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ALX-385-008

Revised 13-Mar-08

Apigenin
SYNONYMS	4',5,7-Trihydroxyflavone
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Flavones

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-385-008-M010		10 mg	35.00 USD
ALX-385-008-M050		50 mg	105.00 USD

Product Specification

FORMULA:	C₁₅H₁₀O₅
MW:	270.2
CAS NUMBER:	520-36-5
MERCK INDEX:	14: 730
SOURCE/HOST:	Synthetic.
PURITY:	≥90% (HPLC)
APPEARANCE:	Light yellow to slightly brown powder.
SOLUBILITY:	Soluble in diluted potassium hydroxide or DMSO; slightly soluble in 100% ethanol (hot). Insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HAZARD:	IRRITANT.

Product Description

Antioxidant flavonoid. Has chemopreventive and antitumor properties. Induces apoptosis. Inhibits the proliferation of malignant tumor cells by G2/M arrest. MAP kinase (MAPK/ERK) inhibitor. Inhibits hypoxia-inducible factor-1 (HIF-1) and vascular endothelial growth factor (VEGF) expression.

Product Specific Literature References

Apigenin and tangeretin enhance gap junctional intercellular communication in rat liver epithelial cells: C. Chaumontet, et al.; Carcinogenesis 15, 2325 (1994) Abstract
Apigenin induces morphological differentiation and G2-M arrest in rat neuronal cells: F. Sato, et al.; BBRC 204, 578 (1994) Abstract
Reversion of v-H-ras-transformed NIH 3T3 cells by apigenin through inhibiting mitogen activated protein kinase and its downstream oncogenes: M.L. Kuo and N.C. Yang; BBRC 212, 767 (1995) Abstract
Structure-antioxidant activity relationships of flavonoids and phenolic acids: C.A. Rice-Evans, et al.; Free Radical Biol. & Med. 20, 933 (1996), (Review) Abstract
Apigenin inhibits endothelial-cell proliferation in G(2)/M phase whereas it stimulates smooth-muscle cells by inhibiting P21 and P27 expression: V. Trochon, et al.; Int. J. Cancer 85, 691 (2000) Abstract
Induction of caspase-dependent, p53-mediated apoptosis by apigenin in human neuroblastoma: R. Torkin, et al.; Mol. Cancer Ther. 4, 1 (2005) Abstract
Apigenin and cancer chemoprevention: progress, potential and promise: D. Patel, et al.; Int. J. Oncol. 30, 233 (2007), (Review) Abstract
Apigenin inhibits tumor angiogenesis through decreasing HIF-1alpha and VEGF expression: J. Fang, et al.; Carcinogenesis 28, 858 (2007) Abstract
Apigenin-induced cell cycle arrest is mediated by modulation of MAPK, PI3K-Akt, and loss of cyclin D1 associated retinoblastoma dephosphorylation in human prostate cancer cells: S. Shukla & S. Gupta; Cell Cycle 6, 1102 (2007) Abstract
Apigenin blocks lipopolysaccharide-induced lethality in vivo and proinflammatory cytokines expression by inactivating NF-kappaB through the suppression of p65 phosphorylation: C. Nicholas, et al.; J. Immunol. 179, 7121 (2007) Abstract

Further Categories Containing This Product:

MAPK Pathway Inhibitors • Hypoxia-inducible Factor [HIF] / Related Products • Antitumor Agents (Enzyme Inhibitors) • Natural Products - Protein Kinase Inhibitors • VEGFs & VEGF-Rs Other Products • Natural Products for Angiogenesis Research • Natural Products - Chemopreventive Agents • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products - Antitumor Reagents • Antitumor Agents (Anti-proliferative) • Natural Products - Antioxidants

ALX-350-219

Revised 28-May-08

Artemisinin
SYNONYMS	Qinghaosu
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Antimalarial Agents

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-219-M100		100 mg	35.00 USD
ALX-350-219-G001		1 g	220.00 USD

Product Specification

FORMULA:	C₁₅H₂₂O₅
MW:	282.4
CAS NUMBER:	63968-64-9
MERCK INDEX:	14: 817
SOURCE/HOST:	Isolated from the traditional Chinese anti-malarial herb Artemisia annua L.
PURITY:	≥98%
APPEARANCE:	White crystalline solid.
SOLUBILITY:	Soluble in methanol, 100% ethanol, dimethyl formamide, DMSO, chloroform or acetone; almost insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light and moisture.
HAZARD:	TOXIC.

Product Description

Powerful antimalarial agent. Inhibits angiogenesis by down-regulating HIF-1α and VEGF expression in mouse embryonic stem cells. Crosses the blood-brain barrier. Inhibitor of human iNOS (NOS II).

Product Specific Literature References

Qinghaosu (artemisinin): an antimalarial drug from China: D.L. Klayman; Science 228, 1049 (1985) Abstract
The chemistry, pharmacology, and clinical applications of qinghaosu (artemisinin) and its derivatives: X.D. Luo & C.C. Shen; Med. Res. Rev. 7, 29 (1987) Abstract
Inhibition of angiogenesis in embryoid bodies by artemisinin: M. Wartenberg, et al.; Pflugers Arch. Eur. J. Physiol. 445, S85 (1994)
Artemisinin drugs in the treatment of malaria: from medicinal herb to registered medication: M.A. van Agtmael, et al.; Trends Pharmacol. Sci. 20, 199 (1999), Review Abstract
Artemisinin inhibits inducible nitric oxide synthase and nuclear factor NF-kB activation: E. Aldieri, et al.; FEBS Lett. 552, 141 (2003) Abstract
The antimalaria agent artemisinin exerts antiangiogenic effects in mouse embryonic stem cell-derived embryoid bodies: M. Wartenberg, et al.; Lab. Invest. 83, 1647 (2003) Abstract
An over four millennium story behind qinghaosu (artemisinin)--a fantastic antimalarial drug from a traditional chinese herb: Y. Li & Y.L. Wu; Curr. Med. Chem. 10, 2197 (2003), Review Abstract
From artemisinin to new artemisinin antimalarials: biosynthesis, extraction, old and new derivatives, stereochemistry and medicinal chemistry requirements: R.K. Haynes; Curr. Top. Med. Chem. 6, 509 (2006), Review Abstract

Further Categories Containing This Product:

NOS Inhibitors (NOS Induction & Enzyme Activity) • Natural Products for Angiogenesis Research • Natural Products - Nitric Oxide Pathway Modulators • Hypoxia-inducible Factor [HIF] / Related Products • Malaria / Related Products

ALX-350-128

Revised 03-Apr-08

Chetomin
SYNONYMS	Chaetomin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Immunomodulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-128-M001		1 mg	185.00 USD
ALX-350-128-M005		5 mg	495.00 USD

Product Specification

FORMULA:	C₃₁H₃₀N₆O₆S₄
MW:	710.9
CAS NUMBER:	1403-36-7
SOURCE/HOST:	Isolated from Chaetomium species.
PURITY:	≥98% (HPLC)
APPEARANCE:	Off-white to fawn solid.
SOLUBILITY:	Soluble in DMSO, ethyl acetate or pyridine; fairly soluble in methanol, 100% ethanol; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HAZARD:	TOXIC.
IDENTITY:	Determined by ¹H-NMR.

Product Description

Dithiodiketopiperazine inhibitor of HIF-1 formation by disrupting the binding of p300 to both HIF-1α and HIF-2α. Inhibitor of tumor growth. Potent immunosuppressor. Antibacterial.

Product Specific Literature References

The structure of chetomin: A.G. McInnes, et al.; JACS 98, 6741 (1976) Abstract
Effects of chetomin on growth and acidic fermentation products of rumen bacteria: W.C. Jen and G.A. Jones; Can. J. Microbiol. 29, 1399 (1983) Abstract
Small molecule blockade of transcriptional coactivation of the hypoxia-inducible factor pathway: A.L. Kung, et al.; Cancer Cell 6, 33 (2004) Abstract
Immunomodulatory constituents from an Ascomycete, Chaetomium seminudum: H. Fujimoto, et al.; J. Nat. Prod. 67, 98 (2004) Abstract
Effects of HIF-1 inhibition by chetomin on hypoxia-related transcription and radiosensitivity in HT 1080 human fibrosarcoma cells: A. Staab, et al.; BMC Cancer 7, 213 (2007) Abstract; Full Text

Further Categories Containing This Product:

Hypoxia-inducible Factor [HIF] / Related Products • Antitumor Antibiotics • Immunomodulators Other Products • Antitumor Agents (Anti-proliferative)

ALX-385-009

Revised 03-Apr-08

Chrysin
SYNONYMS	5,7-Dihydroxyflavone
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Flavones

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-385-009-G001		1 g	15.00 USD

Product Specification

FORMULA:	C₁₅H₁₀O₄
MW:	254.2
CAS NUMBER:	480-40-0
MERCK INDEX:	14: 2256
RTECS:	LK8329050
PURITY:	≥96%
APPEARANCE:	Yellow to tan solid.
SOLUBILITY:	Soluble in pyridine or alkaline solutions; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+20°C

Product Description

Antioxidant flavonoid. Shows anti-inflammatory and antitumor properties. Inhibits hypoxia-inducible factor-1α (HIF-1α). Induces apoptosis.

Product Specific Literature References

Structure-antioxidant activity relationships of flavonoids and phenolic acids: C.A. Rice-Evans, et al.; Free Radical Biol. & Med. 20, 933 (1996), (Review) Abstract
Chrysin-induced apoptosis is mediated through caspase activation and Akt inactivation in U937 leukemia cells: K.J. Woo, et al.; Biochem. Biophys. Res. Commun. 325, 1215 (2004) Abstract
Chrysin induces G1 phase cell cycle arrest in C6 glioma cells through inducing p21Waf1/Cip1 expression: involvement of p38 mitogen-activated protein kinase: M.S. Weng, et al.; Biochem. Pharmacol. 69, 1815 (2005) Abstract
Dietary flavonoids: effects on xenobiotic and carcinogen metabolism:: Y.J. Moon, et al.; Toxicol. In Vitro 20, 187 (2006), (Review) Abstract
Chrysin inhibits expression of hypoxia-inducible factor-1alpha through reducing hypoxia-inducible factor-1alpha stability and inhibiting its protein synthesis: B. Fu, et al.; Mol. Cancer Ther. 6, 220 (2007) Abstract

Further Categories Containing This Product:

Hypoxia-inducible Factor [HIF] / Related Products • Natural Products - Anti-inflammatory Agents • Natural Products - Antitumor Reagents • Natural Products - Apoptosis Inducers & Inhibitors • Natural Products - Antioxidants

ALX-270-372

Revised 08-Jul-08

2,4-Diethylpyridine dicarboxylate
SYNONYMS	2,4-DPD 2,4-Pyridinedicarboxylic acid diethyl ester
PRODUCT LINE	Oxidative Stress
PRODUCT CATEGORY	Hypoxia-inducible Factor [HIF] / Related Products

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-372-M010		10 mg	23.00 USD
ALX-270-372-M025		25 mg	53.00 USD
ALX-270-372-M100		100 mg	177.00 USD

Product Specification

FORMULA:	C₁₁H₁₃NO₄
MW:	223.2
CAS NUMBER:	41438-38-4
CONCENTRATION:	50mg/ml
PURITY:	≥98%
FORMULATION:	Liquid. Solution in ethanol.
SOLUBILITY:	Soluble in 100% ethanol (50mg/ml), DMSO (20mg/ml) or dimethyl formamide (30mg/ml); slightly soluble in PBS, pH 7.2 (1mg/ml).
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stable for at least 1 year after receipt when stored at –20°C. We do not recommend storing aqueous solutions for more than one day.

Product Description

2,4-DPD is a cell permeable, competitive inhibitor of the oxygen-sensing enzyme HIF prolyl hydroxylase (HIF-PH), which destructs HIF-1α when hydroxylated at a specific proline residue (P564). 2,4-DPD inhibits the hydroxylation of P564 by acting as a competitive inhibitor of the HIF-PH cofactor α-keto glutarate, with effective concentrations in the low µM range. 2,4-DPD is therefore expected to act as a pro-angiogenic compound, acting via the HIF-1α system.

Product Specific Literature References

Prolyl 4-hydroxylase is required for viability and morphogenesis in Caenorhabditis elegans: L. Friedman, et al.; PNAS 97, 4736 (2000) Abstract; Full Text
HIFalpha targeted for VHL-mediated destruction by proline hydroxylation: implications for O2 sensing: M. Ivan, et al.; Science 292, 464 (2001) Abstract
Targeting of HIF-alpha to the von Hippel-Lindau ubiquitylation complex by O2-regulated prolyl hydroxylation: P. Jaakkola, et al.; Science 292, 468 (2001) Abstract
A conserved family of prolyl-4-hydroxylases that modify HIF: R.K. Bruick & S.L. McKnight; Science 294, 1337 (2001) Abstract

General Information

BACKGROUND/TECHNICAL INFORMATION

To change the solvent, simply evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice.

