ALEXIS Biochemicals: Sanguinarine chloride

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ALX-380-075

Revised 03-Apr-08

Antimycin A
SYNONYMS	Antipiricullin Virosin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Apoptosis Inducers & Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-075-M005		5 mg	20.00 USD
ALX-380-075-M010		10 mg	33.00 USD

Product Specification

CAS NUMBER:	1397-94-0
MERCK INDEX:	14: 714 (A1) & 715 (A3)
RTECS:	CD0350000
SOURCE/HOST:	Isolated from Streptomyces sp. Mixture of antimycin A's.
APPEARANCE:	White to faint yellow powder.
SOLUBILITY:	Soluble in 100% ethanol (50mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
HAZARD:	TOXIC.

Product Description

Antibiotic. Induces apoptosis, which is not prevented by the presence of Bcl-2. Inhibits mitochondrial electron transport specifically between cytochromes b and c1.

Product Specific Literature References

The isolation and properties of antimycin A: B. R. Dunshee, et al.; J. Am. Chem. Soc. 71, 2436 (1949)
The effect of antimycin A on mouse liver inner mitochondrial membrane channel activity: M.L. Campo, et al.; J. Biol. Chem. 267, 8123 (1992) Abstract; Full Text
Antimycin A mimics a cell-death-inducing Bcl-2 homology domain 3: S.P. Tzung, et al.; Nat. Cell Biol. 3, 183 (2001) Abstract
Biophysical characterization of recombinant human Bcl-2 and its interactions with an inhibitory ligand, antimycin A: K.M. Kim, et al.; Biochemistry 40, 4911 (2001) Abstract
Synthetic peptides and non-peptidic molecules as probes of structure and function of Bcl-2 family proteins and modulators of apoptosis: D. Liu & Z. Huang; Apoptosis 6, 453 (2001) Abstract
Antimycin A mimics a cell-death-inducing Bcl-2 homology domain 3: S.P. Tzung, et al.; Nat. Cell. Biol. 3, 183 (2001) Abstract
Oligomycin and antimycin A prevent nitric oxide-induced apoptosis by blocking cytochrome C leakage: N. Dairaku, et al.; J. Lab. Clin. Med. 143, 143 (2004) Abstract
An ROS generator, antimycin A, inhibits the growth of HeLa cells via apoptosis: W.H. Park, et al.; J. Cell. Biochem. 102, 98 (2007) Abstract

Further Categories Containing This Product:

Bcl-2 Family Modulators • Respiratory Chain Other Products

ALX-350-312

Revised 28-May-08

(-)-Arctigenin
SYNONYMS	(3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(3H)-furanone
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antitumor Reagents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-312-M025		25 mg	70.00 USD

Product Specification

FORMULA:	C₂₁H₂₄O₆
MW:	372.4
CAS NUMBER:	7770-78-7
SOURCE/HOST:	Isolated from Arctium lappa.
PURITY:	≥97% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO (34mg/ml, heating, sonication); sparingly soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C

Product Description

Lignan derivative, which shows antitumor, anti-inflammatory, immunomodulatory and neuroprotective activities. Down-regulates anti-apoptotic protein Bcl-X_L. Potent inhibitor of HIV type-I integrase and DNA topoisomerase II. Shows phytoestrogenic and cytotoxic properties against Hep62 cells. Antagonist for platelet activating factor and Ca²⁺. Blocks the activation of Akt (protein kinase B; PKB) induced by glucose starvation.

