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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-270-109 Revised 14-Apr-08
Ophiobolin A
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SYNONYMS Cochliobolin A
Ophiobalin
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Other Signal Transduction Pathway Modulators
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ALX-270-109-MC01   0.1 mg 50.00 USD Add To Cart
ALX-270-109-M001   1 mg 220.00 USD Add To Cart
Product Specification
FORMULA: C25H36O4
MW: 400.6
CAS NUMBER: 4611-05-6
RTECS: RL1576000
SOURCE/HOST: Isolated from Bipolaris leersia MST-FP107.
PURITY: ≥95% (HPLC)
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in dimethyl formamide, DMSO, 100% ethanol or methanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.
HAZARD: HARMFUL.

Product Description
Cell permeable antagonist of calmodulin. Inhibits Ca2+/calmodulin-dependent phosphodiesterase. Inhibits P-glycoprotein-mediated transport. Exhibits antibacterial, antitumor and nematocidal activities. Phytotoxic.
Product Specific Literature References
The structure of ophiobolin, a C25 terpenoid having a novel skeleton: S. Nozoe, et al.; JACS 87, 4968 (1965) Abstract
The constitution of cochliobolin: L. Canonica, et al.; THL 7, 1211 (1966)
Ophiobolin A. A natural product inhibitor of calmodulin: P.C. Leung, et al.; J. Biol. Chem. 259, 2742 (1984) Abstract; Full Text
Role of Calmodulin Inhibition in the Mode of Action of Ophiobolin A: P.C. Leung, et al.; Plant Physiol. 77, 303 (1985) Abstract; Full Text
Characterization of the interaction of ophiobolin A and calmodulin: P.C. Leung, et al.; Int. J. Biochem. 20, 1351 (1988) Abstract
Microbial metabolites of ophiobolin A and antimicrobial evaluation of ophiobolins: E. Li, et al.; J. Nat. Prod. 58, 74 (1995) Abstract
The biology of ophiobolins: T.K. Au, et al.; Life Sci. 67, 733 (2000), Review Abstract
Calmodulin and lipid binding to synaptobrevin regulates calcium-dependent exocytosis: S. Quetglas, et al.; EMBO J. 21, 3970 (2002) Abstract; Full Text
Herbicidal potential of ophiobolins produced by Drechslera gigantea: A. Evidente, et al.; J. Agric. Food Chem. 54, 1779 (2006) Abstract
Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products: N. Yoshida, et al.; Food Chem. Toxicol. 44, 2033 (2006) Abstract
Further Categories Containing This Product:
Calmodulin Inhibitors • Phosphodiesterases / Related Products • Natural Products with Antibiotic Activity • MDR Inhibitors • P-glycoprotein [Pgp] / Related Products • Other Toxins • Natural Products - Antitumor Reagents
 
 
ALX-270-209 Revised 05-Apr-08
Etoposide
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SYNONYMS 4-Desmethylepipodophyllotoxin 9-(4,6-O-ethylidene)-β-D-glucopyranoside
VP-16-213
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Topoisomerase Inhibitors
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-270-209-M025   25 mg 30.00 USD Add To Cart
ALX-270-209-M100   100 mg 65.00 USD Add To Cart
ALX-270-209-M500   500 mg 260.00 USD Add To Cart
Product Specification
FORMULA: C29H32O13
MW: 588.6
CAS NUMBER: 33419-42-0
MERCK INDEX: 14: 3886
RTECS: KC0190000
SOURCE/HOST: Semisynthetic derivative of podophyllotoxin.
PURITY: ≥99%
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in DMSO, dimethyl formamide, ethyl ether or chloroform:methanol (1:1); slightly soluble in methanol or acetone; insoluble in water.
SHIPPING: AMBIENT
LONG TERM STORAGE: +20°C
USE/STABILITY: Store solutions in DMSO at 4°C. For long term storage prepare aliquots and store at -20°C.
HANDLING: Protect from light and moisture.
HAZARD: MAY BE CARCINOGENIC. TOXIC.

