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Adarotene

Apoptosis inducer/DNA damage agent CAS# 496868-77-0

Adarotene

2D Structure

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Adarotene

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Chemical Properties of Adarotene

Cas No. 496868-77-0 SDF Download SDF
PubChem ID 9864378 Appearance Powder
Formula C25H26O3 M.Wt 374.47
Type of Compound N/A Storage Desiccate at -20°C
Synonyms ST1926
Solubility DMSO : 25 mg/mL (66.76 mM; Need ultrasonic)
Chemical Name (E)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]phenyl]prop-2-enoic acid
SMILES C1C2CC3CC1CC(C2)(C3)C4=C(C=CC(=C4)C5=CC=C(C=C5)C=CC(=O)O)O
Standard InChIKey QAWBIEIZDDIEMW-FPYGCLRLSA-N
Standard InChI 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+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Adarotene

DescriptionAdarotene is a new-in-class potent proapoptotic and cytodifferentiating agent act as a selective activator of RAR β and RAR γ.
TargetsRAR βRAR γ    

Protocol

Cell Assay [2]
Briefly, cells (1×107/mL) are loaded with 1 μM FURA-2 at 37°C in the dark for 30 minutes, washed twice, resuspended in phosphate-buffered saline (PBS) containing 1.26 mM CaCl2 at 106 cells/mL and then used for the experiments. Dual excitation, alternating at 340 nm and 380 nm, is provided by a spectrophotofluorometer equipped with 2 excitation monochromators, and emission is fixed at 480 nm. The temperature is set at 37°C±1°C. In some experiments, to eliminate extracellular calcium, cells preloaded with FURA-2 are resuspended in PBS without Ca2+, and 0.5 mM EGTA (ethylene glycol tetraacetic acid) is added to each sample prior to addition of the appropriate stimulus.

Animal Administration [2]
NB4 cells (3×106) are intraperitoneally inoculated in SCID mice (8 mice/group). ST1926 is dissolved in cremophor/ethanol 1:1 solution, and diluted 1:10 in PBS at the concentration of 50 mg/kg; the doses of 30 mg/kg and 40 mg/kg are then prepared by appropriate dilutions in the same vehicle. ATRA is dissolved in the dark in Cremophor EL and kept magnetically stirred; the solution is then diluted 1:10 in PBS at the final concentration of 40 mg/kg. Both compounds are administered intraperitoneally and orally twice per day for 3 weeks starting from the day after cell inoculation, in a volume of 10 mL/kg. During treatments body weight and lethality are registered.

References:
[1]. Cincinelli R, et al. A novel atypical retinoid endowed with proapoptotic and antitumor activity. J Med Chem. 2003 Mar 13;46(6):909-12. [2]. Garattini E, et al. ST1926, a novel and orally active retinoid-related molecule inducing apoptosis in myeloid leukemia cells: modulation of intracellular calcium homeostasis. Blood. 2004 Jan 1;103(1):194-207.

Adarotene Dilution Calculator

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Adarotene Molarity Calculator

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Preparing Stock Solutions of Adarotene

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6704 mL 13.3522 mL 26.7044 mL 53.4088 mL 66.761 mL
5 mM 0.5341 mL 2.6704 mL 5.3409 mL 10.6818 mL 13.3522 mL
10 mM 0.267 mL 1.3352 mL 2.6704 mL 5.3409 mL 6.6761 mL
50 mM 0.0534 mL 0.267 mL 0.5341 mL 1.0682 mL 1.3352 mL
100 mM 0.0267 mL 0.1335 mL 0.267 mL 0.5341 mL 0.6676 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Adarotene

Retinoid-related molecules are derivatives of retinoic acid and promising antileukemic agents with a mechanism of action different from that of other common chemotherapeutics. Adarotene is a novel atypical retinoid endowed with proapoptotic and antitumor activity.
In vitro: The novel atypical retinoid adarotene exhibited potent antiproliferative activity on a large panel of human tumor cells. It was found that although almost complete loss of ability to activate RARs, adarotene was performing as an effective apoptosis inducer and surprisingly produced DNA damage, which likely contributed to its proapoptotic activity [1].
In vivo: Following oral administration, adarotene was well tolerated and caused tumor growth inhibition in the ovarian carcinoma (A2780/DX) and the human melanoma (MeWo) exnographt in nude mice, supporting the therapeutic interest of this novel agent [1].
Clinical trial: Adarotene is currently only in the preclinical developlent stage and no clinical data are available.
Reference:
[1] Cincinelli R, Dallavalle S, Merlini L, Penco S, Pisano C, Carminati P, Giannini G, Vesci L, Gaetano C, Illy B, Zuco V, Supino R, Zunino F. A novel atypical retinoid endowed with proapoptotic and antitumor activity. J Med Chem. 2003;46(6):909-12.

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References on Adarotene

Stimulation of Erythrocyte Cell Membrane Scrambling by Adarotene.[Pubmed:28214860]

Cell Physiol Biochem. 2017;41(2):519-529.

BACKGROUND/AIMS: The atypical retinoid E23-(40-hydroxyl-30-adamantylbiphenyl-4-yl) acrylic acid (ST1926, Adarotene) is used in the treatment of malignancy. The effect of ST1926 is at least in part due to stimulation of apoptosis. Similar to apoptosis of nucleated cells, erythrocytes may enter eryptosis, the suicidal death of erythrocytes. Hallmarks of eryptosis include cell shrinkage and cell membrane scrambling with phosphatidylserine translocation to the erythrocyte surface. Signaling involved in the stimulation of eryptosis includes increase of cytosolic Ca2+ activity [Ca2+]i, oxidative stress and ceramide. The present study explored, whether Adarotene induces eryptosis and, if so, to test for the involvement of Ca2+ entry, oxidative stress and ceramide. METHODS: Flow cytometry was employed to estimate phosphatidylserine exposure at the cell surface from annexin-V-binding, cell volume from forward scatter, [Ca2+]i from Fluo3-fluorescence, reactive oxygen species (ROS) formation from DCFDA dependent fluorescence, and ceramide abundance utilizing specific antibodies. RESULTS: A 48 hours exposure of human erythrocytes to Adarotene (9 microM) significantly increased the percentage of annexin-V-binding cells, an effect paralleled by significant decrease of forward scatter, as well as significant increase of Fluo3-fluorescence, DCFDA fluorescence, and ceramide abundance. The effect of Adarotene (9 microM) on annexin-V-binding was significantly blunted but not abolished by removal of extracellular Ca2+. CONCLUSIONS: Adarotene stimulates phospholipid scrambling of the erythrocyte cell membrane, an effect paralleled by and at least in part due to Ca2+ entry, oxidative stress and ceramide.

New retinoid derivatives as back-ups of Adarotene.[Pubmed:22365912]

Bioorg Med Chem. 2012 Apr 1;20(7):2405-15.

Adarotene belongs to the so-called class of atypical retinoids. The presence of the phenolic hydroxyl group on Adarotene structure allows a rapid O-glucuronidation as a major mechanism of elimination of the drug, favoring a fast excretion of its glucuronide metabolite in the urines. A series of ether, carbamate and ester derivatives was synthesized. All of them were studied and evaluated for their stability at different pH. The cytotoxic activity in vitro on NCI-H460 non-small cell lung carcinoma and A2780 ovarian tumor cell lines was also tested. A potential back-up of Adarotene has been selected to be evaluated in tumor models.

Description

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

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