Cyclopamine

Modify Date: 2024-01-02 20:28:33

Cyclopamine Structure
Cyclopamine structure
 Common Name Cyclopamine
CAS Number 4449-51-8 Molecular Weight 411.620
Density 1.1±0.1 g/cm3 Boiling Point 550.8±50.0 °C at 760 mmHg
Molecular Formula C27H41NO2 Melting Point 236-238ºC
MSDS N/A Flash Point 286.9±30.1 °C

 Use of Cyclopamine


Cyclopamine is a Hedgehog (Hh) pathway antagonist with an IC50 of 46 nM in the Hh cell assay.

 Names

Name Cyclopamine
Synonym More Synonyms

 Cyclopamine Biological Activity

Description Cyclopamine is a Hedgehog (Hh) pathway antagonist with an IC50 of 46 nM in the Hh cell assay.
Related Catalog
Target

IC50: 46 nM (Hedgehog, in Hh cell assay)[1]
In Vitro Treatment with small molecule Hh inhibitors such as HhAntag and the natural product Cyclopamine, both binding to Smo, induces tumor remission in a genetic mouse model of medulloblastoma[1]. Cyclopamine is a Hedgehog (Hh) pathway antagonist. Cyclopamine suppresses cell growth. Cyclopamine (3 μM) suppression of Hh pathway activity and growth in digestive tract tumour cell lines correlates with expression of PTCHmRNA[2]. Cyclopamine is a steroidal alkaloid that inhibits Hh signalling through direct interaction with Smo[3].
In Vivo Cyclopamine causes durable regression of xenograft tumors. Tumors in Cyclopamine-treated animals, regress completely by 12 days[2]. Cyclopamine (1.2 mg) treatment blocks tumour formation of human pancreatic adenocarcinoma cells after transplantation into nude mice[3].
Cell Assay Cells are cultured in triplicate in 96-well plates in assay media to which 5E1 monoclonal antibody, ShhNp and/or Cyclopamine (3 μM) are added at 0 h at concentrations indicated in the main text. Viable cell mass is determined by optical density measurements at 490 nm (OD490) at 2 and 4 days using the CellTiter96 colorimetric assay. Relative growth is calculated as OD (day 4)-OD (day 2)/OD (day 2)[2].
Animal Admin Mice[3] A total of 0.1 mL Hanks’ balanced salt solution and matrigel (1:1) containing 2×106 cells is injected subcutaneously into CD-1 nude mice. Tumors are grown for 4 days to a minimum volume of 125 mm3; treatment is initiated simultaneously for all subjects. Mice are injected subcutaneously with vector alone (triolein:ethanol 4:1 v/v) or a Cyclopamine suspension (1.2 mg per mouse in triolein:ethanol 4:1 v/v) daily for 7 days. At the end of the treatment period, tumours are excised from mice, weighed and then fixed for 3 h at 4°C with 4% paraformaldehyde, embedded in paraffin wax and sectioned (6 µm). Apoptotic cells are identified by TUNEL using recombinant Tdt. Sections are then counterstained with eosin. Eight ×20-magnified fields from regions corresponding to the exterior, middle and interior of two control and two cyclopamine-treated tumours are chosen at random. We counted the number of TUNEL-positive nuclei manually. Haematoxylin/eosin staining is done.
References

[1]. Peukert S, et al. Identification and structure-activity relationships of ortho-biphenyl carboxamides as potent Smoothened antagonists inhibiting the Hedgehog signaling pathway. Bioorg Med Chem Lett, 2009, 19(2), 328-331.

[2]. Berman DM, et al. Widespread requirement for Hedgehog ligand stimulation in growth of digestive tract tumours. Nature, 2003, 425(6960), 846-851.

[3]. Thayer SP, et al. Hedgehog is an early and late mediator of pancreatic cancer tumorigenesis. Nature, 2003, 425(6960), 851-856.

