ALEXIS Biochemicals: 2-Thio(3-iodobenzyl)-5-(1-pyridyl)-[1,3,4]-oxadiazole

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GSK-3 Antibodies

GSK-3 Inhibitors

GSK-3 Other Products

ALX-270-386

Revised 24-Feb-05

Aloisine
SYNONYMS	RP106 7-n-Butyl-6-(4-methoxyphenyl)[5H]pyrrolo[2,3-b]pyrazine
PRODUCT LINE	Cell Cycle
PRODUCT CATEGORY	CDK & Cyclin Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-386-M001		1 mg	25.00 USD

Product Specification

FORMULA:	C₁₇H₁₉N₃O
MW:	281.4
PURITY:	≥95%
APPEARANCE:	Off-white solid.
SOLUBILITY:	Soluble in DMSO or methanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
HANDLING:	Protect from light. Packaged under inert gas.

Product Description

Potent, cell permeable, selective ATP-competitive inhibitor of CDK1/cyclin B (IC₅₀=700nM), CDK5/p25 (IC₅₀=1.5µM), and GSK-3 (IC₅₀=920nM).

Product Specific Literature References

Aloisines, a new family of CDK/GSK-3 inhibitors. SAR study, crystal structure in complex with CDK2, enzyme selectivity, and cellular effects: Y. Mettey, et al.; J. Med. Chem. 46, 222 (2003) Abstract

Further Categories Containing This Product:

GSK-3 Inhibitors • Cell Cycle Blockers & Inhibitors / Related Products

ALX-270-385

Revised 17-Jul-07

Aloisine A
SYNONYMS	RP107 7-n-Butyl-6-(4-hydroxyphenyl)[5H]pyrrolo[2,3-b]pyrazine
PRODUCT LINE	Cell Cycle
PRODUCT CATEGORY	CDK & Cyclin Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-385-M001		1 mg	30.00 USD

Product Specification

FORMULA:	C₁₆H₁₇N₃O
MW:	267.3
PURITY:	≥95%
APPEARANCE:	Yellow solid.
SOLUBILITY:	Soluble in DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light. Packaged under inert gas.

Product Description

Cell permeable, potent, selective, reversible and ATP-competitive inhibitor of CDK1/cyclin B (IC₅₀=150nM), CDK2/cyclin A (IC₅₀=120nM), CDK2/cyclin E (IC₅₀=400nM), CDK5/p25
(IC₅₀=200nM), CDK5/p35 (IC₅₀=160nM) and GSK-3α (IC₅₀=500nM). Also inhibits GSK-3β (IC₅₀=650nM) and c-Jun N-terminal kinase (JNK) (IC₅₀~3-10µM). Poor inhibitor of CK1, CK2, CDK4/cyclin D1, MAPKK, PKA, PKG, PKCs and c-raf (IC₅₀≥100µM). Blocks cell cycle in both G1 and G2 phase.

Product Specific Literature References

Further Categories Containing This Product:

GSK-3 Inhibitors • JNK [SAPK1] / Related Products • Cell Cycle Blockers & Inhibitors / Related Products

ALX-270-275

Revised 11-Sep-08

Alsterpaullone
SYNONYMS	9-Nitro-7,12-dihydroindolo-[3,2-d][1]benzazepin-6(5H)-one
PRODUCT LINE	Cell Cycle
PRODUCT CATEGORY	CDK & Cyclin Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-275-M001		1 mg	60.00 USD
ALX-270-275-M005		5 mg	270.00 USD

Product Specification

FORMULA:	C₁₆H₁₁N₃O₃
MW:	293.3
CAS NUMBER:	237430-03-4
PURITY:	≥95% (HPLC)
APPEARANCE:	Yellow to brown powder.
SOLUBILITY:	Soluble in DMSO; insoluble in water or 100% ethanol.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
IDENTITY:	Identity determined by IR, ¹H-NMR and ¹³C-NMR.

Product Description

Potent inhibitor of CDK1/cyclin B (IC₅₀=35nM). Potent and selective inhibitor of CDK2/cyclin A, CDK2/cyclin E (IC₅₀=200nM), CDK5/p25 (IC₅₀=40nM), CDK5/p35 (IC₅₀=40nM) and GSK-3β . Induces apoptosis by activation of caspase-8 and caspase-9 followed by disruption of the mitochondrial potential.

