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Natural Products - Other Tumor Promoters
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ALX-270-047 Revised 26-Sep-07
Aristolochic acid
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SYNONYMS 8-Methoxy-6-nitrophenanthrol(3,4-d)-1,3-dioxide-5-carboxylic acid
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Signal Transduction Pathway Modulators
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-270-047-M025   25 mg 25.00 USD Add To Cart
ALX-270-047-M100   100 mg 90.00 USD Add To Cart
Product Specification
FORMULA: C17H11NO7
MW: 341.3
CAS NUMBER: 313-67-7
MERCK INDEX: 14: 786
RTECS: CF3325000
SOURCE/HOST: Isolated from Aristolochia clematis.
PURITY: ≥97% (~1:1 mixture of aristolochic acids I (A) and II (B))
APPEARANCE: Yellow solid.
SOLUBILITY: Soluble in DMSO or 100% ethanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: +20°C
HAZARD: MAY BE CARCINOGENIC. TOXIC. MAY BE MUTAGENIC.

Product Description
Phospholipase A2 (PLA2) inhibitor active against the enzymes found in many snake venoms as well as those of human platelets and synovial fluids. Inhibits ionophore-stimulated PLA2 activity in human neutrophils. Has been shown to be nephropathic and carcinogenic.
Product Specific Literature References
Characterization of three edema-inducing phospholipase A2 enzymes from habu (Trimeresurus flavoviridis) venom and their interaction with the alkaloid aristolochic acid: B.S. Vishwanath, et al.; Toxicon 25, 501 (1987) Abstract
Interaction of aristolochic acid with Vipera russelli phospholipase A2: its effect on enzymatic and pathological activities: B.S. Vishwanath & T.V. Gowda; Toxicon 25, 929 (1987) Abstract
Interaction of phospholipase A2 from Vipera russelli venom with aristolochic acid: a circular dichroism study: B.S. Vishwanath, et al.; Toxicon 25, 939 (1987) Abstract
Edema-inducing activity of phospholipase A2 purified from human synovial fluid and inhibition by aristolochic acid: B.S. Vishwanath, et al.; Inflammation 12, 549 (1988) Abstract
Effects of aristolochic acid on phospholipase A2 activity and arachidonate metabolism of human neutrophils: M.D. Rosenthal, et al.; Biochim. Biophys. Acta 1001, 3 (1989) Abstract
Suramin alters phosphoinositide synthesis and inhibits growth factor receptor binding in HT-29 cells: R. Kopp & A. Pfeiffer; Cancer Res. 50, 6490 (1990) Abstract
The effects of the phospholipase A2 inhibitors aristolochic acid and PGBx on A23187-stimulated mobilization of arachidonate in human neutrophils are overcome by diacylglycerol or phorbol ester: M.D. Rosenthal, et al.; Biochim. Biophys. Acta 1126, 319 (1992) Abstract
Evidence for different mechanisms involved in the formation of lyso platelet-activating factor and the calcium-dependent release of arachidonic acid from human neutrophils: J.D. Winkler, et al.; Biochem. Pharmacol. 44, 2055 (1992) Abstract
Selective inhibition of group II phospholipase A2 by quercetin: M. Lindahl & C. Tagesson; Inflammation 17, 573 (1993) Abstract
Detection of DNA adducts formed by aristolochic acid in renal tissue from patients with Chinese herbs nephropathy: H.H. Schmeiser, et al.; Cancer Res. 56, 2025 (1996) Abstract
Aristolochic acid and ’Chinese herbs nephropathy’: a review of the evidence to date: J.P. Cosyns; Drug Saf. 26, 33 (2003), Review Abstract
Effect of aristolochic acid on intracellular calcium concentration and its links with apoptosis in renal tubular cells: Y.H. Hsin, et al.; Apoptosis 11, 2167 (2006) Abstract
Further Categories Containing This Product:
PLA2 Inhibitors • Carcinogens & Tumor Promoters Other Products • Natural Products - Other Tumor Promoters • Other Toxins • Alkaloids
 