Product Description
Antitumor reagent. Topoisomerase II inhibitor. Induces apoptosis by FasL. Activates p53 resulting in upregulated expression of TRAIL-R2 (DR5) and Bak to overcome TRAIL resistance in Bax-deficient human colon carcinoma cancer cells.
Product Specific Literature References
The podophyllotoxin derivatives VP16-213 and VM26: B.F. Issell; Cancer Chemother. Pharmacol. 7, 73 (1982) Abstract
Etoposide: four decades of development of a topoisomerase II inhibitor: K.R. Hande; Eur. J. Cancer 34, 1514 (1998) Abstract
Etoposide sensitivity of human prostatic cancer cell lines PC-3, DU 145 and LNCaP: M. Salido, et al.; Histol. Histopathol. 14, 125 (1999) Abstract
A systematic review of the role of etoposide and cisplatin in the chemotherapy of small cell lung cancer with methodology assessment and meta-analysis: C. Mascaux, et al.; Lung Cancer 30, 23 (2000) Abstract
Distinct pathways for stimulation of cytochrome c release by etoposide: J.D. Robertson, et al.; J. Biol. Chem. 275, 32438 (2000) Abstract; Full Text
Ordering of ceramide formation, caspase activation, and Bax/Bcl-2 expression during etoposide-induced apoptosis in C6 glioma cells: M. Sawada, et al.; Cell Death Differ. 7, 761 (2000) Abstract
Etoposide-induced apoptosis is not associated with the fas pathway in acute myeloblastic leukemia cells: T. Siitonen, et al.; Leuk. Res. 24, 281 (2000) Abstract
Early caspase activation in leukemic cells subject to etoposide-induced G2-M arrest: evidence of commitment to apoptosis rather than mitotic cell death: R.J. Sleiman & B.W. Stewart; Clin. Cancer Res. 6, 3756 (2000) Abstract; Full Text
Cell cycle phase specificity in the potentiation of etoposide-induced DNA damage and apoptosis by KN-62, an inhibitor of calcium-calmodulin- dependent enzymes: M. Aoyama, et al.; Biochem Pharmacol 61, 49 (2001) Abstract
Deacetylase activity associates with topoisomerase II and is necessary for etoposide-induced apoptosis: C.A. Johnson, et al.; J. Biol. Chem. 276, 4539 (2001) Abstract; Full Text
In vitro topo II-DNA complex accumulation and cytotoxicity of etoposide in leukaemic cells from patients with acute myelogenous and chronic lymphocytic leukaemia: Y. Wang, et al.; Leuk. Res. 25, 133 (2001) Abstract
Etoposide: discovery and medicinal chemistry: P. Meresse, et al.; Curr. Med. Chem. 11, 2443 (2004), Review Abstract
Etoposide, topoisomerase II and cancer: E.L. Baldwin & N. Osheroff; Curr. Med. Chem. Anticancer Agents 5, 363 (2005), Review Abstract
Further Categories Containing This Product:
Other Toxins • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products - Antitumor Reagents • Antitumor Agents (Enzyme Inhibitors) • Antitumor Agents (Apoptosis Inducers)
 
 
ALX-270-341 Revised 28-Sep-07
Epoxyquinone G109 (racemic)
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PRODUCT LINE Neurobiology
PRODUCT CATEGORY Ceramides / Cerebrosides / Sphingolipids / Related Products
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ALX-270-341-M002   2 mg 190.00 USD Add To Cart
Product Specification
FORMULA: C18H27NO4
MW: 321.4
CAS NUMBER: 163972-12-1 ((+)-enantiomer)
PURITY: ≥98%
APPEARANCE: Pale yellow powder.
SOLUBILITY: Soluble in DMSO or methanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.
HAZARD: TOXIC.

Product Description
Potent and selective irreversible inhibitor of neutral sphingomyelinase (N-SMase).
Product Specific Literature References
Manumycin A and its analogues are irreversible inhibitors of neutral sphingomyelinase: C. Arenz, et al.; ChemBioChem 2, 141 (2001) Abstract
Endothelial apoptosis induced by inhibition of integrins αvβ3 and αvβ5 involves ceramide metabolic pathways: A. Erdreich-Epstein, et al.; Blood 105, 4353 (2005) Abstract
Further Categories Containing This Product:
Other Toxins
 
 
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
Related Products
Further Categories Containing This Product:
Other Toxins • Natural Products - Other Tumor Promoters • Carcinogens & Tumor Promoters Other Products • Marine Natural Products
 
 
ALX-350-036 Revised 18-Jan-08
Latrunculin B
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products for Cytoskeletal Research
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-036-C100   100 µg 48.00 USD Add To Cart
ALX-350-036-M001   1 mg 120.00 USD Add To Cart
Product Specification
FORMULA: C20H29NO5S
MW: 395.5
CAS NUMBER: 76343-94-7
MERCK INDEX: 14: 5378
SOURCE/HOST: Isolated from Latrunculia magnifica.
PURITY: ≥97% (HPLC)
APPEARANCE: White to light yellow solid.
SOLUBILITY: Soluble in DMSO (25mg/ml) or 100% ethanol (25mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HAZARD: TOXIC.