Product Specific Literature References

Antiproliferative effect of Arctigenin and Arctiin: S.Y. Ryu, et al.; Arch. Pharm. Res. 18, 462 (1995)
(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase: E. Eich, et al.; J. Med. Chem 39, 86 (1996) Abstract
Immunomodulatory effect of arctigenin, a lignan compound, on tumour necrosis factor-alpha and nitric oxide production, and lymphocyte proliferation: J.Y. Cho, et al.; J. Pharm. Pharmacol. 51, 1267 (1999) Abstract
Arctigenin protects cultured cortical neurons from glutamate-induced neurodegeneration by binding to kainate receptor: Y.P. Jang, et al.; J. Neurosci. Res. 68, 233 (2002) 68, 233 (2002) Abstract
A phytochemical study of lignans in whole plants and cell suspension cultures of Anthriscus sylvestris: A. Koulman, et al.; Planta Med. 69, 733 (2003) Abstract
Naturally occurring lignans efficiently induce apoptosis in colorectal tumor cells: B. Hausott, et al.; J. Cancer Res. Clin. Oncol. 129, 569 (2003) Abstract
Arctigenin, a phenylpropanoid dibenzylbutyrolactone lignan, inhibits MAP kinases and AP-1 activation via potent MKK inhibition: the role in TNF-alpha inhibition: M.K. Cho, et al.; Int. Immunopharmacol. 4, 1419 (2004) Abstract
Arctigenin, a phenylpropanoid dibenzylbutyrolactone lignan, inhibits MAP kinases and AP-1 activation via potent MKK inhibition: the role in TNF-alpha inhibition: M.K. Cho, et al.; Int. Immunopharmacol. 4, 1419 (2004) Abstract
Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation: S. Awale, et al.; Cancer Res. 66, 1751 (2006) Abstract
The chemopreventive effects of Saussurea salicifolia through induction of apoptosis and phase II detoxification enzyme: K. Kang, et al.; Biol. Pharm. Bull. 30, 2352 (2007) Abstract

Further Categories Containing This Product:

Bcl-2 Family Modulators • Platelet Activating Factors [PAF] & Receptors / Related Products • Natural Products - Topoisomerase Inhibitors • Natural Products - Anti-inflammatory Agents • Natural Products - Antiviral / anti-HIV Agents • Natural Products - Immunomodulators • Natural Products - Nitric Oxide Pathway Modulators • HIV / AIDS / Related Products

ALX-350-318

Revised 17-Jun-08

(-)-Arctiin
SYNONYMS	(3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]-3-[[4-(β-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-2(3H)-furanone
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antitumor Reagents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-318-M025		25 mg	60.00 USD

Product Specification

FORMULA:	C₂₇H₃₄O₁₁
MW:	534.6
CAS NUMBER:	20362-31-6
SOURCE/HOST:	Isolated from Arctium lappa.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO (5mg/ml); sparingly soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.

Product Description

Lignan derivative with antitumor activities. Down-regulates anti-apoptotic protein Bcl-X_L. Potent inhibitor of HIV type-I integrase and DNA topoisomerase II. Shows phytoestrogenic activity and is an antagonist for platelet activating factor and Ca²⁺.

Product Specific Literature References

Platelet activating factor (PAF) antagonists contained in medicinal plants: lignans and sesquiterpenes: S. Iwakami, et al.; Chem. Pharm. Bull. (Tokyo) 40, 1196 (1992) Abstract
Antiproliferative effect of Arctigenin and Arctiin: S.Y. Ryu, et al.; Arch. Pharm. Res. 18, 462 (1995)
Cytotoxic components of bardanae fructus (goboshi): S. Moritani, et al.; Biol. Pharm. Bull. 19, 1515 (1996) Abstract
Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection: A.J. Vlietinck, et al.; Planta Med. 64, 97 (1998) Abstract
Anti-tumor-promoting activity of lignans from the aerial part of Saussurea medusa: M. Takasaki, et al.; Cancer Lett. 158, 53 (2000) Abstract
Isolation and identification of arctiin and arctigenin in leaves of burdock (Arctium lappa L.) by polyamide column chromatography in combination with HPLC-ESI/MS: S. Liu, et al.; Phytochem. Anal. 16, 86 (2005) Abstract
Application of preparative high-speed counter-current chromatography for separation and purification of arctiin from Fructus Arctii: X. Wang, et al.; J. Chromatogr. A. 1063, 247 (2005) Abstract
The chemopreventive effects of Saussurea salicifolia through induction of apoptosis and phase II detoxification enzyme: K. Kang, et al.; Biol. Pharm. Bull. 30, 2352 (2007) Abstract

Further Categories Containing This Product:

