[Substituted 6-aminonaphthalene-1-sulfamides as fluorogenic indicators groups for synthetic proteinase substrates].
Alkyl substituted 6-aminonaphthalene-1-sulphamides (ANSA), hydrobromides of substituted 6-(N alpha-benzyloxycarbonyl-L-arginyl)aminonaphthalene-1-sulphamides (Z-Arg-ANSA) and hydrobromides of 6-(benzyloxycarbonylglycylglycyl-L- arginyl)aminonaphthalene-1-sulphamides (Z-Gly-Gly-Arg-ANSA) are synthesized and their absorption and emission spectra measured. ANSA have an emission band at 470-480 nm, comparable or exceeding in intensity that of compounds used as fluorogenic leaving groups in peptide cleavage reactions. The bands of Z-Arg-ANSA and Z-Gly-Gly-Arg-ANSA are shifted to the short-wave side and do not overlap with ANSA's emission band. Reactions of Z-Arg-ANSA and Z-Gly-Gly-Arg-ANSA with trypsin were studied. The kinetic parameters (kcat and Km) of the reaction of Z-Arg-ANSA were found to depend on the nature and the number of substituents in the sulphamide. In the case of Z-Gly-Gly-Arg-ANSA, this dependence is negligible and kcat/Km exceeds by over ten times this parameter of Z-Arg-ANSA. ANSA can apparently be used in the synthesis of fluorogenic substrates of proteases.
Talaĭkite
Z A
ZA
Butenas
S Iu
SIu
Palaĭma
A I
AI
D015081:2-Naphthylamine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D010450:Endopeptidases / Q000378:metabolism*; D005456:Fluorescent Dyes; D007700:Kinetics; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013379:Substrate Specificity; D013449:Sulfonamides / Q000737:chemistry / Q000378:metabolism*
D005456:Fluorescent Dyes; D013449:Sulfonamides; D015081:2-Naphthylamine; D010450:Endopeptidases
Zameshchennye 6-aminonaftalin-1-sul'famidy v kachestve fluorogennykh indikatornykh grupp sinteticheskikh substratov proteinaz.