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A FLOW LINEAR DICHROISM STUDY OF THE ORIENTATION OF 4′,5′‐PSORALEN‐DNA PHOTOADDUCTS
Author(s) -
Vigny Paul,
Blais Jocelyne,
Ibanez Victor,
Geacintov Nicholas E.
Publication year - 1987
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1987.tb07386.x
Subject(s) - psoralen , chemistry , adduct , moiety , linear dichroism , furan , stereochemistry , dna , circular dichroism , stacking , photochemistry , crystallography , organic chemistry , biochemistry
— The flow linear dichroism properties of covalent adducts derived from the photochemical binding of various psoralen derivatives to salmon sperm DNA were investigated. The psoralens studied include bifunctional derivatives (8‐methoxypsoralen,5‐methoxypsoralen, tetrahydropyrido [3,4: 4‘,5’] psoralen) and monofunctional derivatives (pyrido [3,4‐c] psoralen, 7‐methylpyrido [3,4‐c] psoralen, 3‐carbethoxypsoralen). The orientation of the psoralen moieties (furan‐side monoadducts) relative to the orientation of the DNA bases was determined. All of the furan‐side monoadducts are characterized by a similar orientation, with mean angles between the psoralen moiety and the normals of the planes of the DNA bases ranging between 70° and values close—but not equal—to 90°. The results are consistent with a pseudo‐intercalative adduct geometry, most probably involving stacking interactions with the DNA bases.