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Natural Products - ATPase Inhibitors
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ALX-350-004 Revised 08-Apr-08
Thapsigargin
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Tumor Promoters
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-004-M001   1 mg 50.00 USD Add To Cart
ALX-350-004-M005   5 mg 200.00 USD Add To Cart
ALX-350-004-M010   10 mg 350.00 USD Add To Cart
ALX-350-004-M025   25 mg 690.00 USD Add To Cart
Product Specification
FORMULA: C34H50O12
MW: 650.8
CAS NUMBER: 67526-95-8
MERCK INDEX: 14: 9272
PURITY: ≥95% (HPLC)
APPEARANCE: Clear colorless film.
SOLUBILITY: Soluble in DMSO or 100% ethanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light and oxygen.
HAZARD: HIGHLY IRRITANT. HARMFUL.

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Product Description
Cell permeable tumor promoter by specific inhibition of the (sarco)endoplasmatic reticulum Ca2+-ATPase (SERCA). Inhibition of SERCA reveals a significant change in intracellular Ca2+ homeostasis and pH regulation in tumor cells. Does not increase inositol phosphates. Shows no effect on protein kinase C (PKC). Increases Ca2+-dependent Na+ influx in human platelets in a dose-dependent manner. Induces apoptosis. Stimulates nitric oxide (NO) production, contributing to hepatocyte apoptosis.
Product Specific Literature References
Brefeldin A, thapsigargin, and AIF4- stimulate the accumulation of GRP78 mRNA in a cycloheximide dependent manner, whilst induction by hypoxia is independent of protein synthesis: B.D. Price, et al.; J. Cell. Physiol. 152, 545 (1992) Abstract
Thapsigargin, a Ca(2+)-ATPase inhibitor, depletes the intracellular Ca2+ pool and induces apoptosis in human hepatoma cells: A. Tsukamoto & Y. Kaneko; Cell Biol. Int. 17, 969 (1993) Abstract
The role of calcium, pH, and cell proliferation in the programmed (apoptotic) death of androgen-independent prostatic cancer cells induced by thapsigargin: Y. Furuya, et al.; Cancer Res. 54, 6167 (1994) Abstract
Intracellular Ca2+ signals activate apoptosis in thymocytes: studies using the Ca(2+)-ATPase inhibitor thapsigargin: S. Jiang, et al.; Exp. Cell Res. 212, 84 (1994) Abstract
Role of EGR-1 in thapsigargin-inducible apoptosis in the melanoma cell line A375-C6: S. Muthukkumar, et al.; Mol. Cell. Biol. 15, 6262 (1995) Abstract; Full Text
Baculovirus p35 and Z-VAD-fmk inhibit thapsigargin-induced apoptosis of breast cancer cells: X.M. Qi, et al.; Oncogene 15, 1207 (1997) Abstract
Signal transduction of thapsigargin-induced apoptosis in osteoblast: H.J. Chae, et al.; Bone 25, 453 (1999) Abstract
Nitric oxide is involved in apoptosis induced by thapsigargin in rat mesangial cells: A.M. Rodriguez-Lopez, et al.; Cell Physiol. Biochem. 9, 285 (1999) Abstract
Thapsigargin induces apoptosis in cultured human aortic smooth muscle cells: C. Peiro, et al.; J. Cardiovasc. Pharmacol. 36, 676 (2000) Abstract
Thapsigargin induces a calmodulin/calcineurin-dependent apoptotic cascade responsible for the death of prostatic cancer cells: B. Tombal, et al.; Prostate 43, 303 (2000) Abstract
Changes in intracellular Ca2+ and pH in response to thapsigargin in human glioblastoma cells and normal astrocytes: G.G. Kovacs, et al.; Am. J. Physiol. Cell. Physiol. 289, C361 (2005) Abstract
Thapsigargin, a selective inhibitor of sarco-endoplasmic reticulum Ca2+ -ATPases, modulates nitric oxide production and cell death of primary rat hepatocytes in culture: N.K. Canova, et al.; Cell Biol. Toxicol. 23, 337 (2007) Abstract
General Information
BACKGROUND/TECHNICAL INFORMATION Dissolving of 0.65mg Thapsigargin in 1ml gives a stock solution of 1mM.
General Literature References
Role of Ca2(+)-ATPases in regulation of cellular Ca2+ signalling, as studied with the selective microsomal Ca2(+)-ATPase inhibitor, thapsigargin: O. Thastrup; Agents Actions 29, 8 (1990), (Review) Abstract
Thapsigargin, a high affinity and global inhibitor of intracellular Ca2+ transport ATPases: G. Inesi and Y. Sagara; Arch. Biochem. Biophys. 298, 313 (1992), (Review) Abstract
Use of thapsigargin to study Ca2+ homeostasis in cardiac cells: T.B. Rogers, et al.; Biosci. Rep. 15, 341 (1995), (Review) Abstract
The sarcoplasmic reticulum Ca2+ pump: inhibition by thapsigargin and enhancement by adenovirus-mediated gene transfer: G. Inesi, et al.; Ann. NY Acad. Sci. 853, 195 (1998), (Review) Abstract; Full Text
A tool coming of age: thapsigargin as an inhibitor of sarco-endoplasmic reticulum Ca(2+)-ATPases: M. Treiman, et al.; TIPS 19, 131 (1998), (Review) Abstract
Further Categories Containing This Product:
Ca2+-ATPase/Related Products • Other Natural Products - DNA Regulation/Transcription • Nuclear Envelope & Nuclear Transport • Endoplasmatic Reticulum Stress • Carcinogens & Tumor Promoters Other Products • Natural Products - Nitric Oxide Pathway Modulators • Natural Products - ATPase Inhibitors • Autophagy Other Products • Natural Products - Apoptosis Inducers & Inhibitors
 
