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Calcipotriol

Catalog No.
A3271
Vitamin D3 analog,regulates cell differentiation and proliferation
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$60.00
In stock
10mg
$56.00
In stock
50mg
$252.00
In stock
100mg
$448.00
In stock
500mg
$1,960.00
In stock
For scientific research use only and should not be used for diagnostic or medical purposes.

Tel: +1-832-696-8203

Email: [email protected]

Worldwide Distributors

Background

Calcipotriol is an analogue of vitamin D3. [1]

Calcipotriol is a ligand of VDR-like receptors and is used as a first-line topical agent in the treatment of psoriasis.[1-2] Calcipotriol is much less effective in causing hypercalcemia.[3] The vitamin D receptor is found on the cells of many different tissues including T cells of the immune system. T cells are known to play a role in psoriasis, and the binding of calcipotriol to VDR modulates the T cells gene transcription of cell differentiation and proliferation related genes. Calcipotriol induced apoptosis in eratinocytes isolated from psoriatic plaques at 100 nM for 20 h.[4] Calcipotriol also induced autophagy in both HeLa cells and keratinocytes.[2] Calcipotriol inhibited the proliferation of HL-60 and MCF-7 cells dose-dependently from 1 nM-1000 nM.[5] Calcipotriol is a potent inducer of terminal differentiation in cultured human keratinocytes.[3] Calcipotriol also decreased the mRNA expression/production of human cathelicidin antimicrobial protein (hCAP18) and LL37 peptide by IL-17A/IL-22-stimulated keratinocytes at 40 nM.[6]

References:
1.?M. R. Klaber, P. E. Hutchinson, A. Pedvis-Leftick, K. Kragballe, T. L. Reunala, P. C. Van de Kerkhof, M. K. Johnsson, L. Molin, M. S. Corbett and N. Downess, Br J Dermatol 1994, 131, 678-683.
2.?R. C. Wang and B. Levine, J Invest Dermatol 2011, 131, 990-993.
3.?K. Kragballe and I. L. Wildfang, Arch Dermatol Res 1990, 282, 164-167.
4.?R. Tiberio, C. Bozzo, G. Pertusi, F. Graziola, M. Gattoni, P. Griffanti, P. Boggio, E. Colombo and G. Leigheb, Clin Exp Dermatol 2009, 34, e972-974.
5.?M. Milczarek, M. Chodynski, B. Filip-Psurska, A. Martowicz, M. Krupa, K. Krajewski, A. Kutner and J. Wietrzyk, Cancers (Basel) 2013, 5, 1355-1378.
6.?J. Sakabe, T. Umayahara, M. Hiroike, T. Shimauchi, T. Ito and Y. Tokura, Acta Derm Venereol 2014, 94, 512-516.

Chemical Properties

StorageStore at -20°C
M.Wt412.60
Cas No.112965-21-6
FormulaC27H40O3
SynonymsMC 903; Calcipotriene
Solubility≥16.7 mg/mL in DMSO
Chemical Name(1R,3S,Z)-5-((E)-2-((1R,3aS,7aR)-1-((2R,5S,E)-5-cyclopropyl-5-hydroxypent-3-en-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol
SDFDownload SDF
Canonical SMILESO[C@@H]1C/C(C([C@@H](O)C1)=C)=C/C=C2[C@@](CC[C@]3([H])[C@H](C)/C=C/[C@@H](O)C4CC4)([H])[C@]3(C)CCC/2
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment [1]:

Cell lines

Human HL-60 and MCF-7 cell lines

Preparation method

Soluble in DMSO > 16.7mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reacting condition

1, 10, 100, 1000 nM for 24 h

Applications

Calcipotriol revealed a strong proliferation inhibition in HL-60 cells, the potentiation of the antiproliferative effect of CIS(cisplatin) could be observed. In MCF-7 cells, a lower dose of TX (tamoxifen) in combination with calcipotriol caused an increase in the G0/G1 and a decrease in the G2/M stage as compared to TX alone.
Clinical experiment [2]:

Diseases models

Patients with vulgaris psoriasis aged ≥18 years

Dosage form

Foam of calcipotriol 50μg/g plus betamethasone 0.5 mg/g, 4, 8, 12 weeks, topical treatment

Application

A greater proportion of patients achieved modified Psoriasis Area and Severity Index 75 and 90 at weeks 4, 8, and 12 with the calcipotriol 50μg/g plus betamethasone 0.5 mg/g (Cal/BD) foam.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Milczarek M1, Chodyński M, et al, Synthesis and Biological Activity of Diastereomeric and Geometric Analogs of Calcipotriol, PRI-2202 and PRI-2205, Against Human HL-60 Leukemia and MCF-7 Breast Cancer Cells. Cancers (Basel). 2013 Oct 31;5(4):1355-78. doi: 10.3390/cancers5041355.

[2]. Paul C1, Leonardi C2, et al, Calcipotriol Plus Betamethasone Dipropionate Aerosol Foam in Patients with Moderate-to-Severe Psoriasis: Sub-Group Analysis of the PSO-ABLE Study. Am J Clin Dermatol. 2017 Jun;18(3):405-411. doi: 10.1007/s40257-017-0258-0.

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