ALEXIS Biochemicals: UK-1

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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-380-220

Revised 13-Nov-07

Steffimycin B
SYNONYMS	Antibiotic U 40615
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Antibiotics - DNA Regulation / Transcription

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-220-M001		1 mg	260.00 USD

Product Specification

FORMULA:	C₂₉H₃₂O₁₃
MW:	588.6
CAS NUMBER:	54526-94-2
RTECS:	QI9450000
SOURCE/HOST:	Isolated from Streptomyces sp. MST-AS5455.
PURITY:	≥99% (HPLC)
APPEARANCE:	Orange to red solid.
SOLUBILITY:	Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C

Product Description

DNA-binding agent. Displays antibacterial and antineoplastic properties. Potential antitumor agent.

Product Specific Literature References

Steffimycin B, a new member of the steffimycin family: isolation and characterization: T.F. Brodasky and F. Reusser; J. Antibiot. (Tokyo) 27, 809 (1974) Abstract
Steffimycin B, a DNA binding agent: F. Reusser; Biochim. Biophys. Acta 383, 266 (1975) Abstract
Screening of antibiotics preferentially active against ras oncogene-expressed cells: K. Suzukake-Tsuchiya, et al.; J. Antibiot. (Tokyo) 43, 1489 (1990) Abstract
Molecular structure of antitumor drug steffimycin and modelling of its binding to DNA: M. Sriram, et al.; J. Biomol. Struct. Dyn. 9, 251 (1991) Abstract

Further Categories Containing This Product:

Antitumor Antibiotics • Antitumor Agents (DNA Interaction & Gene Regulation)

ALX-380-010

Revised 08-Oct-08

Streptozotocin
SYNONYMS	Streptozocin 2-Deoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose STZ
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Nitric Oxide Pathway Modulators

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-010-M100		100 mg	25.00 USD
ALX-380-010-5100		5x100 mg	65.00 USD
ALX-380-010-G001		1 g	74.00 USD

Product Specification

FORMULA:	C₈H₁₅N₃O₇
MW:	265.2
CAS NUMBER:	18883-66-4
MERCK INDEX:	14: 8832
RTECS:	LZ5775000
PURITY:	≥97%
APPEARANCE:	White to pale yellow solid.
SOLUBILITY:	Soluble in water or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	TOXIC. MAY BE CARCINOGENIC.

Product Description

Widely used diabetes inducer in rodents. Inhibition of β-cell O-GlcNAcase by streptozotocin is the mechanism that accounts for its diabetogenic toxicity. N-nitroso-containing antibiotic, acting as a nitric oxide (NO) donor. Potent methylating agent for DNA.

Product Specific Literature References

Studies on the diabetogenic action of streptozotocin: N. Rakieten, et al.; Cancer Chemother. Rep. 29, 91 (1963)
The structure of streptozotocin: R.R. Herr, et al.; JACS 89, 4808 (1967) Abstract
Alkylation of DNA in rat tissues following administration of streptozotocin: R.A. Bennett & A.E. Pegg; Cancer Res. 41, 2786 (1981) Abstract
Streptozotocin: a nitric oxide carrying molecule and its effect on vasodilation: G. Thomas & P. Ramwell; Eur. J. Pharmacol. 161, 279 (1989) Abstract
NO- and NO2-carrying molecules potentiate photorelaxation in rat trachea and aorta: K.C. Chang, et al.; BBRC 191, 509 (1993) Abstract
Biochemical evidence for nitric oxide formation from streptozotocin in isolated pancreatic islets: J. Turk, et al.; BBRC 197, 1458 (1993) Abstract
Nitric oxide generation from streptozotocin: N.S. Kwon, et al.; FASEB J. 8, 529 (1994) Abstract
Nitric oxide generation during cellular metabolization of the diabetogenic N-methyl-N-nitroso-urea streptozotozin contributes to islet cell DNA damage: K.-D. Kroncke, et al.; Biol. Chem. Hoppe Seyler 376, 179 (1995) Abstract
The mechanism of alloxan and streptozotocin action in B cells of the rat pancreas: T. Szkudelski; Physiol. Res. 50, 537 (2001), (Review) Abstract
Genotoxicity of streptozotocin: A.D. Bolzan & M.S. Bianchi; Mutat. Res. 512, 121 (2002), (Review) Abstract
Streptozotocin induces G2 arrest in skeletal muscle myoblasts and impairs muscle growth in vivo: A.P. Johnston, et al.; Am. J. Physiol. Cell Physiol. 292, C1033 (2007) Abstract

Further Categories Containing This Product:

Nitric Oxide Donors • Antitumor Antibiotics • Obesity & Diabetes Other Products

ALX-350-317

Revised 08-Apr-08

Tenuazonic acid
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antitumor Antibiotics

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-317-MC05		0.5 mg	150.00 USD

Product Specification

FORMULA:	C₁₀H₁₅NO₃
MW:	197.3
CAS NUMBER:	610-88-8
MERCK INDEX:	14: 9149
RTECS:	UY7425000
SOURCE/HOST:	Isolated from Alternaria sp.
PURITY:	≥97% (HPLC)
APPEARANCE:	Brown oily solid.
SOLUBILITY:	Soluble in DMSO or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
IDENTITY:	Identity determined by ¹H-NMR, ¹³C-NMR and MS.