Licensed from NCI.

Product Specific Literature References

ATP-site directed inhibitors of cyclin-dependent kinases: N. Gray, et al.; Curr. Med. Chem. 6, 859 (1999) Abstract
Fused azepinones with antitumor activity: C. Kunick; Curr. Pharm. Des. 5, 181 (1999), (Review) Abstract
Paullones, a series of cyclin-dependent kinase inhibitors: synthesis, evaluation of CDK1/cyclin B inhibition, and in vitro antitumor activity: C. Schultz, et al.; J. Med. Chem. 42, 2909 (1999) Abstract
Discovery and initial characterization of the paullones, a novel class of small-molecule inhibitors of cyclin-dependent kinases: D.W. Zaharevitz, et al.; Cancer Res. 59, 2566 (1999) Abstract
2-Substituted paullones: CDK1/cyclin B-inhibiting property and in vitro antiproliferative activity: C. Kunick, et al.; Bioorg. Med. Chem. Lett. 10, 567 (2000) Abstract
Paullones are potent inhibitors of glycogen synthase kinase-3beta and cyclin-dependent kinase 5/p25: M. Leost, et al.; Eur. J. Biochem. 267, 5983 (2000) Abstract
Inhibition of CDKs as a therapeutic modality: E.A. Sausville, et al.; Ann. NY Acad. Sci. 910, 207 (2000) Abstract
A novel, extraneuronal role for cyclin-dependent protein kinase 5 (CDK5): modulation of cAMP-induced apoptosis in rat leukemia cells: T. Sandal, et al.; J. Biol. Chem. 277, 20783 (2002) Abstract; Full Text
Intracellular Targets of Paullones. Identification following affinity purification on immobilized inhibitor: M. Knockaert, et al.; J. Biol. Chem. 277, 25493 (2002) Abstract; Full Text
Alsterpaullone, a novel cyclin-dependent kinase inhibitor, induces apoptosis by activation of caspase-9 due to perturbation in mitochondrial membrane potential: T. Lahusen, et al.; Mol Carcinog 36, 183 (2003) Abstract
The specificities of protein kinase inhibitors: an update: J. Bain, et al.; Biochem. J. 371, 199 (2003) Abstract

Further Categories Containing This Product:

GSK-3 Inhibitors • Apoptosis Inducers & Inhibitors Other Products

ALX-270-387

Revised 18-Jul-07

3-Amino-1H-pyrazolo[3,4-b]quinoxaline
PRODUCT LINE	Cell Cycle
PRODUCT CATEGORY	CDK & Cyclin Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-387-M001		1 mg	40.00 USD
ALX-270-387-M005		5 mg	160.00 USD

Product Specification

FORMULA:	C₉H₇N₅
MW:	185.2
CAS NUMBER:	40254-90-8
PURITY:	≥98% (HPLC)
APPEARANCE:	Red solid.
SOLUBILITY:	Soluble in DMSO.
SHIPPING:	SHIPPED ON BLUE ICE
LONG TERM STORAGE:	+4°C
HANDLING:	Protect from light. Packaged under inert gas.

Product Description

Selective inhibitor of CDK1/cyclin B (IC₅₀=600nM), CDK5/p25 (IC₅₀=400nM) and GSK-3β (IC₅₀=1µM). Does not inhibit Cdc25 phosphatase activity (IC₅₀>10µM).

Product Specific Literature References

Pyrazolo[3,4-b]quinoxalines. A new class of cyclin-dependent kinases inhibitors: M.A. Ortega, et al.; Bioorg. Med. Chem. 10, 2177 (2002) Abstract

Further Categories Containing This Product:

GSK-3 Inhibitors

ALX-270-468

Revised 02-Oct-07

AR-A014418
SYNONYMS	N-(4-Methoxybenzyl)-N′-(5-nitro-1,3-thiazol-2-yl)urea
PRODUCT LINE	Signal Transduction
PRODUCT CATEGORY	GSK-3 Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-468-M001		1 mg	55.00 USD

Product Specification

FORMULA:	C₁₂H₁₂N₄O₄S
MW:	308.3
CAS NUMBER:	487021-52-3
SOURCE/HOST:	Synthetic.
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO, methanol, 100% ethanol or ethyl acetate.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
HAZARD:	HARMFUL. MAY BE CARCINOGENIC.
IDENTITY:	Identity determined by ¹H-NMR.

