10Z-Hymenialdisine (CAS: 82005-12-7)

C₁₁H₁₀BrN₅O₂

• Insecticidal and cytotoxic [1].
• Potent NF-κB inhibitor. Inhibits various pro-inflammatory cytokines such as IL-1, IL-2, IL-6, IL-8, TNF-α and nitric oxide (NO) in a variety of cell lines [2, 3, 4, 9].
• ATP-competitive kinase inhibitor. Inhibits DNA damage checkpoint at G2, cyclin-dependent kinases CDK1/cyclin B, CDK2/cyclin A, CDK2/cyclin E, CDK4/cyclin D1, CDK5/p25, GSK-3β and casein kinase 1 (CK1) [5, 6].
• Potent mitogen-activated protein kinase kinase-1 (MEK-1) inhibitor [7].
• MARK (microtubule affinity-regulating kinase) inhibitor [8].

1. Bioactive alkaloids from the tropical marine sponge Axinella carteri: A. Supriyono, et al.; Z. Naturforsch. [C] 50, 669 (1995)
2. 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)
3. 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)
4. 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)
5. Inhibition of cyclin-dependent kinases, GSK-3beta and CK1 by hymenialdisine, a marine sponge constituent: L. Meijer, et al.; Chem. Biol. 7, 51 (2000)
6. 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)
7. 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)
8. Protein kinase MARK/PAR-1 is required for neurite outgrowth and establishment of neuronal polarity: J. Biernat et al.; Mol. Biol. Cell. 13, 4013 (2002)
9. Inhibition of cytokine production by hymenialdisine derivatives: V. Sharma, et al.; J. Med. Chem. 47, 3700 (2004)