6955-16-4Relevant academic research and scientific papers
Pro-apoptotic activity of lipidic α-amino acids isolated from Protopalythoa variabilis
Wilke, Diego Veras,Jimenez, Paula Christine,Araújo, Renata Mendona,Da Silva, Wildson Max Barbosa,Pessoa, Otília Deusdênia Loiola,Silveira, Edilberto Rocha,Pessoa, Claudia,De Moraes, Manoel Odorico,Skwarczynski, Mariusz,Simerska, Pavla,Toth, Istvan,Costa-Lotufo, Letícia Veras
scheme or table, p. 7997 - 8004 (2011/02/23)
Lipidic α-amino acids (LAAs) have been described as non-natural amino acids with long saturated or unsaturated aliphatic chains. In the continuing prospect to discover anticancer agents from marine sources, we have obtained a mixture of two cytotoxic LAAs (1a and 1b) from the zoanthid Protopalythoa variabilis. The anti-proliferative potential of 14 synthetic LAAs and 1a/1b were evaluated on four tumor cell lines (HCT-8, SF-295, MDA-MB-435, and HL-60). Five of the synthetic LAAs showed high percentage of tumor cell inhibition, while 1a/1b completely inhibited tumor cell growth. Additionally, apoptotic effects of 1a/1b were studied on HL-60 cell line. 1a/1b-treated cells showed apoptosis morphology, loss of mitochondrial potential, and DNA fragmentation.
New GM1 ganglioside derivatives for selective single and double labelling of the natural glycosphingolipid skeleton
Polyakova, Svetlana M.,Belov, Vladimir N.,Yan, Sergey F.,Eggeling, Christian,Ringemann, Christian,Schwarzmann, Guenter,De Meijere, Armin,Hell, Stefan W.
scheme or table, p. 5162 - 5177 (2010/01/11)
Selective single and double labelling of the natural ganglioside GM1. enables one to introduce various markers into different parts of the glycosphingolipid molecule without changing the natural skeleton. To that end, N-Fmoc-2amino-, N-Fmoc-18-amino- and S-(ethoxythiocarbonyl)-18mercaptostearic acids have been prepared, and. coupled with the primary amino group in the sphingosine part of lyso-GM1 and. deAc-deAcyl-GM1. gangliosides. The products of these coupling reactions - building blocks 16a, 16b, 16c, 26 and 27 - may be used for the synthesis of GM1 derivatives with one or two fluorescent dye moieties or other labels of various polarities. Examples of various labelling strategies, using hydrophilic and lipophilic photostable fluorescent dyes, have been made available. The GM1. derivatives 17a, 22a and 23c labelled with the fluorescent dye ATTO 647N or the doubly labelled derivative 25b can be used as probes in fluorescence correlation spectroscopy (in conventional, microscopy or stimulated emission depletion nanoscopy) to study the diffusion of lipid analogues in model or live cell membranes.
