204853-33-8
Chemical Structure
Tolcapone 3-β-D-glucuronide
Synonym(s): Ro 61-1448
- CAS No.: 204853-33-8
- Formula:C20H19NO11
- Molecular Weight:449.36
IUPAC Name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxy-5-(4-methylbenzoyl)-3-nitrophenoxy)tetrahydro-2H-pyran-2-carboxylic acid
InChIKey: QQQCXCUCFPMHBX-HBWRTXEVSA-N
SMILES: O[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1OC2=CC(C(C3=CC=C(C=C3)C)=O)=CC([N+]([O-])=O)=C2O)C(O)=O
Biological Activity: Tolcapone 3-β-D-glucuronide (Ro 61-1448) is an O-methyl metabolite of Tolcapone (HY-17406) and is pharmacologically inactive. Tolcapone (Ro 40-7592) is a selective, potent and orally active COMT inhibitor with an IC50of 773 nM. Tolcapone can inhibits α-syn and Aβ42 oligomerization and fibrillogenesis. Tolcapone can cause oxidative stress and induce cancer cells apoptosis and ROS production. Tolcapone can be used for the researches of cancer and neurological disease, such as Parkinson disease and neuroblastoma[1][2][3][4][5].
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Tolcapone 3-β-D-glucuronide | Tolcapone 3-β-D-glucuronide (Ro 61-1448) is an O-methyl metabolite of Tolcapone (HY-17406) and is pharmacologically inactive. Tolcapone (Ro 40-7592) is a selective, potent and orally active COMT inhibitor with an IC50of 773 nM. Tolcapone can inhibits α-syn and Aβ42 oligomerization and fibrillogenesis. Tolcapone can cause oxidative stress and induce cancer cells apoptosis and ROS production. Tolcapone can be used for the researches of cancer and neurological disease, such as Parkinson disease and neuroblastoma. | |||||||||||||||||||||
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- [1]. P Heizmann, et al. Determination of the catechol-O-methyltransferase inhibitor tolcapone and three of its metabolites in animal and human plasma and urine by reversed-phase high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 1999 Jul 9;730(2):153-60. [Content Brief]
- [2]. De Santi C, et al. Catechol-O-methyltransferase: variation in enzyme activity and inhibition by entacapone and tolcapone. Eur J Clin Pharmacol. 1998 May;54(3):215-9. [Content Brief]
- [3]. Di Giovanni S, et al. Entacapone and tolcapone, two catechol O-methyltransferase inhibitors, block fibril formation of alpha-synuclein and beta-amyloid and protect against amyloid-induced toxicity. J Biol Chem. 2010 May 14;285(20):14941-14954. [Content Brief]
- [4]. Ceravolo R, et al. 18F-dopa PET evidence that tolcapone acts as a central COMT inhibitor in Parkinson's disease. Synapse. 2002 Mar 1;43(3):201-7. [Content Brief]
- [5]. Maser T, et al. Tolcapone induces oxidative stress leading to apoptosis and inhibition of tumor growth in Neuroblastoma. Cancer Med. 2017 Jun;6(6):1341-1352. [Content Brief]
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