Narciclasine

• CAT Number: I003024
• CAS Number: 29477-83-6
• Molecular Formula: C14H13NO7
• Molecular Weight: 307.3
• Purity: ≥95%
• Synonyms: (2S,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
• Target: ROCK
• Solubility: DMSO > 10 mg.mL
• Storage: Store at -20°C
• InChI: InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1
• InChIKey: LZAZURSABQIKGB-AEKGRLRDSA-N
• SMILES: OC1=C(C(N[C@]2([H])C3=C[C@H](O)[C@@H](O)[C@H]2O)=O)C3=CC4=C1OCO4

Narciclasine is a Rho/Rho kinase/LIM kinase/cofilin signaling pathway activator.IC50 Value:Target: Apoptosis inducerNarciclasine modulates the Rho/ROCK/LIM kinase/cofilin pathway; stimulates RhoA activation and induces actin polymerization. The cytostatic activity of Narciclasine involves the impairment of actin cytoskeleton organization by targeting GTPases, including RhoA and the elongation factor eEF1A. Thus, Narciclasine is a potentially promising agent for the treatment of primary brain cancers and various brain metastases. Also Narciclasine is an actin stress fiber formation inducer; a plant growth modulator.

Reference

1:Metabolism: Narciclasine boosts energy metabolism. Greenhill C.Nat Rev Endocrinol. 2017 Apr;13(4):189. doi: 10.1038/nrendo.2017.25. Epub 2017 Mar 3. No abstract available. PMID: 28256628 2:Narciclasine attenuates diet-induced obesity by promoting oxidative metabolism in skeletal muscle. Julien SG, Kim SY, Brunmeir R, Sinnakannu JR, Ge X, Li H, Ma W, Yaligar J, Kn BP, Velan SS, Röder PV, Zhang Q, Sim CK, Wu J, Garcia-Miralles M, Pouladi MA, Xie W, McFarlane C, Han W, Xu F.PLoS Biol. 2017 Feb 16;15(2):e1002597. doi: 10.1371/journal.pbio.1002597. eCollection 2017 Feb. PMID: 28207742 Free PMC Article3:Narciclasine – an Amaryllidaceae Alkaloid with Potent Antitumor and Anti-Inflammatory Properties. Fürst R.Planta Med. 2016 Nov;82(16):1389-1394. Epub 2016 Aug 19. Review. PMID: 27542176 4:Transcriptomic analysis reveals key early events of narciclasine signaling in Arabidopsis root apex. Cao X, Ma F, Xu T, Wang J, Liu S, Li G, Su Q, Qiao Z, Na X.Plant Cell Rep. 2016 Nov;35(11):2381-2401. Epub 2016 Aug 25. PMID: 27562382 5:Narciclasine, a potential allelochemical, affects subcellular trafficking of auxin transporter proteins and actin cytoskeleton dynamics in Arabidopsis roots. Hu Y, Na X, Li J, Yang L, You J, Liang X, Wang J, Peng L, Bi Y.Planta. 2015 Dec;242(6):1349-60. doi: 10.1007/s00425-015-2373-6. Epub 2015 Aug 2. PMID: 26232920 6:Haemanthus coccineus extract and its main bioactive component narciclasine display profound anti-inflammatory activities in vitro and in vivo. Fuchs S, Hsieh LT, Saarberg W, Erdelmeier CA, Wichelhaus TA, Schaefer L, Koch E, Fürst R.J Cell Mol Med. 2015 May;19(5):1021-32. doi: 10.1111/jcmm.12493. Epub 2015 Mar 5. PMID: 25754537 Free PMC Article7:Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide. Vshyvenko S, Reisenauer MR, Rogelj S, Hudlicky T.Bioorg Med Chem Lett. 2014 Sep 1;24(17):4236-8. doi: 10.1016/j.bmcl.2014.07.034. Epub 2014 Jul 19. PMID: 25108300 Free PMC Article8:Inhibition of root growth by narciclasine is caused by DNA damage-induced cell cycle arrest in lettuce seedlings. Hu Y, Li J, Yang L, Nan W, Cao X, Bi Y.Protoplasma. 2014 Sep;251(5):1113-24. doi: 10.1007/s00709-014-0619-y. Epub 2014 Jan 31. PMID: 24482192 9:Narciclasine inhibits the responses of Arabidopsis roots to auxin. Hu Y, Yang L, Na X, You J, Hu W, Liang X, Liu J, Mao L, Wang X, Wang H, Bi Y.Planta. 2012 Aug;236(2):597-612. doi: 10.1007/s00425-012-1632-z. Epub 2012 Apr 5. PMID: 22476291 10:Narciclasine as well as other Amaryllidaceae isocarbostyrils are promising GTP-ase targeting agents against brain cancers. Van Goietsenoven G, Mathieu V, Lefranc F, Kornienko A, Evidente A, Kiss R.Med Res Rev. 2013 Mar;33(2):439-55. doi: 10.1002/med.21253. Epub 2012 Mar 14. Review. PMID: 22419031