[4]. Ma W, et al. Reduced Smoothened level rescued Aβ-induced memory deficits and neuronal inflammation in animal models of Alzheimer's disease. J Genet Genomics. 2018 May 20;45(5):237-246.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 550.8±50.0 °C at 760 mmHg
Melting Point 236-238ºC
Molecular Formula C27H41NO2
Molecular Weight 411.620
Flash Point 286.9±30.1 °C
Exact Mass 411.313721
PSA 41.49000
LogP 5.44
Vapour Pressure 0.0±3.4 mmHg at 25°C
Index of Refraction 1.583
Storage condition 2-8°C
Stability Store in Freezer at - 20°C
Water Solubility DMSO: soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GY0750000
CHEMICAL NAME :
Cyclopamine
CAS REGISTRY NUMBER :
4449-51-8
LAST UPDATED :
199712
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C27-H41-N-O2
MOLECULAR WEIGHT :
411.69
WISWESSER LINE NOTATION :
L D6 B566 FX DU LUTJ A1 E1 OQ F-& CT56 BOX FMTJ D1 H1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
180 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
170 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
120 mg/kg
SEX/DURATION :
female 6-9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,1187,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
300 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 29(2),22A,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
44500 ug/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 136,1174,1971
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
116 mg/kg
SEX/DURATION :
female 7-8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - eye/ear
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 136,1174,1971
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
250 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
170 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
54546 ug/kg
SEX/DURATION :
female 30-31 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 142,1287,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
30 mg/kg
SEX/DURATION :
female 14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 192,153,1989 *** REVIEWS *** TOXICOLOGY REVIEW AEMBAP Advances in Experimental Medicine and Biology. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.1- 1967- Volume(issue)/page/year: 27,107,1972

 Safety Information

Hazard Codes Xi: Irritant;
Safety Phrases 22-24/25
WGK Germany 3
RTECS GY0750000

 Synthetic Route

(2'R,3S,3'R,3a'S,6aS,6bS,6'S,7a'R,11aS,11bR)-3',6',10,11b-tetramethyl-4'-(phenylsulfonyl)-1,2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol structure

(2'R,3S,3'R,3a'...

CAS#:1198184-95-0

~91%

Cyclopamine Structure

Cyclopamine

CAS#:4449-51-8
Literature: Giannis, Athanassios; Heretsch, Philipp; Sarli, Vasiliki; Stoessel, Anne Angewandte Chemie - International Edition, 2009 , vol. 48, # 42 p. 7911 - 7914
Jervine structure

Jervine

CAS#:469-59-0

~51%

Cyclopamine Structure

Cyclopamine

CAS#:4449-51-8
Literature: Suginome, Hiroshi; Yonekura, Norihisa; Masamune, Tadashi Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 1 p. 210 - 213
N/A structure

N/A

CAS#:1224886-42-3

~%

4-hydroxy-2-nitrophenol structure

4-hydroxy-2-nit...

CAS#:41833-13-0
Cyclopamine Structure

Cyclopamine

CAS#:4449-51-8
Literature: Hamon, Florian; Renoux, Brigitte; Chadeneau, Corinne; Muller, Jean-Marc; Papot, Sebastien European Journal of Medicinal Chemistry, 2010 , vol. 45, # 4 p. 1678 - 1682

 Synonyms

11-DEOXYJERVINE
alkaloidv
Spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol, 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-, (3S,3'R,3a'S,6'S,6aS,6bS,7a'R,9R,11aS,11bR)-
deoxojervine
11-Desoxo-jervin
Veratraman-3-ol, 17,23-epoxy-, (3β,23β)-
Cyclopamine
(3β,22S,23R)-17,23-Epoxyveratraman-3-ol
Spiro(9H-benzo(a)fluorene-9,2'(3'H)-furo(3,2-b)pyridin)-3-ol, 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-, (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-
11-deoxojervine
MFCD01735266
(3β,17β,22S,23R)-17,23-Epoxyveratraman-3-ol
11-deoxo-jervin
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Chemsrc provides Cyclopamine(CAS#:4449-51-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Cyclopamine are included as well.>> amp version: Cyclopamine

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