81203-50-1
Chemical Structure
Calcitriol lactone
Synonym(s): 1α,25-Dihydroxyvitamin D3-26,23-lactone
- CAS No.: 81203-50-1
- Formula:C27H40O5
- Molecular Weight:444.60
IUPAC Name: (3R,5S)-5-((R)-2-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propyl)-3-hydroxy-3-methyldihydrofuran-2(3H)-one
InChIKey: WMYIVSWWSRCZFA-RWVJFQLJSA-N
SMILES: O=C1O[C@@H](C[C@H]([C@H]2CC[C@@]3([H])/C(CCC[C@]23C)=C/C=C4C([C@@H](O)C[C@H](O)C\4)=C)C)C[C@]1(O)C
Biological Activity: Calcitriol lactone (1α,25-Dihydroxyvitamin D3-26,23-lactone) is an endogenous metabolite of vitamin D3. Calcitriol lactone has the biological activity of inhibiting bone resorption and lowering blood calcium. Calcitriol lactone acts as a natural antagonist or partial agonist of VDR by binding to the vitamin D receptor (VDR) and inducing specific conformational changes, thereby regulating the transcription of downstream target genes. Calcitriol lactone can be used in research on bone metabolic diseases (such as osteoporosis) and breast cancer[1][2][3][4][5][6][7].
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Calcitriol lactone | Calcitriol lactone (1α,25-Dihydroxyvitamin D3-26,23-lactone) is an endogenous metabolite of vitamin D3. Calcitriol lactone has the biological activity of inhibiting bone resorption and lowering blood calcium. Calcitriol lactone acts as a natural antagonist or partial agonist of VDR by binding to the vitamin D receptor (VDR) and inducing specific conformational changes, thereby regulating the transcription of downstream target genes. Calcitriol lactone can be used in research on bone metabolic diseases (such as osteoporosis) and breast cancer. | |||||||||||||||||||||
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References
- [1]. Siu-Caldera ML, et al. Enhanced biological activity of 1α, 25-dihydroxy-20-epi-vitamin D3, the C-20 epimer of 1α, 25-dihydroxyvitamin D3, is in part due to its metabolism into stable intermediary metabolites with significant biological activity. The Journal of Steroid Biochemistry and Molecular Biology. 1999 Dec 15;71(3-4):111-21.
- [2]. Ishizuka S, et al. The difference of biological activity among four diastereoisomers of 1 alpha,25-dihydroxycholecalciferol-26,23-lactone. Journal of steroid biochemistry. 1986 Oct;25(4):505-10.
- [3]. Uskokovic MR, et al. Highly active analogs of 1alpha,25-dihydroxyvitamin D(3) that resist metabolism through C-24 oxidation and C-3 epimerization pathways. Steroids. 2001;66(3-5):463-71.
- [4]. Vanham G, et al. The effect of vitamin D analogs and of vitamin D-binding protein on lymphocyte proliferation. Journal of steroid biochemistry. 1988 Apr;29(4):381-6.
- [5]. Ochiai E, et al. Molecular mechanism of the vitamin D antagonistic actions of (23S)-25-dehydro-1alpha-hydroxyvitamin D3-26,23-lactone depends on the primary structure of the carboxyl-terminal region of the vitamin d receptor. Molecular endocrinology (Baltimore, Md.). 2005 May;19(5):1147-57.
- [6]. WOVKULICH P M, et al. Total synthesis of 1α,25(R)-dihydroxy vitamin D₃ 26,23(S)-lactone (calcitriol lactone), a natural metabolite of vitamin D₃[J]. *The Journal of Organic Chemistry*, 1983, 48(23): 4433-4436.
- [7]. Gupta S, et al. Role of Acorus calamus extract in reducing exosome secretion by targeting Rab27a and nSMase2: a therapeutic approach for breast cancer. Molecular biology reports. 2025 Jan 15;52(1):124. [Content Brief]
