Premium
Intercalating Nucleic Acids Containing Insertions of Naphthalimide
Author(s) -
Wamberg Michael C.,
Walczak Krzysztof,
Andersen Lars,
Hassan Allam A.,
Pedersen Erik B.
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690177
Subject(s) - chemistry , linker , nucleic acid , dna , intercalation (chemistry) , base pair , rna , nucleobase , monomer , stereochemistry , pyrene , combinatorial chemistry , biochemistry , organic chemistry , gene , polymer , operating system , computer science
In a study of linker‐length dependence, we evaluated naphthalimide (= 1 H ‐benzo[ de ]isoquinoline‐1,3(2 H )‐dione) and 4‐bromonaphthalimide as intercalating nucleic acids. We used a vicinal dihydroxy system when incorporating the six different naphthalimide monomers into DNA, and found the minimum linker‐length to be five C‐atoms. With this length of the linker, naphthalimide was discriminating between DNA and RNA – stabilizing DNA, while destabilizing RNA. Furthermore, naphthalimide showed universal base character by hybridizing to the four natural bases with a range as narrow as 1.4°. When compared to pyrene, naphthalimide with the same linker‐length gave significantly higher thermal meltings when hybridized to DNA.