ALEXIS Biochemicals: Debromohymenialdisine

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ALX-430-159

Revised 19-Aug-08

Cyclopamine
SYNONYMS	11-Deoxyjervine
PRODUCT LINE	Signal Transduction
PRODUCT CATEGORY	Hedgehog [Hh] Signalling Pathway

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-430-159-M001		1 mg	80.00 USD
ALX-430-159-M005		5 mg	320.00 USD

Product Specification

FORMULA:	C₂₇H₄₁NO₂
MW:	411.6
CAS NUMBER:	4449-51-8
MERCK INDEX:	14: 10201
RTECS:	GY0750000
PURITY:	≥98% (TLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in 100% ethanol (20mg/ml), DMF (10mg/ml), methanol (7mg/ml) or DMSO (4mg/ml). Heating to 50-60°C may be necessary. Insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
HAZARD:	MAY BE TERATOGENIC. HARMFUL.

Product Description

Steroidal alkaloid. Blocks activation of the Hedgehog (Hh) response pathway. Binds to the heptahelical protein bundle of Smoothened. Induces expression of the transcription factor Pdx-1. Disrupts cholesterol biosynthesis. Displays anti-tumor properties. Induces apoptosis. Causes cyclopia.

Product Specific Literature References

The teratogenic Veratrum alkaloid cyclopamine inhibits sonic hedgehog signal transduction: J.P. Incardona, et al.; Development 125, 3553 (1998) Abstract; Full Text
Pancreas development is promoted by cyclopamine, a hedgehog signaling inhibitor: S.K. Kim & D.A. Melton; PNAS 95, 13036 (1998) Abstract; Full Text
Teratogen-mediated inhibition of target tissue response to Shh signaling: M.K. Cooper, et al.; Science 280, 1603 (1998) Abstract
Effects of oncogenic mutations in Smoothened and Patched can be reversed by cyclopamine: J. Taipale, et al.; Nature 406, 1005 (2000) Abstract
Cyclopamine inhibition of Sonic hedgehog signal transduction is not mediated through effects on cholesterol transport: J.P. Incardona, et al.; Dev. Biol. 224, 440 (2000) Abstract
Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened: J.K. Chen, et al.; Genes Dev. 16, 2743 (2002) Abstract; Full Text
Small molecule modulation of Smoothened activity: J.K. Chen, et al.; PNAS 99, 14071 (2002) Abstract; Full Text
Medulloblastoma growth inhibition by hedgehog pathway blockade: D.M. Berman, et al.; Science 297, 1559 (2002) Abstract
Hedgehog signalling within airway epithelial progenitors and in small-cell lung cancer: D.N. Watkins, et al.; Nature 422, 313 (2003) Abstract
Widespread requirement for Hedgehog ligand stimulation in growth of digestive tract tumours: D.M. Berman, et al.; Nature 425, 846 (2003) Abstract
Hedgehog is an early and late mediator of pancreatic cancer tumorigenesis: S.P. Thayer, et al.; Nature 425, 851 (2003) Abstract
Hedgehog signalling in colorectal tumour cells: induction of apoptosis with cyclopamine treatment: D. Qualtrough, et al.; Int. J. Cancer 110, 831 (2004) Abstract
Induction of the differentiation and apoptosis of tumor cells in vivo with efficiency and selectivity: S. Tabs & O. Avci; Eur. J. Dermatol. 14, 96 (2004) Abstract; Full Text
In vitro directed differentiation of mouse embryonic stem cells into insulin-producing cells: T. Leon-Quinto, et al.; Diabetologia 47, 1442 (2004) Abstract
Transforming growth factor (TGF)beta, fibroblast growth factor (FGF) and retinoid signalling pathways promote pancreatic exocrine gene expression in mouse embryonic stem cells: A. Skoudy, et al.; Biochem. J. 379, 749 (2004) Abstract; Full Text
Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway: X. Wu, et al.; Chem. Biol. 11, 1229 (2004) Abstract