Product Description

Antineoplastic compound exhibiting antitumor, antiviral and antibacterial activity. Inhibits protein synthesis by suppression at the ribosome. May act as a mycotoxin.

Product Specific Literature References

Microbial metabolites with insecticidal properties: M. Cole & G.N. Rolinson; Appl. Microbiol. 24, 660 (1972) Abstract
Microbial production of tenuazonic acid analogues: S. Gatenbeck & J. Sierankiewicz; Antimicrob. Agents Chemother. 3, 308 (1973) Abstract
Inhibition of mouse skin tumor promotion by tenuazonic acid: M. Antony, et al.; Cancer Lett. 61, 21 (1991) Abstract

Further Categories Containing This Product:

Antitumor Agents (Anti-proliferative) • Mycotoxins • Antibiotics - Antiviral / Anti-HIV

ALX-380-068

Revised 09-Apr-08

Trichostatin A
SYNONYMS	TSA [R-(E,E)]-7-[4-(Dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide]
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Other Antibiotics - DNA Regulation / Transcription

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-068-M001		1 mg	115.00 USD
ALX-380-068-M005		5 mg	385.00 USD

Product Specification

FORMULA:	C₁₇H₂₂N₂O₃
MW:	302.4
CAS NUMBER:	58880-19-6
MERCK INDEX:	14: 9649
SOURCE/HOST:	Isolated from Streptomyces hygroscopicus.
PURITY:	≥98% (HPLC)
APPEARANCE:	Whitish film adhered to inside of vial.
SOLUBILITY:	Soluble in DMSO, dimethyl formamide, acetonitrile, methanol or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HAZARD:	HARMFUL.

Product Description

Potent, reversible inhibitor of histone deacetylase (HDAC). Mediates the activation of O⁶-methylguanine-DNA methyltransferase (MGMT). May be involved in cell cycle progression of several cell types. Induces cell growth arrest at both G1 and G2/M phases. May induce apoptosis in some cases. Induces acetylation of histone-3/4 and expression of p300.

Product Specific Literature References

A new antifungal antibiotic, trichostatin: N. Tsuji, et al.; J. Antibiot. 29, 1 (1976) Abstract
Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A: M. Yoshida, et al.; J. Biol. Chem. 265, 17174 (1990) Abstract; Full Text
Trichostatin A induces morphological changes and gelsolin expression by inhibiting histone deacetylase in human carcinoma cell lines: Y. Hoshikawa, et al.; Exp. Cell Res. 214, 189 (1994) Abstract
Trichostatin A inhibits both ras-induced neurite outgrowth of PC12 cells and morphological transformation of NIH3T3 cells: M. Futamura, et al.; Oncogene 10, 1119 (1995) Abstract
Trichostatin A and trapoxin: novel chemical probes for the role of histone acetylation in chromatin structure and function: M. Yoshida, et al.; Bioessays 17, 423 (1995) Abstract
Selective inhibition of IL-2 gene expression by trichostatin A, a potent inhibitor of mammalian histone deacetylase: I. Takahashi, et al.; J. Antibiot. 49, 453 (1996) Abstract
A mammalian histone deacetylase related to the yeast transcriptional regulator Rpd3p: J. Taunton, et al.; Science 272, 408 (1996) Abstract
Transcriptional activation and chromatin remodeling of the HIV-1 promoter in response to histone acetylation: C. Van Lint, et al.; EMBO J. 15, 1112 (1996) Abstract
Induction of caspase-3 protease activity and apoptosis by butyrate and trichostatin A (inhibitors of histone deacetylase): dependence on protein synthesis and synergy with a mitochondrial/cytochrome c- dependent pathway:: V. Medina, et al.; Cancer Res. 57, 3697 (1997) Abstract
A histone deacetylase inhibitor potentiates retinoid receptor action in embryonal carcinoma cells: S. Minucci, et al.; PNAS 94, 11295 (1997) Abstract; Full Text
Histone deacetylase inhibitor activates the WAF1/Cip1 gene promoter through the Sp1 sites: Y. Sowa, et al.; BBRC 241, 142 (1997) Abstract
Retinoblastoma protein recruits histone deacetylase to repress transcription: A. Brehm, et al.; Nature 391, 597 (1998) Abstract
Effects of cell density and trichostatin A on the expression of HDAC1 and p57Kip2 in Hep 3B cells: S.G. Gray & T.J. Ekstrom; BBRC 245, 423 (1998) Abstract
Regulation of the human O6-methylguanine-DNA methyltransferase gene by transcriptional coactivators cAMP response element-binding protein- binding protein and p300: K.K. Bhakat & S. Mitra; J. Biol. Chem. 275, 34197 (2000) Abstract; Full Text
Histone deacetylase inhibitors: inducers of differentiation or apoptosis of transformed cells: P.A. Marks, et al.; J. Natl. Cancer Inst. 92, 1210 (2000) Abstract
Trichostatin A is a histone deacetylase inhibitor with potent antitumor activity against breast cancer in vivo: D.M. Vigushin, et al.; Clin. Cancer Res. 7, 971 (2001) Abstract
Chromatin remodeling agent trichostatin A: a key-factor in the hepatic differentiation of human mesenchymal stem cells derived of adult bone marrow: S. Snykers, et al.; BMC Dev. Biol. 7, 24 (2007) Abstract
Trichostatin A induces myocardial differentiation of monkey ES cells: M. Hosseinkhani, et al.; BBRC 356, 386 (2007) Abstract

