4254-88-0Relevant academic research and scientific papers
A simple route to [11C]N-Me labeling of aminosuberic acid for proof of feasibility imaging of the xC- transporter
Yang, Hua,Miao, Qing,Johnson, Bruce F.,Rishel, Michael J.,Sossi, Vesna,Dinelle, Katherine,Bénard., Fran?ois,Yapp, Donald T.,Webster, Jack M.,Schaffer, Paul
, p. 5512 - 5515 (2015/02/19)
Oxidative stress has been implicated in a variety of conditions, including cancer, heart failure, diabetes, neurodegeneration and other diseases. A potential biomarker for oxidative stress is the cystine/glutamate transporter, system xC-. l-Aminosuberic acid (l-ASu) has been identified as a system xC- substrate. Here we report a facile method for [11C]N-Me labeling of l-ASu, automation of the radiochemical process, and preliminary PET imaging with EL4 tumor bearing mice. The results demonstrate uptake in the tumor above background, warranting further studies on the use of radiolabeled analogs of l-ASu as a PET imaging agent for system xC-.
Structure elucidation and antimalarial activity of apicidin F: An apicidin-like compound produced by Fusarium fujikuroi
Von Bargen, Katharina Walburga,Niehaus, Eva-Maria,Bergander, Klaus,Brun, Reto,Tudzynski, Bettina,Humpf, Hans-Ulrich
, p. 2136 - 2140 (2014/01/06)
Apicidins are cyclic tetrapeptides with histone deacetylase inhibitory activity. Since their discovery in 1996 a multitude of studies concerning the activity against protozoa and certain cancer cell lines of natural and synthetic apicidin analogues have been published. Until now, the only published natural sources of apicidin are the fungus Fusarium pallidoroseum, later known as F. semitectum and two unspecified Fusarium strains. The biosynthetic origin of apicidins could be associated with a gene cluster, and a biosynthetic pathway has been proposed. Recently, our group was able to identify for the first time an apicidin-like gene cluster in F. fujikuroi that apparently does not lead to the production of any known apicidin analogue. By overexpressing the pathway-specific transcription factor we were able to identify a new apicidin-like compound. The present study provides the complete structure elucidation of the new compound, named apicidin F. Activity evaluation against Plasmodium falciparum showed good in vitro activity with an IC50 value of 0.67 μM.
Design, synthesis, potency, and cytoselectivity of anticancer agents derived by parallel synthesis from α-aminosuberic acid
Kahnberg, Pia,Lucke, Andrew J.,Glenn, Matthew P.,Boyle, Glen M.,Tyndall, Joel D. A.,Parsons, Peter G.,Fairlie, David P.
, p. 7611 - 7622 (2007/10/03)
Chemotherapy in the last century was characterized by cytotoxic drugs that did not discriminate between cancerous and normal cell types and were consequently accompanied by toxic side effects that were often dose limiting. The ability of differentiating agents to selectively kill cancer cells or transform them to a nonproliferating or normal phenotype could lead to cell- and tissue-specific drugs without the side effects of current cancer chemotherapeutics. This may be possible for a new generation of histone deacetylase inhibitors derived from amino acids. Structure-activity relationships are now reported for 43 compounds derived from 2-aminosuberic acid that kill a range of cancer cells, 26 being potent cytotoxins against MM96L melanoma cells (IC50 20 nM-1 μM), while 17 were between 5- and 60-fold more selective in killing MM96L melanoma cells versus normal (neonatal foreskin fibroblasts, NFF) cells. This represents a 10- to 100-fold increase in potency and up to a 10-fold higher selectivity over previously reported compounds derived from cysteine (J. Med. Chem. 2004, 47, 2984). Selectivity is also an underestimate, because the normal cells, NFF, are rarely all killed by the drugs that also induce selective blockade of the cell cycle for normal but not cancer cells. Selected compounds were tested against a panel of human cancer cell lines (melanomas, prostate, breast, ovarian, cervical, lung, and colon) and found to be both selective and potent cytotoxins (IC50 20 nM-1 μM). Compounds in this class typically inhibit human histone deacetylases, as evidenced by hyperacetylation of histones in both normal and cancer cells, induce expression of p21, and differentiate surviving cancer cells to a nonproliferating phenotype. These compounds may be valuable leads for the development of new chemotherapeutic agents.
Diheteropeptin, a novel substance with TGF-β-like activity, produced by a fungus, Diheterospora chlamydosporia. II. Physico-chemical properties and structure elucidation
Masuoka,Shin-ya,Furihata,Matsumoto,Takebayashi,Nagai,Suzuki,Hayakawa,Seto
, p. 793 - 798 (2007/10/03)
The structure of diheteropeptin (1), a TGF-β-like active substance from Diheterospora chlamydosporia Q58044, was determined to be a new cyclotetrapeptide, cyclo[2- aminoisobutyryl-(S)-phenylalanyl-(R)-prolyl-(2S,8R,9R)-2-amino-8, 9-dihydroxydecanoyl-] by NMR, mass spectrometric and chemical studies.