Related Products

ALX-350-377	Tomatidine . hydrochloride
ALX-350-378	Jervine

Further Categories Containing This Product:

Antitumor Agents (Apoptosis Inducers) • Alkaloids

ALX-350-023

Revised 03-Jun-08

Cyclopiazonic acid
SYNONYMS	CPA
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - ATPase Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-023-M005		5 mg	42.00 USD
ALX-350-023-M025		25 mg	145.00 USD
ALX-350-023-M100		100 mg	460.00 USD

Product Specification

FORMULA:	C₂₀H₂₀N₂O₃
MW:	336.4
CAS NUMBER:	18172-33-3
RTECS:	UY8587000
SOURCE/HOST:	Isolated from Penicillium griseofulvum.
PURITY:	≥98% (TLC)
APPEARANCE:	Off-white to yellow powder.
SOLUBILITY:	Soluble in DMSO (50mg/ml), methylene chloride or methanol (10mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	TOXIC.

Product Description

Mycotoxin. Cell permeable, reversible inhibitor of Ca²⁺-ATPases.

Product Specific Literature References

Cyclopiazonic acid is a specific inhibitor of the Ca2+-ATPase of sarcoplasmic reticulum: N.W. Seidler, et al.; J. Biol. Chem. 264, 17816 (1989) Abstract; Full Text
Acetylcholine Ca2+ stores refilling directly involves a dihydropyridine- sensitive channel in dog trachea: J.P. Bourreau, et al.; Am. J. Physiol. 261, C497 (1991) Abstract
Discrimination of Ca(2+)-ATPase activity of the sarcoplasmic reticulum from actomyosin-type ATPase activity of myofibrils in skinned mammalian skeletal muscle fibres: distinct effects of cyclopiazonic acid on the two ATPase activities: N. Kurebayashi & Y. Ogawa; J. Muscle Res. Cell Motility 12, 355 (1991) Abstract
Coupling between intracellular Ca2+ stores and the Ca2+ permeability of the plasma membrane. Comparison of the effects of thapsigargin, 2,5-di- (tert-butyl)-1,4-hydroquinone, and cyclopiazonic acid in rat thymic lymphocytes: M.J. Mason, et al.; J. Biol. Chem. 266, 20856 (1991) Abstract; Full Text
Cyclopiazonic acid depletes intracellular Ca2+ stores and activates an influx pathway for divalent cations in HL-60 cells: N. Demaurex, et al.; J. Biol. Chem. 267, 2318 (1992) Abstract; Full Text
Cyclopiazonic acid, an inhibitor of the sarcoplasmic reticulum Ca(2+)- pump, reduces Ca(2+)-dependent K+ currents in guinea-pig smooth muscle cells: M. Suzuki, et al.; Br. J. Pharmacol. 107, 134 (1992) Abstract
Effects of cyclopiazonic acid, a novel Ca(2+)-ATPase inhibitor, on contractile responses in skinned ileal smooth muscle: Y. Uyama, et al.; Br. J. Pharmacol. 106, 208 (1992) Abstract
Effects of cyclopiazonic acid and ryanodine on cytosolic calcium and contraction in vascular smooth muscle: F. Abe, et al.; Br. J. Pharmacol. 118, 1711 (1996) Abstract
Natural and in vitro coproduction of cyclopiazonic acid and aflatoxins: M.L. Martins & H.M. Martins; J. Food Prot. 62, 292 (1999) Abstract
Recent advances in analytical methodology for cyclopiazonic acid: J.W. Dorner; Adv. Exp. Med. Biol. 504, 107 (2002), Review Abstract
Cyclopiazonic acid reduces the coupling factor of the Ca2+-ATPase acting on Ca2+ binding: F. Martinez-Azorin; FEBS Lett. 576, 73 (2004) Abstract

Further Categories Containing This Product:

Ca2+-ATPase / Related Products • Neurotoxins • Mycotoxins

ALX-106-028

Revised 03-Apr-08

D-Cycloserine
SYNONYMS	R(+)-4-Amino-3-isoxazolidinone
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products for Neurological Research

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-106-028-M050		50 mg	20.00 USD
ALX-106-028-M250		250 mg	80.00 USD

Product Specification

FORMULA:	C₃H₆N₂O₂
MW:	102.1
CAS NUMBER:	68-41-7
RTECS:	NY2975000
SOURCE/HOST:	Synthetic.
PURITY:	≥97%
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HANDLING:	Hygroscopic.

