ALEXIS Biochemicals: Actinomycin X0β

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ALX-380-032

Revised 19-Mar-08

Decoyinine
SYNONYMS	Angustmycin A U-7984 9-(6-Deoxy-D-β-erythro-hex-5-en-2-ulofuranosyl)-adenine
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Other Signal Transduction Pathway Modulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-032-M001		1 mg	20.00 USD
ALX-380-032-M005		5 mg	60.00 USD

Product Specification

FORMULA:	C₁₁H₁₃N₅O₄
MW:	279.3
CAS NUMBER:	2004-04-8
RTECS:	AU6256000
SOURCE/HOST:	Natural fermentation product.
PURITY:	≥95%
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO (warm), water or 100% ethanol; poorly soluble in methanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stable for at least 1 year after receipt when stored at +4°C. Stock solutions are stable for 3 months when stored at -20°C.

Product Description

Nucleoside antibiotic. Antitumor compound. Inhibitor of xanthosin monophosphate (XMP) aminase. Inhibitor of RNA synthesis. Specific inhibitor of GMP synthase. Reduces intracellular GTP levels.

Product Specific Literature References

Studies on a new antibiotic, angustmycin: H. Sakai, et al.; J. Antibiot. 7, 116 (1954) Abstract
Studies on a new antibiotic, angustmycin. I: H. Yuntsen, et al.; J. Antibiot. 7, 113 (1954) Abstract
Studies on angustmycin. III: H. Yuntsen, et al.; J. Antibiot. 9, 195 (1956) Abstract
On the studies of angustmycins. VI. Chemical structure of angustmycin A: H. Yuntsen; J. Antibiot. 11, 79 (1958) Abstract
Purine nucleosides. XXII. The synthesis of angustmycin A (decoyinine) and related unsaturated nucleosides: J.R. McCarthy, Jr., et al.; J. Am. Chem. Soc. 90, 4993 (1968) Abstract
Effects of several tumor-inhibitory antibiotics on immunological responses: H. Yamaki, et al.; J. Antibiot. 22, 315 (1969) Abstract
Halo sugar nucleosides. 5. Synthesis of angustmycin A and some base analogues: E.J. Prisbe, et al.; J. Org. Chem. 41, 1836 (1976) Abstract
A decrease in GTP content is associated with aerial mycelium formation in Streptomyces MA406-A-1: K. Ochi; J. Gen. Microbiol. 132, 299 (1986) Abstract
Extracellular control of spore formation in Bacillus subtilis: A.D. Grossman & R. Losick; PNAS 85, 4369 (1988) Abstract; Full Text
Nucleoside antibiotics: structure, biological activity, and biosynthesis: K. Isono; J. Antibiot. 41, 1711 (1988) Abstract
A target for carbon source-dependent negative regulation of the citB promoter of Bacillus subtilis: A. Fouret & A.L. Sonenshein; J. Bacteriol. 172, 835 (1990) Abstract; Full Text
Sporulation of Streptomyces venezuelae in submerged cultures: M.A. Glazebrook, et al.; J. Gen. Microbiol. 136, 581 (1990) Abstract
Conformational studies on some Cl’-branched beta-D-nucleosides by 1H-NMR spectroscopy and molecular mechanics calculations: J. Plavec, et al.; J. Biochem. Biophys. Meth. 26, 317 (1993) Abstract
Biochemical characterization of human GMP synthetase: J. Nakamura & L. Lou; J. Biol. Chem. 270, 7347 (1995) Abstract; Full Text
Guanine nucleotides guanosine 5’-diphosphate 3’-diphosphate and GTP co-operatively regulate the production of an antibiotic bacilysin in Bacillus subtilis: T. Inaoka, et al.; J. Biol. Chem. 278, 2169 (2003) Abstract; Full Text

Further Categories Containing This Product:

Antitumor Agents (Enzyme Inhibitors) • Antitumor Antibiotics

ALX-380-034

Revised 30-Jul-08

Concanamycin A
SYNONYMS	Folimycin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - ATPase Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-034-C025		25 µg	55.00 USD
ALX-380-034-C100		100 µg	180.00 USD
ALX-380-034-M001		1 mg	750.00 USD

Product Specification

FORMULA:	C₄₆H₇₅NO₁₄
MW:	866.1
CAS NUMBER:	80890-47-7
RTECS:	CB9732000
SOURCE/HOST:	Isolated from Streptomyces sp.
PURITY:	≥96% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in methanol, DMSO or acetonitrile; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
HAZARD:	VERY TOXIC.
IDENTITY:	Identity determined by ¹H-NMR.