Further Categories Containing This Product:

Cell Cycle Blockers & Inhibitors / Related Products • Antibiotics - Other Signal Transduction Pathway Modulators • Antibiotics - Apoptosis Inducers & Inhibitors • HDAC Inhibitors • PKC Activators • Antitumor Antibiotics • Antibiotics for Cell Cycle Research • DNA Repair Other Products • DNA & RNA Methyl & Alkyl Transferases / Related Products • Antibiotics - Antifungal

ALX-380-222

Revised 19-Aug-08

UCN-01
SYNONYMS	7-Hydroxystaurosporine Staurosporine, 7-Hydroxy-
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Staurosporine / Related Products

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-222-MC25		0.25 mg	85.00 USD
ALX-380-222-M001		1 mg	265.00 USD

Product Specification

FORMULA:	C₂₈H₂₆N₄O₄
MW:	482.5
CAS NUMBER:	112953-11-4
RTECS:	KC6600010
SOURCE/HOST:	Isolated from Streptomyces sp. MST-AS5345.
PURITY:	≥98% (HPLC)
APPEARANCE:	Light tan to light yellow solid.
SOLUBILITY:	Soluble in methanol, 100% ethanol, dimethyl formamide or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.

Product Description

Inhibitor of protein kinase C (PKC) and cyclin-dependent kinases (CDKs) resulting in accumulation of cells in the G1 phase and induction of apoptosis. Enhances the cytotoxicity of other anticancer drugs, such as DNA-damaging agents and anti-metabolite drugs, through putative abrogation of G2 and/or S phase accumulation induced by these agents.

Product Specific Literature References

[1] UCN-01, a selective inhibitor of protein kinase C from Streptomyces: I. Takahashi, et al.; J. Antibiot. (Tokyo) 40, 1782 (1987) Abstract
[2] UCN-01 and UCN-02, new selective inhibitors of protein kinase C. II. Purification, physico-chemical properties, structural determination and biological activities: I. Takahashi, et al.; J. Antibiot. (Tokyo) 42, 571 (1989) Abstract
[3] UCN-01, 7-hydroxyl-staurosporine, inhibits kinase activity of cyclin-dependent kinases and reduces the phosphorylation of the retinoblastoma susceptibility gene product in A549 human lung cancer cell line: K. Kawakami, et al.; BBRC 219, 778 (1996) Abstract
[4] UCN-01 (7-hydroxystaurosporine) and other indolocarbazole compounds: a new generation of anti-cancer agents for the new century?: S. Akinaga, et al.; Anticancer Drug Des. 15, 43 (2000) Abstract
[5] UCN-01-induced cell cycle arrest requires the transcriptional induction of p21(waf1/cip1) by activation of mitogen-activated protein/extracellular signal-regulated kinase kinase/extracellular signal-regulated kinase pathway: M.M. Facchinetti, et al.; Cancer Res. 64, 3629 (2004) Abstract; Full Text

General Information

BACKGROUND/TECHNICAL INFORMATION

Note: Some interconversion of UCN-01 to UCN-02 may occur under acidic HPLC conditions (see [2]).

