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Volumn 51, Issue 21, 2008, Pages 6646-6649

Semisynthetic cyclopamine analogues as potent and orally bioavailable hedgehog pathway antagonists

Author keywords

[No Author keywords available]

Indexed keywords

4 EN 3 ONE CYCLOPAMINE; ALLYL COMPOUND; ANTINEOPLASTIC AGENT; CYCLOPAMINE; CYCLOPROPYLCYCLOPAMINE; DEXTRO HOMOCYCLOPAMINE DERIVATIVE; IPI 269609; KETONE; UNCLASSIFIED DRUG; VERATRAMINE;

EID: 56249121238     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8008508     Document Type: Article
Times cited : (102)

References (39)
  • 1
    • 0036559186 scopus 로고    scopus 로고
    • Gli and Hedgehog in Cancer: Tumours, Embryos and Stem Cells
    • Ruiz i Altaba, A.; Sanchez, M. P.; Dahmane, N. Gli and Hedgehog in Cancer: Tumours, Embryos and Stem Cells. Nat. Rev. Cancer 2002, 2, 361-372.
    • (2002) Nat. Rev. Cancer , vol.2 , pp. 361-372
    • Ruiz i Altaba, A.1    Sanchez, M.P.2    Dahmane, N.3
  • 2
    • 0345059765 scopus 로고    scopus 로고
    • Hedgehog Signalling in Cancer Formation and Maintenance
    • di Magliano, M. P.; Hebrok, M. Hedgehog Signalling in Cancer Formation and Maintenance. Nat. Rev. Cancer 2003, 3, 903-911.
    • (2003) Nat. Rev. Cancer , vol.3 , pp. 903-911
    • di Magliano, M.P.1    Hebrok, M.2
  • 3
    • 9244221172 scopus 로고    scopus 로고
    • Tissue Repair and Stem Cell Renewal in Carcinogenesis
    • Beachy, P. A.; Karhadkar, S. S.; Berman, D. M. Tissue Repair and Stem Cell Renewal in Carcinogenesis. Nature 2004, 432, 324-331.
    • (2004) Nature , vol.432 , pp. 324-331
    • Beachy, P.A.1    Karhadkar, S.S.2    Berman, D.M.3
  • 4
    • 0030844141 scopus 로고    scopus 로고
    • Activation of the Transcription Factor Gli1 and the Sonic Hedgehog Signalling Pathway in Skin Tumours
    • Dahmane, N.; Lee, J.; Robins, P.; Heller, P.; Ruiz i Altaba, A. Activation of the Transcription Factor Gli1 and the Sonic Hedgehog Signalling Pathway in Skin Tumours. Nature 1997, 389, 876-881.
    • (1997) Nature , vol.389 , pp. 876-881
    • Dahmane, N.1    Lee, J.2    Robins, P.3    Heller, P.4    Ruiz i Altaba, A.5
  • 5
    • 19944429892 scopus 로고    scopus 로고
    • Sustained Hedgehog Signaling Is Required for Basal Cell Carcinoma Proliferation and Survival: Conditional Skin Tumorigenesis Recapitulates the Hair Growth Cycle
    • Hutchin, M. E.; Kariapper, M. S. T.; Gratchtchouk, M.; Wang, A.; Wei, L.; Cummings, D.; Liu, J.; Michael, L. R.; Glick, A.; Dlugosz, A. A. Sustained Hedgehog Signaling Is Required for Basal Cell Carcinoma Proliferation and Survival: Conditional Skin Tumorigenesis Recapitulates the Hair Growth Cycle. Genes Dev. 2004, 19, 214-224.
    • (2004) Genes Dev , vol.19 , pp. 214-224
    • Hutchin, M.E.1    Kariapper, M.S.T.2    Gratchtchouk, M.3    Wang, A.4    Wei, L.5    Cummings, D.6    Liu, J.7    Michael, L.R.8    Glick, A.9    Dlugosz, A.A.10
  • 8
    • 0032409157 scopus 로고    scopus 로고
    • Hedgehog and Patched in Neural Development and Disease
    • Goodrich, L. V.; Scott, M. P. Hedgehog and Patched in Neural Development and Disease. Neuron 1998, 21, 1243-1257.
