97780-30-8Relevant academic research and scientific papers
Antiproliferative and uncoupling effects of delocalized, lipophilic, cationic gallic acid derivatives on cancer cell lines. Validation in vivo in singenic mice
Jara, José A.,Castro-Castillo, Vicente,Saavedra-Olavarría, Jorge,Peredo, Liliana,Pavanni, Mario,Ja?a, Fabián,Letelier, María Eugenia,Parra, Eduardo,Becker, María Inés,Morello, Antonio,Kemmerling, Ulrike,Maya, Juan Diego,Ferreira, Jorge
, p. 2440 - 2454 (2014/04/17)
Tumor cells principally exhibit increased mitochondrial transmembrane potential (Δψm) and altered metabolic pathways. The therapeutic targeting and delivery of anticancer drugs to the mitochondria might improve treatment efficacy. Gallic acid e
Synthesis and biological characterization of new aminophosphonates for mitochondrial pH determination by 31P NMR spectroscopy
Culcasi, Marcel,Casano, Gilles,Lucchesi, Céline,Mercier, Anne,Clément, Jean-Louis,Pique, Valérie,Michelet, Laure,Krieger-Liszkay, Anja,Robin, Maxime,Pietri, Sylvia
, p. 2487 - 2499 (2013/05/22)
A series of mitochondria targeted α-aminophosphonates combining a diethoxyphosphoryl group and an alkyl chain-connected triphenylphosphonium bromide tail were designed and synthesized, and their pH-sensitive 31P NMR properties and biological activities in vitro and in vivo were evaluated. The results showed a number of these mito-aminophosphonates exhibiting pKa values fitting the mitochondrial pH range, short relaxation, and chemical shift parameters compatible with sensitive 31P NMR detection, and low cytotoxicity on green algae and murine fibroblasts cell cultures. Of these, two selected compounds demonstrated to distribute at NMR detectable levels within the cytosolic and mitochondrial sites following their perfusion to isolated rat livers, with no detrimental effects on cell energetics and aerobic respiration. This study provided a new molecular scaffold for further development of in situ spectroscopic real-time monitoring of mitochondrion/cytosol pH gradients.
A practical route to long-chain non-natural α,ω-diamino acids
Brasile, Giuseppina,Mauri, Laura,Sonnino, Sandro,Compostella, Federica,Ronchetti, Fiamma
, p. 435 - 441 (2013/07/27)
An efficient method for the synthesis of long-chain α,ω-diamino acids, starting from natural α-amino acids, has been developed. The long-chain skeleton has been generated through condensation between a protected aldehyde, derived from l-aspartic acid, and an ylide obtained from an ω-hydroxy-alkyl phosphonium salt. After conversion of the ω-hydroxy group into an amine, catalytic hydrogenation produced the N,N'-protected α,ω-diamino acid. The present route to α,ω-diamino acids allows the modulation of the chain length depending on the length of the ylide used for the Wittig olefination reaction.
Molecular design, synthesis, and evaluation of novel potent apoptosis inhibitors inspired from bongkrekic acid
Okuda, Katsuhiro,Hasui, Keisuke,Abe, Masato,Matsumoto, Kenji,Shindo, Mitsuru
, p. 2253 - 2260 (2013/01/15)
Bongkrekic acid (BKA) is an inhibitor of adenine nucleotide translocase (ANT). Since inhibition of ANT is connected to the inhibition of cytochrome c release from mitochondria, which then results in the suppression of apoptosis, it has been used as a tool for the mechanistic investigation of apoptosis. BKA consists of a long carbon chain with two asymmetric centers, a nonconjugated olefin, two conjugated dienes, three methyl groups, a methoxyl group, and three carboxylic acids. This complicated chemical structure has caused difficulties in synthesis, supply, and biochemical mechanistic investigations. In this study, we designed and synthesized more simple tricarboxylic acids that were inspired by the molecular structure of BKA. Their cytotoxicity and apoptosis-preventing activity in HeLa cells and the effect on the mitochondrial inner membrane potential (Δψm) in HL-60 cells were then evaluated. All tested tricarboxylic acid derivatives including BKA showed little toxicity against HeLa cells. BKA and two of the synthesized derivatives significantly suppressed staurosporine (STS)-induced reductions in cell viability. Furthermore, STS-induced Δψm collapse was significantly restored by pretreatment with BKA and a tricarboxylic acid derivative. Other derivatives, in which one of three carboxylic acids was esterified, exhibited potent toxicity, especially a derivative bearing a carbon chain of the same length as that of BKA. In conclusion, we have developed a new lead compound as an apoptosis inhibitor bearing three carboxylic acids connected with the proper length of a long carbon chain.
An Efficient Synthesis of the Plant Growth Hormone 1-Triacontanol
Tran-Thi, N. H.,Falk, H.
, p. 565 - 568 (2007/10/02)
A high yield synthesis of 1-triacontanol was based on the cheap and easily available starting materials 1-octadecanol and 1,12-dodecanediol.The first one was converted to octadecanal using a phase transfer system, whereas the second one after phase transfer bromination and reaction with triphenylphosphine provided 1-hydroxy-12-triphenylphosphonium bromide.Wittig reaction of these two synthons and subsequent hydrogenation furnished the desired product. - Keywords: 1-Triacontanol: Wittig reaction; Phase transfer reaction; Plant growth hormone
Studies on Synthesis of Linear Aliphatic Compounds. Part 2. The Realisation of a Strategy for Repeated Molecular Doubling.
Igner, Eva,Paynter, Oliver I.,Simmonds, Derek J.,Whiting, Mark C.
, p. 2447 - 2454 (2007/10/02)
Routes from C11 and C12 starting-materials, obtainable free from near homologues, to compounds of doubled chain length have been explored as approaches to the synthesis of n-paraffins and of terminally mono- or bi-functional derivatives.Acetylene alkylation routes lead to problems with prtotecting groups, but the use of the Wittig reaction provides a method of molecular doubling convenient for repeated use, with formation of chain-lengths rising in a geometrical progression.The general problems inherent in the synthesis of very long-chain paraffins are discussed, earlier work is reviewed, and criteria for success are suggested.A useful protecting group for hydroxyl, the tri-p-tolylmethyl(trimtyl) ether, is described.
