Photo-induced DNA cleavage by (heterocyclo)carbonyl oxime esters of anthraquinone

DNA damage induced by carbon ions (C3+) beam accessed by independent component analysis of infrared spectra

“…Oxime groups are also evidenced by reactions between the native abasic sites, a product of oxidation of 2-deoxyribose in DNA with methoxyamine (Zhou et al 2005) which can be formed by the carbon ion beam action. The presence of these oxime groups in DNA indicate that reactions can occur in the DNA bases, similarly to those occurring with various (heterocyclo) carbonyl mono-oxime esters of anthraquinone who exhibited ability for DNA cleavage upon UV irradiation (Hwu et al 2008). giving rise to the formation of C  O bonds: The fragmentation of PO 4 2 groups and the decrease in the number of thymine, cytosine, adenine and guanine groups.…”

(E)-3-Methyl-2,6-diphenylpiperidin-4-oneO-(3-methylbenzoyl)oxime

“…For the biological activity of oxime esters, see: Crichlow et al (2007); Hwu et al (2008); Neely et al (2013); Liu et al (2011). For ring conformations, see: Cremer & Pople (1975).…”

p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

“…O-Acyl amidoximes, ketoximes and aldoximes (I, II and III, respectively, Figure 1) are also recognized as DNA "photocleavage" agents owing their action to the homolysis of their vulnerable N-O bond, at 312 nm [9,[39][40][41][42][43] or 365 nm [44,45] yielding photogenerated carbonyloxyl radicals (CRs), which are able to cause oxidative DNA damage. We have recently reported the DNA photocleavage from sulfonylamidoximes and ethanone oximes (IV and V, Figure 1), which were found to attack DNA via sulfonyloxyl radicals (SRs) [10,11].…”