    • (1998) Neuron , vol.21 , pp. 1243-1257
    • Goodrich, L.V.1    Scott, M.P.2
  • 11
    • 0242669237 scopus 로고    scopus 로고
    • Hedgehog Signalling within Airway Epithelial Progenitors and in Small-Cell Lung Cancer
    • Watkins, D. N.; Berman, D. M.; Burkholder, S. G.; Wang, B.; Beachy, P. A.; Baylin, S. B. Hedgehog Signalling within Airway Epithelial Progenitors and in Small-Cell Lung Cancer. Nature 2003, 422, 313-317.
    • (2003) Nature , vol.422 , pp. 313-317
    • Watkins, D.N.1    Berman, D.M.2    Burkholder, S.G.3    Wang, B.4    Beachy, P.A.5    Baylin, S.B.6
  • 12
    • 33751549095 scopus 로고    scopus 로고
    • Target the Hedgehog Pathway in Cancer
    • Rubin, L. L.; de Sauvage, F. J. Target the Hedgehog Pathway in Cancer. Nat. Rev. Cancer 2006, 5, 1026-1033.
    • (2006) Nat. Rev. Cancer , vol.5 , pp. 1026-1033
    • Rubin, L.L.1    de Sauvage, F.J.2
  • 14
    • 2442767513 scopus 로고
    • Teratogenic Compounds of Veratrum californicum (Durand)-IV. First Isolation of Veratramine and Alkaloid Q and a Reliable Method for Isolation of Cyclopamine
    • Kecler, R. F. Teratogenic Compounds of Veratrum californicum (Durand)-IV. First Isolation of Veratramine and Alkaloid Q and a Reliable Method for Isolation of Cyclopamine. Phytochemisiry 1968, 7, 303-306.
    • (1968) Phytochemisiry , vol.7 , pp. 303-306
    • Kecler, R.F.1
  • 15
    • 0036829397 scopus 로고    scopus 로고
    • Inhibition of Hedgehog Signaling by Direct Binding of Cyclopamine to Smoothened
    • Chen, J. K.; Taipale, J.; Cooper, M. K.; Beachy, P. A. Inhibition of Hedgehog Signaling by Direct Binding of Cyclopamine to Smoothened. Genes Dev. 2002, 16, 2743-2748.
    • (2002) Genes Dev , vol.16 , pp. 2743-2748
    • Chen, J.K.1    Taipale, J.2    Cooper, M.K.3    Beachy, P.A.4
  • 17
    • 0024449555 scopus 로고
    • Osmotic Minipump, and Intramuscular Administration to Sheep of the Veratrum Alkaloid Cyclopamine
    • Keeler, R. F.; Baker, D. C. Oral, Osmotic Minipump, and Intramuscular Administration to Sheep of the Veratrum Alkaloid Cyclopamine. Proc. Soc. Exp. Biol. Med. 1989, 192, 153-156.
    • (1989) Proc. Soc. Exp. Biol. Med , vol.192 , pp. 153-156
    • Keeler, R.F.1    Baker, D.2    Oral, C.3
  • 18
    • 0014786872 scopus 로고
    • Teratogenic Compounds in Veratrum californicum (Durand) IX. Structure-Activity Relation
    • Keeler, R. F. Teratogenic Compounds in Veratrum californicum (Durand) IX. Structure-Activity Relation. Teratology 1970, 3, 169-174.
    • (1970) Teratology , vol.3 , pp. 169-174
    • Keeler, R.F.1
  • 19
    • 0032890406 scopus 로고    scopus 로고
    • Pharmacological Tests of the Mechanism of the Periodic Rhythm Caused by Veratramine in the Sinoatrial Node of the Guinea Pig
    • Thron, C. D.; McCann, F. V. Pharmacological Tests of the Mechanism of the Periodic Rhythm Caused by Veratramine in the Sinoatrial Node of the Guinea Pig. Gen. Pharmacol. 1998, 32, 81-89.
    • (1998) Gen. Pharmacol , vol.32 , pp. 81-89
    • Thron, C.D.1    McCann, F.V.2
  • 20
    • 0026092559 scopus 로고
