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Synthesis of Two Acridine Conjugates of the Bis(phenanthroline) Ligand “Clip‐Phen” and Evaluation of the Nuclease Activity of the Corresponding Copper Complexes
Author(s) -
Ross Steven A.,
Pitié Marguerite,
Meunier Bernard
Publication year - 1999
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199903)1999:3<557::aid-ejic557>3.0.co;2-y
Subject(s) - chemistry , phenanthroline , nuclease , hexafluorophosphate , acridine , dna , conjugate , copper , stereochemistry , ligand (biochemistry) , cleavage (geology) , medicinal chemistry , crystallography , organic chemistry , receptor , biochemistry , catalysis , mathematical analysis , ionic liquid , mathematics , geotechnical engineering , fracture (geology) , engineering
The synthesis of three novel derivatives [ N ‐acetyl‐Clip‐Phen ( 1 ), Clip‐Phen‐hexylaminoacridine ( 4 ) and Clip‐Phen‐hexylchloromethoxyaminoacridine ( 5 )] of the bis(phenanthroline) ligand “ Clip‐Phen ”, are described. Complexation of these ligands with copper(II) afforded the 1:1 complexes as hexafluorophosphate salts. The relaxation of ϕX 174 DNA was used as a DNA cleavage assay, with the following results. [Cu( 1 )] 2+ was found to show a diminished activity relative to the parent complex [Cu( Clip‐Phen )] 2+ . However, the acridine‐containing complexes [Cu( 4 )H] 3+ and [Cu( 5 )H] 3+ exhibited significantly enhanced cleavage efficiencies, which has been attributed to increased affinity of the complexes for DNA. UV/Vis‐spectral data of the complexes in the presence of calf‐thymus DNA was consistent with an intercalative mode of binding.