Natural Products - Immunomodulators • Bcl-2 Family Modulators • Antitumor Agents (Anti-proliferative) • Platelet Activating Factors [PAF] & Receptors / Related Products • Natural Products - Topoisomerase Inhibitors • Natural Products - Antiviral / anti-HIV Agents • HIV / AIDS / Related Products

ALX-430-122

Revised 23-Feb-05

BH3I-1
SYNONYMS	5-(p-Bromobenzylidine)-α-isopropyl-4-oxo-2-thioxo-3-thiozolidineacetic acid
PRODUCT LINE	Cell Death / Apoptosis / Autophagy
PRODUCT CATEGORY	Bcl-2 Family Modulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-430-122-M005		5 mg	160.00 USD

Product Specification

FORMULA:	C₁₅H₁₄BrNO₃S₂
MW:	400.3
PURITY:	≥95% (HPLC)
APPEARANCE:	Yellow solid.
SOLUBILITY:	Soluble in DMSO or 100% ethanol.
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stock solutions are stable for up to 3 months when stored at –20°C.
HANDLING:	After reconstitution, prepare aliquots and store at -20°C. Packaged under inert gas. Protect from light.
HAZARD:	HARMFUL.

Product Description

Cell permeable BH3 mimetic. Binds to Bcl-X_L.

ALX-430-123

Revised 24-Feb-05

BH3I-1"
SYNONYMS	5-Benzylidine-α-isopropyl-4-oxo-2-thioxo-3-thiozolidineacetic acid
PRODUCT LINE	Cell Death / Apoptosis / Autophagy
PRODUCT CATEGORY	Bcl-2 Family Modulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-430-123-M005		5 mg	125.00 USD

Product Specification

FORMULA:	C₁₅H₁₅NO₃S₂
MW:	321.4
PURITY:	≥95% (HPLC)
APPEARANCE:	Yellow solid.
SOLUBILITY:	Soluble in DMSO or 100% ethanol.
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stable for 2 years after receipt when stored at -20°C. Stock solutions are stable for up to 3 months when stored at –20°C.
HANDLING:	After reconstitution, prepare aliquots and store at -20°C. Packaged under inert gas. Protect from light.
HAZARD:	HARMFUL.

Product Description

Cell permeable BH3 mimetic. Binds to Bcl-X_L.

ALX-350-008

Revised 02-Oct-07

Chelerythrine chloride
SYNONYMS	1,2-Dimethoxy-N-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium chloride
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Protein Kinase Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-008-M001		1 mg	25.00 USD
ALX-350-008-M005		5 mg	75.00 USD
ALX-350-008-M025		25 mg	300.00 USD

Product Specification

FORMULA:	C₂₁H₁₈NO₄Cl
MW:	383.8
CAS NUMBER:	3895-92-9
MERCK INDEX:	14: 2051
RTECS:	FL9200000
SOURCE/HOST:	Synthetic.
PURITY:	≥97% (completely free of biologically active impurities, such as sanguinarine)
APPEARANCE:	Yellow to orange solid.
SOLUBILITY:	Soluble in DMSO, water, 100% ethanol or methanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Heating to 40-50°C with gentle agitation may support complete solubilization. Further dilute with buffer just prior to use. Stock solutions should be refrigerated or frozen between for storage.
HAZARD:	HARMFUL.

Product Description

Potent, selective and cell permeable protein kinase C (PKC) inhibitor. Induces apoptosis. BH3 mimetic which inhibits Bcl-X_L function.

