Synthesis and properties of novel psoralen derivatives.
We have synthesized a set of new trimethylpsoralen derivatives that are characterized by a chain extending from the 4'-position of the furan ring and linked to this ring by an aminomethylene group. The nature of the side chain can be varied widely. In these derivatives, the chains contain either amino or ethylene oxide units for enhanced water solubility and allow the introduction of a thiol or amine group to nucleic acids. These compounds represent the first set of thiolated psoralen derivatives, and their usefulness is demonstrated in several nucleic acid cross-linking experiments. The reagents can be used to create both intraduplex reversible cross-links between the two single-strand partners in a DNA double helix and interduplex reversible cross-links between two DNA double helices.
Goldenberg
M
M
Department of Chemistry, Columbia University, New York, New York 10027.
Welsh
J
J
Haas
R
R
Rideout
D C
DC
Cantor
C R
CR
D003432:Cross-Linking Reagents; D004247:DNA / Q000187:drug effects*; D011564:Furocoumarins / Q000494:pharmacology*; D010777:Photochemistry; D012995:Solubility; D013438:Sulfhydryl Compounds; D014307:Trioxsalen / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*
D003432:Cross-Linking Reagents; D011564:Furocoumarins; D013438:Sulfhydryl Compounds; D004247:DNA; D014307:Trioxsalen