Product Description

Excitatory amino acid. Partial agonist at the glycine modulatory site of the NMDA receptor.

Further Categories Containing This Product:

Excitatory Amino Acids • Special Amino Acids • NMDA Receptors / Related Products

ALX-106-037

Revised 09-Oct-07

L-Cycloserine
SYNONYMS	S(-)-4-Amino-3-isoxazolidinone
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products for Neurological Research

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-106-037-M025		25 mg	50.00 USD
ALX-106-037-M100		100 mg	150.00 USD

Product Specification

FORMULA:	C₃H₆N₂O₂
MW:	102.1
CAS NUMBER:	339-72-0; 4834-58-6
MERCK INDEX:	14: 2751
RTECS:	NY2976000
PURITY:	≥98%
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Hygroscopic.

Product Description

Excitatory amino acid. Inhibitor of ketosphinganine synthase (serine-palmitoyl-CoA transferase, EC 2.3.1.50), leading to blockade of sphingosine biosynthesis. Partial agonist at the glycine modulatory site of the NMDA receptor.

Product Specific Literature References

Inhibition of sphingolipid synthesis by cycloserine in vitro and in vivo: K.S. Sundaram & M. Lev; J. Neurochem. 42, 577 (1984) Abstract
Inhibition of serine palmitoyltransferase activity in rabbit aorta by L-cycloserine: R.D. Williams, et al.; J. Lipid Res. 28, 1478 (1987) Abstract; Full Text
D-cycloserine acts as a partial agonist at the glycine modulatory site of the NMDA receptor expressed in Xenopus oocytes: G.B. Watson, et al.; Brain Res. 510, 158 (1990) Abstract
D-cycloserine, a putative cognitive enhancer, facilitates activation of the N-methyl-D-aspartate receptor-ionophore complex in Alzheimer brain: I.P. Chessell, et al.; Brain Res. 565, 345 (1991) Abstract
Rapid kidney changes resulting from glycosphingolipid depletion by treatment with a glucosyltransferase inhibitor: G.S. Shukla, et al.; Biochim. Biophys. Acta 1083, 101 (1991) Abstract

Further Categories Containing This Product:

Special Amino Acids • Excitatory Amino Acids • NMDA Receptors / Related Products

ALX-380-002

Revised 03-Apr-08

Cyclosporin A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-002-M100		100 mg	46.00 USD
ALX-380-002-5100		5x100 mg	190.00 USD
ALX-380-002-G001		1 g	290.00 USD
ALX-380-002-5001		5x1 g	1'150.00 USD

Product Specification

FORMULA:	C₆₂H₁₁₁N₁₁O₁₂
MW:	1202.6
CAS NUMBER:	59865-13-3
MERCK INDEX:	14: 2752
RTECS:	GZ4120000
SOURCE/HOST:	Isolated from Fusarium solani.
PURITY:	≥99% (Assay)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in methanol, 100% ethanol, acetone or petroleum ether; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HAZARD:	MAY BE TERATOGENIC. TOXIC. MAY BE CARCINOGENIC.

Product Description

Antibiotic. Potent immunosuppressor. Widely used after organ transplantation. Binds to cytosolic proteins of the cyclophilin family. Cyclosporin A-cyclophilin complexes block protein phosphatase 2B (PP2B; calcineurin), a key enzyme in T cell activation. As a result of the calcineurin inhibition, cyclosporine A blocks various cellular processes such as activation of T cells and expression of several lymphokines (especially IL-2). Inhibits cytochrome c release from mitochondria. Inhibits nitric oxide (NO) synthesis.

