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ALX-350-346

Revised 12-Sep-08

Silybin
SYNONYMS	Silibinin 2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl)benzodioxin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Chemopreventive Agents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-346-G001		1 g	10.00 USD
ALX-350-346-G005		5 g	35.00 USD

Product Specification

FORMULA:	C₂₅H₂₂O₁₀
MW:	482.4
CAS NUMBER:	22888-70-6; 65666-07-1
MERCK INDEX:	14: 8532
RTECS:	DJ2981770
SOURCE/HOST:	Originally isolated from Silybum marianum.
PURITY:	≥98%
APPEARANCE:	White to light yellow solid.
SOLUBILITY:	Soluble in 100% ethanol (0.1mg/ml), DMSO (10mg/ml), dimethyl formamide (20mg/ml), acetone or methanol; 0.5mg/ml soluble in a 1:9 solution of dimethyl formamide:PBS (pH 7.2) (dilute the dimethyl formamide solution with PBS).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	We do not recommend storing aqueous solutions for more than one day.
HAZARD:	IRRITANT.

Product Description

Mixture of silybin A and silybin B. Major active constituent of silymarin. Anti-inflammatory, cytoprotective and anti-cancer compound. Shows chemopreventive effect against skin cancer. Inhibits mitogen-activated protein kinase (MAPK). Inhibits P-glycoprotein (Pgp)-mediated cellular efflux. Inhibits cytochrome P450 enzymes. Apoptosis inducer. Blocks the production of superoxide in Kupffer cells (EC₅₀=100µM). Antioxidant. Free radical scavenger.