 
ALX-350-003 Revised 23-May-08
Okadaic acid (high purity)
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SYNONYMS Halochondrine A (high purity)
9,10-Deepithio-9,10-didehydroacanthifolicin (high purity)
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Okadaic Acids
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-003-C025   25 µg 60.00 USD Add To Cart
ALX-350-003-C050   50 µg 110.00 USD Add To Cart
ALX-350-003-C100   100 µg 180.00 USD Add To Cart
ALX-350-003-M001   1 mg 990.00 USD Add To Cart
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Product Specification
FORMULA: C44H68O13
MW: 805.0
CAS NUMBER: 78111-17-8
MERCK INDEX: 14: 6819
RTECS: AA8227800
SOURCE/HOST: Isolated from Prorocentrum concavum by preparative flash, medium pressure and high performance liquid chromatography.
PURITY: ≥98% (HPLC)
APPEARANCE: White crystalline solid.
SOLUBILITY: Soluble in DMSO, 100% ethanol or methanol (1mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
USE/STABILITY: Use only fresh solutions.
HANDLING: Protect from light. Packaged under inert gas.
HAZARD: MAY BE CARCINOGENIC. HIGHLY IRRITANT. TOXIC.

Product Description
Potent inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A) in numerous cell types. Does not affect activity of acid phosphatase, alkaline phosphatase and tyrosine phosphatase. Non-phorbol type tumor promoter. Induces apoptosis in human breast carcinoma cells (MB-231 and MCF-7) and in myeloid cells, but inhibits glucocorticoid-induced apoptosis in T cell hybridomas. Tumor promoter. Has shown contractile effect on smooth muscle and heart muscle. Significantly increases cyclin B1 expression in adult neurons.
Product Specific Literature References
Okadaic acid: an additional non-phorbol-12-tetradecanoate-13-acetate- type tumor promoter: M. Suganuma, et al.; PNAS 85, 1768 (1988) Abstract
Protein phosphatases come of age: P. Cohen & P.T.W. Cohen; J. Biol. Chem. 264, 21435 (1989) Abstract; Full Text
The structure and regulation of protein phosphatases: P. Cohen; Ann. Rev. Biochem. 58, 453 (1989) Abstract
Effects of the tumour promoter okadaic acid on intracellular protein phosphorylation and metabolism: T.A. Haystead, et al.; Nature 337, 78 (1989) Abstract
Okadaic acid: a new probe for the study of cellular regulation: P. Cohen, et al.; TIPS 15, 98 (1990), (Review) Abstract
Nonphorbol tumor promoters okadaic acid and calyculin-A induce membrane translocation of protein kinase C: R. Gopalakrishna, et al.; BBRC 189, 950 (1992) Abstract
Protein phosphatase inhibitors okadaic acid and calyculin A alter cell shape and F-actin distribution and inhibit stimulus-dependent increases in cytoskeletal actin of human neutrophils: P. Kreienbuehl, et al.; Blood 80, 2911 (1992) Abstract
Site-specific dephosphorylation of smooth muscle myosin light chain kinase by protein phosphatases 1 and 2A: M. Nomura, et al.; Biochemistry 31, 11915 (1992) Abstract
Inhibition of apoptosis in human tumour cells by okadaic acid: Q. Song, et al.; J. Cell Physiol. 153, 550 (1992) Abstract
Okadaic acid enhances human T cell activation and phosphorylation of an internal substrate induced by phorbol myristate acetate: Y. Tada, et al.; Immunopharmacol. 24, 17 (1992) Abstract
Okadaic acid inhibits glucocorticoid-induced apoptosis in T cell hybridomas at its late stage: Y. Ohoka, et al.; BBRC 197, 916 (1993) Abstract
Multiple apoptotic death types triggered through activation of separate pathways by cAMP and inhibitors of protein phosphatases in one (IPC leukemia) cell line: B.T. Gjertsen, et al.; J. Cell. Sci. 107, 3363 (1994) Abstract
Differential induction of apoptosis in human breast tumor cells by okadaic acid and related inhibitors of protein phosphatases 1 and 2A: K. Kiguchi, et al.; Cell Growth Differentiation 5, 995 (1994) Abstract
Unique features of the okadaic acid activity class of tumor promoters: H. Fujiki & M. Suganuma; J. Cancer Res. Clin. Oncol. 125, 150 (1999), Review Abstract
Okadaic acid: the archetypal serine/threonine protein phosphatase inhibitor: A.B. Dounay & C.J. Forsyth; Curr. Med. Chem. 9, 1939 (2002), Review Abstract
Mechanism of Ca2+-mediated regulation of NDR protein kinase through autophosphorylation and phosphorylation by an upstream kinase: R. Tamaskovic, et al.; J. Biol. Chem. 278, 6710 (2003) Abstract; Full Text
Okadaic acid induced cyclin B1 expression and mitotic catastrophe in rat cortex: B. Chen, et al.; Neurosci. Lett. 406, 178 (2006) Abstract
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Further Categories Containing This Product:
Vesicles & Membrane Trafficking Other Products • Neurotoxins • Protein Serine / Threonine Phosphatases Other Products • Natural Products - Other Tumor Promoters • Natural Products - Apoptosis Inducers & Inhibitors • Marine Natural Products
 