Product Description

Antibiotic. More potent and specific H⁺-ATPase inhibitor than bafilomycin A₁(Prod. No. ALX-380-030). Inhibits acidification of organelles such as lysosomes and the Golgi apparatus. Blocks cell surface expression of viral glycoproteins without affecting their synthesis. Exhibits cytotoxic effects in a number of cell lines in a cell viability assay. Induces nitric oxide (NO) production.

Product Specific Literature References

Isolation and characterization of concanamycins A, B and C: H. Kinashi, et al.; J. Antibiot. (Tokyo) 37, 1333 (1984) Abstract
Bafilomycins: a class of inhibitors of membrane ATPases from microorganisms, animal cells, and plant cells: E.J. Bowman, et al.; PNAS 85, 7972 (1988) Abstract
Structure and function of vacuolar class of ATP-driven proton pumps: M. Forgac; Physiol. Rev. 69, 765 (1989) Abstract
Intravesicular acidification correlates with binding of ADP- ribosylation factor to microsomal membranes: S. Zeuzem, et al.; PNAS 89, 6619 (1992) Abstract
Inhibitory effect of modified bafilomycins and concanamycins on P- and V-type adenosinetriphosphatases: S. Drose, et al.; Biochemistry 32, 3902 (1993) Abstract
Folimycin (concanamycin A), a specific inhibitor of V-ATPase, blocks intracellular translocation of the glycoprotein of vesicular stomatitis virus before arrival to the Golgi apparatus: M. Muroi, et al.; Cell Struct. Funct. 18, 139 (1993) Abstract
Folimycin (concanamycin A), an inhibitor of V-type H(+)-ATPase, blocks cell-surface expression of virus-envelope glycoproteins: M. Muroi, et al.; BBRC 193, 999 (1993) Abstract
Purification of vacuolar ATPase with bafilomycin C1 affinity chromatography: T.J. Rautiala, et al.; BBRC 194, 50 (1993) Abstract
Involvement of the vacuolar H(+)-ATPases in the secretory pathway of HepG2 cells: M. Yilla, et al.; J. Biol. Chem. 268, 19092 (1993) Abstract; Full Text
Specific inhibitors of vacuolar type H(+)-ATPases induce apoptotic cell death: T. Nishihara, et al.; BBRC 212, 255 (1995) Abstract
Characterization of the ATPase activity of P-glycoprotein from multidrug-resistant Chinese hamster ovary cells: F.J. Sharom, et al.; Biochem. J. 308 (Pt2), 381 (1995) Abstract
Concanamycin A, the specific inhibitor of V-ATPases, binds to the V(o) subunit c: M. Huss, et al.; J. Biol. Chem. 277, 40544 (2002) Abstract
Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449: S.F. Haydock, et al.; Microbiology 151, 3161 (2005) Abstract; Full Text
Nitric oxide production by the vacuolar-type (H+)-ATPase inhibitors bafilomycin A1 and concanamycin A and its possible role in apoptosis in RAW 264.7 cells: J. Hong, et al.; J. Pharmacol. Exp. Ther. 319, 672 (2006) Abstract

Related Products

ALX-380-030

Bafilomycin A₁

Further Categories Containing This Product:

Antibiotics - Nitric Oxide Pathway Modulators • H+-ATPase / Related Products • Antitumor Antibiotics

ALX-380-036

Revised 10-Dec-07

Oligomycin A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Apoptosis Inducers & Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-036-M005		5 mg	140.00 USD

Product Specification

FORMULA:	C₄₅H₇₄O₁₁
MW:	791.1
CAS NUMBER:	579-13-5
MERCK INDEX:	14: 6833
RTECS:	RK3328000
SOURCE/HOST:	Isolated from Streptomyces sp. MST-AS5339.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	MAY BE MUTAGENIC. HARMFUL.