Product Description
Structurally unique marine toxin. Actin filament modulator. 10- to 100-fold more potent than cytochalasins. Whereas cytochalasin D (Prod. No. ALX-380-031) induces dissolution of F-actin and stress fiber contraction in fibroblasts in culture, latrunculin B causes a shortening and thickening of stress fibers.
Product Specific Literature References
Latrunculins: novel marine toxins that disrupt microfilament organization in cultured cells: I. Spector, et al.; Science 219, 493 (1983) Abstract
Latrunculin inhibits the microfilament-mediated processes during fertilization, cleavage and early development in sea urchins and mice: G. Schatten, et al.; Exp. Cell. Res. 166, 191 (1986) Abstract
Inhibition of actin polymerization by latrunculin: M. Coue, et al.; FEBS Lett. 213, 316 (1987) Abstract
Latrunculin A is a potent inhibitor of phagocytosis by macrophages: C.A. de Oliveira & B. Mantovani; Life Sci. 43, 1825 (1988) Abstract
Latrunculins--novel marine macrolides that disrupt microfilament organization and affect cell growth: I. Comparison with cytochalasin D: I. Spector, et al.; Cell Motility & Cytoskeleton 13, 127 (1989) Abstract
Effects of cytochalasin D and latrunculin B on mechanical properties of cells: T. Wakatsuki, et al.; J. Cell. Sci. 114, 1025 (2001) Abstract
Further Categories Containing This Product:
Other Toxins • Actin / Related Products • Marine Natural Products
 
 
ALX-350-043 Revised 06-Jun-08
Microcystin-RR
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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-350-043-C050   50 µg 70.00 USD Add To Cart
ALX-350-043-C100   100 µg 125.00 USD Add To Cart
ALX-350-043-C250   250 µg 240.00 USD Add To Cart
ALX-350-043-C500   500 µg 470.00 USD Add To Cart
ALX-350-043-M001   1 mg 850.00 USD Add To Cart
Product Specification
FORMULA: C49H75N13O12
MW: 1038.2
CAS NUMBER: 111755-37-4
SOURCE/HOST: Isolated from Microcystis aeruginosa.
PURITY: ≥95% (HPLC)
APPEARANCE: Clear to whitish film adhered to inside of vial.
SOLUBILITY: Soluble in 80% aqueous methanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: For maximum product recovery after thawing, centrifuge the vial before opening the cap.
HAZARD: MAY BE CARCINOGENIC. VERY TOXIC. HIGHLY IRRITANT.
IDENTITY: Identity determined by MS.

Product Description
Arg-Arg analog of microcystin-LR (Prod. No. ALX-350-012). Hepatotoxic, although found to be up to 10-fold less toxic than microcystin-LR on i.p. injection in mice. Potent inhibitor of protein phosphatase 2A (PP2A).
Product Specific Literature References
The structure of a cyclic peptide toxin, cyanogenosin-RR from Microcystis aeruginosa: P. Painuly, et al.; THL 29, 11 (1988)
Toxicity and toxins of natural blooms and isolated strains of Microcystis spp. (Cyanobacteria) and improved procedure for purification of cultures: M. Shirai, et al.; Appl. Environ. Microbiol. 57, 1241 (1991) Abstract
Inhibition of protein phosphatases activates glucose-6-phosphatase in isolated rat hepatocytes: S. Claeyssens, et al.; FEBS Lett. 315, 7 (1993) Abstract
Extraction and high-performance liquid chromatographic method for the determination of microcystins in raw and treated waters: L.A. Lawton, et al.; Analyst 119, 1525 (1994) Abstract
Determination of some physicochemical parameters of microcystins (cyanobacterial toxins) and trace level analysis in environmental samples using liquid chromatography: C. Rivasseau, et al.; J. Chromatogr. A 799, 155 (1998) Abstract
Physiological and biochemical analyses of microcystin-RR toxicity to the cyanobacterium Synechococcus elongatus: Z.Q. Hu, et al.; Environ. Toxicol. 19, 571 (2004) Abstract
Microcystin-RR-induced accumulation of reactive oxygen species and alteration of antioxidant systems in tobacco BY-2 cells: L. Yin, et al.; Toxicon. 46, 507 (2005) Abstract
Related Products
Further Categories Containing This Product:
Other Toxins • Marine Natural Products • Oxidative Stress Markers & Reagents / Related Products