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Natural Products for Cytoskeletal Research
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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
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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
 
 
ALX-350-069 Revised 15-Jul-08
Vincristine . sulfate
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SYNONYMS VCR . sulfate
Leukocristine . sulfate
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products for Cell Cycle Research
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ALX-350-069-M001   1 mg 35.00 USD Add To Cart
ALX-350-069-M005   5 mg 95.00 USD Add To Cart
Product Specification
FORMULA: C46H56N4O10 . H2SO4
MW: 825.0 . 98.1
CAS NUMBER: 2068-78-2
MERCK INDEX: 14: 9986
RTECS: OH6340000
SOURCE/HOST: Semisynthetic from catharanthine or vindoline.
PURITY: ≥95%
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in water (25mg/ml) or methanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HAZARD: MAY BE TERATOGENIC. TOXIC.

Product Description
Plant alkaloid that arrests the cell cycle in G2/M phase by blocking mitotic spindle formation. Depolymerizes microtubules and blocks binding of tubulin to microtubule proteins. Induces apoptosis. Triggers Raf-1 activation, phosphorylation of Bcl-2 family proteins and induction of p53 expression.
Product Specific Literature References
Cell death induced by vincristine in the intestinal crypts of mice and in a human Burkitt's lymphoma cell line: B.V. Harmon, et al.; Cell Prolif. 25, 523 (1992) Abstract
Binding selectivity of rhizoxin, phomopsin A, vinblastine, and ansamitocin P-3 to fungal tubulins: differential interactions of these antimitotic agents with brain and fungal tubulins [published erratum appears in BBRC 190, 1180 (1993)]: Y. Li, et al.; BBRC 187, 722 (1992) Abstract
Interaction of vinca alkaloids with tubulin: a comparison of vinblastine, vincristine, and vinorelbine: S. Lobert, et al.; Biochemistry 35, 6806 (1996) Abstract
Raf-1/bcl-2 phosphorylation: a step from microtubule damage to cell death: M.V. Blagosklonny, et al.; Cancer Res. 57, 130 (1997) Abstract
Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle: A. Jordan, et al.; Med. Res. Rev. 18, 259 (1998) Abstract
Bcl-xL is phosphorylated in malignant cells following microtubule disruption: M.S. Poruchynsky, et al.; Cancer Res. 58, 3331 (1998) Abstract
The effect of antimicrotubule agents on signal transduction pathways of apoptosis: a review: L.G. Wang, et al.; Cancer Chemother. Pharmacol. 44, 355 (1999), (Review) Abstract
Vincristine-induced apoptosis in vivo in peripheral blood mononuclear cells of children with acute lymphoblastic leukaemia (ALL): E. Groninger, et al.; Br. J. Haematol. 111, 875 (2000) Abstract
Selective toxicity of vincristine against chronic lymphocytic leukemia cells in vitro: J.A. Vilpo, et al.; Eur. J. Haematol. 65, 370 (2000) Abstract
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Further Categories Containing This Product:
Antitumor Agents (Anti-proliferative) • Cell Cycle Blockers & Inhibitors/Related Products • Natural Products for Cytoskeletal Research • Alkaloids • Microtubule Modulators • Natural Products - Antitumor Reagents • Natural Products - Apoptosis Inducers & Inhibitors • Antitumor Agents (Apoptosis Inducers) • Antitumor Agents (DNA Interaction & Gene Regulation)
 
 
ALX-350-088 Revised 16-Jun-08
Swinholide A
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products for Cytoskeletal Research
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Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
ALX-350-088-C010   10 µg 95.00 USD Add To Cart
ALX-350-088-C050   50 µg 285.00 USD Add To Cart
Product Specification
FORMULA: C78H132O20
MW: 1389.9
CAS NUMBER: 95927-67-6
SOURCE/HOST: Isolated from marine sponge Theonella swinhoei.
PURITY: ≥97% (HPLC)
APPEARANCE: Colorless oil or amorphous solid.
SOLUBILITY: Soluble in 100% ethanol, methanol, acetone or ethyl acetate.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Keep under inert gas. Protect from light.
HAZARD: TOXIC.
IDENTITY: Identity determined by 1H-NMR, 13C-NMR and MS.

