ALEXIS Biochemicals: Ilimaquinone

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ALX-270-047

Revised 26-Sep-07

Aristolochic acid
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
ALX-270-047-M100		100 mg	90.00 USD

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 PLA₂activity 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 • Alkaloids • Other Toxins

ALX-270-157

Revised 03-Apr-08

Australine . hydrochloride
SYNONYMS	(1R,2R,3R,7S,7aR)-3-Hydroxymethyl-1,2,7-trihydroxypyrrolizidine . HCI
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-270-157-M001		1 mg	180.00 USD

Product Specification

FORMULA:	C₈H₁₅NO₄. HCl
MW:	189.2 . 36.5
CAS NUMBER:	186766-07-4
SOURCE/HOST:	Isolated from Castanospermum australe seeds.
PURITY:	≥95%
APPEARANCE:	Crystalline solid.
SOLUBILITY:	Soluble in water, methanol and 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HANDLING:	After reconstitution, prepare aliquots and store at -20°C.
HAZARD:	HARMFUL.

Product Description

Alkaloid. Inhibitor of α-glucosidase, amyloglucosidase and glucosidase I. Does not inhibit glucosidase II, and is reported to be the first glucosidase inhibitor which differentiates glucosidase I from glucosidase II. Does not inhibit α-galactosidase, β-galactosidase, β-glucosidase, α-mannosidase and β-mannosidase.

Product Specific Literature References

Australine, a pyrrolizidine alkaloid that inhibits amyloglucosidase and glycoprotein processing: J.E. Tropea, et al.; Biochemistry 28, 2027 (1989) Abstract
Calystegins, a novel class of alkaloid glycosidase inhibitors: R.J. Molyneux, et al.; Arch. Biochem. Biophys. 304, 81 (1993) Abstract
Stereoselective synthesis of the glycosidase inhibitor australine through a one-pot, double-cyclization strategy: C. Ribes, et al.; Org. Lett. 9, 77 (2007) Abstract

Further Categories Containing This Product:

Alkaloids • Glycosidases/Related Products

ALX-350-366

Revised 03-Apr-08

Azaspiracid-1
SYNONYMS	AZA-1
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Toxins

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-366-C001		1 µg	180.00 USD

Product Specification

FORMULA:	C₄₇H₇₁NO₁₂
MW:	842.1
CAS NUMBER:	214899-21-5
SOURCE/HOST:	Islolated from marine mussel.
CONCENTRATION:	2μg/ml
PURITY:	≥95%
FORMULATION:	Liquid. In methanol.
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
HAZARD:	VERY TOXIC. MAY BE TERATOGENIC.

Product Description

Activator of JNK (c-Jun-N-terminal kinase). Cellular growth inhibitor and inducer of cytoskeletal alterations. Activator of caspases. Modulator of intracellular cAMP (cyclic adenosine monophosphate) and calcium levels. Inhibitor of cholesterol biosynthesis in human T lymphocyte cells. Potent teratogen to finfish. Cytotoxic to mammalian cells.

Product Specific Literature References

Multiple organ damage caused by a new toxin azaspiracid, isolated from mussels produced in Ireland: E. Ito, et al.; Toxicon 38, 917 (2000) Abstract
Azaspiracid-1, a potent, nonapoptotic new phycotoxin with several cell targets: Y. Roman, et al.; Cell. Signal. 14, 703 (2002) Abstract
Teratogenic effects of azaspiracid-1 identified by microinjection of Japanese medaka (Oryzias latipes) embryos: J.R. Coleman, et al.; Toxicon 45, 881 (2005) Abstract
Cytotoxic and cytoskeletal effects of azaspiracid-1 on mammalian cell lines: M.J. Twiner, et al.; Toxicon 45, 891 (2005) Abstract
Azaspiracids modulate intracellular pH levels in human lymphocytes: A. Alfonso, et al.; BBRC 346, 1091 (2006) Abstract
Cell growth inhibition and actin cytoskeleton disorganization induced by azaspiracid-1 structure-activity studies: N. Vilarino, et al.; Chem. Res. Toxicol. 19, 1459 (2006) Abstract
The c-Jun-N-terminal kinase is involved in the neurotoxic effect of azaspiracid-1: C. Vale, et al.; Cell Physiol. Biochem. 20, 957 (2007) Abstract
Effects of azaspiracid-1, a potent cytotoxic agent, on primary neuronal cultures. A structure-activity relationship study: C. Vale, et al.; J. Med. Chem. 50, 356 (2007) Abstract
Irreversible cytoskeletal disarrangement is independent of caspase activation during in vitro azaspiracid toxicity in human neuroblastoma cells: N. Vilarino, et al.; Biochem. Pharmacol. 74, 327 (2007) Abstract
Transcriptional profiling and inhibition of cholesterol biosynthesis in human T lymphocyte cells by the marine toxin azaspiracid: M.J. Twiner, et al.; Genomics 91, 289 (2008) Abstract