Product Specific Literature References

[On the chemistry of silymarin (silybin), the active principle of the fruits from Silybum marianum (L.) Gaertn. (Carduus marianus L.)]: H. Wagner, et al.; Arzneimittelforschung 18, 688 (1968) Abstract
Inhibition of Kupffer cell functions as an explanation for the hepatoprotective properties of silibinin: C. Dehmlow, et al.; Hepatology 23, 749 (1996) Abstract; Full Text
Silibinin decreases prostate-specific antigen with cell growth inhibition via G1 arrest, leading to differentiation of prostate carcinoma cells: implications for prostate cancer intervention: X. Zi & R. Agarwal; PNAS 96, 7490 (1999) Abstract; Full Text
The flavanolignan silybin and its hemisynthetic derivatives, a novel series of potential modulators of P-glycoprotein: M. Maitrejean, et al.; Bioorg. Med. Chem. Lett. 10, 157 (2000) Abstract
Silibinin inhibits constitutive and TNFalpha-induced activation of NF-kappaB and sensitizes human prostate carcinoma DU145 cells to TNFalpha-induced apoptosis: S. Dhanalakshmi, et al.; Oncogene 21, 1759 (2002) Abstract; Full Text
Silibinin upregulates the expression of cyclin-dependent kinase inhibitors and causes cell cycle arrest and apoptosis in human colon carcinoma HT-29 cells: C. Agarwal, et al.; Oncogene 22, 8271 (2003) Abstract; Full Text
Epidermal growth factor receptor mediates silibinin-induced cytotoxicity in a rat glioma cell line: L. Qi, et al.; Cancer Biol. Ther. 2, 526 (2003) Abstract; Full Text
Silibinin down-regulates survivin protein and mRNA expression and causes caspases activation and apoptosis in human bladder transitional-cell papilloma RT4 cells: A.K. Tyagi, et al.; BBRC 312, 1178 (2003) Abstract
Silibinin causes cell cycle arrest and apoptosis in human bladder transitional cell carcinoma cells by regulating CDKI-CDK-cyclin cascade, and caspase 3 and PARP cleavages: A. Tyagi, et al.; Carcinogenesis 25, 1711 (2004) Abstract; Full Text
Silibinin protects against photocarcinogenesis via modulation of cell cycle regulators, mitogen-activated protein kinases, and Akt signaling: G. Mallikarjuna, et al.; Cancer Res. 64, 6349 (2004) Abstract; Full Text
Silibinin up-regulates DNA-protein kinase-dependent p53 activation to enhance UVB-induced apoptosis in mouse epithelial JB6 cells: S. Dhanalakshmi, et al.; J. Biol. Chem. 280, 20375 (2005) Abstract; Full Text
Silibinin inhibits invasion of oral cancer cells by suppressing the MAPK pathway: P.N. Chen, et al.; J. Dent. Res. 85, 220 (2006) Abstract; Full Text
Pilot study of oral silibinin, a putative chemopreventive agent, in colorectal cancer patients: silibinin levels in plasma, colorectum, and liver and their pharmacodynamic consequences: C. Hoh, et al.; Clin. Cancer Res. 12, 2944 (2006) Abstract; Full Text
Silibinin prevents UV-induced HaCaT cell apoptosis partly through inhibition of caspase-8 pathway: L.H. Li, et al.; Biol. Pharm. Bull. 29, 1096 (2006) Abstract; Full Text
Silibinin inhibits UVB- and epidermal growth factor-induced mitogenic and cell survival signaling involving activator protein-1 and nuclear factor-kappaB in mouse epidermal JB6 cells: R.P. Singh, et al.; Mol. Cancer Ther. 5, 1145 (2006) Abstract; Full Text
Silibinin activates p53-caspase 2 pathway and causes caspase-mediated cleavage of Cip1/p21 in apoptosis induction in bladder transitional-cell papilloma RT4 cells: evidence for a regulatory loop between p53 and caspase 2: A. Tyagi, et al.; Carcinogenesis 27, 2269 (2006) Abstract; Full Text
Silibinin inhibits constitutive activation of Stat3, and causes caspase activation and apoptotic death of human prostate carcinoma DU145 cells: C. Agarwal, et al.; Carcinogenesis 28, 1463 (2007) Abstract
Effects and mechanisms of silibinin on human hepatoma cell lines: J.J. Lah, et al.; World J. Gastroenterol. 13, 5299 (2007) Abstract; Full Text
Silibinin suppresses PMA-induced MMP-9 expression by blocking the AP-1 activation via MAPK signaling pathways in MCF-7 human breast carcinoma cells: S.O. Lee, et al.; BBRC 354, 165 (2007) Abstract
Immunosuppressive effect of silibinin in experimental autoimmune encephalomyelitis: K. Min, et al.; Arch. Pharm. Res. 30, 1265 (2007) Abstract
Silibinin sensitizes human glioma cells to TRAIL-mediated apoptosis via DR5 up-regulation and down-regulation of c-FLIP and survivi: Y.G. Son, et al.; Cancer Res. 67, 8274 (2007) Abstract
Silibinin impairs constitutively active TGFalpha-EGFR autocrine loop in advanced human prostate carcinoma cells: A. Tyagi, et al.; Pharm. Res. Epub ahead of print, (2008) Abstract

Further Categories Containing This Product:

Free Radical Scavengers • Flavanones • MAPK Pathway Inhibitors • Cytochrome P450 [CYP450] / Related Products • Natural Products - Antioxidants • MDR Inhibitors • P-glycoprotein [Pgp] / Related Products • Natural Products - Anti-inflammatory Agents • Antitumor Agents (Enzyme Inhibitors)

ALX-350-358

Revised 08-Apr-08

Sipholenol A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antitumor Reagents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-358-C100		100 µg	140.00 USD

Product Specification

FORMULA:	C₃₀H₅₂O₄
MW:	476.7
SOURCE/HOST:	Isolated from marine sponge Callyspongia siphonella formerly known as Siphonochalina siphonella.
PURITY:	≥98% (HPLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in DMSO or 100% ethanol (25mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C

Product Description

Efficiently inhibits the function of P-glycoprotein (Pgp). A new reversing agent for treatment of multidrug resistance (MDR) in Pgp-overexpressing tumors. Antiproliferative activity. Cytotoxic.