Product Description
Disrupts the actin cytoskeleton of cells grown in culture. Stabilizes actin dimers and severs actin filaments.
Product Specific Literature References
Marine natural products. XXIII. Three new cytotoxic dimeric macrolides, swinholides B and C and isoswinholide A, congeners of swinholide A, from the Okinawan marine sponge Theonella swinhoei: M. Kobayashi, et al.; Chem. Pharm. Bull. (Tokyo) 38, 2960 (1990) Abstract
Marine natural products. XXXI. Structure-activity correlation of a potent cytotoxic dimeric macrolide swinholide A, from the Okinawan marine sponge Theonella swinhoei, and its isomers: M. Kobayashi, et al.; Chem. Pharm. Bull. (Tokyo) 42, 19 (1994) Abstract
Swinholide A is a microfilament disrupting marine toxin that stabilizes actin dimers and severs actin filaments: M.R. Bubb, et al.; J. Biol. Chem. 270, 3463 (1995) Abstract; Full Text
Two classes of metabolites from Theonella swinhoei are localized in distinct populations of bacterial symbionts: C.A. Bewley, et al.; Experientia 52, 716 (1996) Abstract
Autoregulation of actin synthesis responds to monomeric actin levels: A. Lyubimova, et al.; J. Cell. Biochem. 65, 469 (1997) Abstract
Misakinolide A is a marine macrolide that caps but does not sever filamentous actin: D.R. Terry, et al.; J. Biol. Chem. 272, 7841 (1997) Abstract; Full Text
Actin-depolymerizing effect of dimeric macrolides, bistheonellide A and swinholide A: S.Y. Saito, et al.; J. Biochem. 123, 571 (1998) Abstract
Structural basis of swinholide A binding to actin: V.A. Klenchin, et al.; Chem. Biol. 12, 287 (2005) Abstract; Full Text
Hurghadolide A and swinholide I, potent actin-microfilament disrupters from the Red Sea sponge Theonella swinhoei: D.T. Youssef & S.L. Mooberry; J. Nat. Prod. 69, 154 (2006) Abstract
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Further Categories Containing This Product:
Actin/Related Products
 
 
ALX-350-101 Revised 03-Apr-08
Catharanthine . tartrate
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SYNONYMS 3,4-Didehydroibogamine-18-carboxylic acid methyl ester . tartrate
7-Ethyl-9,10,12,13-tetrahydro-6,9-methano-5H-pyrido[1’,2’:1,2]azepino[4,5-b]indole-6(6aH)-carboxylic acid methyl ester . tartrate
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products for Cytoskeletal Research
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ALX-350-101-M100   100 mg 160.00 USD Add To Cart
ALX-350-101-G001   1 g 430.00 USD Add To Cart
Product Specification
FORMULA: C21H24N2O2 . C4H6O6
MW: 336.4 . 150.1
CAS NUMBER: 2648-21-5
MERCK INDEX: 14: 1904
SOURCE/HOST: Isolated from Catharanthus roseus.
PURITY: ≥90%
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in 100% ethanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Very hygroscopic. Keep cool and dry.

Product Description

Starting material for the synthesis of the antitumor drugs vinblastine and vincristine.  It is less active as an inhibitor of tubulin self-assembly into microtubules than the latter two compounds.

Product Specific Literature References
Photochemical one-pot synthesis of vinblastine and vincristine: S. Pennanen & A. Huhtikangas; Photochem. Photobiol. 51, 515 (1990) Abstract
Mechanism of interaction of vinca alkaloids with tubulin: catharanthine and vindoline: V. Prakash & S.N. Timasheff; Biochemistry 30, 873 (1991) Abstract
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Further Categories Containing This Product:
Alkaloids • Microtubule Modulators • Natural Products - Antitumor Reagents
 
 
ALX-350-102 Revised 25-Mar-08
Vindoline
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SYNONYMS (2β,3β,4β,5α,12β,19α)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-aspidospermidine-3-carbox
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products for Cytoskeletal Research
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ALX-350-102-M100   100 mg 160.00 USD Add To Cart
ALX-350-102-G001   1 g 430.00 USD Add To Cart
Product Specification
FORMULA: C25H32N2O6
MW: 456.5
CAS NUMBER: 2182-14-1
MERCK INDEX: 14: 9988
SOURCE/HOST: Isolated from Catharanthus roseus.
PURITY: ≥90%
APPEARANCE: White to off-white powder.
SOLUBILITY: Soluble in 100% ethanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Very hygroscopic.

