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Cyclopamine



Cyclopamine

Systematic (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
Synonyms
11-deoxojervine
(3-β,23-β)-17,23-epoxy-3-hydroxy-veratraman
Identifiers
PubChem         442972
Chemical data
Formula C27H41NO2 
Molar mass 411.62
Complete data

Cyclopamine (11-deoxojervine) is 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).

Additional recommended knowledge

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]

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, for four times or every 3 months over a year, August 2006-August 2007. M marker was measured and decreased from 1.0 to 0.2 during that time.

Two new Cyclopamine like Alkaloids have been discoverd by Logan Natural Products ( www.logannaturalproducts.com ), their Hydrochloride salts are stable and water soluble. They have been named Amkurdamine and Bijaramine.Initial results exibits activity against Lung Cancer Cell , with positive inhibitory effect toward the Hedgehog Signaling pathway.

References

  1. ^ (2000-08-31) "Effects of oncogenic mutations in Smoothened and Patched can be reversed by cyclopamine". Nature 406 (6799): 1005-9. PubMed
  2. ^ Herper, Matthew (2005-11-28). The Curious Case of The One-Eyed Sheep. Forbes.


3. 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.
4. Tas,S.,Avci , O.,Rapid Clearance of Psoriatic Skin Lesions Induced by Topical Cyclopamine, Dermatology, Vol.209,No:2, 2004.

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cyclopamine". A list of authors is available in Wikipedia.
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