ChemInform Abstract: THE PHOTOCHEMICAL SYNTHESIS OF AZOXYBENZENES

Mattison, Louis E.; O'Dell, Dale E.

doi:10.1002/chin.197937182

Cited by 1 publication

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…ficient than their corresponding 4-nitrobenzamido analogues, since it is well-known that hydrogen abstraction is less efficient with nitrobenzenes having an electronwithdrawing group in the 3-position rather than in the 4-position (Mattison et al, 1979;Dopp, 1975). This photocleavage reaction is independent of pH and only slightly influenced by the distance between the nitrobenzamido and the acridinyl moiety of the reagent.…”

Section: Discussionmentioning

confidence: 99%

Photolytic cleavage of DNA by nitrobenzamido ligands linked to 9-aminoacridines gives DNA polymerase substrates in a wavelength-dependent reaction

Nielsen¹,

Egholm²,

Koch³

et al. 1991

Bioconjugate Chem.

View full text Add to dashboard Cite

A series of reagents containing 3- or 4-nitrobenzamido ligands tethered to 9-aminoacridine via variable-length linkers have been prepared and their properties as photochemical DNA cleavers (photonucleases) examined. When irradiated with approximately 300-nm light, where the nitrobenzamido ligand can absorb, they cleave DNA in an oxygen-independent reaction presumably involving oxygen transfer from the nitro group to the deoxyribose units of the DNA backbone (Nielsen et al., 1988b). This reaction is pH independent and only slightly affected by the linker length, and the DNA fragments are not substrates for DNA polymerase. When approximately 420-nm light is used, were only the 9-aminoacridinyl ligands absorb, the DNA cleavage is also oxygen-independent but pH dependent, requires DNA saturation with the reagent (base pair:reagent less than or equal to 2), and is most efficient with the longer linkers. The cleavage is specific for guanine residues and results in 5'-phosphate termini and heterogeneous (more than four products) 3'-termini. One of the products is presumably 3'-hydroxy since DNA photocleaved with nitrobenzamido acridine reagents and 420-nm radiation are substrates for DNA polymerase in a nick translation assay as well as for the Klenow fragment. An electron-transfer mechanism is suggested.

show abstract

Section: Discussionmentioning

confidence: 99%