Product Description
Lacks physiological activity itself, but is contained as the pentacyclic moiety in the antineoplastic agents vinblastine and vincristine.
Product Specific Literature References
Photochemical one-pot synthesis of vinblastine and vincristine: S. Pennanen & A. Huhtikangas; Photochem. Photobiol. 51, 515 (1990) Abstract
Mechanism of interaction of vinca alkaloids with tubulin: catharanthine and vindoline: V. Prakash & S.N. Timasheff; Biochemistry 30, 873 (1991) Abstract
Antimitotic agents: chemistry and recognition of tubulin molecule: S. Iwasaki; Med. Res. Rev. 13, 183 (1993) Abstract
Catharanthus roseus L. plants and explants infected with phytoplasmas: alkaloid production and structural observations: M.A. Favali, et al.; Protoplasma 223, 45 (2004) Abstract
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Further Categories Containing This Product:
Alkaloids • Microtubule Modulators • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products - Antitumor Reagents • Antitumor Agents (Apoptosis Inducers)
 
 
ALX-350-130 Revised 07-Apr-08
Latrunculin A
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PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products for Cytoskeletal Research
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ALX-350-130-C100   100 µg 150.00 USD Add To Cart
Product Specification
FORMULA: C22H31NO5S
MW: 421.6
CAS NUMBER: 76343-93-6
MERCK INDEX: 14: 5378
SOURCE/HOST: Isolated from Latrunculia magnifica.
PURITY: ≥98% (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
USE/STABILITY: Stable for 1 year after receipt when stored at -20°C. Stock solutions are stable for up to 3 months when stored at -20°C.
HANDLING: Protect from light.
HAZARD: TOXIC.

Product Description
Inhibits actin polymerization via a different mechanism and 10- to 20-fold more potently than cytochalasins. Inhibits phagocytosis by macrophages.
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: A: M. Coue, et al.; FEBS Lett. 213, 316 (1987) Abstract
Latrunculin A is a potent inhibitor of phagocytosis by macrophages: C.A. de Oliveira and 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 Motil. Cytoskeleton 13, 127 (1989) Abstract
High rates of actin filament turnover in budding yeast and roles for actin in establishment and maintenance of cell polarity revealed using the actin inhibitor latrunculin-A: K.R. Ayscough, et al.; J. Cell Biol. 137, 399 (1997) Abstract; Full Text
Differential effects of latrunculin-A on myofibrils in cultures of skeletal muscle cells: Insights into mechanisms of myofibrillogenesis: J. Wang, et al.; Cell Motil. Cytoskeleton 62, 35 (2005) Abstract
Seizures induced by microperfusion of glutamate and glycine in the hippocampus of rats pretreated with latrunculin A: A. Vazquez-Lopez; Neurosci. Lett. 388, 81 (2005) Abstract
Latrunculin A depolarizes starfish oocytes: F. Moccia; Comp. Biochem. Physiol. A Mol. Integr. Physiol. 148, 845 (2007) Abstract
Further Categories Containing This Product:
Other Toxins • Actin/Related Products
 
 
ALX-350-153 Revised 28-Jul-08
Withaferin A
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SYNONYMS 5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products - Antitumor Reagents
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ALX-350-153-M001   1 mg 60.00 USD Add To Cart
ALX-350-153-M005   5 mg 240.00 USD Add To Cart
Product Specification
FORMULA: C28H38O6
MW: 470.6
CAS NUMBER: 5119-48-2
MERCK INDEX: 14: 10048
RTECS: KE7288500
SOURCE/HOST: Isolated from Withania somnifera.
PURITY: ≥94% (HPLC)
APPEARANCE: White to off-white solid.
SOLUBILITY: Soluble in DMSO (20 mg/ml), methanol (10 mg/ml) or 100% ethanol.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.
HAZARD: MAY BE MUTAGENIC. MAY BE CARCINOGENIC. HARMFUL.