ALX-270-371

Revised 18-Jun-07

Dimethyloxalyl glycine
SYNONYMS	DMOG N-(Methoxyoxoacetyl)-glycine methyl ester
PRODUCT LINE	Oxidative Stress
PRODUCT CATEGORY	Hypoxia-inducible Factor [HIF] / Related Products

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-371-M010		10 mg	18.00 USD
ALX-270-371-M050		50 mg	72.00 USD
ALX-270-371-M100		100 mg	120.00 USD

Product Specification

FORMULA:	C₆H₉NO₅
MW:	175.1
CAS NUMBER:	89464-63-1
PURITY:	≥98%
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in 100% ethanol, DMSO or dimethyl formamide; also soluble in PBS.
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stable for at least 1 year when stored at -20°C. Stock solutions are stable for at least 6 months if stored at -20°C.

Product Description

Cell permeable, competitive inhibitor of PHDs (prolyl hydroxylase domain-containing proteins; HIF-PHs), which destructs HIF-1α when hydroxylated at a specific proline residue (P⁵⁶⁴). Stabilizes HIF-1α expression at normal oxygen tensions in cultured cells at concentrations between 0.1 and 1mM. Expected to act pro-angiogenic.

Product Specific Literature References

Targeting of HIF-alpha to the von Hippel-Lindau ubiquitylation complex by O2-regulated prolyl hydroxylation: P. Jaakkola, et al.; Science 292, 468 (2001) Abstract
A conserved family of prolyl-4-hydroxylases that modify HIF: R.K. Bruick & S.L. McKnight; Science 294, 1337 (2001) Abstract
HIFalpha targeted for VHL-mediated destruction by proline hydroxylation: implications for O2 sensing: M. Ivan, et al.; Science 292, 464 (2001) Abstract

General Information

BACKGROUND/TECHNICAL INFORMATION

A stock solution may be made by dissolving the DMOG in an organic solvent purged with an inert gas. DMOG is soluble in organic solvents such as ethanol, DMSO and dimethyl formamide.The solubility of DMOG in these solvents is at least 30mg/ml. DMOG will be stable for at least six months in these solvents if stored at -20°C.
Further dilutions of the stock solution into aqueous buffers or isotonic saline should be made prior to performing biological experiments. Ensure that the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. Organic solvent-free aqueous solutions of DMOG can be prepared by directly dissolving the crystalline compound powder in aqueous buffers. The solubility of DMOG in PBS (pH 7.2) is at least 10mg/ml.

ALX-380-201

Revised 27-Jun-08

Echinomycin
SYNONYMS	Quinomycin A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - DNA Replication Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-201-M001		1 mg	80.00 USD
ALX-380-201-M005		5 mg	320.00 USD

Product Specification

FORMULA:	C₅₁H₆₄N₁₂O₁₂S₂
MW:	1101.3
CAS NUMBER:	512-64-1
MERCK INDEX:	14: 3497
RTECS:	JW5250000
SOURCE/HOST:	Isolated from Streptomyces echinatus (DSM 40013).
PURITY:	≥98% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in 100% ethanol, dimethyl formamide or DMSO; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Hygroscopic.
HAZARD:	TOXIC. MAY BE MUTAGENIC.
IDENTITY:	Identity determined by ¹H-NMR.

Product Description

Antitumor antibiotic. Powerful, selective inhibitor of nucleic acid synthesis in vitro. Potent inhibitor of hypoxia-inducible factor 1 (HIF-1) DNA binding activity. Induces apoptosis. Displays antibacterial, antifungal and antiviral activities.