Product Specific Literature References

The Sipholanes: A novel group of triterpenes from the marine sponge Siphonochalina siphonella: S. Carmely & Y. Kashman; J. Org. Chem. 48, 3517 (1983) Full Text
Reversal of P-glycoprotein-mediated multidrug resistance by Sipholane triterpenoids: S. Jain, et al.; J. Nat. Prod. 70, 928 (2007) Abstract
Sipholenol A, a marine-derived sipholane triterpene, potently reverses P-glycoprotein (ABCB1)-mediated multidrug resistance in cancer cells: Z. Shi, et al.; Cancer Sci. 98, 1373 (2007) Abstract
Biocatalysis of the anticancer sipholane triterpenoids: S. Jain, et al.; Planta Med. 73, 591 (2007) Abstract

Related Products

ALX-350-358

Sipholenol A

Further Categories Containing This Product:

MDR Inhibitors • P-glycoprotein [Pgp] / Related Products • Marine Natural Products

ALX-350-232

Revised 06-Oct-08

DL-Sulforaphane
SYNONYMS	R,S-Sulforaphane 1-Isothiocyanato-4-methylsulfinyl-butane
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Chemopreventive Agents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-232-M025		25 mg	140.00 USD

Product Specification

FORMULA:	C₆H₁₁NOS₂
MW:	177.3
CAS NUMBER:	142825-10-3; 4478-93-7 (unspecified stereo)
MERCK INDEX:	14: 8962
SOURCE/HOST:	Synthetic.
PURITY:	≥98% (UPLC)
APPEARANCE:	Slightly yellowish liquid.
SOLUBILITY:	Soluble in methanol or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
IDENTITY:	Identity determined by ¹H-NMR and MS.

Product Description

Potent, selective inducer of phase II detoxification enzymes. Inhibits chemically induced mammary tumor formation in rats. Inhibits LPS-induced HMGB1 (high mobility group box 1) secretion.

Product Specific Literature References

A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure: Y. Zhang, et al.; PNAS 89, 2399 (1992) Abstract; Full Text
Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates: Y. Zhang, et al.; PNAS 91, 3147 (1994) Abstract; Full Text
A novel mechanism of chemoprotection by sulforaphane: inhibition of histone deacetylase: M.C. Myzak, et al.; Cancer Res. 64, 5767 (2004) Abstract; Full Text
The phase 2 enzyme inducers ethacrynic acid, DL-sulforaphane, and oltipraz inhibit lipopolysaccharide-induced high-mobility group box 1 secretion by RAW 264.7 cells: M.E. Killeen, et al.; J. Pharmacol. Exp. Ther. 316, 1070 (2006) Abstract
Sulforaphane targets pancreatic tumor-initiating cells by NF-{kappa}B-induced anti-apoptotic signaling: G. Kallifatidis, et al.; Gut Epub ahead of print, (2008) Abstract

Further Categories Containing This Product:

Antitumor Agents (Enzyme Activators & Inducers) • Cytochrome P450 [CYP450] / Related Products • Glutathione S-Transferase • Respiratory Chain Other Products • Natural Products - Apoptosis Inducers & Inhibitors • Active Substances from Fruit and Vegetables

ALX-350-230

Revised 03-Nov-08

L-Sulforaphane
SYNONYMS	R-Sulforaphane (-)-1-Isothiocyanato-(4R)-(methylsulfinyl)butane
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Chemopreventive Agents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-230-M010		10 mg	180.00 USD

Product Specification

FORMULA:	C₆H₁₁NOS₂
MW:	177.3
CAS NUMBER:	142825-10-3; 4478-93-7
MERCK INDEX:	14: 8962
SOURCE/HOST:	Chiral natural product isolated from broccoli.
PURITY:	≥98% (UPLC)
APPEARANCE:	Slightly yellowish liquid.
SOLUBILITY:	Soluble in methanol, 100% ethanol, DMSO or ethyl acetate.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C

Product Description

Potent, selective inducer of phase II detoxification enzymes. Inhibits chemically induced mammary tumor formation in rats.