 
ALX-350-023 Revised 03-Jun-08
Cyclopiazonic acid
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SYNONYMS CPA
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - ATPase Inhibitors
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Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-023-M005   5 mg 42.00 USD Add To Cart
ALX-350-023-M025   25 mg 145.00 USD Add To Cart
ALX-350-023-M100   100 mg 460.00 USD Add To Cart
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-350-066 Revised 14-Nov-07
Ouabain . octahydrate
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SYNONYMS Strophanthin G
3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-1,5,11α-14,19-penta-hydroxycard-20(22)-enolide
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - ATPase Inhibitors
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ALX-350-066-M100   100 mg 20.00 USD Add To Cart
Product Specification
FORMULA: C29H44O12 . 8H2O
MW: 584.6 . 144.2
CAS NUMBER: 630-60-4
MERCK INDEX: 14: 6901
PURITY: ≥98%
APPEARANCE: White solid.
SOLUBILITY: Soluble in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: +4°C
HANDLING: Protect from light.
HAZARD: TOXIC.

Product Description
Selective inhibitor of Na+- and K+-dependent ATPases.
Product Specific Literature References
Subacute noradrenergic agonist infusions in vivo increase Na+, K+- ATPase and ouabain binding in rat cerebral cortex: A.C. Swann & J.D. Steketee; J. Neurochem. 52, 1598 (1989) Abstract
Actions of bufalin and cinobufotalin, two bufadienolides respectively more active and less active than ouabain, on ouabain binding and 86Rb uptake by human erythrocytes: A.A. Brownlee, et al.; Clin. Sci. (Lond.) 78, 169 (1990) Abstract
Subchronic methamphetamine treatment enhances ouabain-induced striatal dopamine efflux in vivo: A. Kanzaki, et al.; Brain Res. 569, 181 (1992) Abstract
Resting membrane potential and potassium currents in cultured parasympathetic neurones from rat intracardiac ganglia: Z.J. Xu & D.J. Adams; J. Physiol. 456, 405 (1992) Abstract
Allosteric regulation of the access channels to the Rb+ occlusion sites of (Na+ + K+)-ATPase: J. Hasenauer, et al.; J. Biol. Chem. 268, 3289 (1993) Abstract; Full Text
Charge movement by the Na/K pump in Xenopus oocytes: R.F. Rakowski; J. Gen. Physiol. 101, 117 (1993) Abstract
Cardiotonic steroids differentially affect intracellular Na+ and [Na+]i/[K+]i-independent signaling in C7-MDCK cells: O.A. Akimova, et al.; J. Biol. Chem. 280, 832 (2005) Abstract
Vascular endothelium as a target for endogenous ouabain: studies on the effect of ouabain on human endothelial cells: L. Trevisi, et al.; Cell. Mol. Biol. 52, 64 (2006), (Review) Abstract
Na+,K+-ATPase and hormone ouabain:new roles for an old enzyme and an old inhibitor: R.G. Contreras, et al.; Cell. Mol. Biol. 52, 31 (2006), (Review) Abstract
Further Categories Containing This Product:
Na+/K+-ATPase/Related Products
 
