Adarotene

Adarotene is a synthetic, phenolic hydroxyl retinoid with proapoptotic activity. As an atypical retinoid, adarotene has the ability to induce apoptosis which is independent of retinoid receptor signaling.

Methyl E-3-(3’-Adamantan-1-yl-4’-hydroxybiphenyl-4-yl)acrylate. (3.28 g, 8.45 mmol) was added to asolution of LiOH.HGeneral procedure: Chemical stability of Adarotene derivatives was ascertained at 37 °C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5percent DMSO and 5percent Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12percent and 36percent resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 °C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5percent DMSO and 5percent Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12percent and 36percent resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 °C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5percent DMSO and 5percent Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12percent and 36percent resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.General procedure: Chemical stability of Adarotene derivatives was ascertained at 37 °C at the stomach pH (1.2), intestine pH (6.8) and blood pH (7.4). Due to the low water solubility of the compounds, stability experiments were performed in aqueous buffer containing 5percent DMSO and 5percent Tween 80. The stability results are reported (Table 1a, S.I.) as percentage of recovery, as determined by HPLC and UPLC measurements (see Section 5). All compounds appeared unchanged after 12 h at pH 1.2. Compounds 6b-d, 6h and 7b were partially hydrolysed at pH 6.8 and 7.4, with the lowest percentage of recovery for 6d and 7b (12percent and 36percent resp.) at pH 7.4. All the partially hydrolysed compounds contain a basic nitrogen in the side chain.

Molecular Weight:374.5
XLogP3:6.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:374.18819469
Monoisotopic Mass:374.18819469
Topological Polar Surface Area:57.5
Heavy Atom Count:28
Complexity:574
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes