ALEXIS Biochemicals: Compound A

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ALX-350-298

Revised 03-Apr-08

Betulinic acid (~95%)
SYNONYMS	3β-Hydroxy-20(29)-lupaene-28-oic acid
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antitumor Reagents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-298-M100		100 mg	55.00 USD
ALX-350-298-M500		500 mg	180.00 USD
ALX-350-298-G001		1 g	290.00 USD

Product Specification

FORMULA:	C₃₀H₄₈O₃
MW:	456.7
CAS NUMBER:	472-15-1
SOURCE/HOST:	Isolated from Platanus acerifolia (plane tree) bark.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C

Product Description

Antitumor and anti-HIV agent. Induces apoptosis by activating mitochondrial permeability transition (MPT). Inhibits NF-κB activation and NF-κB-regulated gene expression induced by carcinogens and inflammatory stimuli. Decreases expression of Bcl-2 and cyclin D1. Potent proteasome activator.

Product Specific Literature References

Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids: T. Fujioka, et al.; J. Nat. Prod. 57, 243 (1994) Abstract
Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis: E. Pisha, et al.; Nat. Med. 1, 1046 (1995) Abstract
Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents: Y. Kashiwada, et al.; J. Med. Chem. 39, 1016 (1996) Abstract
Betulinic acid triggers CD95 (APO-1/Fas)- and p53-independent apoptosis via activation of caspases in neuroectodermal tumors: S. Fulda, et al.; Cancer Res. 57, 4956 (1997) Abstract
Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives: F. Hashimoto, et al.; Bioorg. Med. Chem. 5, 2133 (1997) Abstract
Betulinic acid induces apoptosis in human neuroblastoma cell lines: M.L. Schmidt, et al.; Eur. J. Cancer 33, 2007 (1997) Abstract
Induction of p53 without increase in p21WAF1 in betulinic acid-mediated cell death is preferential for human metastatic melanoma: M. Rieber & M. Strasberg Rieber; DNA Cell Biol. 17, 399 (1998) Abstract
Activation of mitochondria and release of mitochondrial apoptogenic factors by betulinic acid: S. Fulda, et al.; J. Biol. Chem. 273, 33942 (1998) Abstract; Full Text
Betulinic acid inhibits aminopeptidase N activity: M.F. Melzig & H. Bormann; Planta Med. 64, 655 (1998) Abstract
Correspondence re: S. Fulda et al., Betulinic acid triggers CD95 (Apo1/Fas)- and p53-independent apoptosis via activation of caspases in neuroectodermal tumors. Cancer Res., 57: 4956, 1997: M. Rieber & M. Strasberg Rieber; Cancer. Res. 58, 5876 (1998) Abstract
Betulinic acid: a new cytotoxic agent against malignant brain-tumor cells: S. Fulda, et al.; Int. J. Cancer 82, 435 (1999) Abstract
Betulinic acid-induced apoptosis in glioma cells: A sequential requirement for new protein synthesis, formation of reactive oxygen species, and caspase processing: W. Wick, et al.; J Pharmacol. Exp. Ther. 289, 1306 (1999) Abstract; Full Text
Effects of betulinic acid alone and in combination with irradiation in human melanoma cells: E. Selzer, et al.; J. Invest. Dermatol. 114, 935 (2000) Abstract
Betulinic acid suppresses carcinogen-induced NF-kappa B activation through inhibition of I kappa B alpha kinase and p65 phosphorylation: abrogation of cyclooxygenase-2 and matrix metalloprotease-9: Y. Takada & B.B. Aggarwal; J. Immunol. 171, 3278 (2003) Abstract
Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection: R.H. Cichewicz & S.A. Kouzi; Med. Res. Rev. 24, 90 (2004), Review Abstract
Betulinic acid-induced apoptosis in leukemia cells: H. Ehrhardt, et al.; Leukemia 18, 1406 (2004) Abstract
Betulinic acid and its derivatives: a review on their biological properties: P. Yogeeswari & D. Sriram; Curr. Med. Chem. 12, 657 (2005), Review Abstract
Betulinic acid decreases expression of bcl-2 and cyclin D1, inhibits proliferation, migration and induces apoptosis in cancer cells: W. Rzeski, et al.; Naunyn Schmiedebergs Arch. Pharmacol. 374, 11 (2006) Abstract
Activation and inhibition of the proteasome by betulinic acid and its derivatives: L. Huang, et al.; FEBS Lett. 581, 4955 (2007) Abstract

Further Categories Containing This Product:

CDK & Cyclin Inhibitors • NF-kB Pathway Inhibitors • Other Natural Products - DNA Regulation / Transcription • Natural Products - NF-kB Pathway Inhibitors • MPTP [Mitochondrial Transition Pore] / Related Products • Natural Products - Anti-inflammatory Agents • Natural Products - Antiviral / anti-HIV Agents • Antitumor Agents (Apoptosis Inducers) • Ubiquitin & Proteasome Other Products • Natural Products - Apoptosis Inducers & Inhibitors • HIV / AIDS / Related Products

ALX-350-336

Revised 05-Apr-08

Galiellalactone
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Natural Products - DNA Regulation / Transcription

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-336-MC05		0.5 mg	320.00 USD

Product Specification

FORMULA:	C₁₁H₁₄O₃
MW:	194.2
CAS NUMBER:	133613-71-5
SOURCE/HOST:	Isolated from an unidentified fungus, MST-FP1889.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to light tan solid.
SOLUBILITY:	Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C

Product Description

Originally isolated from Galiella rufa as a plant growth regulator. Inhibits IL-6 mediated signal transduction by blocking the binding of the activated STAT3 dimers to their DNA binding sites without inhibiting the tyrosine and serine phosphorylation site of the STAT3 transcription factor.

Product Specific Literature References

Screening of basidiomycetes and ascomycetes for plant regulating substances: R. Hautzel and H. Anke; Z. Naturforsch. 45c, 1094 (1990)
Inhibition of interleukin-6 signaling by galiellalactone: M. Weidler, et al.; FEBS Lett. 484, 1 (2000) Abstract
Synthesis of (-)-galiellalactone: M. Johansson and O. Sterner; J. Antibiot. (Tokyo) 55, 663 (2002) Abstract
Biologically active secondary metabolites from the ascomycete A111-95. 1. Production, isolation and biological activities: B. Kopcke, et al.; J. Antibiot. (Tokyo) 55, 36 (2002) Abstract
Galiellalactone and its biogenetic precursors as chemotaxonomic markers of the Sarcosomataceae (Ascomycota): B. Kopcke, et al.; Phytochemistry 60, 709 (2002) Abstract

ALX-350-371

Revised 10-Mar-08

Harmine
SYNONYMS	Leucoharmine Banisterine Telepathine Yageine 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Natural Products - DNA Regulation / Transcription

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-371-M250		250 mg	22.00 USD

Product Specification

FORMULA:	C₁₃H₁₂N₂O
MW:	212.3
CAS NUMBER:	442-51-3
MERCK INDEX:	14: 4616
RTECS:	UV0175000
SOURCE/HOST:	Originally isolated from Peganum harmala.
PURITY:	≥98%
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO, dimethyl formamide or 100% ethanol; slightly soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	HARMFUL.

Product Description

Alkaloid of the β-carboline family. Regulates PPARγ expression. Inhibits the Wnt signalling pathway in a cell-specific manner. Down-regulates inflammatory gene expression (TNF-α, IL-1β, iNOS). Reversibly inhibits monoamine oxidase inhibitor A (MAO-A), but has no effect on MAO-B.

Product Specific Literature References

The chemotherapy of derivatives of harmine and harmaline. I: C.E. Coulthard, et al.; Biochee. J. 27, 727 (1933) Abstract; Full Text
The chemotherapy of derivatives of harmine and harmaline. II: C.E. Coulthard; Biochem. J. 28, 264 (1934) Abstract; Full Text
Interrelationships between amphetamine and harmala alkaloids: H. Schmitt; Nature 203, 877 (1964) Abstract
Effect of moclobemide on rat brain monoamine oxidase A and B: comparison with harmaline and clorgyline: J. Gerardy; Prog. Neuropsychopharmacol. Biol. Psychiatry 18, 793 (1994) Abstract
Hypothermic effect of harmala alkaloid in rats: involvement of serotonergic mechanism: A.F. Abdel-Fattah, et al.; Pharmacol. Biochem. Behav. 52, 421 (1995) Abstract
The mode of action of thiazolidinediones: H. Hauner; Diabet. Metab. Res. Rev. 18, S10 (2002) Abstract
Antitumor and neurotoxic effects of novel harmine derivatives and structure-activity relationship analysis: Q. Chen, et al.; Int. J. Cancer 114, 675 (2005) Abstract
The small molecule harmine is an antidiabetic cell-type-specific regulator of PPARgamma expression: H. Waki, et al.; Cell Metab. 5, 357 (2007) Abstract

Further Categories Containing This Product:

Natural Products - Other Signal Transduction Pathway Modulators • Interleukin-1 [IL-1] & Receptors / Related Products • TNF-alpha & TNF Receptors Other Products • Wnt Signalling Pathway Other Products • NOS Regulation • Antidiabetic Agents / Related Products • Alkaloids

ALX-380-243

Revised 08-Apr-08

Siomycin
SYNONYMS	Mutabilycin Sporangiomycin Antibiotic 6741-21 Mutabillicin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antitumor Antibiotics

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-243-MC05		0.5 mg	390.00 USD

Product Specification

FORMULA:	C₇₁H₈₁N₁₉O₁₈S₅
MW:	1648.9
CAS NUMBER:	12656-09-6
RTECS:	VX0600000
SOURCE/HOST:	Isolated from Streptomyces sp. MST-AS4617.
PURITY:	≥95% (HPLC)
APPEARANCE:	White solid.
SOLUBILITY:	Soluble in DMSO or dimethyl formamide; partially soluble in methanol or 100% ethanol; poorly soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C

Product Description

Macrocyclic thiazole antibiotic with potent and selective antibacterial activity. Potent inhibitor of the oncogenic transcription factor forkhead box M1 (FoxM1) that downregulates protein and mRNA levels of FoxM1. Inhibits FoxM1 induced cell growth.

Product Specific Literature References

Studies on siomycin. I. Physicochemical properties of siomycins A, B and C: M. Ebata, et al.; J. Antibiot. 22, 364 (1969)
Identification of a chemical inhibitor of the oncogenic transcription factor forkhead box M1: S.K. Radhakrishnan, et al.; Cancer Res. 22, 364 (2006) Abstract; Full Text
Future roles for FoxM1 inhibitors in cancer treatments: G.R. Adami & H. Ye; Future Oncol. 3, 1 (2007) Abstract; Full Text

Further Categories Containing This Product:

Forkhead Box [FOX] Proteins / Related Products • Other Natural Products - DNA Regulation / Transcription

ALX-385-025

Revised 07-Apr-08

8-Isopentenylnaringenin
SYNONYMS	8-Prenylnaringenin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Flavanones

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-385-025-M005		5 mg	155.00 USD

Product Specification

FORMULA:	C₂₀H₂₀O₅
MW:	340.4
SOURCE/HOST:	Isolated from hops (Humulus lupulus L.).
PURITY:	≥97% (HPLC)
APPEARANCE:	Light yellow powder
SOLUBILITY:	Soluble in methanol or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C

Product Description

Prenyl flavonoid. Phytoestrogen. Selective, non-steroidal estrogen receptor α (ERα) ligand. Potent inhibitor of angiogenesis in vitro and in vivo. Chemopreventive agent against cancer induced by heterocyclic amines.