Product Specific Literature References

A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure: Y. Zhang, et al.; PNAS 89, 2399 (1992) Abstract; Full Text
Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates: Y. Zhang, et al.; PNAS 91, 3147 (1994) Abstract; Full Text
Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors: J.W. Fahey, et al.; PNAS 99, 7610 (2002) Abstract; Full Text
A novel mechanism of chemoprotection by sulforaphane: inhibition of histone deacetylase: M.C. Myzak ,et al.; Cancer Res. 64, 5767 (2004) Abstract; Full Text
Reprogramming of keratin biosynthesis by sulforaphane restores skin integrity in epidermolysis bullosa simplex: M.L. Kerns, et al.; PNAS 104, 14460 (2007) Abstract
Sulforaphane targets pancreatic tumor-initiating cells by NF-{kappa}B-induced anti-apoptotic signaling: G. Kallifatidis, et al.; Gut Epub ahead of print, (2008) Abstract

Further Categories Containing This Product:

ALX-350-231

Revised 30-Jun-08

L-Sulforaphene
SYNONYMS	S-Sulforaphene (-)-4-Isothiocyanato-(1S)-(methylsulfinyl)-1-butene Raphanin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Chemopreventive Agents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-231-M010		10 mg	180.00 USD

Product Specification

FORMULA:	C₆H₉NOS₂
MW:	175.3
CAS NUMBER:	592-95-0
SOURCE/HOST:	Chiral natural product isolated from radish seeds (Raphanus sativus L.) and broccoli.
PURITY:	≥97% (GC)
APPEARANCE:	Slightly yellowish liquid.
SOLUBILITY:	Soluble in methanol or DMSO; slightly soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
IDENTITY:	Identity determined by MS and NMR.

Product Description

Shows antitumor activity.

Product Specific Literature References

Phytochemicals as modulators of cancer risk: H.L. Bradlow, et al.; Adv. Exp. Med. Biol. 472, 207 (1999), Review Abstract
Glucosinolates of seven medicinal plants from Thailand: T. Songsak & G.B. Lockwood; Fitoterapia 73, 209 (2002) Abstract

Further Categories Containing This Product:

Antitumor Agents (Enzyme Activators & Inducers) • Natural Products with Antibiotic Activity • Active Substances from Fruit and Vegetables

ALX-350-077

Revised 30-Jun-08

Swainsonine
SYNONYMS	8α,β-Octahydroindolizidine-1α,2α,8β-triol
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antitumor Reagents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-077-MC05		0.5 mg	85.00 USD
ALX-350-077-M001		1 mg	148.00 USD

Product Specification

FORMULA:	C₈H₁₅NO₃
MW:	173.2
CAS NUMBER:	72741-87-8
SOURCE/HOST:	Synthetic.
PURITY:	≥98% (TLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO, methanol or water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
IDENTITY:	Identity determined by ¹H-NMR.

Product Description

Reversibly inhibits the active site of lysosomal α-mannosidase. Also inhibits the growth of tumors and prevents metastasis in murine models. Could inhibit cell proliferation in vitro and the growth of human gastric carcinoma in vivo. Blocks the processing of high mannose oligosaccharides to form complex type oligosaccharides.

Product Specific Literature References

Inhibitors of glycoprotein synthesis: A.D. Elbein; Meth. Enzymol. 98, 135 (1983) Abstract
Purification and characterization of Ca2+/calmodulin-dependent protein kinase V from rat cerebrum: H. Mochizuki, et al.; J. Biol. Chem. 268, 9143 (1993) Abstract; Full Text
Swainsonine protects both murine and human haematopoietic systems from chemotherapeutic toxicity: J.L. Klein, et al.; Br. J. Cancer 80, 87 (1999) Abstract
Swainsonine stimulates bone marrow cell proliferation and differentiation in different strains of inbred mice: O.A. Oredipe, et al.; Pharmacol. Res. 47, 69 (2003) Abstract
Inhibition of the growth of human gastric carcinoma in vivo and in vitro by swainsonine: J.Y. Sun, et al.; Phytomedicine 14, 353 (2007) Abstract

Further Categories Containing This Product:

Natural Products with Antibiotic Activity • Glycosidases / Related Products • Alkaloids

ALX-350-356

Revised 12-Mar-08

Swinholide I
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-350-356-C010		10 µg	120.00 USD

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

FORMULA:	C₃₀H₅₀O₄
MW:	474.7
SOURCE/HOST:	Isolated from marine sponge Callyspongia siphonella formerly known as Siphonochalina siphonella.
PURITY:	≥98% (HPLC)
APPEARANCE:	White to off-white powder.
FORMULATION:	Lyophilized.
SOLUBILITY:	Soluble in DMSO or 100% ethanol (25mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C