Further Categories Containing This Product:

Natural Products - Other Signal Transduction Pathway Modulators • MAPK Pathway Activators • Natural Products for Cytoskeletal Research • Caspases Other Products • cAMP Pathways Other Products

ALX-350-367

Revised 31-Mar-08

Azaspiracid-2
SYNONYMS	AZA-2
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Toxins

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-367-C001		1 µg	360.00 USD

Product Specification

FORMULA:	C₄₈H₇₃NO₁₂
MW:	855.5
CAS NUMBER:	265996-92-7
SOURCE/HOST:	Isolated from marine mussel.
CONCENTRATION:	2µg/ml
PURITY:	≥95%
APPEARANCE:	Liquid. In methanol.
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
HAZARD:	VERY TOXIC.

Product Description

Modulator of intracellular cAMP (cyclic adenosine monophosphate) and calcium levels.

Product Specific Literature References

Effects of Azaspiracids 2 and 3 on intracellular cAMP, [Ca2+], and pH: Y. Roman, et al.; Chem. Res. Toxicol. 17, 1338 (2004) Abstract
Azaspiracids modulate intracellular pH levels in human lymphocytes: A. Alfonso, et al.; BBRC 346, 1091 (2006) Abstract

Further Categories Containing This Product:

Natural Products - Other Signal Transduction Pathway Modulators • cAMP Pathways Other Products

ALX-350-368

Revised 31-Mar-08

Azaspiracid-3
SYNONYMS	AZA-3
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Toxins

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-368-C001		1 µg	540.00 USD

Product Specification

FORMULA:	C₄₆H₆₉NO₁₂
MW:	827.5
CAS NUMBER:	265996-93-8
SOURCE/HOST:	Isolated from marine mussel.
CONCENTRATION:	2µg/ml
PURITY:	≥95%
APPEARANCE:	Liquid. In methanol.
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
HAZARD:	VERY TOXIC.

Product Description

Modulator of intracellular cAMP (cyclic adenosine monophosphate), calcium and pH levels.

Product Specific Literature References

Further Categories Containing This Product:

Natural Products - Other Signal Transduction Pathway Modulators • cAMP Pathways Other Products

ALX-350-144

Revised 03-Apr-08

Bakuchiol
SYNONYMS	4-(3-Ethenyl-3,7-dimethyl-1,6-octadienyl)phenol
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-350-144-M001		1 mg	170.00 USD

Product Specification

FORMULA:	C₁₈H₂₄O
MW:	256.4
CAS NUMBER:	10309-37-2
SOURCE/HOST:	Isolated from plant Psoralea corylifolia.
PURITY:	≥97% (HPLC)
APPEARANCE:	Yellow to brownish oil.
SOLUBILITY:	Soluble in DMSO or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
IDENTITY:	Determined by ¹H-NMR, ¹³C-NMR and MS.

Product Description

Inhibitor of protein tyrosine phosphatase 1B (PTB1B). Antioxidant. Inhibitor of mitochondrial lipid peroxidation. Inhibitor of inducible nitric oxide synthase (iNOS; NOS II) expression. DNA polymerase inhibitor. Shows antimicrobial and cytotoxic activity.

