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| Cyclopamine | |
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| IUPAC name | (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)- 1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b- octadecahydro-3',6',10,11b-tetramethyl-spiro [9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol |
| Other names | 11-deoxojervine (3-β,23-β)-17,23-epoxy-3-hydroxy-veratraman |
| Identifiers | |
| CAS number | [4449-51-8] |
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| Properties | |
| Molecular formula | C27H41NO2 |
| Molar mass | 411.62 g∙mol-1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Cyclopamine (11-deoxojervine) is a naturally-occurring chemical that belongs to the group of steroidal jerveratrum alkaloids. It is a teratogen isolated from the corn lily (Veratrum californicum) that can lead to cyclopia (holoprosencephaly).
Cyclopamine inhibits the hedgehog signaling pathway (Hh) by influencing the balance between the active and inactive forms of the Smoothened protein. Cyclopamine is currently being investigated as a treatment agent in basal cell carcinoma, medulloblastoma, and rhabdomyosarcoma, tumors that result from excessive Hh activity [1], glioblastoma, and as a treatment agent for multiple myeloma.
Cyclopamine was named for one-eyed lambs which were born to sheep which grazed on wild corn lily at a farm in Idaho. In 1957 the US Department of Agriculture started an eleven-year investigation which led to the identification of cyclopamine as the cause of the birth defect.[2]
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See also
Patient trial conducted in Dallas, Texas through APQ research center. Myeloma patient was given 200 mg of cyclopamine daily for two 2 weeks every 3 months for a year, for a total of eight weeks or four times, August 2006-August 2007. M marker was measured and decreased from 1.0 to 0.2 during that time. There is now a new water-soluble version of cyclopamine that will be tested soon.dubious Cyclopamine Tartarate Salt (All Hydroxy Carboxylic Acids) is a white crystaline compound that has been filed for a provisional patent by Logan Natural Products on 2/10/2008.
Notes
References
- Tas,S.,Avci , O., Induction of the differentiation and apotosis of tumor cells in vivo with efficiency and selectivity, Eur. J. Dermatology , 14: 96-102, 2004.
- Tas,S.,Avci , O.,Rapid Clearance of Psoriatic Skin Lesions Induced by Topical Cyclopamine, Dermatology, Vol.209,No:2, 2004.
- Garrossian, M. et al. "Synthesis and Anticancer Activity Studies of Cyclopamine Derivatives." Bioorganic & Medicinal Chemistry Letters 18 (2008): 1359-1363.
External links
- Cancer Drug Behind Cyclops Birth? (Wired News Article)
- Experimental Anti-cancer Drug Kills Brain Tumor Stem Cells (Science Daily)
Wikipedia content modification information:
- This page was last modified on 27 September 2008, at 19:25.
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