Product Description

Cell permeable, specific and potent inhibitor of glycogen synthase kinase-3 (GSK-3) (IC₅₀=104nM). Inhibition is competitive with respect to ATP (K_i=38nM).

Product Specific Literature References

Structural insights and biological effects of glycogen synthase kinase 3-specific inhibitor AR-A014418: R. Bhat, et al.; J. Biol. Chem. 278, 45937 (2003) Abstract; Full Text
AR-A014418, a selective GSK-3 inhibitor, produces antidepressant-like effects in the forced swim test: T.D. Gould, et al.; Int. J. Neuropsychopharmacol. 7, 387 (2004) Abstract
Inhibition of glycogen synthase kinase-3 by lithium correlates with reduced tauopathy and degeneration in vivo: W. Noble, et al.; PNAS 102, 6990 (2005) Abstract; Full Text

ALX-270-430

Revised 23-Mar-06

1-Azakenpaullone
SYNONYMS	9-Bromo-7,12-dihydropyrido[3',2':2,3]azepino[4,5-b]indol-6(5H)-one
PRODUCT LINE	Signal Transduction
PRODUCT CATEGORY	GSK-3 Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-430-M001		1 mg	95.00 USD
ALX-270-430-M005		5 mg	380.00 USD

Product Specification

FORMULA:	C₁₅H₁₀BrN₃O
MW:	328.2
PURITY:	≥95% (HPLC)
APPEARANCE:	Off-white to tan powder.
SOLUBILITY:	Soluble in DMSO; insoluble in water.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stock solutions are stable for up to 6 months when stored at -20°C.
HANDLING:	Protect from light.

Product Description

Analog of kenpaullone (Prod. No. ALX-270-274) acting as a potent and ATP-competitive inhibitor of GSK-3β (IC₅₀=18nM). Displays ~100-200 fold greater selectivity on
GSK-3β than over CDK1/cyclin B and CDK5/p25 (IC₅₀=2.0µM and 4.2µM, respectively).

Product Specific Literature References

1-Azakenpaullone is a selective inhibitor of glycogen synthase kinase-3 beta: C. Kunick, et al.; Bioorg. Med. Chem. Lett. 14, 413 (2004) Abstract
Novel CDK inhibition profiles of structurally varied 1-aza-9-oxafluorenes: B. Voigt, et al.; Bioorg. Med. Chem. Lett. 15, 823 (2005) Abstract

Related Products

ALX-270-274

Kenpaullone

ALX-270-442

Revised 06-Oct-08

CDK1/2 Inhibitor III
SYNONYMS	5-Amino-3-((4-(aminosulfonyl)phenyl)amino)-N-(2,6-difluorophenyl)-1H-1,2,4-triazole-1-carbothioamide
PRODUCT LINE	Cell Cycle
PRODUCT CATEGORY	CDK & Cyclin Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-442-M001		1 mg	118.00 USD

Product Specification

FORMULA:	C₁₅H₁₃F₂N₇O₂S₂
MW:	425.4
CAS NUMBER:	443798-55-8
PURITY:	≥95% (HPLC)
APPEARANCE:	White to off-white solid.
SOLUBILITY:	Soluble in DMSO (10mg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
USE/STABILITY:	Stock solutions are stable for up to 6 months when stored at -20°C.
HANDLING:	Protect from light.
HAZARD:	HARMFUL.
IDENTITY:	Identity determined by NMR.

Product Description

Cell permeable triazolo-diamine compound that displays anti-proliferative properties in various human cancer cells (IC₅₀=20nM, 35nM and 92nM in HCT-116, HeLa, and A375 cells). Acts as a highly potent, ATP-competitive inhibitor of CDK1/cyclin B and CDK2/cyclin A (IC₅₀=600pM and 500pM) with selectivity over VEGF-R2 and GSK-3β (IC₅₀=32nM and 140nM).

