisano C, Carminati P, Riccardi R. The novel atypical retinoid ST1926 is active in ATRA resistant neuroblastoma cells acting by a different mechanism. Biochem Pharmacol. 2007 Mar 1;73(5):643-55. Epub 2006 Nov 7. PubMed PMID: 17150196. 8: Parrella E, GiannÃ¬ M, Fratelli M, Barzago MM, Raska I Jr, Diomede L, Kurosaki M, Pisano C, Carminati P, Merlini L, Dallavalle S, Tavecchio M, Rochette-Egly C, Terao M, Garattini E. Antitumor activity of the retinoid-related molecules (E)-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid (ST1926) and 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid (CD437) in F9 teratocarcinoma: Role of retinoic acid receptor gamma and retinoid-independent pathways. Mol Pharmacol. 2006 Sep;70(3):909-24. Epub 2006 Jun 20. PubMed PMID: 16788091. 9: Zuco V, Zanchi C, Lanzi C, Beretta GL, Supino R, Pisano C, Barbarino M, Zanier R, Bucci F, Aulicino C, Carminati P, Zunino F. Development of resistance to the atypical retinoid, ST1926, in the lung carcinoma cell line H460 is associated with reduced formation of DNA strand breaks and a defective DNA damage response. Neoplasia. 2005 Jul;7(7):667-77. PubMed PMID: 16026646; PubMed Central PMCID: PMC1501428. 10: Zanchi C, Zuco V, Lanzi C, Supino R, Zunino F. Modulation of survival signaling pathways and persistence of the genotoxic stress as a basis for the synergistic interaction between the atypical retinoid ST1926 and the epidermal growth factor receptor inhibitor ZD1839. Cancer Res. 2005 Mar 15;65(6):2364-72. PubMed PMID: 15781651.