 
ALX-350-004 Revised 08-Apr-08
Thapsigargin
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Tumor Promoters
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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 • Endoplasmatic Reticulum Stress • Other Natural Products - DNA Regulation / Transcription • Carcinogens & Tumor Promoters Other Products • Natural Products - ATPase Inhibitors • Natural Products - Nitric Oxide Pathway Modulators • Natural Products - Apoptosis Inducers & Inhibitors • Nuclear Envelope & Nuclear Transport • Autophagy Other Products
 
 
ALX-350-010 Revised 02-Apr-08
Okadaic acid . ammonium salt (high purity)
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SYNONYMS Halochondrine A . Na (high purity)
9,10-Deepithio-9,10-didehydroacanthifolicin . Na (high purity)
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Okadaic Acids
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-010-C025   25 µg 55.00 USD Add To Cart
ALX-350-010-C100   100 µg 145.00 USD Add To Cart
ALX-350-010-M001   1 mg 980.00 USD Add To Cart
Product Specification
FORMULA: C44H67O13 . NH4
MW: 804.0 . 18.0
CAS NUMBER: 155716-06-6
SOURCE/HOST: Isolated from Prorocentrum concavum by preparative flash, medium pressure and high performance liquid chromatography. Salt form generated in aqueous ammonium hydroxide-methanol solution.
PURITY: ≥98% (HPLC)
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in DMSO, 100% ethanol, methanol, acetone, ethyl acetate or distilled water. Dissolve first in organic solvent before diluting in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Packaged under inert gas. Protect from light.
HAZARD: TOXIC. MAY BE CARCINOGENIC. HIGHLY IRRITANT.

Product Description
Salt form of okadaic acid (Prod. No. ALX-350-003), with slightly greater stability than the free acid after it is put into stock solution (in organic solvents). Potent inhibitor of protein phosphatase 1 (PP1) and 2A (PP2A). Potent tumor promotor and neurotoxin.
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Further Categories Containing This Product:
Vesicles & Membrane Trafficking Other Products • Neurotoxins • Natural Products - Other Tumor Promoters • Protein Serine / Threonine Phosphatases Other Products • Natural Products - Apoptosis Inducers & Inhibitors • Marine Natural Products
 
 
ALX-350-011 Revised 10-Apr-08
Okadaic acid . sodium salt (high purity)
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SYNONYMS Halochondrine A . sodium salt (high purity)
9,10-Deepithio-9,10-didehydroacanthifolicin . sodium salt (high purity)
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Okadaic Acids
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-011-C025   25 µg 58.00 USD Add To Cart
ALX-350-011-C100   100 µg 160.00 USD Add To Cart
ALX-350-011-M001   1 mg 980.00 USD Add To Cart
Product Specification
FORMULA: C44H67O13 . Na
MW: 804.0 . 23.0
CAS NUMBER: 209266-80-8
SOURCE/HOST: Isolated from Prorocentrum concavum by preparative flash, medium pressure and high performance liquid chromatography. Salt form generated in aqueous sodium hydroxide-methanol solution.
PURITY: ≥98% (HPLC)
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in DMSO (1mg/ml), 100% ethanol, methanol, acetone, ethyl acetate or distilled water. Dissolve first in organic solvent before diluting in water. 
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.
HAZARD: HIGHLY IRRITANT. MAY BE CARCINOGENIC. TOXIC.

Product Description
Salt form of okadaic acid (Prod. No. ALX-350-003), with slightly greater stability than the free acid after it is put into stock solution (in organic solvents). Potent inhibitor of protein phosphatase 1 (PP1) and 2A (PP2A). Potent tumor promotor and neurotoxin.
Related Products
Further Categories Containing This Product:
Vesicles & Membrane Trafficking Other Products • Natural Products - Other Tumor Promoters • Neurotoxins • Protein Serine / Threonine Phosphatases Other Products • Natural Products - Apoptosis Inducers & Inhibitors • Marine Natural Products
 