Product Specific Literature References

1-Acyl-1H-[1,2,4]triazole-3,5-diamine analogues as novel and potent anticancer cyclin-dependent kinase inhibitors: synthesis and evaluation of biological activities: R. Lin, et al.; J. Med. Chem. 48, 4208 (2005) Abstract

Further Categories Containing This Product:

Tyrosine Kinase Inhibitors • GSK-3 Inhibitors • Antitumor Agents (Anti-proliferative) • VEGFs & VEGF-Rs Other Products

ALX-350-289

Revised 05-Apr-08

10Z-Hymenialdisine
SYNONYMS	4-(2-Amino-4-oxo-2-imidazolin-5-ylidene)-2-bromo-4,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one
PRODUCT LINE	Natural Products / Antibiotics
PRODUCT CATEGORY	Natural Products - Protein Kinase Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-350-289-C500		500 µg	190.00 USD

Product Specification

FORMULA:	C₁₁H₁₀BrN₅O₂
MW:	324.1
CAS NUMBER:	82005-12-7
SOURCE/HOST:	Isolated from sponge Axinella damicornis (Stylissa damicornis).
PURITY:	≥97%
APPEARANCE:	Yellow needles.
SOLUBILITY:	Soluble in DMSO.
SHIPPING:	AMBIENT
LONG TERM STORAGE:	-20°C
HANDLING:	Protect from light.
HAZARD:	TOXIC.

Product Description

Originally isolated from the sponges Axinella verrucosa and Acantella aurantiaca. Potent inhibitor of mitogen-activated protein kinase kinase-1 (MEK-1) (IC₅₀=6nM). Blocks the in vivo phosphorylation of the microtubule-binding protein tau at sites that are hyperphosphorylated by glycogen synthase kinase-β (GSK-3β) and CDK5/p35 in Alzheimer’s disease. Inhibitor of DNA damage checkpoint at G2 phase (IC₅₀=6µM), cyclin-dependent kinases CDK1/cyclin B (IC₅₀=22nM), CDK2/cyclin A (IC₅₀=70nM), CDK2/cyclin E (IC₅₀=40nM), CDK4/cyclin D1 (IC₅₀=600nM), CDK5/p25 (IC₅₀=28nM), GSK-3β (IC₅₀=10nM), and casein kinase 1 (CK1) (IC₅₀=35nM). Inhibitor of NF-κB activation and of various pro-inflammatory cytokines such as IL-1, IL-2 (IC₅₀=2.4µM), IL-6, IL-8, TNF-α (IC₅₀=1.4µM) and nitric oxide (NO) (IC₅₀=0.8µM) in a variety of cell lines.

Product Specific Literature References

Isolation and x-ray crystal structure of a novel bromo-compound from two marine sponges: G. Cimino, et al.; Tetrahedron Lett. 23, 767 (1982)
Bioactive alkaloids from the tropical marine sponge Axinella carteri: A. Supriyono, et al.; Z. Naturforsch. [C] 50, 669 (1995) Abstract
The natural product hymenialdisine inhibits interleukin-8 production in U937 cells by inhibition of nuclear factor-kappaB: J.J. Breton & M.C. Chabot-Fletcher; J. Pharmacol. Exp. Ther. 282, 459 (1997) Abstract; Full Text
Inhibition of NFkappaB-mediated interleukin-1beta-stimulated prostaglandin E2 formation by the marine natural product hymenialdisine: A. Roshak, et al.; J. Pharmacol. Exp. Ther. 283, 955 (1997) Abstract; Full Text
Inhibition of interleukin-1-induced proteoglycan degradation and nitric oxide production in bovine articular cartilage/chondrocyte cultures by the natural product, hymenialdisine: A.M. Badger, et al.; J. Pharmacol. Exp. Ther. 290, 587 (1999) Abstract; Full Text
Inhibition of cyclin-dependent kinases, GSK-3beta and CK1 by hymenialdisine, a marine sponge constituent: L. Meijer, et al.; Chem. Biol. 7, 51 (2000) Abstract
Inhibition of the G2 DNA damage checkpoint and of protein kinases Chk1 and Chk2 by the marine sponge alkaloid debromohymenialdisine: D. Curman, et al.; J. Biol. Chem. 276, 17914 (2001) Abstract; Full Text
An investigation of cell proliferation and soluble mediators induced by interleukin 1beta in human synovial fibroblasts: comparative response in osteoarthritis and rheumatoid arthritis: H. Inoue, et al.; Inflamm. Res. 50, 65 (2001) Abstract
Aldisine alkaloids from the Philippine sponge Stylissa massa are potent inhibitors of mitogen-activated protein kinase kinase-1 (MEK-1): D. Tasdemir, et al.; J. Med. Chem. 45, 529 (2002) Abstract
Inhibition of cytokine production by hymenialdisine derivatives: V. Sharma, et al.; J. Med. Chem. 47, 3700 (2004) Abstract