Product Specific Literature References

Cyclosporin A and C-New metabolites from Trichodermapolysporum (Link ex Pers.) Rifai: Dreyfuss M., et al.; Europ. J. appl. Microbiol. 3, 125 (1976)
Immunosuppression for organ grafting - observations on cyclosporin A: R. Y. Calne; Immunol. Rev. 46, 113 (1976), Review Abstract
Immunological actions of cyclosporin A in rheumatoid arthritis: D. Yocum; Br. J. Rheumatol. 32, 38 (1993), Review Abstract
Cyclosporin A binding to mitochondrial cyclophilin inhibits the permeability transition pore and protects hearts from ischaemia/reperfusion injury: A.P. Halestrap, et al; Mol. Cell. Biochem. 174, 167 (1997), Review Abstract
New aspects of cyclosporin a mode of action: from gene silencing to gene up-regulation: L. Mascarell & P. Truffa-Bachi; Mini Rev. Med. Chem. 3, 205 (2003), Review Abstract
Rationale for T cell inhibition by cyclosporin A in major autoimmune diseases: G.F. Ferraccioli, et al.; Ann. N. Y. Acad. Sci. 1051, 658 (2005), Review Abstract

Further Categories Containing This Product:

MPTP [Mitochondrial Transition Pore] / Related Products • Antibiotics - Nitric Oxide Pathway Modulators • Antibiotics - Apoptosis Inducers & Inhibitors • Non-apoptotic Cell Death / Necrosis

ALX-380-282

Revised 19-Mar-08

Cyclosporin C
SYNONYMS	Thr²-cyclosporin A 7-L-Threonine-cyclosporin A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-282-M001		1 mg	50.00 USD
ALX-380-282-M005		5 mg	200.00 USD

Product Specification

FORMULA:	C₆₂H₁₁₁N₁₁O₁₃
MW:	1218.6
CAS NUMBER:	59787-61-0
MERCK INDEX:	14: 2752
SOURCE/HOST:	Isolated from Fusarium solani.
PURITY:	≥95% (HPLC)
APPEARANCE:	Colorless to off-white crystalline solid.
SOLUBILITY:	Soluble in 100% ethanol, acetone or ethyl acetate; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	MAY BE CARCINOGENIC. TOXIC. MAY BE TERATOGENIC.

Product Description

Potent immunosuppressor.

Product Specific Literature References

Cyclosporin A and C-New metabolites from Trichodermapolysporum (Link ex Pers.) Rifai: M. Dreyfuss, et al.; Europ. J. Appl. Microbiol. 3, 125 (1976)
[The structure of cyclosporin c (author’s transl)]: R. Traber, et al.; Helv. Chim. Acta 60, 1247 (1977) Abstract
Dosage, timing, and route of administration of cyclosporin A and nonimmunosuppressive derivatives of dihydrocyclosporin A and cyclosporin C against Schistosoma mansoni in vivo and in vitro: L.H. Chappell, et al.; Antimicrob. Agents Chemother. 31, 1567 (1987) Abstract
Cyclosporin C is the main antifungal compound produced by Acremonium luzulae: M. Moussaif, et al.; Appl. Environ. Microbiol. 63, 1739 (1997) Abstract; Full Text
Cyclosporin C(2) and C(0) concentration monitoring in stable, long-term heart transplant recipients receiving metabolic inhibitors: J.E. Ray, et al.; J. Heart Lung Transplant. 22, 715 (2003) Abstract

Further Categories Containing This Product:

Non-apoptotic Cell Death / Necrosis

ALX-380-284

Revised 08-Apr-08

Cyclosporin D
SYNONYMS	Val²-cyclosporin 7-L-Valine-cyclosporin A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-284-M001		1 mg	80.00 USD
ALX-380-284-M005		5 mg	320.00 USD

Product Specification

FORMULA:	C₆₃H₁₁₃N₁₁O₁₂
MW:	1216.6
CAS NUMBER:	63775-96-2
MERCK INDEX:	14: 2752
SOURCE/HOST:	Isolated from Fusarium solani.
PURITY:	≥95% (HPLC)
APPEARANCE:	Colorless to off-white crystalline solid.
SOLUBILITY:	Soluble in 100% ethanol, acetone or ethyl acetate; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	MAY BE TERATOGENIC. TOXIC. MAY BE CARCINOGENIC.

