71204-89-2
Chemical Structure
Calcitroic acid
- CAS. Nr.: 71204-89-2
- Formula:C23H34O4
- Molecular Weight:374.51
IUPAC Name: 6-methyl-1,5,6,7-tetrahydro-4H-indol-4-one
InChIKey: MBLYZRMZFUWLOZ-ZTIKAOTBSA-N
SMILES: C[C@@]12[C@](CC[C@]2([H])[C@H](C)CC(O)=O)([H])/C(CCC1)=C/C=C3C([C@H](C[C@@H](C\3)O)O)=C
Biological Activity: Calcitroic acid is a water-soluble terminal vitamin D metabolite and also a ligand for vitamin D receptor (VDR). Calcitroic acid binds to the ligand-binding domain of VDR, forms a retinoic X receptor complex, recruits the coactivator peptide MED1, mediates partial VDR-dependent transcription, inhibits Calcitriol (HY-10002)-induced VDR activation, and reduces the transcription level of CYP24A1 in the presence of 1α,25-dihydroxyvitamin D3. Calcitroic acid exerts selective activating effects on VDR, upregulates the expression of CYP24A1 and CYP3A4, decreases the transcription levels of iNOS and IL-1β, reduces the secretion of nitric oxide and IL-1β, and possesses metabolic stability due to its resistance to phase I oxidation and hepatic glucuronidation. Calcitroic acid can be used in research related to colon cancer, inflammatory bowel disease and rickets[1][2][3][4][5][6][7].
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Calcitroic acid | 85.0% | Calcitroic acid is a water-soluble terminal vitamin D metabolite and also a ligand for vitamin D receptor (VDR). Calcitroic acid binds to the ligand-binding domain of VDR, forms a retinoic X receptor complex, recruits the coactivator peptide MED1, mediates partial VDR-dependent transcription, inhibits Calcitriol (HY-10002)-induced VDR activation, and reduces the transcription level of CYP24A1 in the presence of 1α,25-dihydroxyvitamin D3. Calcitroic acid exerts selective activating effects on VDR, upregulates the expression of CYP24A1 and CYP3A4, decreases the transcription levels of iNOS and IL-1β, reduces the secretion of nitric oxide and IL-1β, and possesses metabolic stability due to its resistance to phase I oxidation and hepatic glucuronidation. Calcitroic acid can be used in research related to colon cancer, inflammatory bowel disease and rickets. | ||||||||||||||||||||
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Calcitroic acid-13C | Calcitroic acid-13C is the 13C-labeled Calcitroic acid (HY-N10508). Calcitroic acid is a water-soluble terminal vitamin D metabolite and also a ligand for vitamin D receptor (VDR). Calcitroic acid binds to the ligand-binding domain of VDR, forms a retinoic X receptor complex, recruits the coactivator peptide MED1, mediates partial VDR-dependent transcription, inhibits Calcitriol (HY-10002)-induced VDR activation, and reduces the transcription level of CYP24A1 in the presence of 1α,25-dihydroxyvitamin D3. Calcitroic acid exerts selective activating effects on VDR, upregulates the expression of CYP24A1 and CYP3A4, decreases the transcription levels of iNOS and IL-1β, reduces the secretion of nitric oxide and IL-1β, and possesses metabolic stability due to its resistance to phase I oxidation and hepatic glucuronidation. Calcitroic acid can be used in research related to colon cancer, inflammatory bowel disease and rickets. | |||||||||||||||||||||
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References
- [1]. Teske KA, et al. Synthesis and evaluation of vitamin D receptor-mediated activities of cholesterol and vitamin D metabolites. European journal of medicinal chemistry. 2016 Feb 15;109:238-46. [Content Brief]
- [2]. Yu OB, et al. Biological evaluation and synthesis of calcitroic acid. Bioorg Chem. 2021 Nov;116:105310. [Content Brief]
- [3]. Di Milo E. Determination of the metabolism, distribution, and concentration of calcitroic acid [dissertation]. Milwaukee (WI): University of Wisconsin-Milwaukee; 2021 May
- [4]. Yu OB. Part I: an investigation of calcitroic acid and its phase II conjugates. Part II: toward the development of a novel orally-available asthma treatment targeting GABAA receptors in the lungs [dissertation]. Milwaukee (WI): University of Wisconsin-Milwaukee; 2019 May.
- [5]. Yu OB, et al. Synthesis and biological evaluation of calcioic acid. Steroids. 2020 Feb;154:108536. [Content Brief]
- [6]. Zimmerman DR, et al. Calcitroic acid is a major catabolic metabolite in the metabolism of 1 alpha-dihydroxyvitamin D(2). Arch Biochem Biophys. 2001 Aug 1;392(1):14-22. [Content Brief]
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[7]. Esvelt RP, et al. Calcitroic acid: biological activity and tissue distribution studies. Arch Biochem Biophys. 1981 Feb;206(2):403–413.