Product Specific Literature References

Antiplatelet effects of chelerythrine chloride isolated from Zanthoxylum simulans: F.-N. Ko, et al.; Biochim. Biophys. Acta 1052, 360 (1990) Abstract
Chelerythrine is a potent and specific inhibitor of protein kinase C: J.M. Herbert, et al.; BBRC 172, 993 (1990) Abstract
Induction of apoptotic DNA fragmentation and cell death in HL-60 human promyelocytic leukemia cells by pharmacological inhibitors of protein kinase C: W.D. Jarvis, et al.; Cancer Res. 54, 1707 (1994) Abstract
Identification of chelerythrine as an inhibitor of BclXL function: S.L. Chan, et al.; J. Biol. Chem. 278, 20453 (2003) Abstract
Chelerythrine and sanguinarine dock at distinct sites on BclXL that are not the classic BH3 binding cleft: Y.H. Zhang, et al.; J. Mol. Biol. 364, 536 (2006) Abstract
The effect of chelerythrine on cell growth, apoptosis, and cell cycle in human normal and cancer cells in comparison with sanguinarine: J. Malikova, et al.; Cell Biol. Toxicol. 22, 439 (2006) Abstract

Further Categories Containing This Product:

Bcl-2 Family Modulators • PKC Inhibitors • Natural Products - Apoptosis Inducers & Inhibitors • Alkaloids

ALX-350-113

Revised 28-May-08

Gossypol
SYNONYMS	2,2’-bis[8-Formyl-1,6,7-trihydroxy-5-isopropyl-3- methylnaphthalene]
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antitumor Reagents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-113-M100		100 mg	90.00 USD

Product Specification

FORMULA:	C₃₀H₃₀O₈
MW:	518.6
CAS NUMBER:	303-45-7
MERCK INDEX:	14: 4528
RTECS:	DU3100000
SOURCE/HOST:	Isolated from Gossypium genus, Malvaceae.
PURITY:	≥90%
APPEARANCE:	Off-white to yellow solid.
SOLUBILITY:	Soluble in acetone or DMSO; sparingly soluble in 100% ethanol (2mg/ml) or methanol (2mg/ml). Insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HANDLING:	Protect from light.
HAZARD:	MAY BE CARCINOGENIC. HARMFUL.

Product Description

Mixture of ~65% (+)- and ~35% (-)-enantiomers. Male antifertility agent. Shows antitumor, antiviral and antioxidant actions. Small molecule inhibitor of Bcl-2/Bcl-X_L. Induces apoptosis. Synergizes with radiation and chemotherapy in vitro. Reversible inhibitor of protein phosphatase 2B (PP2B; calcineurin). Protein kinase C (PKC) inhibitor.

Product Specific Literature References

Binding of gossypol to purified tubulin and inhibition of its assembly into microtubules: F.J. Medrano and J.M. Andreu; Eur. J. Biochem. 158, 63 (1986) Abstract
Differential inhibition of protein kinase C subtypes: J.M. Pelosin, et al.; BBRC 169, 1040 (1990) Abstract
Induction of apoptotic DNA fragmentation and cell death in HL-60 human promyelocytic leukemia cells by pharmacological inhibitors of protein kinase C: W.D. Jarvis, et al.; Cancer Res. 54, 1707 (1994) Abstract
Gossypol arrests human benign prostatic hyperplastic cell growth at G0/G1 phase of the cell cycle: F. Shidaifat, et al.; Anticancer Res. 17, 1003 (1997) Abstract
Inhibition of huntingtin fibrillogenesis by specific antibodies and small molecules: implications for Huntington’s disease therapy: V. Heiser, et al.; PNAS 97, 6739 (2000) Abstract; Full Text
Cytotoxic effect of gossypol on colon carcinoma cells: X. Wang, et al.; Life Sci. 67, 2663 (2000) Abstract
Reversible inhibition of calcineurin by the polyphenolic aldehyde gossypol: R. Baumgrass, et al.; J. Biol. Chem. 276, 47914 (2001) Abstract; Full Text
Toxicity of (+)- and (-)-gossypol to the plant pathogen, Rhizoctonia solani: L.S. Puckhaber, et al.; J. Agric. Food Chem. 50, 7017 (2002) Abstract
Telomerase inhibitors in anticancer therapy: gossypol as a potential telomerase inhibitor: M. Mego; Bratisl. Lek. Listy 103, 378 (2002) Abstract
An in vitro study of inhibitory activity of gossypol, a cottonseed extract, in human carcinoma cell lines: M. Le Blanc, et al.; Pharmacol. Res. 46, 551 (2002) Abstract
Gossypol induces chloride secretion in rat proximal colon: G. Kuhn, et al.; Eur. J. Pharmacol. 457, 187 (2002) Abstract
Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism: T.B. Freedman, et al.; Chirality 15, 196 (2003) Abstract
In vitro effects of the BH3 mimetic, (-)-gossypol, on head and neck squamous cell carcinoma cells: C.L. Oliver, et al.; Clin. Cancer Res. 10, 7757 (2004) Abstract; Full Text
The inhibitory effects of gossypol on human prostate cancer cells-PC3 are associated with transforming growth factor beta1 (TGFbeta1) signal transduction pathway: J. Jiang, et al.; Anticancer Res. 24, 19 (2004) Abstract
(-)-Gossypol enhances response to radiation therapy and results in tumor regression of human prostate cancer: L. Xu, et al.; Mol. Cancer Ther. 4, 197 (2005) Abstract; Full Text
Investigations on gossypol: past and present developments: K. Dodou; Expert Opin. Investig. Drugs 14, 1419 (2005) Abstract
An in vitro study of cytotoxic effects of gossypol on human epidermoid larynx carcinoma cell line (HEp-2): E. Konac, et al.; Exp. Oncol. 27, 81 (2005) Abstract; Full Text

