Premium
Selective Ruthenium Labeling of the Tryptophan Residue in the Bee Venom Peptide Melittin
Author(s) -
Perekalin Dmitry S.,
Novikov Valentin V.,
Pavlov Alexander A.,
Ivanov Igor A.,
Anisimova Natalia Yu.,
Kopylov Alexey N.,
Volkov Dmitry S.,
Seregina Irina F.,
Bolshov Michail A.,
Kudinov Alexander R.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406510
Subject(s) - melittin , peptide , chemistry , ruthenium , bee venom , tryptophan , biodistribution , residue (chemistry) , conjugate , combinatorial chemistry , stereochemistry , biochemistry , amino acid , biology , catalysis , zoology , mathematical analysis , mathematics , in vitro
Melittin is a membrane‐active peptide from bee venom with promising antimicrobial and anticancer activity. Herein we report on a simple and selective method for labeling of the tryptophan residue in melittin by the organometallic fragment [(C 5 H 5 )Ru] + in aqueous solution and in air. Ruthenium coordination does not disturb the secondary structure of the peptide (as verified by 2D NMR spectroscopy), but changes the pattern of its intermolecular interactions resulting in an 11‐fold decrease of hemolytic activity. The high stability of the organometallic conjugate allowed the establishment of the biodistribution of the labeled melittin in mice by inductively coupled plasma MS analysis of ruthenium.