Product Description

Major component of the oligomycin complex. Macrolide antibiotic that inhibits membrane bound mitochondrial ATPase (F₁F₀), preventing phosphoryl group transfer. Induces apoptosis. Induces autophagy in the IPLB-LdFB insect cell line.

Product Specific Literature References

Production and isolation of the antibiotic, oligomycin: J. Visser, et al.; J. Biochem. Microbiol. Technol. Egr. 2, 31 (1960) Abstract
The BH3 domain is required for caspase-independent cell death induced by Bax and oligomycin: M.E. Fitch, et al.; Cell Death Differ. 7, 338 (2000) Abstract; Full Text
Oligomycin, inhibitor of the F0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis: L.A. Shchepina, et al.; Oncogene 21, 8149 (2000) Abstract; Full Text
Mitochondria-targeting drug oligomycin blocked P-glycoprotein activity and triggered apoptosis in doxorubicin-resistant HepG2 cells: Y.C. Li, et al.; Chemotherapy 50, 55 (2004) Abstract
Oligomycin A induces autophagy in the IPLB-LdFB insect cell line: G. Tettamanti, et al.; Cell Tissue Res. 326, 179 (2006) Abstract

Further Categories Containing This Product:

Antibiotics - ATPase Inhibitors • H+-ATPase / Related Products • Antitumor Antibiotics • Respiratory Chain Other Products • Antibiotics - Antifungal

ALX-380-037

Revised 20-Jun-08

Oligomycin
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Apoptosis Inducers & Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-037-M005		5 mg	50.00 USD
ALX-380-037-M010		10 mg	95.00 USD

Product Specification

MW:	789.3
CAS NUMBER:	1404-19-9
MERCK INDEX:	14: 6833
RTECS:	RK3325000
SOURCE/HOST:	Isolated from Streptomyces diastatochromogens.
PURITY:	≥90% (mixture of oligomycin A, B, and C (~65% oligomycin A))
APPEARANCE:	White to faint yellow powder.
SOLUBILITY:	Soluble in 100% ethanol, methanol (10mg/ml) or acetone (50mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	HARMFUL. MAY BE MUTAGENIC.

Product Description

Macrolide antibiotic that inhibits membrane bound mitochondrial ATPase (F₁), preventing phosphoryl group transfer. Induces apoptosis.

Product Specific Literature References

Inhibition of the Na(+)-Ca++ exchanger enhances anoxia and glucopenia- induced [3H]aspartate release in hippocampal slices: S. Amoroso, et al.; J. Pharmacol. Exp. Ther. 264, 515 (1993) Abstract
Cyclosporin A suppression of uncoupling in liver mitochondria of ground squirrel during arousal from hibernation: N.N. Brustovetsky, et al.; FEBS Lett. 315, 233 (1993) Abstract
The lipophilic weak base (Z)-5-methyl-2-[2-(1-naphthyl)ethenyl]-4- piperidinopyridine (AU-1421) is a potent protonophore type cationic uncoupler of oxidative phosphorylation in mitochondria: H. Nagamune, et al.; Biochim. Biophys. Acta 1141, 231 (1993) Abstract
Mitochondrial respiratory chain inhibitors induce apoptosis: E.J. Wolvetang, et al.; FEBS Lett. 339, 40 (1994) Abstract
Dissociation of phagocyte recognition of cells undergoing apoptosis from other features of the apoptotic program: J. Zhuang, et al.; J. Biol. Chem. 273, 15628 (1998) Abstract; Full Text
Apoptosis in factor-dependent haematopoietic cells is linked to calcium- sensitive mitochondrial rearrangements and cytoskeletal modulation: J. Garland, et al.; Br. J. Haematol. 109, 221 (2000) Abstract
Properties of DNA fragmentation activity generated by ATP depletion: N. Nakamura & Y. Wada; Cell Death Differ. 7, 477 (2000) Abstract

Further Categories Containing This Product:

ALX-380-038

Revised 10-Dec-07

Oligomycin B
SYNONYMS	28-Oxooligomycin A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Apoptosis Inducers & Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-038-M005		5 mg	140.00 USD

Product Specification

FORMULA:	C₄₅H₇₂O₁₂
MW:	805.1
CAS NUMBER:	11050-94-5
MERCK INDEX:	14: 6833
RTECS:	RK3330000
SOURCE/HOST:	Isolated from Streptomyces sp. MST-AS5339.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	HARMFUL. MAY BE MUTAGENIC.

Product Description

Minor component of the oligomycin complex. Macrolide antibiotic that inhibits membrane bound mitochondrial ATPase (F₁F₀), preventing phosphoryl group transfer. Induces apoptosis.

Product Specific Literature References

Further Categories Containing This Product:

ALX-380-039

Revised 10-Dec-07

Oligomycin C
SYNONYMS	12-Deoxyoligomycin A
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Apoptosis Inducers & Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-039-M001		1 mg	330.00 USD

Product Specification

FORMULA:	C₄₅H₇₄O₁₀
MW:	775.1
CAS NUMBER:	11052-72-5
MERCK INDEX:	14: 6833
RTECS:	RK3335000
SOURCE/HOST:	Isolated from Streptomyces sp. MST-AS5339.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white powder.
SOLUBILITY:	Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	MAY BE MUTAGENIC. HARMFUL.

Product Description

Minor component of the oligomycin complex. Macrolide antibiotic that inhibits membrane bound mitochondrial ATPase (F₁F₀), preventing phosphoryl group transfer. Induces apoptosis.

Product Specific Literature References

Production and isolation of the antibiotic, oligomycin: J. Visser, et al.; J. Biochem. Microbiol. Technol. Engr. 2, 31 (1960) Abstract
The BH3 domain is required for caspase-independent cell death induced by Bax and oligomycin: M.E. Fitch, et al.; Cell Death Differ. 7, 338 (2000) Abstract; Full Text
Oligomycin, inhibitor of the F0 part of H+-ATP-synthase, suppresses the TNF-induced apoptosis: L.A. Shchepina, et al.; Oncogene 21, 8149 (2002) Abstract; Full Text
Mitochondria-targeting drug oligomycin blocked P-glycoprotein activity and triggered apoptosis in doxorubicin-resistant HepG2 cells: Y.C. Li, et al.; Chemotherapy 50, 55 (2004) Abstract

Further Categories Containing This Product:

ALX-380-042

Revised 05-May-08

Doxorubicin . hydrochloride
SYNONYMS	DXR . HCl 14-Hydroxydaunomycin . HCl Adriamycin . HCl
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antitumor Antibiotics

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-042-M005		5 mg	60.00 USD
ALX-380-042-M010		10 mg	110.00 USD
ALX-380-042-M025		25 mg	250.00 USD

Product Specification

FORMULA:	C₂₇H₂₉NO₁₁ . HCl
MW:	543.5 . 36.5
CAS NUMBER:	25316-40-9
MERCK INDEX:	14: 3439
RTECS:	QI9295900
SOURCE/HOST:	Isolated from Streptomyces peucetius var. caesius.
PURITY:	≥98%
APPEARANCE:	Red solid.
SOLUBILITY:	Soluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HAZARD:	MAY BE CARCINOGENIC. MAY BE TERATOGENIC. TOXIC. MAY BE MUTAGENIC.

Product Description

Antitumor antibiotic. Induces DNA damage by intercalating into DNA and inhibiting topoisomerase II. Binds covalently to DNA. Inhbibits reverse transcriptase, RNA polymerase and the catalytic activity of Dnmt1. Immunosuppressive. Antineoplastic. Induces apoptosis.