Further Categories Containing This Product:

Bcl-2 Family Modulators • PKC Inhibitors • Natural Products - Protein Kinase Inhibitors • PP2B [Calcineurin] / Related Products • Antitumor Agents (Apoptosis Inducers) • Natural Products - Antioxidants • Polyphenols Other Products • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products - Antiviral / anti-HIV Agents

ALX-430-101

Revised 08-Aug-08

HA14-1
SYNONYMS	Ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate
PRODUCT LINE	Cell Death / Apoptosis / Autophagy
PRODUCT CATEGORY	Bcl-2 Family Modulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-430-101-M005		5 mg	40.00 USD
ALX-430-101-M025		25 mg	160.00 USD

Product Specification

FORMULA:	C₁₇H₁₇N₂O₅Br
MW:	409.2
CAS NUMBER:	65673-63-4
PURITY:	≥95% (¹H-NMR)
APPEARANCE:	Off-white to light yellow powder.
SOLUBILITY:	Soluble in DMSO, dimethyl formamide or halogenated solvents; also soluble in 100% ethanol (hot).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Unstable in solution. Prepare fresh solution for each application.
HANDLING:	Keep cool and dry.
IDENTITY:	Identity determined by IR, ¹H-NMR.

Product Description

Cell permeable Bcl-2 ligand.

Product Specific Literature References

Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells: J.L. Wang, et al.; PNAS 97, 7124 (2000) Abstract
Synthetic peptides and non-peptidic molecules as probes of structure and function of Bcl-2 family proteins and modulators of apoptosis: D. Liu & Z. Huang; Apoptosis 6, 453 (2001) Abstract
Synergistic induction of apoptosis by simultaneous disruption of the Bcl-2 and MEK/MAPK pathways in acute myelogenous leukemia: M. Milella, et al.; Blood 99, 3461 (2002) Abstract

Further Categories Containing This Product:

Apoptosis Inducers & Inhibitors Other Products

ALX-350-120

Revised 01-Apr-08

Helenalin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Anti-inflammatory Agents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-120-MC05		0.5 mg	240.00 USD

Product Specification

FORMULA:	C₁₅H₁₈O₄
MW:	262.3
CAS NUMBER:	6754-13-8
SOURCE/HOST:	Isolated from Arnica chamissonis.
PURITY:	≥97% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO (10mg/ml) or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	TOXIC.
IDENTITY:	Identity determined by ¹H-NMR.

Product Description

Potent anti-inflammatory and antineoplastic agent. Induces a CD95 death receptor-independent apoptosis even when the mitochondria protecting proteins Bcl-X_Lor Bcl-2 are overexpressed. Also an inhibitor of NF-κB.

Product Specific Literature References

Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-kappaB: G. Lyss, et al.; J. Biol. Chem. 378, 951 (1997) Abstract
The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65: G. Lyss, et al; J. Biol. Chem. 27