Further Categories Containing This Product:

CDK & Cyclin Inhibitors • MAPK Pathway Inhibitors • Natural Products - NF-kB Pathway Inhibitors • Natural Products for Cell Cycle Research • Natural Products - Nitric Oxide Pathway Modulators • NF-kB Pathway Inhibitors • DNA Damage Checkpoint Other Products • Alkaloids • GSK-3 Inhibitors

ALX-270-361

Revised 28-Sep-07

Indirubin
PRODUCT LINE	Cell Cycle
PRODUCT CATEGORY	CDK & Cyclin Inhibitors

Ordering Information

Product Numbers:	Format:	Size:	Unit Price:	Quantity:	Add To Cart
ALX-270-361-M001		1 mg	50.00 USD
ALX-270-361-M005		5 mg	200.00 USD

Product Specification

FORMULA:	C₁₆H₁₀N₂O₂
MW:	262.3
CAS NUMBER:	479-41-4
SOURCE/HOST:	Synthetic.
PURITY:	≥98% (¹H-NMR, HPLC)
APPEARANCE:	Purple powder.
SOLUBILITY:	Soluble in DMSO (10mg/ml) or methanol (0.3mg/ml). Sparingly soluble in aqueous buffers (12.5µg/ml).
SHIPPING:	AMBIENT
LONG TERM STORAGE:	+4°C
USE/STABILITY:	Stable for at least 2 years when stored at +4°C in the dark. Stock solutions should be stored in the dark and used within 1 month.
HANDLING:	Keep cool and dry. Protect from light.
IDENTITY:	Identity determined by ¹H-NMR, ¹³C-NMR, IR, ESI-MS and UV.

Product Description

Inhibitor of cyclin-dependent kinases (CDK1/cyclin B (IC₅₀=10µM), CDK2/cyclin A (IC₅₀=2.2µM), CDK2/cyclin E (IC₅₀=7.5µM), CDK4/cyclin D1 (IC₅₀=12µM), CDK5/p35 (IC₅₀=5.5µM)) [1] and of GSK-3β (IC₅₀=600nM) [2]. Inhibits inflammatory reaction in delayed-type hypersensitivity in mice [3]. Ligand of human aryl hydrocarbon receptor [4]. Exhibits anti-cancer activity [5] [6].

Product Specific Literature References

[1] Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases: R. Hoessel, et al.; Nature Cell Biol. 1, 60 (1999) Abstract
[2] Indirubins inhibit glycogen synthase kinase-3 beta and CDK5/p25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer’s disease. A property common to most cyclin-dependent kinase inhibitors?: S. Leclerc, et al.; J. Biol. Chem. 276, 251 (2001) Abstract; Full Text
[3] Indirubin inhibits inflammatory reactions in delayed-type hypersensitivity: T. Kunikata, et al.; Eur. J. Pharmacol. 410, 93 (2000) Abstract
[4] Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine: J. Adachi, et al.; J. Biol. Chem. 276, 31475 (2001) Abstract; Full Text
[5] Molecular mechanisms of indirubin and its derivatives: novel anticancer molecules with their origin in traditional Chinese phytomedicine: G. Eisenbrand, et al.; J. Cancer Res. Clin. Oncol. 130, 627 (2004) Abstract
[6] Indirubin enhances tumor necrosis factor-induced apoptosis through modulation of nuclear factor-kappa B signaling pathway: G. Sethi, et al.; J. Biol. Chem. 281, 23425 (2006) Abstract

General Information

BACKGROUND/TECHNICAL INFORMATION

Indirubin is derived from various natural sources, such as Indigofera indica, Isatis tinctoria and I. indigotica by fermentation, oxidation and the presence of light as a by product of indigo formation. Indirubin is also present in human urine and fetal bovine serum [4]. Preclinical studies of indirubin its confirmed anti-tumor activity. Efficacy against chronic myelocytic leukemia was demonstrated in clinical trials in China [2].

ALX-270-271	Indirubin-3'-monoxime
ALX-270-296	Indirubin-5-sulfonic acid . sodium salt
ALX-270-424	5-Iodo-indirubin-3'-monoxime
ALX-430-149	7BIO
ALX-430-157	Me-7BIO
ALX-430-156	6BIO