7252-31-5Relevant 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.
Syntheses of polycationic dendrimers on lipophilic peptide core for complexation and transport of oligonucleotides
Wimmer, Norbert,Marano, Robert J.,Kearns, Philip S.,Rakoczy, Elizabeth P.,Toth, Istvan
, p. 2635 - 2637 (2007/10/03)
Synthesis of novel polycationic lipophilic peptide core(s) was accomplished and these agents successfully transfected human retinal pigment epithelium cells with ODN1 upon complexation with the oligonucleotide. The level of transfection was indirectly measured by the decreased production of the protein hVEGF (human vascular endothelial growth factor) in comparison to the transfection agent cytofectin GSV.
Potent immunosuppressants, 2-alkyl-2-aminopropane-1,3-diols
Fujita, Tetsuro,Hirose, Ryoji,Yoneta, Masahiko,Sasaki, Shigeo,Inoue, Kenichiro,Kiuchi, Masatoshi,Hirase, Susumu,Chiba, Kenji,Sakamoto, Hiroshi,Arita, Masafumi
, p. 4451 - 4459 (2007/10/03)
Several immunosuppressants, ISP-I [(2S,3R,4R)-(E)-2-amino-3,4-dihydroxy- 2-(hydroxymethyl)-14-oxoeicos-6-enoic acid, myriocin = thermozymocidin] and mycestericins A-G, were isolated from culture broths of Isaria sinclairii and Mycelia sterilia, respectively. In order to investigate structure-activity relationships, extensive modifications of ISP-I were conducted, and it was established that the fundamental structure possessing the immunosuppressive activity is a symmetrical 2-alkyl-2-aminopropane-1,3-diol. The tetradecyl, pentadecyl, and hexadecyl derivatives prolonged rat skin allograft survival in the combination of LEW donor and F344 recipient and were more effective than cyclosporin A. Among them, 2-amino-2-tetradecylpropane-1,3-diol hydrochloride, ISP-I-55, showed the lowest toxicity. ISP-I-55 is a promising lead compound for the development of effective immunosuppressants for organ transplantations and for the treatment of autoimmune diseases.
Alkylation of diethyl acetamidomalonate by weak electrophiles
Zhu,Galons,Pigeon,Loupy
, p. 215 - 218 (2007/10/02)
Diethyl acetamidomalonate was efficiently alkylated with electrophiles of low reactivity under modified phase transfer-catalysis conditions in the absence of organic solvent using potassium ten-butoxide as a base.
Lipidic Peptides, I Synthesis, Resolution and Structural Elucidation of Lipidic Amino Acids and Their Homo- and Hetero-Oligomers
Gibbons, William A.,Hughes, Richard A.,Charalambous, Mario,Christodoulou, Marika,Szeto, Alice,et al.
, p. 1175 - 1183 (2007/10/02)
The α-amino acids with long alkyl side chains, the so-called lipidic amino acids 1a-e, and their homo-oligomers, the lipidic peptides 1p-aj, represent a class of compounds which combine the structural properties of peptides and proteins with the characteristics of lipids and membranes.The amino acids were synthesised from the appropriate alkyl bromide and diethyl acetamidomalonate.Resolution was made chemically, by forming diastereomers of the amino acid esters with an optically pure α-pinene derivative.The protected homo-oligomers were synthesised in solution with the assistance of a water-soluble carbodiimide coupling agent.In order to modify the physical and chemical properties of the peptides, a series of protected hetero-oligomers were prepared, by similar methods, incorporating either other amino acids (3a-d, 7a-i) or side-chain-substituted lipidic amino acids (6a-d).