Further Categories Containing This Product:

Antibiotics - Apoptosis Inducers & Inhibitors • PKC Inhibitors • Antibiotics - Protein Kinase Inhibitors • CDK & Cyclin Inhibitors • Cell Cycle Blockers & Inhibitors / Related Products • Antibiotics for Cell Cycle Research • Antitumor Antibiotics • Alkaloids

ALX-380-206

Revised 19-Aug-08

UCN-02
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Staurosporine / Related Products

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-206-MC25		0.25 mg	85.00 USD
ALX-380-206-M001		1 mg	265.00 USD

Product Specification

FORMULA:	C₂₈H₂₆N₄O₄
MW:	482.5
CAS NUMBER:	121569-61-7
RTECS:	KC6600000
SOURCE/HOST:	Isolated from Streptomyces sp. MST-AS5345.
PURITY:	≥98% (HPLC)
APPEARANCE:	White to pale yellow solid.
SOLUBILITY:	Soluble in ethyl acetate, 100% ethanol, dimethyl formamide or DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.

Product Description

Inhibitor of protein kinase C (PKC) and protein kinase A (PKA). Although less selective than its isomer UCN-01 (Prod. No. ALX-380-222), UCN-02 exhibits comparable activity and probably acts by similar mechanisms.

Product Specific Literature References

[1] UCN-01 and UCN-02, new selective inhibitors of protein kinase C. II. Purification, physico-chemical properties, structural determination and biological activities: I. Takahashi, et al.; J. Antibiot. (Tokyo) 42, 571 (1989) Abstract

General Information

BACKGROUND/TECHNICAL INFORMATION

Note: Some interconversion of UCN-02 to UCN-01 may occur under acidic HPLC conditions (see [1]).

Further Categories Containing This Product:

Antibiotics - Apoptosis Inducers & Inhibitors • Antitumor Antibiotics • PKC Inhibitors • Antibiotics - Protein Kinase Inhibitors • Cell Cycle Blockers & Inhibitors / Related Products • CDK & Cyclin Inhibitors • Antibiotics for Cell Cycle Research • Alkaloids

ALX-380-117

Revised 10-Apr-07

UK-1
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Antibiotics - Antifungal

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-380-117-C250		250 µg	140.00 USD
ALX-380-117-M001		1 mg	420.00 USD

Product Specification

FORMULA:	C₂₂H₁₄N₂O₅
MW:	386.4
CAS NUMBER:	151271-53-3
SOURCE/HOST:	Isolated from Streptomyces sp.
PURITY:	≥98% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO, dimethyl formamide or acetone.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C

Product Description

Antibiotic. Antifungal. Inhibitor of topoisomerase II (Topo II). Mg²⁺- and Zn²⁺-dependent DNA binding agent. Displays a wide spectrum of potent anticancer activities.

Product Specific Literature References

UK-1, a novel cytotoxic metabolite from Streptomyces sp. 517-02. I. Taxonomy, fermentation, isolation, physico-chemical and biological properties: M. Ueki, et al.; J. Antibiot. 46, 1089 (1993) Abstract
UK-1, a novel cytotoxic metabolite from Streptomyces sp. 517-02. II. Structural elucidation: K. Shibata, et al.; J. Antibiot. 46, 1095 (1993) Abstract
UK-1, a novel cytotoxic metabolite from Streptomyces sp. 517-02. III. Antibacterial action of demethyl UK-1: M. Ueki and M. Taniguchi; J. Antibiot. 50, 788 (1997) Abstract
UK-1, a novel cytotoxic metabolite from Streptomyces sp. 517-02. IV. Antifungal action of methyl UK-1: M. Ueki, et al.; J. Antibiot. 51, 883 (1998) Abstract
The novel bis(benzoxazole) cytotoxic natural product UK-1 is a magnesium ion-dependent DNA binding agent and inhibitor of human topoisomerase II: M.B. Reynolds, et al.; Bioorg. Chem. 27, 326 (1999)
Evaluation of complexation of metal-mediated DNA-binding drugs to oligonucleotides via electrospray ionization mass spectrometry: M.L. Reyzer, et al.; Nucl. Acids Res. 29, E103 (2001) Abstract; Full Text
Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1: D. Kumar, et al.; Bioorg. Med. Chem. 10, 3997 (2002) Abstract
Critical structural motif for the catalytic inhibition of human topoisomerase II by UK-1 and analogs: B.B. Wang, et al.; Bioorg. Med. Chem. Lett. 14, 3221 (2004) Abstract
Synthesis and antimicrobial activity of some 5-[2-(morpholin-4-yl)acetamido] and/or 5-[2-(4-substituted piperazin-1-yl)acetamido]-2-(p-substituted phenyl)benzoxazoles: O. Temiz-Arpaci, et al.; Arch. Pharm. 338, 105 (2005) Abstract
Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles: S.T. Huang, et al.; Bioorg. Med. Chem. 14, 6106 (2006) Abstract

Further Categories Containing This Product:

Antibiotics - Topoisomerase Inhibitors • Antitumor Agents (DNA Interaction & Gene Regulation) • Antitumor Antibiotics