ALEXIS Biochemicals: 10Z-Hymenialdisine

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

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