A class of novel nitronyl nitroxide labeling basic and acidic amino acids: synthesis, application for preparing ESR optionally labeling peptides, and bioactivity investigations.
Aimed at optional ESR label 2-(4'-hydroxyl)phenyl-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl was introduced into the guanido of L-Arg-OH, the omega-amino group of L-Lys-OH with methylcarboxyl as a linker, and into the beta-carboxyl of L-Asp-OH and the gamma-carboxyl of L-Glu-OH with ethylamino as a linker. It was explored that the synthetic 30 novel ESR labeling amino acid derivatives were stable enough to the reaction conditions of peptide synthesis. Their incorporation led to 12 novel ESR optionally labeling PAK, RGDS, RGDV, and ECG. A series of NO related chemical tests, the in vitro and in vivo assays of these peptides confirmed that this strategy was practical.
Zhang
Jianwei
J
College of Pharmaceutical Sciences, Capital Medical University, Beijing 100069, PR China.
Zhao
Ming
M
Cui
Guohui
G
Peng
Shiqi
S
D024342:Amino Acids, Acidic / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification / Q000494:pharmacology; D024361:Amino Acids, Basic / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification / Q000494:pharmacology; D000818:Animals; D019610:Cytoprotection / Q000187:drug effects; D004578:Electron Spin Resonance Spectroscopy; D005343:Fibrinolytic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000145:classification / Q000494:pharmacology; D005609:Free Radicals / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D016716:PC12 Cells; D010455:Peptides / Q000737:chemistry; D010974:Platelet Aggregation / Q000187:drug effects; D051381:Rats; D013329:Structure-Activity Relationship; D014664:Vasodilation / Q000187:drug effects
D024342:Amino Acids, Acidic; D024361:Amino Acids, Basic; D005343:Fibrinolytic Agents; D005609:Free Radicals; D009589:Nitrogen Oxides; D010455:Peptides