 
ALX-350-076 Revised 16-Jun-08
Sanguinarine chloride
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SYNONYMS Pseudochelerythrine
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - ATPase Inhibitors
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ALX-350-076-M005   5 mg 75.00 USD Add To Cart
Product Specification
FORMULA: C20H14NO4Cl
MW: 367.8
CAS NUMBER: 5578-73-4
MERCK INDEX: 14: 8356
RTECS: VP5220000
SOURCE/HOST: Isolated from the leaves and stems of Macleaya cordata and M. microcarpa.
PURITY: ≥98% (HPLC)
APPEARANCE: Orange solid.
SOLUBILITY: Soluble in methanol; slightly soluble in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: +4°C
HAZARD: HARMFUL.

Product Description
Na+/K+-and Mg2+-ATPase inhibitor. Antimicrobial, anti-inflammatory and antioxidant properties. Induces apoptosis. Modulates the Bcl-2 family. Shows antiplaque activity in humans.
Product Specific Literature References
Sanguinarine, inhibitor of Na-K dependent ATP'ase: K.D. Straub & P. Carver; BBRC 62, 913 (1975) Abstract
Isoquinoline alkaloids. Inhibitory actions on cation-dependent ATP-phosphohydrolases: L.R. Meyerson, et al.; Neurochem. Res. 3, 239 (1978) Abstract
Sanguinarine, a new antiplaque agent: retention and plaque specificity: G.L. Southard, et al.; J. Am. Dent. Assoc. 108, 338 (1984) Abstract
Sanguinarine-induced apoptosis is associated with an early and severe cellular glutathione depletion: E. Debiton, et al.; Cancer Chemother. Pharmacol. 51, 474 (2003) Abstract
Activation of prodeath Bcl-2 family proteins and mitochondrial apoptosis pathway by sanguinarine in immortalized human HaCaT keratinocytes: V.M. Adhami, et al.; Clin. Cancer Res. 9, 3176 (2003) Abstract
The effect of chelerythrine on cell growth, apoptosis, and cell cycle in human normal and cancer cells in comparison with sanguinarine: J. Malikova, et al.; Cell Biol. Toxicol. 22, 439 (2006) Abstract
Chelerythrine and sanguinarine dock at distinct sites on BclXL that are not the classic BH3 binding cleft: Y.H. Zhang, et al.; J. Mol. Biol. 364, 538 (2006) Abstract
Induction of apoptosis by sanguinarine in C6 rat glioblastoma cells is associated with the modulation of the Bcl-2 family and activation of caspases through downregulation of extracellular signal-regulated kinase and Akt: M.H. Han, et al.; Anticancer Drugs 18, 913 (2007) Abstract
Metabolism of sanguinarine: the facts and the myths: Z. Dvorak & V. Simanek; Curr. Drug Metab. 8, 173 (2007), Review Abstract
Further Categories Containing This Product:
Na+/K+-ATPase/Related Products • Bcl-2 Family Modulators • Alkaloids • Natural Products - Anti-inflammatory Agents • Natural Products - Antioxidants • Natural Products - Apoptosis Inducers & Inhibitors
 