Product Specific Literature References

Plant antimutagenic agents, 2. Flavonoids: M.E. Wall, et al.; J. Nat. Prod. 51, 1084 (1988) Abstract
DNA polymerase and topoisomerase II inhibitors from Psoralea corylifolia: N.J. Sun, et al.; J. Nat. Prod. 61, 362 (1998) Abstract
Inhibition of mitochondrial lipid peroxidation by Bakuchiol, a meroterpene from Psoralea corylifolia: H. Haraguchi, et al.; Planta Med. 66, 569 (2000) Abstract
Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities: C.N. Backhouse, et al.; J. Ethnopharmacol. 78, 27 (2001) Abstract
Bakuchiol: a hepatoprotective compound of Psoralea corylifolia on tacrine-induced cytotoxicity in Hep G2 cells: H. Cho, et al.; Planta Med. 67, 750 (2001) Abstract
In vitro antimicrobial activities of bakuchiol against oral microorganisms: H. Katsura, et al.; Antimicrob. Agents Chemother. 45, 3009 (2001) Abstract; Full Text
Bakuchiol from Psoralea corylifolia inhibits the expression of inducible nitric oxide synthase gene via the inactivation of nuclear transcription factor-kappaB in RAW 264.7 macrophages: H.O. Pae, et al.; Int. Immunopharmacol. 1, 1849 (2001) Abstract
Antioxidative components of Psoralea corylifolia (Leguminosae): H. Haraguchi, et al.; Phytother. Res. 16, 539 (2002) Abstract
The evaluation of forty-three plant species for in vitro antimycobacterial activities; isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis: S.M. Newton, et al.; J. Ethnopharmacol. 79, 57 (2002) Abstract
Antioxidant activity of bakuchiol: experimental evidences and theoretical treatments on the possible involvement of the terpenoid chain: S. Adhikari, et al.; Chem. Res. Toxicol. 16, 1062 (2003) Abstract
Preparation and in vitro evaluation of radioiodinated bakuchiol as an anti tumor agent: K. Bapat, et al.; Appl. Radiat. Isot. 62, 389 (2005) Abstract
In vitro protein tyrosine phosphatase 1B inhibitory phenols from the seeds of Psoralea corylifolia: Y.C. Kim, et al.; Planta Med. 71, 87 (2005) Abstract
Protective effect of (S)-bakuchiol from Psoralea corylifolia on rat liver injury in vitro and in vivo: E.J. Park, et al.; Planta Med. 71, 508 (2005) Abstract
Bakuchiol-induced caspase-3-dependent apoptosis occurs through c-Jun NH2-terminal kinase-mediated mitochondrial translocation of Bax in rat liver myofibroblasts: E.J. Park, et al.; Eur. J. Pharmacol. 559, 115 (2007) Abstract

Further Categories Containing This Product:

Natural Products - DNA Replication Inhibitors • NOS Inhibitors (NOS Induction & Enzyme Activity) • Lipid Peroxidation • Natural Products - Nitric Oxide Pathway Modulators • Natural Products - Topoisomerase Inhibitors • Natural Products with Antibiotic Activity • Protein Tyrosine Phosphatases Other Products • Natural Products - Antioxidants

ALX-350-005

Revised 02-Oct-07

Bryostatin 1
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-350-005-C010		10 µg	85.00 USD

Product Specification

FORMULA:	C₄₇H₆₈O₁₇
MW:	905.0
CAS NUMBER:	83314-01-6
MERCK INDEX:	14: 1457
PURITY:	≥97%
APPEARANCE:	Colorless oil.
SOLUBILITY:	25mg/ml soluble in 100% ethanol or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Store tightly sealed. Binds to glass and plastic surfaces in aqueous solutions.

Product Description

Binds to and activates protein kinase C (PKC). Antineoplastic.

Product Specific Literature References

Isolation and structure of Bryostatin 1: G.R. Pettit, et al.; J. Am. Chem. Soc. 104, 6846 (1982)
Bryostatin 1: differentiating agent from the depths: R.M. Stone; Leuk. Res. 21, 399 (1997) Abstract
Chemistry and clinical biology of the bryostatins: R. Mutter & M. Wills; Bioorg. Med. Chem. 8, 1841 (2000), (Review) Abstract
The clinical development of the bryostatins: A. Clamp and G.C. Jayson; Anticancer Drugs 13, 673 (2002) Abstract
The chemistry and biology of the bryostatin antitumour macrolides: K.J. Hale, et al.; Nat. Prod. Rep. 19, 413 (2002), Review Abstract
Bryostatin-1: pharmacology and therapeutic potential as a CNS drug: M.K. Sun & D.L. Alkon; CNS Drug Rev. 12, 1 (2006), Review Abstract

