Latrunculin A is a thiazolidine macrolide found in the Red Sea sponge. Latrunculin A binds actin, releasing RhoA effector mDia1 and inhibiting microtubule polymerization in vitro. Latrunculin A may have anticancer or anti-angiogenic activities, as a synthetic derivative inhibits cell invasion and activation of HIF-1α in breast cancer cells.
| Cas No. | 76343-93-6 |
|---|---|
| Formula | C22H31NO5S |
| Formula Wt. | 421.55 |
| IUPAC Name | (4R)-4-[(1R,4S,5Z,7E,11Z,15R,17R)-17-hydroxy-4,11-dimethyl-13-oxo-14,18-dioxabicyclo[13.3.1]nonadeca-5,7,11-trien-17-yl]-1,3-thiazolidin-2-one |
| Appearance | White to off white powder |
| Store Temp | 4°C |
|---|---|
| Ship Temp | Ambient |
| Info Sheet | L0076 Info Sheet PDF |
|---|
Helal MA, Khalifa S, Ahmed S. Differential binding of latrunculins to G-actin: a molecular dynamics study. J Chem Inf Model. 2013 Sep 23;53(9):2369-75. PMID: 23988111.
Bartolini F, Ramalingam N, Gundersen GG. Actin-capping protein promotes microtubule stability by antagonizing the actin activity of mDia1. Mol Biol Cell. 2012 Oct;23(20):4032-40. PMID: 22918941.
Rennebaum S, Caflisch A. Inhibition of interdomain motion in g-actin by the natural product latrunculin: a molecular dynamics study. Proteins. 2012 Aug;80(8):1998-2008. PMID: 22488806.
Khanfar MA, Youssef DT, El Sayed KA. Semisynthetic latrunculin derivatives as inhibitors of metastatic breast cancer: biological evaluations, preliminary structure-activity relationship and molecular modeling studies. ChemMedChem. 2010 Feb 1;5(2):274-85. PMID: 20043312.
Sayed KA, Khanfar MA, Shallal HM, et al. Latrunculin A and its C-17-O-carbamates inhibit prostate tumor cell invasion and HIF-1 activation in breast tumor cells. J Nat Prod. 2008 Mar;71(3):396-402. PMID: 18298079.
