68709-94-4Relevant academic research and scientific papers
An effective and safe enkephalin analog for antinociception
Durgarao Viswanadham,B?ttger, Roland,Hohenwarter, Lukas,Nguyen, Anne,Rouhollahi, Elham,Smith, Alexander,Tsai, Yi-Hsuan,Chang, Yuan-Yu,Ortiz, Christopher Llynard,Yang, Lee-Wei,Jimenez, Liliana,Li, Siyuan,Hur, Chan,Li, Shyh-Dar
, (2021/07/10)
Opioids account for 69,000 overdose deaths per annum worldwide and cause serious side effects. Safer analgesics are urgently needed. The endogenous opioid peptide Leu-Enkephalin (Leu-ENK) is ineffective when introduced peripherally due to poor stability a
Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent
Singh, Palwinder,Kaur, Sukhmeet,Kaur, Jagroop,Singh, Gurjit,Bhatti, Rajbir
supporting information, p. 3920 - 3934 (2016/05/24)
Among the small peptides 2-31, (H)Gly-Gly-Phe-Leu(OMe) (30) reduced prostaglandin production of COX-2 with an IC50 of 60 nM relative to 6000 nM for COX-1. The 5 mg kg-1 dose of compound 30 rescued albino mice by 80% from capsaicin-induced paw licking and recovered it by 60% from carrageenan-induced inflammation. The mode of action of compound 30 for targeting COX-2, iNOS, and VGSC was investigated by using substance P, l-arginine, and veratrine, respectively, as biomarkers. The interactions of 30 with COX-2 were supported by isothermal calorimetry experiments showing a Ka of 6.10 ± 1.10 × 104 M-1 and ΔG of -100.3 kJ mol-1 in comparison to a Ka 0.41 × 103 ± 0.09 M-1 and ΔG of -19.2 ± 0.06 kJ mol-1 for COX-1. Moreover, compound 30 did not show toxicity up to a 2000 mg kg-1 dose. Hence, we suggest peptide 30 as a highly potent and promising candidate for further development into an anti-inflammatory drug.
Silver-catalyzed late-stage fluorination
Tang, Pingping,Furuya, Takeru,Ritter, Tobias
supporting information; experimental part, p. 12150 - 12154 (2010/10/04)
Carbon-fluorine bond formation by transition metal catalysis is difficult, and only a few methods for the synthesis of aryl fluorides have been developed. All reported transition-metal-catalyzed fluorination reactions for the synthesis of functionalized arenes are based on palladium. Here we present silver catalysis for carbon-fluorine bond formation. Our report is the first example of the use of the transition metal silver to form carbon-heteroatom bonds by cross-coupling catalysis. The functional group tolerance and substrate scope presented here have not been demonstrated for any other fluorination reaction to date.
DIASTEREOSELECTIVE HYDROGENATION OF MONODEHYDRO ENKEPHALINS CONTROLLED BY CHIRAL RHODIUM CATALYSTS
Hammadi, A.,Nuzillard, J. M.,Poulin, J. C.,Kagan, H. B.
, p. 1247 - 1262 (2007/10/02)
Protected (Z)dehydrophenylalanyl-Leu-enkephalin, (Z)dehydrotyrosyl-Leu-enkephalin and (Z)dehydrotyrosyl-(R)Ala2-Leu-enkephalin, have been synthesized.These compounds have been hydrogenated to give protected Leu-enkephalins in the presence of various chiral rhodium complexes.Deprotection of the product gave Leu-enkephalins or epimers, ytterbium in liquid ammonia allows smooth deprotection of NHCBz or OTs groups on small amounts of peptides.Strong stereocontrol could be achieved by suitable choice of the chiral catalyst.This method has good potential for stereospecific labelling of enkephalins and other small peptides.