Further Categories Containing This Product:

Antitumor Agents (Enzyme Activators & Inducers) • PKC Activators • Natural Products - Antitumor Reagents • Natural Products - Immunomodulators

ALX-550-322

Revised 29-Oct-07

Caffeine
SYNONYMS	1,3,7-Trimethylxanthine 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products for Neurological Research

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-550-322-G005		5 g	10.00 USD

Product Specification

FORMULA:	C₈H₁₀N₄O₂
MW:	194.2
CAS NUMBER:	58-08-2
MERCK INDEX:	14: 1636
SOURCE/HOST:	Found in tea leaves, coffee beans, cocoa beans, maté leaves, guarana paste and kola nuts.
PURITY:	≥99%
APPEARANCE:	White powder.
SOLUBILITY:	Soluble in chloroform, 100% alcohol or hot water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+20°C
HAZARD:	TOXIC.

Product Description

CNS stimulant. Blocks adenosine A1 and A2A receptors. cAMP phosphodiesterase inhibitor. Interferes with the uptake and storage of Ca2+ by the sarcoplasmic reticulum in skeletal muscle. Prevents apoptosis and cell cycle effects induced by various chemicals. Inhibits cellular DNA repair mechanisms. Anti-inflammatory.

Product Specific Literature References

Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors: J.W. Daly, et al.; J. Med. Chem. 29, 1305 (1986) Abstract
Caffeine as an analgesic adjuvant: a review of pharmacology and mechanisms of action: J. Sawynok & T.L. Yaksh; Pharmacol. Rev. 45, 43 (1993) Abstract
Caffeine prevents apoptosis and cell cycle effects induced by camptothecin or topotecan in HL-60 cells: F. Traganos, et al.; Cancer Res. 53, 4613 (1993) Abstract
Multiple effects of caffeine on calcium current in rat ventricular myocytes: I. Zahradnik & P. Palade; Pfluegers Arch. 424, 129 (1993) Abstract
Acute effects of caffeine on arterial stiffness, wave reflections, and central aortic pressures: T.G. Papaioannou, et al.; Am. J. Hypertens. 18, 129 (2005), (Review) Abstract
Caffeine and the dopaminergic system: O. Cauli & M. Morelli; Behav. Pharmacol. 16, 63 (2005), (Review) Abstract
Immunomodulatory effects of caffeine: friend or foe: L. A. Horrigan, et al.; Pharmacol. Ther. 111, 877 (2006), (Review) Abstract
Novel neuroprotection by caffeine and adenosine A(2A) receptor antagonists in animal models of Parkinson’s disease: A. Kalda, et al.; J. Neurol. Sci. 248, 9 (2006), (Review) Abstract
The enigmatic effects of caffeine in cell cycle and cancer: A. M. & Bode and Z. Dong; Cancer Lett. 247, 26 (2007), (Review) Abstract

Further Categories Containing This Product:

Ca2+ Modulators • Natural Products - Other Signal Transduction Pathway Modulators • Phosphodiesterases/Related Products • DNA Repair Other Products • Neuroactive Agents Other Products • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products for Cell Cycle Research • Natural Products - Anti-inflammatory Agents • Natural Products - Chemopreventive Agents • Alkaloids • Active Substances from Fruit and Vegetables • Other Natural Products - DNA Regulation/Transcription

ALX-350-014

Revised 03-Apr-08

Calyculin A
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-350-014-C010		10 µg	65.00 USD
ALX-350-014-C025		25 µg	110.00 USD
ALX-350-014-C050		50 µg	190.00 USD
ALX-350-014-C100		100 µg	320.00 USD

Product Specification

FORMULA:	C₅₀H₈₁N₄O₁₅P
MW:	1009.2
CAS NUMBER:	101932-71-2
SOURCE/HOST:	Isolated from Discodermia calyx.
PURITY:	≥95%
APPEARANCE:	Lyophilized.
SOLUBILITY:	Soluble in DMSO, 100% ethanol, methanol, acetonitrile, chloroform, methylene chloride or benzene. Insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	May by subject to isomerization when in solution. Biological activity is not affected by isomerization.
HANDLING:	Protect from light and moisture.
HAZARD:	TOXIC. MAY BE CARCINOGENIC.

Product Description