Product Specific Literature References

Adriamycin and daunomycin induce programmed cell death (apoptosis) in tumour cells: A. Skladanowski & J. Konopa; Biochem. Pharmacol. 46, 375 (1993) Abstract
A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin: D.A. Gewirtz; Biochem. Pharmacol. 57, 727 (1999) Abstract
Doxorubicin treatment activates a Z-VAD-sensitive caspase, which causes deltapsim loss, caspase-9 activity, and apoptosis in Jurkat cells: S. Gamen, et al.; Exp. Cell Res. 258, 223 (2000) Abstract
Involvement of cyclin-dependent kinases in doxorubicin-induced apoptosis in human tumor cells: Y. Lu, et al.; Mol. Carcinog. 29, 1 (2000) Abstract
Characterization of Adriamycin-Induced G2 Arrest and Its Abrogation by Caffeine in FL-Amnion Cells with or without p53: Y. Minemoto, et al.; Exp. Cell Res. 262, 37 (2001) Abstract
Enhancement of Fas-mediated apoptosis in renal cell carcinoma cells by adriamycin: X.X. Wu, et al.; Cancer Res. 60, 2912 (2000) Abstract
Doxorubicin-induced apoptosis in endothelial cells and cardiomyocytes is ameliorated by nitrone spin traps and ebselen. Role of reactive oxygen and nitrogen species: S. Kotamraju, et al.; J. Biol. Chem. 275, 33585 (2000) Abstract; Full Text
The power and potential of doxorubicin-DNA adducts: S.M. Cutts, et al.; IUBMB Life 57, 73 (2005), Review Abstract
Adriamycin-induced interference with cardiac mitochondrial calcium homeostasis: K.B. Wallace; Cardiovasc. Toxicol. 7, 101 (2007), Review Abstract
Doxorubicin-induced cardiomyopathy from the cardiotoxic mechanisms to managemen: G. Takemura & H. Fujiwara; Prog. Cardiovasc. Dis. 49, 330 (2007), Review Abstract

Further Categories Containing This Product:

Other Toxins • Antitumor Agents (Enzyme Inhibitors) • Antibiotics - Immunomodulators • Antitumor Agents (Apoptosis Inducers) • Antibiotics - Topoisomerase Inhibitors • Antibiotics - Apoptosis Inducers & Inhibitors • DNA Intercalators & Crosslinkers • Antitumor Agents (DNA Interaction & Gene Regulation)

ALX-380-043

Revised 03-Apr-08

Daunorubicin . hydrochloride
SYNONYMS	Daunomycin . HCl
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antitumor Antibiotics

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-043-M010		10 mg	95.00 USD

Product Specification

FORMULA:	C₂₇H₂₉NO₁₀. HCl
MW:	527.5 . 36.5
CAS NUMBER:	23541-50-6
MERCK INDEX:	14: 2832
SOURCE/HOST:	Isolated from Streptomyces spec.
PURITY:	≥98% (HPLC)
APPEARANCE:	Orange to red solid.
SOLUBILITY:	Soluble in water or methanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	TOXIC.

Product Description

Anthracycline anticancer antibiotic. Induces DNA damage by intercalating into DNA and inhibiting topoisomerase I and II. Inhibits RNA and DNA synthesis. Induces DNA single strand breaks and apoptosis in tumor cells.

Product Specific Literature References

Ceramide synthase mediates daunorubicin-induced apoptosis: an alternative mechanism for generating death signals: R. Bose, et al.; Cell 82, 405 (1995) Abstract
Daunorubicin activates NFkappaB and induces kappaB-dependent gene expression in HL-60 promyelocytic and Jurkat T lymphoma cells: M.P. Boland, et al.; J. Biol. Chem. 272, 12952 (1997) Abstract; Full Text
Alteration of the daunorubicin-triggered sphingomyelin-ceramide pathway and apoptosis in MDR cells: influence of drug transport abnormalities: M.G. Come, et al.; Int. J. Cancer 81, 580 (1999) Abstract
A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin: D.A. Gewirtz; Biochem. Pharmacol. 57, 727 (1999) Abstract
Altered multidrug resistance phenotype caused by anthracycline analogues and cytosine arabinoside in myeloid leukemia: X.F. Hu, et al.; Blood 93, 4086 (1999) Abstract
Implication of radical oxygen species in ceramide generation, c-Jun N- terminal kinase activation and apoptosis induced by daunorubicin: V. Mansat-de Mas, et al.; Mol. Pharmacol. 56, 867 (1999) Abstract
The phosphoinositide 3-kinase/Akt pathway is activated by daunorubicin in human acute myeloid leukemia cell lines: I. Plo, et al.; FEBS Lett 452, 150 (1999)