Product Specific Literature References

A “quinoxaline antibiotic” similar to the triostins, q.v.: I. Kuroya, et al.; J. Antibiot. 14A, 324 (1961)
Identity of levomycin and quinomycin A (echimomycin): K. Katagiri, et al.; J. Antibiot. 15, 273 (1962) Abstract
The mode of action of quinoxaline antibiotics. Interaction of quinomycin A with deoxyribonucleic acid: K. Sato, et al.; J. Antibiot. 20, 270 (1967) Abstract
The binding of echinomycin to deoxyribonucleic acid: S.P. Wakelin & M.J. Waring; Biochem. J. 157, 721 (1976) Abstract; Full Text
Bifunctional intercalation and sequence specificity in the binding of quinomycin and triostin antibiotics to deoxyribonucleic acid: J.S. Lee & M.J. Waring; Biochem. J. 173, 115 (1978) Abstract; Full Text
Kinetics of the interaction between echinomycin and deoxyribonucleic acid: K.R. Fox, et al.; Biochemistry 20, 5768 (1981) Abstract
Sequence-specific binding of echinomycin to DNA: evidence for conformational changes affecting flanking sequences: C.M. Low, et al.; Nucl. Acids Res. 12, 4865 (1984) Abstract; Full Text
Echinomycin binding sites on DNA: M.M. Van Dyke & P.B. Dervan; Science 225, 1122 (1984) Abstract
Kinetic evidence that echinomycin migrates between potential DNA binding sites: K.R. Fox & M.J. Waring; Nucl. Acids Res. 13, 595 (1985) Abstract; Full Text
Effect of echinomycin on DNA methylation: R.L. Adams & A. Rinaldi; FEBS Lett. 215, 266 (1987) Abstract
Interaction of echinomycin with An.Tn. and (AT)n regions flanking its CG binding site: K. Waterloh & K.R. Fox; Nucl. Acids Res. 19, 6719 (1991) Abstract; Full Text
Localized chemical reactivity in DNA associated with the sequence-specific bisintercalation of echinomycin: C. Bailly, et al.; Biochem. J. 300, 165 (1994) Abstract; Full Text
Energetics of echinomycin binding to DNA: F. Leng, et al.; Nucl. Acids Res. 31, 6191 (2003) Abstract; Full Text
Echinomycin inhibits chromosomal DNA replication and embryonic development in vertebrates: L.G. May, et al.; Nucl. Acids Res. 32, 65 (2004) Abstract; Full Text
Echinomycin and a novel analogue induce apoptosis of HT-29 cells via the activation of MAP kinases pathway: J.Y. Park, et al.; Pharmacol. Res. 50, 201 (2004) Abstract
Echinomycin, a small-molecule inhibitor of hypoxia-inducible factor-1 DNA-binding activity: D. Kong, et al.; Cancer Res. 65, 9047 (2005) Abstract; Full Text
Molecular signaling cascade in DNA bisintercalator, echinomycin-induced apoptosis of HT-29 cells: evidence of the apoptotic process via activation of the cytochrome c-ERK-caspase-3 pathway: J.Y. Park, et al.; Int. J. Biochem. Cell Biol. 38, 244 (2006) Abstract
Synergistic effects of CoCl(2) and ROCK inhibition on mesenchymal stem cell differentiation into neuron-like cells: E. Pacary, et al.; J. Cell Sci. 119, 2667 (2006) Abstract; Full Text
Metabolic targeting of hypoxia and HIF1 in solid tumors can enhance cytotoxic chemotherapy: R.A. Cairns, et al.; PNAS 104, 9445 (2007) Abstract

Further Categories Containing This Product:

Hypoxia-inducible Factor [HIF] / Related Products • Antibiotics - Antiviral / Anti-HIV • Antibiotics - Antifungal • Antitumor Agents (Apoptosis Inducers) • Antitumor Antibiotics

ALX-350-092

Revised 03-Apr-08

Emetine . dihydrochloride
SYNONYMS	6’,7’,10,11-Tetramethoxyemetan . 2HCl
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - DNA Replication Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-092-M050		50 mg	10.00 USD

Product Specification

FORMULA:	C₂₉H₄₀N₂O₄ . 2HCl
MW:	480.7 . 73.0
CAS NUMBER:	316-42-7
MERCK INDEX:	14: 3559
SOURCE/HOST:	Isolated from ground roots of Uragoga ipecacuanha.
PURITY:	≥98%
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in water or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HANDLING:	Protect from light. Hygroscopic.
HAZARD:	TOXIC.

Product Description

Irreversibly blocks protein synthesis by inhibiting the movement of ribosome along the mRNA. Induces hypotension by blocking adrenoreceptors. Inhibits DNA replication in the early S phase. Inhibits HIF-1 activation by hypoxia. Induces apoptosis in leukemia cells. Antiamebic.

Product Specific Literature References

Inhibitors of protein biosynthesis. V. Effects of emetine on protein and nucleic acid biosynthesis in HeLa cells: A.P. Grollman; J. Biol. Chem. 243, 4089 (1968) Abstract
Cytometric analysis of DNA replication inhibited by emetine and cyclosporin A:: A: T. Schweighoffer, et al.; Histochemistry 96, 93 (1991) Abstract
Emetine allows identification of origins of mammalian DNA replication by imbalanced DNA synthesis, not through conservative nucleosome segregation: W.C. Burhans, et al.; EMBO J. 10, 4351 (1991) Abstract
Role of newly synthesized MH