Product Description
Cell permeable and potent angiogenesis inhibitor from the family of withanolides. Inhibits endothelial cells (HUVEC) sprouting in vitro (IC50=12nM) and in vivo. Exhibits antitumor, anti-inflammatory, radiosensitizing, and immunosuppressive properties. Potently inhibits NF-κB activation by preventing the TNF-induced activation of IκB kinase β (IKKβ). Affects AP1 transcription and induces cell death. Alters cytoskeletal architecture by covalently binding annexin II and stimulating its basal F-actin cross-linking activity which inhibits the migratory and invasive capability of endothelial cells. Displays neuronal regenerative properties. Targets the intermediate filament protein vimentin.
Product Specific Literature References
Tumor inhibitors. XXXIX. Active principles of Acnistus arborescens. Isolation and structural and spectral studies of withaferin A and withacnistin: S.M. Kupchan, et al.; J. Org. Chem. 34, 3858 (1969) Abstract
In vivo growth inhibitory and radiosensitizing effects of withaferin A on mouse Ehrlich ascites carcinoma: P.U. Devi, et al.; Cancer Lett. 95, 189 (1995) Abstract
Growth inhibition of human tumor cell lines by withanolides from Withania somnifera leaves: B. Jayaprakasam, et al.; Life Sci. 74, 125 (2003) Abstract
Withaferin A is a potent inhibitor of angiogenesis: R. Mohan, et al.; Angiogenesis 7, 115 (2004) Abstract
Neuritic regeneration and synaptic reconstruction induced by withanolide: A: T. Kuboyama, et al.; Br. J. Pharmacol. 144, 961 (2005) Abstract; Full Text
Actin microfilament aggregation induced by withaferin A is mediated by annexin II: R.R. Falsey, et al.; Nat. Chem. Biol. 2, 33 (2006) Abstract
Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity: M. Kaileh, et al.; J. Biol. Chem. 282, 4253 (2007) Abstract; Full Text
The tumor inhibitor and antiangiogenic agent withaferin A targets the intermediate filament protein vimentin: P. Bargagna-Mohan, et al.; Chem. Biol. 14, 623 (2007) Abstract
Further Categories Containing This Product:
Natural Products for Angiogenesis Research • NF-kB Pathway Inhibitors • Natural Products - NF-kB Pathway Inhibitors • Natural Products for Cytoskeletal Research • Natural Products - Anti-inflammatory Agents • Natural Products - Immunomodulators • Antitumor Agents (Apoptosis Inducers)
 
 
ALX-350-257 Revised 08-Apr-08
Vinblastine . sulfate
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SYNONYMS Vincaleukoblastine . sulfate
PRODUCT LINE Natural Products / Antibiotics
PRODUCT CATEGORY Natural Products for Cell Cycle Research
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ALX-350-257-M005   5 mg 45.00 USD Add To Cart
ALX-350-257-M025   25 mg 190.00 USD Add To Cart
Product Specification
FORMULA: C46H58N4O9 . H2SO4
MW: 811.0 . 98.1
CAS NUMBER: 143-67-9
MERCK INDEX: 14: 9982
SOURCE/HOST: Semisynthetic from catharanthine or vindoline.
PURITY: ≥98%
APPEARANCE: White powder.
SOLUBILITY: Soluble in DMSO, methanol or water.
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HAZARD: CARCINOGENIC. TOXIC.

Product Description
Plant alkaloid that arrests the cell cycle in G2/M phase by blocking mitotic spindle formation. Depolymerizes microtubules and blocks binding of tubulin to microtubule proteins. Induces apoptosis. Triggers Raf-1 activation, phosphorylation of Bcl-2 family proteins and induction of p53 expression.
Product Specific Literature References
Microtubule antagonists activate programmed cell death (apoptosis) in cultured rat hepatocytes: K. Tsukidate, et al.; Am. J. Pathol. 143, 918 (1993) Abstract
Resistance of Ehrlich tumor cells to apoptosis can be due to accumulation of heat shock proteins: V.L. Gabai, et al.; FEBS Lett. 375, 21 (1995) Abstract
The interaction of taxol and vinblastine with radiation induction of p53 and p21 WAF1/CIP1: R.B. Tishler & D.M. Lamppu; Br. J. Cancer. Suppl. 27, S82 (1996) Abstract
Raf-1/bcl-2 phosphorylation: a step from microtubule damage to cell death: M.V. Blagosklonny, et al.; Cancer Res. 57, 130 (1997) Abstract
Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle: A. Jordan, et al.; Med. Res. Rev. 18, 259 (1998) Abstract
The C terminus of beta-tubulin regulates vinblastine-induced tubulin polymerization: S.S. Rai & J. Wolff; PNAS 95, 4253 (1998) Abstract; Full Text
Caspase-3 activation is not responsible for vinblastine-induced Bcl-2 phosphorylation and G2/M arrest in human small cell lung carcinoma Ms-1 cells: E. Tashiro, et al.; Jpn. J. Cancer Res. 89, 940 (1998)