 
ALX-350-105 Revised 05-Apr-08
Hellebrin
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SYNONYMS 3β-(O4-β-D-Glucopyranosyl-α-L-rhamnopyranosyloxy)-5,14-dihydroxy-19-oxo-5β,14-β-bufa-20,22-dienolide
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - ATPase Inhibitors
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Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-105-M001   1 mg 45.00 USD Add To Cart
ALX-350-105-M005   5 mg 180.00 USD Add To Cart
Product Specification
FORMULA: C36H52O15
MW: 724.8
CAS NUMBER: 13289-18-4
SOURCE/HOST: Isolated from Helleborus sp.
PURITY: ≥99%
APPEARANCE: White solid.
SOLUBILITY: Soluble in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HAZARD: TOXIC.

Product Description
Cardiotonic glycoside which presents a bufadienolide-steroid structure. Besides ouabain (Prod. No. ALX-350-066), from the class of cardenolides hellebrin is the second unique water soluble cardiotonic glycoside. Extremely potent inhibitor of Na+/K+-ATPase  (sodium pump) blocking the active efflux of Na+ and reuptake of K+ of this membrane enzyme. Shows a positive inotropic effect by increasing the intracellular Ca2+ concentration. Strong immunosuppressor inhibiting T cell activity with much higher potency than cortisol or cyclosporin A (Prod. No. ALX-380-002). Induces caspase-dependent apoptosis.
Product Specific Literature References
Über Hellebrin, ein krystallisiertes Glykosid aus Radix Hellebori nigri: W. Karrer; Helv. Chim. Acta 26, 1353 (1943)
The structure of hellebrin: P. Muhr, et al.; Liebigs Ann. Org. Bioorg. Chem. 2, 443 (1995)
In search of ideal inotropic steroids: recent progress: K.R. Repke, et al.; Prog. Drug Res. 47, 9 (1996) Abstract
Exquisitely small amounts of nonglucocorticoid natural steroids suppress the human allogeneic T-cell response: P. Terness, et al.; Transplant Proc. 33, 547 (2001) Abstract
Apoptosis-mediated selective killing of malignant cells by cardiac steroids: maintenance of cytotoxicity and loss of cardiac activity of chemically modified derivatives: D. Daniel, et al.; Int. Immunopharmacol. 3, 1791 (2003) Abstract
Further Categories Containing This Product:
Na+/K+-ATPase/Related Products • Calcium Signalling (Intracellular) Other Products • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products - Immunomodulators
 
 
ALX-350-132 Revised 25-Mar-08
Tentoxin
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SYNONYMS cyclo-(N-Methyl-L-alanyl-L-leucyl-N-methyl-(Z)-dihydrophenylalanyl-glycyl)
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Plant Research Reagents
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ALX-350-132-MC05   0.5 mg 180.00 USD Add To Cart
Product Specification
FORMULA: C22H30N4O4
MW: 414.5
SOURCE/HOST: Isolated from Alternaria alternata.
PURITY: ≥99% (HPLC)
PURITY DETAIL: Free of any peptide contaminations, especially dihydrotentoxin.
SOLUBILITY: Soluble in water (60°C, sonification) up to 6mg/ml.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C

Product Description
Cyclic tetrapeptide. Inhibitor of chloroplast F1-ATPase (CF1). Does not inhibit the homologous enzymes from chloroplasts of insusceptible plant species or from bacteria or mitochondria.
Product Specific Literature References
Effects of tentoxin and dihydrotentoxin on human erythrocytes: K. Gwozdzinski, et al.; Cytobios. 67, 183 (1991) Abstract
Metabolism of tentoxin by hepatic cytochrome P-450 3A isozymes: M. Delaforge, et al.; Eur. J. Biochem. 250, 150 (1997) Abstract
Complete inhibition and partial Re-activation of single F1-ATPase molecules by tentoxin: new properties of the re-activated enzyme: P. Pavlova, et al.; J. Biol. Chem. 279, 9685 (2004) Abstract; Full Text
Further Categories Containing This Product:
Other Toxins • Natural Products - ATPase Inhibitors • Plant Research Reagents/Related Products
 