Product Description

Weak immunosuppressor. Potent inhibitor of tumor promoting phorbol ester TPA/PMA (Prod. No. ALX-445-004) in vivo. Potent inhibitor of Ca²⁺/calmodulin dependent EF-2 phosphorylation in vitro.

Product Specific Literature References

Further Categories Containing This Product:

MPTP [Mitochondrial Transition Pore] / Related Products • CAM Kinase Inhibitors

ALX-380-286

Revised 08-Apr-08

Cyclosporin H
SYNONYMS	Csh-cyclosporin 5-(N-Methyl-D-valine)-cyclosporin A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-286-M001		1 mg	80.00 USD
ALX-380-286-M005		5 mg	320.00 USD

Product Specification

FORMULA:	C₆₂H₁₁₁N₁₁O₁₂
MW:	1202.6
CAS NUMBER:	83602-39-5
SOURCE/HOST:	Isolated from Fusarium solani.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in 100% ethanol, acetone or ethyl acetate; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	MAY BE TERATOGENIC. TOXIC. MAY BE CARCINOGENIC.

Product Description

Immunologically inactive. Does not bind to immunophilin. Potent inhibitor of tumor promoting phorbol ester TPA/PMA (Prod. No. ALX-445-004) in mouse skin in vivo. Potent inhibitor of Ca²⁺/calmodulin dependent EF-2 phosphorylation in vitro. Potent and selective antagonist of formyl peptide receptor. Inhibits formyl peptide-induced superoxide formation.

Product Specific Literature References

The weak immunosuppressant cyclosporine D as well as the immunologically inactive cyclosporine H are potent inhibitors in vivo of phorbol ester TPA-induced biological effects in mouse skin and of Ca2+/calmodulin dependent EF-2 phosphorylation in vitro: M. Gschwendt, et al.; BBRC 150, 545 (1988) Abstract
Differential inhibition of human neutrophil activation by cyclosporins A, D, and H. Cyclosporin H is a potent and effective inhibitor of formyl peptide-induced superoxide formation: K. Wenzel-Seifert, et al.; J. Immunol. 147, 1940 (1991) Abstract
Cyclosporin H is a potent and selective formyl peptide receptor antagonist. Comparison with N-t-butoxycarbonyl-L-phenylalanyl-L-leucyl-L-phenylalanyl-L- leucyl-L-phenylalanine and cyclosporins A, B, C, D, and E: K. Wenzel-Seifert & R. Seifert; J. Immunol. 150, 4591 (1993) Abstract
Cyclosporin H is a potent and selective competitive antagonist of human basophil activation by N-formyl-methionyl-leucyl-phenylalanine: A. de Paulis, et al.; J. Allergy Clin. Immunol. 98, 152 (1996) Abstract
Cyclosporin H, Boc-MLF and Boc-FLFLF are antagonists that preferentially inhibit activity triggered through the formyl peptide receptor: A.L. Stenfeldt, et al.; Inflammation 30, 224 (2007) Abstract

Further Categories Containing This Product:

MPTP [Mitochondrial Transition Pore] / Related Products • Antibiotics - Apoptosis Inducers & Inhibitors • CAM Kinase Inhibitors • Antibiotics - Nitric Oxide Pathway Modulators • Non-apoptotic Cell Death / Necrosis

ALX-350-149

Revised 23-Oct-07

Cylindrospermopsin