UAB30

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

MedKoo CAT#: 206470

CAS#: 205252-59-1

Description: UAB30, also known 9cUAB30 or 9-cis UAB30, is conformationally defined retinoic acid analogue, and is a potent, selective and low toxicity of specific ligand for the retinoid X receptor.. UAB30 down-regulates the DNA methyltransferases and has anti-telomerase activity in human breast cancer cells. 9-cis-UAB30 is a potential chemopreventative agent that has been shown to be effective on many different types of tumors.


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UAB30 is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206470
Name: UAB30
CAS#: 205252-59-1
Chemical Formula: C20H22O2
Exact Mass: 294.16198
Molecular Weight: 294.39
Elemental Analysis: C, 81.60; H, 7.53; O, 10.87


Synonym: 9cUAB30, 9-cis UAB30, (all-E)-UAB 30, all-trans-UAB 30, UAB30, UAB-30, UAB 30

IUPAC/Chemical Name: (2E,4E,6E)-8-((E)-3,4-dihydronaphthalen-1(2H)-ylidene)-3,7-dimethylocta-2,4,6-trienoic acid

InChi Key: PPGNMFUMZSAZCW-FRCHHHHOSA-N

InChi Code: InChI=1S/C20H22O2/c1-15(7-5-8-16(2)14-20(21)22)13-18-11-6-10-17-9-3-4-12-19(17)18/h3-5,7-9,12-14H,6,10-11H2,1-2H3,(H,21,22)/b8-5+,15-7+,16-14+,18-13+

SMILES Code: O=C(O)/C=C(C)/C=C/C=C(C)/C=C1CCCC2=C\1C=CC=C2


Technical Data

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).

Harmonized System Code:
291639


References

1: Atigadda VR, Xia G, Desphande A, Boerma LJ, Lobo-Ruppert S, Grubbs CJ, Smith CD, Brouillette WJ, Muccio DD. Methyl substitution of a rexinoid agonist improves potency and reveals site of lipid toxicity. J Med Chem. 2014 Jun 26;57(12):5370-80. doi: 10.1021/jm5004792. Epub 2014 Jun 5. PubMed PMID: 24801499; PubMed Central PMCID: PMC4216212.

2: Boerma LJ, Xia G, Qui C, Cox BD, Chalmers MJ, Smith CD, Lobo-Ruppert S, Griffin PR, Muccio DD, Renfrow MB. Defining the communication between agonist and coactivator binding in the retinoid X receptor α ligand binding domain. J Biol Chem. 2014 Jan 10;289(2):814-26. doi: 10.1074/jbc.M113.476861. Epub 2013 Nov 1. PubMed PMID: 24187139; PubMed Central PMCID: PMC3887207.

3: Vedell PT, Lu Y, Grubbs CJ, Yin Y, Jiang H, Bland KI, Muccio DD, Cvetkovic D, You M, Lubet R. Effects on gene expression in rat liver after administration of RXR agonists: UAB30, 4-methyl-UAB30, and Targretin (Bexarotene). Mol Pharmacol. 2013 Mar;83(3):698-708. doi: 10.1124/mol.112.082404. Epub 2013 Jan 4. PubMed PMID: 23292798; PubMed Central PMCID: PMC3583492.

4: Lindeblad M, Kapetanovic IM, Kabirov KK, Dinger N, Mankovskaya I, Morrisey R, Martín-Jiménez T, Lyubimov A. Assessment of oral toxicity and safety of 9-cis-UAB30, a potential chemopreventive agent, in rat and dog studies. Drug Chem Toxicol. 2011 Jul;34(3):300-10. doi: 10.3109/01480545.2010.536771. PubMed PMID: 21649485.

5: Kolesar JM, Hoel R, Pomplun M, Havighurst T, Stublaski J, Wollmer B, Krontiras H, Brouillette W, Muccio D, Kim K, Grubbs CJ, Bailey HE. A pilot, first-in-human, pharmacokinetic study of 9cUAB30 in healthy volunteers. Cancer Prev Res (Phila). 2010 Dec;3(12):1565-70. doi: 10.1158/1940-6207.CAPR-10-0149. PubMed PMID: 21149332; PubMed Central PMCID: PMC3204611.

6: Kapetanovic IM, Horn TL, Johnson WD, Cwik MJ, Detrisac CJ, McCormick DL. Murine oncogenicity and pharmacokinetics studies of 9-cis-UAB30, an RXR agonist, for breast cancer chemoprevention. Int J Toxicol. 2010 Mar-Apr;29(2):157-64. doi: 10.1177/1091581809360070. PubMed PMID: 20335511.

7: Jiang W, Deng W, Bailey SK, Nail CD, Frost AR, Brouillette WJ, Muccio DD, Grubbs CJ, Ruppert JM, Lobo-Ruppert SM. Prevention of KLF4-mediated tumor initiation and malignant transformation by UAB30 rexinoid. Cancer Biol Ther. 2009 Feb;8(3):289-98. Epub 2009 Feb 21. PubMed PMID: 19197145; PubMed Central PMCID: PMC2776760.

8: Jackson JP, Kabirov KK, Kapetanovic IM, Lyubimov A. In vitro assessment of P450 induction potential of novel chemopreventive agents SR13668, 9-cis-UAB30, and pentamethychromanol in primary cultures of human hepatocytes. Chem Biol Interact. 2009 May 15;179(2-3):263-72. doi: 10.1016/j.cbi.2008.12.005. Epub 2008 Dec 16. PubMed PMID: 19135037.

9: Gorman GS, Coward L, Kerstner-Wood C, Cork L, Kapetanovic IM, Brouillette WJ, Muccio DD. In vitro metabolic characterization, phenotyping, and kinetic studies of 9cUAB30, a retinoid X receptor-specific retinoid. Drug Metab Dispos. 2007 Jul;35(7):1157-64. Epub 2007 Apr 19. PubMed PMID: 17446266.

10: Hansen NJ, Wylie RC, Phipps SM, Love WK, Andrews LG, Tollefsbol TO. The low-toxicity 9-cis UAB30 novel retinoid down-regulates the DNA methyltransferases and has anti-telomerase activity in human breast cancer cells. Int J Oncol. 2007 Mar;30(3):641-50. PubMed PMID: 17273765; PubMed Central PMCID: PMC2435481.

11: Grubbs CJ, Hill DL, Bland KI, Beenken SW, Lin TH, Eto I, Atigadda VR, Vines KK, Brouillette WJ, Muccio DD. 9cUAB30, an RXR specific retinoid, and/or tamoxifen in the prevention of methylnitrosourea-induced mammary cancers. Cancer Lett. 2003 Nov 10;201(1):17-24. PubMed PMID: 14580682.

12: Atigadda VR, Vines KK, Grubbs CJ, Hill DL, Beenken SL, Bland KI, Brouillette WJ, Muccio DD. Conformationally defined retinoic acid analogues. 5. Large-scale synthesis and mammary cancer chemopreventive activity for (2E,4E,6Z,8E)-8-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3,7-dimethyl-2,4,6- octatrienoic acid (9cUAB30). J Med Chem. 2003 Aug 14;46(17):3766-9. PubMed PMID: 12904083.

13: Muccio DD, Brouillette WJ, Breitman TR, Taimi M, Emanuel PD, Zhang X, Chen G, Sani BP, Venepally P, Reddy L, Alam M, Simpson-Herren L, Hill DL. Conformationally defined retinoic acid analogues. 4. Potential new agents for acute promyelocytic and juvenile myelomonocytic leukemias. J Med Chem. 1998 May 7;41(10):1679-87. PubMed PMID: 9572893.