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9-cis-Retinoic Acid (Synonyms: Alitretinoin, NSC 659772, Panretin, 9-cis RA)

Catalog No.GC14596

9-cis-Retinoic acid (ALRT1057), a vitamin A derivative, is a potent RAR/RXR agonist.

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9-cis-Retinoic Acid Chemical Structure

Cas No.: 5300/3/8

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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

Ki: 0.5-27 nM for RAR; 3.8-12 nM for RXR

9-cis-Retinoic acid (9cRA) is a RAR and RXR activator.

Metabolism activates vitamin A into retinoic acid (RA), which controls physiological processes such as nervous system function, immune response, cell proliferation and differentiation, as well as reproduction. Much of the activity of RA is mediated via two subfamilies of nuclear receptors, retinoic acid receptor (RAR) and retinoid X receptor (RXR).

In vitro: The 9cRA effect in pancreatic β-cells line INS-1 832/13 led to a decreased expression of Mptn associated to a concomitant increase of miR-375. Moreover, in the breast cancer model, 9cRA showed different effect on both Mtpn and miR-375 expression. Moreover, in INS-1 832/13, 3T3-L1 pre-adipocytes and MCF-7 but not in MDA-MB-231, the effect of 9cRA on Mptn gene expression and its miR was under the control of RARs and RXRs receptors [1].

In vivo: A chemoprevention study was conducted to evaluate the activity of 9cRA as an inhibitor of prostate carcinogenesis in male Wistar-Unilever rats. Results showed that continuous dietary administration of 9cRA reduced cancer incidence in the dorsolateral + anterior prostate. Similarly, 9cRA with same doses reduced the incidence of cancer in all accessory sex glands. Moreover, chronic dietary administration of 9cRA induced no gross or organ-specific toxicity and did not suppress group mean body weight gain [2].

Clinical trial: The impact of 9cRA on quality of life of alitretinoin in severe chronic hand eczema has been evaluated. At baseline, most patients had CHE characterized as severe by PGA (83 %). At last visit, 48 % of patients had a PGA response of clear/almost clear. Mean improvement in DLQI scores at week 24 was 58 % and 70 %. The overall incidence of AEs was low and similar in both groups [3].

References:
[1] Perri M, Caroleo MC, Liu N, Gallelli L, De Sarro G, Kagechika H, Cione E.  9-cis Retinoic acid modulates myotrophin expression and its miR in physiological and pathophysiological cell models. Exp Cell Res. 2017 Mar 12. pii: S0014-4827(17)30126-X.
[2] McCormick DL, Rao KV, Steele VE, Lubet RA, Kelloff GJ, Bosland MC.  Chemoprevention of rat prostate carcinogenesis by 9-cis-retinoic acid. Cancer Res. 1999 Feb 1;59(3):521-4.
[3] Augustin M, Thai D, Kamps A.  Impact on quality of life of alitretinoin in severe chronic hand eczema: FUGETTA real-world study. J Dtsch Dermatol Ges. 2016 Dec;14(12):1261-1270.

Chemical Properties

Cas No. 5300/3/8 SDF
Synonyms Alitretinoin, NSC 659772, Panretin, 9-cis RA
Chemical Name (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Canonical SMILES CC1(C)C(/C=C/C(C)=C\C=C\C(C)=C\C(O)=O)=C(C)CCC1
Formula C20H28O2 M.Wt 300.44
Solubility ≤0.5mg/ml in ethanol;20mg/ml in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 3.3285 mL 16.6423 mL 33.2845 mL
5 mM 0.6657 mL 3.3285 mL 6.6569 mL
10 mM 0.3328 mL 1.6642 mL 3.3285 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 23 reference(s) in Google Scholar.)

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