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Natural Products for Cytoskeletal Research
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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
Ordering Information
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 • Marine Natural Products
 
 
ALX-350-356 Revised 12-Mar-08
Swinholide I
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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-350-356-C010   10 µg 120.00 USD Add To Cart
Product Specification
FORMULA: C78H132O21
MW: 1405.9
SOURCE/HOST: Isolated from marine sponge Theonella swinhoei.
PURITY: ≥98% (HPLC)
APPEARANCE: Colorless oil.
SOLUBILITY: Soluble in DMSO (25mg/ml) or 100% ethanol (25mg/ml).
SHIPPING: AMBIENT
LONG TERM STORAGE: -20°C
HANDLING: Protect from light.

Product Description
First analog of swinholide A (Prod. No. ALX-350-088) with a hydroxylated side-chain. It shows potent cytotoxicity against the human colon adenocarcinoma cell line HCT-116 by disruption of the actin cytoskeleton. Has antifungal activity against Candida albicans.
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:
Natural Products - Antifungal Agents • Natural Products - Antitumor Reagents • Actin / Related Products • Marine Natural Products
 
 
ALX-350-372 Revised 10-Jul-08 New product
Thiocolchicine
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SYNONYMS N-[(7S)-5,6,7,9-Tetrahydro-1,2,3-trimethoxy-10-(methylthio)-9-oxobenzo[a]heptalen-7-yl]acetamide
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-350-372-M001   1 mg 50.00 USD Add To Cart
ALX-350-372-M005   5 mg 150.00 USD Add To Cart
ALX-350-372-M025   25 mg 450.00 USD Add To Cart
Product Specification
FORMULA: C22H25NO5S
MW: 415.5
CAS NUMBER: 2730-71-4
MERCK INDEX: 14: 9324
SOURCE/HOST: Semisynthetic.
PURITY: ≥95% (HPLC)
APPEARANCE: Yellow solid.
SOLUBILITY: Soluble in 100% ethanol or acetone; almost insoluble in water or ether.
SHIPPING: SHIPPED ON BLUE ICE
LONG TERM STORAGE: -20°C
HANDLING: Protect from light and moisture.
HAZARD: VERY TOXIC.
IDENTITY: Identity determined by 1H-NMR.

Product Description
Inhibitor of microtubules by specific binding to tubulin. Modulator of axonal cytoskeleton. Induces apoptosis. Topoisomerase I inhibitor.
Product Specific Literature References
Association of thiocolchicine with tubulin: R.M. Chabin & S.B. Hastie; BBRC 161, 544 (1989) Abstract
Antiproliferative activity of colchicine analogues on MDR-positive and MDR-negative human cancer cell lines: R. De Vincenzo, et al.; Anticancer Drug Des. 13, 19 (1998) Abstract
Biological evaluation on different human cancer cell lines of novel colchicine analogs: R. De Vincenzo, et al.; Oncol. Res. 11, 145 (1999) Abstract
Effects of thiocolchicine on axonal cytoskeleton of the rat peroneus nerve: P. Ferri, et al.; Exp. Toxicol. Pathol. 54, 211 (2002) Abstract
Thiocolchicine dimers: a novel class of topoisomerase-I inhibitors: G. Raspaglio, et al.; Biochem. Pharmacol. 69, 113 (2005) Abstract
Further Categories Containing This Product:
Natural Products - Apoptosis Inducers & Inhibitors • Microtubule Modulators • Natural Products with Antibiotic Activity • Alkaloids
 
 
ALX-350-257 Revised 08-Oct-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: TOXIC. MAY BE CARCINOGENIC.

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) Abstract
Use of drugs to study role of microtubule assembly dynamics in living cells: A. Jordan & L. Wilson; Meth. Enzymol. 298, 252 (1998) Abstract
Vinblastine-induced phosphorylation of Bcl-2 and Bcl-XL is mediated by JNK and occurs in parallel with inactivation of the Raf-1/MEK/ERK cascade: M. Fan, et al.; J. Biol. Chem. 275, 29980 (2000) Abstract; Full Text
Vinblastine, a chemotherapeutic drug, inhibits palmitoylation of tubulin in human leukemic lymphocytes: J.M. Caron & M. Herwood; Chemotherapy 53, 51 (2007) Abstract
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Further Categories Containing This Product:
Cell Cycle Blockers & Inhibitors / Related Products • Natural Products for Cytoskeletal Research • Natural Products - Antitumor Reagents • Antitumor Agents (Apoptosis Inducers) • Microtubule Modulators • Natural Products - Apoptosis Inducers & Inhibitors • Alkaloids
 
 
ALX-350-069 Revised 02-Oct-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
USE/STABILITY: Stable for at least 1 year after receipt when stored at -20°C. Stock solutions are stable for up to 3 months at -20°C.
HANDLING: Protect from light and moisture.
HAZARD: MAY BE TERATOGENIC.

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:
Cell Cycle Blockers & Inhibitors / Related Products • Natural Products for Cytoskeletal Research • Microtubule Modulators • Natural Products - Antitumor Reagents • Antitumor Agents (DNA Interaction & Gene Regulation) • Antitumor Agents (Apoptosis Inducers) • Antitumor Agents (Anti-proliferative) • Natural Products - Apoptosis Inducers & Inhibitors • Alkaloids
 
 
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
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
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:
Microtubule Modulators • Natural Products - Antitumor Reagents • Antitumor Agents (Apoptosis Inducers) • Natural Products - Apoptosis Inducers & Inhibitors • Alkaloids
 
 
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
Ordering Information
Product Numbers: Format: Size: Unit Price: Quantity: Add To Cart
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 - Immunomodulators • Natural Products for Angiogenesis Research • Natural Products - NF-kB Pathway Inhibitors • Natural Products for Cytoskeletal Research • Antitumor Agents (Apoptosis Inducers) • Vimentin / Related Products • Natural Products - Anti-inflammatory Agents • NF-kB Pathway Inhibitors
 
 
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