95548-26-8Relevant articles and documents
Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration
Lin, Hua,Long, Jonathan Z.,Roche, Alexander M.,Svensson, Katrin J.,Dou, Florence Y.,Chang, Mi Ra,Strutzenberg, Timothy,Ruiz, Claudia,Cameron, Michael D.,Novick, Scott J.,Berdan, Charles A.,Louie, Sharon M.,Nomura, Daniel K.,Spiegelman, Bruce M.,Griffin, Patrick R.,Kamenecka, Theodore M.
supporting information, p. 3224 - 3230 (2018/04/23)
N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.
Synthesis of lipid a analogues containing glucose instead of glucosamine and their LPS-antagonistic activities
Shiozaki, Masao,Watanabe, Yukiko,Iwano, Yuji,Kaneko, Toshio,Doi, Hiromi,Tanaka, Daisuke,Shimozato, Takaichi,Kurakata, Shin-Ichi
, p. 5101 - 5122 (2007/10/03)
Lipid A analogues containing glucose in substitution for glucosamine on the reducing end were synthesized, and the inhibitory activities on LPS-induced TNFα production (LPS-antagonistic activity) in vitro using human whole blood cells were measured. The I
Syntheses of glucose-containing lipid A analogues and their LPS-antagonistic activities
Shiozaki, Masao,Doi, Hiromi,Tanaka, Daisuke,Shimozato, Takaichi,Kurakata, Shin-Ichi
, p. 1091 - 1104 (2007/10/03)
Three anomeric pairs of lipid A-type disaccharides containing a glucose on their reducing end were synthesized, and their LPS-antagonistic activities were measured. The inhibitory activities (IC50) on the LPS-induced TNFα production of these six compounds (16α, 16β, 28α, 28β, 40α, and 40β) toward human whole blood cells were 0.35, 0.42, 2.37, 1.16, 2.89, and 7.70 nM, respectively.
Vanilloids. 1. Analogs of Capsaicin with Antinociceptive and Antiinflammatory Activity
Janusz, John M.,Buckwalter, Brian L.,Young, Patricia A.,LaHann, Thomas R.,Farmer, Ralph W.,et al.
, p. 2595 - 2604 (2007/10/02)
As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion the parent structure (and related compounds derived from homovanillic acid) was varied.In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures were active.Short-chain compounds were active by systemic administration in the assays mentioned above but they retained the high pungency and acute toxicity characteristic of capsaicin.In contrast, the long chain cis-unsaturates, NE-19550 (vanillyloleamide) and NE-28345 (oleylhomovanillamide), were orally active, less pungent, and less acutely toxic than capsaicin.The potential of these compounds as antiinflammatory/analgesic agents is discussed in light of recent data on the mechanism of action of vanilloids on sensory nerve fibers.