 
ALX-350-012 Revised 23-Oct-08
Microcystin-LR
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Microcystins
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-012-C050   50 µg 24.00 USD Add To Cart
ALX-350-012-C100   100 µg 46.00 USD Add To Cart
ALX-350-012-C500   500 µg 175.00 USD Add To Cart
ALX-350-012-M001   1 mg 330.00 USD Add To Cart
Product Specification
FORMULA: C49H74N10O12
MW: 995.2
CAS NUMBER: 101043-37-2
RTECS: GT2810000
SOURCE/HOST: Isolated from Microcystis aeruginosa.
PURITY: ≥95% (HPLC)
APPEARANCE: Whitish film adhered to inside of the vial.
SOLUBILITY: Soluble in 100% ethanol, methanol or DMSO.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
USE/STABILITY: Stock solutions are stable for up to 6 months when stored at -20°C. Unstable at pH>7.7.
HANDLING: For maximum product recovery after thawing, centrifuge the vial before opening the cap.
HAZARD: MAY BE CARCINOGENIC. VERY TOXIC. HIGHLY IRRITANT.

Product Description
Heptapeptide ester hepatotoxin. Tumor promoter. Equally potent and selective inhibitor of protein phosphatase 1 (PP1) and 2A (PP2A). PP2B is less sensitive and PP2C is not inhibited up to 4µM. Useful for affinity-purification of PP2A. The product is not cell permeable except in liver cells, which appear to have a functional uptake system. Has no effect on protein kinases. Less toxic than the more hydrophobic analogs microcystin-LY, -LW and -LF. Frequently contaminates fresh-water lakes and ponds. Causes livestock poisonings. Ozonation did lead to complete loss of toxicity and toxins from contaminated samples.
Product Specific Literature References
Structural studies on cyanoginosins-LR, -YR, -YA, and -YM, peptide toxins from Microcystis aeruginosa: D.P. Botes, et al.; JCS Perkin Trans. I, 2747 (1985)
Nodularin, microcystin, and the configuration of Adda: K.L. Rinehart, et al.; JACS 110, 8557 (1988)
Characterization of microcystin-LR, a potent inhibitor of type 1 and type 2A protein phosphatases: R.E. Honkanen, et al.; J. Biol. Chem. 265, 19401 (1990) Abstract; Full Text
Cyanobacterial microcystin-LR is a potent and specific inhibitor of protein phosphatases 1 and 2A from both mammals and higher plants: C. MacKintosh, et al.; FEBS Lett. 264, 187 (1990) Abstract
Protein phosphatase 2A is a specific protamine-kinase-inactivating phosphatase: G.D. Amick, et al.; Biochem. J. 287, 1019 (1992) Abstract
Evidence for the regulation of exocytic transport by protein phosphorylation: H.W. Davidson, et al.; J. Cell. Biol. 116, 1343 (1992) Abstract
Liver tumor promotion by the cyanobacterial cyclic peptide toxin microcystin-LR: R. Nishiwaki-Matsushima, et al.; J. Cancer Res. Clin. Oncol. 118, 420 (1992) Abstract
Two significant aspects of microcystin-LR: specific binding and liver specificity: R. Nishiwaki, et al.; Cancer Lett. 83, 283 (1994) Abstract
Comparative toxicity of four microcystins of different hydrophobicities to the protozoan, Tetrahymena pyriformis: C.J. Ward & G.A. Codd; J. Appl. Microbiol. 86, 874 (1999) Abstract
Unique features of the okadaic acid activity class of tumor promoters: H. Fujiki & M. Suganuma; J. Cancer Res. Clin. Oncol. 125, 150 (1999), Review Abstract
The toxicology of microcystin-LR: occurrence, toxicokinetics, toxicodynamics, diagnosis and treatment: K. Bischoff; Vet. Hum. Toxicol. 43, 294 (2001), Review Abstract
Negative regulation of ERK and Elk by protein kinase B modulates c-Fos transcription: I. Galetic, et al.; J. Biol. Chem. 278, 4416 (2003) Abstract; Full Text
Decrease in toxicity of microcystins LA and LR in drinking water by ozonation: S. Brooke, et al.; Toxicon. 48, 1054 (2006) Abstract
Mitochondria a key role in microcystin-LR kidney intoxication: R. La-Salete, et al.; J. Appl. Toxicol. 28, 55 (2008) Abstract
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Further Categories Containing This Product:
Other Toxins • Natural Products - Other Tumor Promoters • Carcinogens & Tumor Promoters Other Products • Marine Natural Products
 
 
ALX-350-014 Revised 03-Apr-08
Calyculin A
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