    • Veratramine-Induced Behavior Associated with Serotonergic Hyperfunction in Mice
    • Nagata, R.; Izumi, K. Veratramine-Induced Behavior Associated with Serotonergic Hyperfunction in Mice. J. Pharmacol. 1991, 55, 129.
    • (1991) J. Pharmacol , vol.55 , pp. 129
    • Nagata, R.1    Izumi, K.2
  • 21
    • 0029061675 scopus 로고
    • Time Course and Inhibition of Stavaroside K, Veratramine and Cevine-Induced Hemolysis by Other Pregnane Glycosides and Veratrum Alkaloids
    • Badria, F. A.; McChesney, J. D.; Halim, A. F.; Zaghloul, A. M.; El Sayed, K. A. Time Course and Inhibition of Stavaroside K, Veratramine and Cevine-Induced Hemolysis by Other Pregnane Glycosides and Veratrum Alkaloids. Pharmazie 1995, 50, 421-423.
    • (1995) Pharmazie , vol.50 , pp. 421-423
    • Badria, F.A.1    McChesney, J.D.2    Halim, A.F.3    Zaghloul, A.M.4    El Sayed, K.A.5
  • 23
    • 0017964787 scopus 로고
    • Structure-Activity Relation of Steroid Teratogens. 1 Jervine Ring System
    • Brown, B.; Keeler, R. F. Structure-Activity Relation of Steroid Teratogens. 1 Jervine Ring System. J. Agric. Food Chem. 1978, 26, 561-563.
    • (1978) J. Agric. Food Chem , vol.26 , pp. 561-563
    • Brown, B.1    Keeler, R.F.2
  • 25
    • 41249085384 scopus 로고    scopus 로고
    • Targeted Inhibition of Hedgehog Signaling by Cyclopamine Prodrugs for Advanced Prostate Cancer
    • Kumar, S. K.; Roy, I.; Anchoori, R. K.; Fazli, S.; Maitra, A.; Beachy, P. A.; Khan, S. R. Targeted Inhibition of Hedgehog Signaling by Cyclopamine Prodrugs for Advanced Prostate Cancer. Bioorg. Med. Chem. 2008, 16, 2764-2768.
    • (2008) Bioorg. Med. Chem , vol.16 , pp. 2764-2768
    • Kumar, S.K.1    Roy, I.2    Anchoori, R.K.3    Fazli, S.4    Maitra, A.5    Beachy, P.A.6    Khan, S.R.7
  • 26
    • 56249097147 scopus 로고    scopus 로고
    • Cyclopamine Analogs and Methods of Use Thereof
    • US 7,230,004 B2, June 12, 2007
    • Adams, J.; Castro, A. C.; Foley, M. A.; Nair, S. N. J.; Nevalainen, M.; Cyclopamine Analogs and Methods of Use Thereof. US 7,230,004 B2, June 12, 2007.
    • Adams, J.1    Castro, A.C.2    Foley, M.A.3    Nair, S.N.J.4    Nevalainen, M.5
  • 27
    • 46449106374 scopus 로고    scopus 로고
    • Oatis, J. E.; Brunsfeld, P.; Rushing, J. W.; Moeller, P. D.; Bearden, D. W. Isolation, Purification, and Full NMR Assignments of Cyclopamine from Veratrum californicum. Chem. Cent. J. 2008, 2, 12.
    • Oatis, J. E.; Brunsfeld, P.; Rushing, J. W.; Moeller, P. D.; Bearden, D. W. Isolation, Purification, and Full NMR Assignments of Cyclopamine from Veratrum californicum. Chem. Cent. J. 2008, 2, 12.
  • 28
  • 29
    • 0000008041 scopus 로고
    • A Comparison of (Chloromethyl)-and (Iodomethyl)zinc Cyclopropanation Reagents
    • Denmark, S. E.; Edwards, J. P. A Comparison of (Chloromethyl)-and (Iodomethyl)zinc Cyclopropanation Reagents. J. Org. Chem. 1991, 56, 6974-6981.
    • (1991) J. Org. Chem , vol.56 , pp. 6974-6981
    • Denmark, S.E.1    Edwards, J.P.2
  • 30
    • 0032548133 scopus 로고    scopus 로고
    • Exploring New Reactive Species for Cyclopropanation