 
ALX-350-281 Revised 11-Jun-07
Bufalin
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SYNONYMS (3β,5β)-3,14-Dihydroxybufa-20,22-dienolide
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - ATPase Inhibitors
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ALX-350-281-M005   5 mg 160.00 USD Add To Cart
Product Specification
FORMULA: C24H34O4
MW: 386.5
CAS NUMBER: 465-21-4
MERCK INDEX: 14: 1471
SOURCE/HOST: Isolated from Bufonis venom.
PURITY: ≥98%
APPEARANCE: White powder.
SOLUBILITY: Soluble in chloroform.
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: +4°C
HAZARD: TOXIC.

Product Description
Cardiotonic steroid specific Na+/K+-ATPase inhibitor. More potent than ouabain (Prod. No. ALX-350-066). Induces cell differentiation and apoptosis.
Product Specific Literature References
Actions of bufalin and cinobufotalin, two bufadienolides respectively more active and less active than ouabain, on ouabain binding and 86Rb uptake by human erythrocytes: A.A. Brownlee, et al.; Clin. Sci. (Lond.) 78, 169 (1990) Abstract
Neutralization of cardiac toxins oleandrin, oleandrigenin, bufalin, and cinobufotalin by digibind: monitoring the effect by measuring free digitoxin concentrations: A. Dasgupta & L. Emerson; Life Sci. 63, 781 (1998) Abstract
Bufadienolides from animal and plant sources: L. Krenn & B. Kopp; Phytochemistry 48, 1 (1998), (Review) Abstract
The T-cell suppressive effect of bufadienolides: structural requirements for their immunoregulatory activity: P. Terness, et al.; Int. Immunopharmacol. 1, 19 (2001) Abstract
Simultaneous determination of four bufadienolides in human liver by high-performance liquid chromatography: Z. Wang, et al.; Biomed. Chromatogr. 18, 318 (2004) Abstract
Cardiotonic steroids differentially affect intracellular Na+ and [Na+]i/[K+]i-independent signaling in C7-MDCK cells: O.A. Akimova, et al.; J. Biol. Chem. 280, 832 (2005) Abstract
Further Categories Containing This Product:
Na+/K+-ATPase/Related Products • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products - Immunomodulators
 
 
ALX-350-282 Revised 16-Jun-06
Bufotalin
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SYNONYMS (3β,5β,16β)-16-(Acetyloxy)-3-,14-dihydroxybufa-20,22-dienolide
3β,14,16β-Trihydroxy-5β bufa-20,22-dienolide 16-acetate
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - ATPase Inhibitors
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ALX-350-282-M005   5 mg 85.00 USD Add To Cart
Product Specification
FORMULA: C26H36O6
MW: 444.6
CAS NUMBER: 471-95-4
MERCK INDEX: 14: 1477
SOURCE/HOST: Isolated from Bufonis venom.
PURITY: ≥98% (HPLC)
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in 100% ethanol or chloroform.
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: +4°C
HAZARD: TOXIC.

Product Description
Less potent Na+/K+-ATPase inhibitor than other bufadienolides. Potent immunosuppressor.
Product Specific Literature References
Bufadienolides from animal and plant sources: L. Krenn & B. Kopp; Phytochemistry 48, 1 (1999), (Review) Abstract
The T-cell suppressive effect of bufadienolides: structural requirements for their immunoregulatory activity: P. Terness, et al.; Int. Immunopharmacol. 1, 119 (2001) Abstract
Further Categories Containing This Product:
Na+/K+-ATPase/Related Products • Natural Products - Immunomodulators
 
 
ALX-350-283 Revised 11-Jun-07
Cinobufagin