Product Specific Literature References

Prenylflavonoids: a new class of non-steroidal phytoestrogen (Part 1). Isolation of 8-isopentenylnaringenin and an initial study on its structure-activity relationship: M. Kitaoka, et al.; Planta Med. 64, 511 (1998) Abstract
Prenylflavonoids: a new class of non-steroidal phytoestrogen (Part 2). Estrogenic effects of 8-isopentenylnaringenin on bone metabolism: M. Miyamoto, et al.; Planta Med. 64, 516 (1998) Abstract
Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer: S.R. Milligan, et al.; J. Clin. Endocrinol. Metab. 84, 2249 (1999) Abstract
Prenylflavonoids from hops inhibit the metabolic activation of the carcinogenic heterocyclic amine 2-amino-3-methylimidazo[4, 5-f]quinoline, mediated by cDNA-expressed human CYP1A2: C.L. Miranda, et al.; Drug Metab. Dispos. 28, 1297 (2000) Abstract; Full Text
The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids: S.R. Milligan, et al.; J. Clin. Endocrinol. Metab. 85, 4912 (2000) Abstract; Full Text
8-prenylnaringenin, a novel phytoestrogen, inhibits angiogenesis in vitro and in vivo: M.S. Pepper, et al.; J. Cell Physiol. 199, 98 (2004) Abstract
Xanthohumol and related prenylflavonoids from hops and beer: to your good health!: J.F. Stevens & J.E. Page; Phytochemistry 65, 1317 (2004), (Review) Abstract
Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types: T.F. Bovee, et al.; J. Steroid Biochem. Mol. Biol. 91, 99 (2004) Abstract
8-Prenylnaringenin, inhibits estrogen receptor-alpha mediated cell growth and induces apoptosis in MCF-7 breast cancer cells: E. Brunelli, et al.; J. Steroid Biochem. Mol. Biol. 107, 140 (2007) Abstract

Further Categories Containing This Product:

Active Substances from Fruit and Vegetables • Estrogen & Estrogen Receptors / Related Products • Natural Products for Angiogenesis Research • Natural Products - Chemopreventive Agents • Other Natural Products - DNA Regulation / Transcription

ALX-550-322

Revised 11-Nov-08

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 to colorless powder.
SOLUBILITY:	Soluble in chloroform, 100% alcohol or hot water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+20°C
HAZARD:	HARMFUL.
IDENTITY:	Identity determined by NIR.

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:

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

ALX-550-516

Revised 21-May-08

Compound A
SYNONYMS	CpdA 2-((4-Acetophenyl)-2-chloro-N-methyl)ethylammonium chloride
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-550-516-M005		5 mg	40.00 USD
ALX-550-516-M025		25 mg	120.00 USD

Product Specification

FORMULA:	C₁₁H₁₄ClNO₂ . HCl
MW:	227.7 . 36.5
PURITY:	≥98% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO, 100% ethanol or water.
SHIPPING:	SHIPPED ON DRY ICE
LONG TERM STORAGE:	-80°C
USE/STABILITY:	Stock solutions in ethanol are stable for up to 1 month when stored at -80°C.
HANDLING:	Protect from moisture. After reconstitution, prepare aliquots and store at -80°C.

Product Description

Cell permeable, nonsteroidal glucocorticoid receptor modulator with high binding affinity. Exerts anti-inflammatory potential by down-modulating TNF-induced pro-inflammatory gene expression, such as IL-6 and E-selectin. Unlike dexamethasone (Prod. No. ALX-370-002) it does not enhance glucocorticoid response element (GRE)-driven gene expression or induce glucocorticoid receptor (GR) binding to GRE-dependent genes in vivo.

Product Specific Literature References

A fully dissociated compound of plant origin for inflammatory gene repression: K. De Bosscher, et al.; PNAS 102, 15827 (2005) Abstract
A plant-derived ligand favoring monomeric glucocorticoid receptor conformation with impaired transactivation potential attenuates collagen-induced arthritis: P. Dewint, et al.; J. Immunol. 180, 2608 (2008) Abstract