    • Yang, Z.; Lorenz, J. C.; Shi, Y. Exploring New Reactive Species for Cyclopropanation. Tetrahedron Lett. 1998, 39, 8621-8624.
    • (1998) Tetrahedron Lett , vol.39 , pp. 8621-8624
    • Yang, Z.1    Lorenz, J.C.2    Shi, Y.3
  • 32
    • 49049137510 scopus 로고
    • Biogenesis-like Conversion of Marasmane to Lactarane and seco-Lactarane Skeleton
    • DeBernadi, M.; Vidari, G.; Vita-Finzi, P.; Fiasson, K. G. Biogenesis-like Conversion of Marasmane to Lactarane and seco-Lactarane Skeleton. Tetrahedron Lett. 1982, 23, 4623-4624.
    • (1982) Tetrahedron Lett , vol.23 , pp. 4623-4624
    • DeBernadi, M.1    Vidari, G.2    Vita-Finzi, P.3    Fiasson, K.G.4
  • 33
    • 0000646553 scopus 로고
    • Total Synthesis of the Marine Sesquiterpenes Dactylol and Africanol. De Novo Construction of a Cyclooctanoid Natural Product from Cycloheptane Precursors
    • Paquette, L. A.; Ham, W. H. Total Synthesis of the Marine Sesquiterpenes Dactylol and Africanol. De Novo Construction of a Cyclooctanoid Natural Product from Cycloheptane Precursors. J. Am. Chem. Soc. 1987, 109, 3025-3036.
    • (1987) J. Am. Chem. Soc , vol.109 , pp. 3025-3036
    • Paquette, L.A.1    Ham, W.H.2
  • 34
    • 0026472609 scopus 로고
    • Total Synthesis of Some Marasmane and Lactarane Sesquiterpenes
    • Thompson, S. K.; Heathcock, C. H. Total Synthesis of Some Marasmane and Lactarane Sesquiterpenes. J. Org. Chem. 1992, 57, 5979-5989.
    • (1992) J. Org. Chem , vol.57 , pp. 5979-5989
    • Thompson, S.K.1    Heathcock, C.H.2
  • 35
    • 34247844371 scopus 로고    scopus 로고
    • Oxysterols Are Novel Activators of the Hedgehog Signaling Pathway in Pluripotent Mesenchymal Cells
    • Dwyer, J. R.; Sever, N.; Carlson, M.; Nelson, S. F.; Beachy, P. A.; Parhami, F. Oxysterols Are Novel Activators of the Hedgehog Signaling Pathway in Pluripotent Mesenchymal Cells. J. Biol. Chem. 2007, 282, 8959-8968.
    • (2007) J. Biol. Chem , vol.282 , pp. 8959-8968
    • Dwyer, J.R.1    Sever, N.2    Carlson, M.3    Nelson, S.F.4    Beachy, P.A.5    Parhami, F.6
  • 36
    • 42749097286 scopus 로고
    • Syntheses and NMR Spectra of 22,27-Imino-17,23-oxidojervane Derivatives
    • Masamune, T.; Sato, N.; Kobayashi, K.; Yamazaki, I.; Mori, Y. Syntheses and NMR Spectra of 22,27-Imino-17,23-oxidojervane Derivatives. Tetrahedron 1967, 23, 1591-1612.
    • (1967) Tetrahedron , vol.23 , pp. 1591-1612
    • Masamune, T.1    Sato, N.2    Kobayashi, K.3    Yamazaki, I.4    Mori, Y.5
  • 37
    • 56249146243 scopus 로고    scopus 로고
    • Regulators of the Hedgehog Pathway, Compositions and Use Related Thereto
    • WO 01/27135 A2, April 19, 2001
    • Beachy, P. A. Regulators of the Hedgehog Pathway, Compositions and Use Related Thereto. WO 01/27135 A2, April 19, 2001.
    • Beachy, P.A.1
  • 38
    • 56249097513 scopus 로고    scopus 로고
    • McGovern, K. J.; Pien, C. S.; Wright, J. L. Dosing Regimen for the Treatment of Cancer. WO 2007/123511 A2, November 1, 2007.
    • McGovern, K. J.; Pien, C. S.; Wright, J. L. Dosing Regimen for the Treatment of Cancer. WO 2007/123511 A2, November 1, 2007.


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