N,O-Diacyl-4-benzoyl-N-phenylhydroxylamines as photoinduced DNA cleaving agents

Chowdhury, Nilanjana; Dutta, Sansa; Nishitha, Boda; Dasgupta, Swagata; Singh, N. D. Pradeep

doi:10.1016/j.bmcl.2010.07.116

Cited by 12 publications

(8 citation statements)

References 33 publications

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“…The organic solution was concentrated and then purified by flash column chromatography using ethyl acetate/hexane (1:1) as eluent to give 2,6-diazaanthracene-9,10-dione (2, 15.8 mg, 84%). The aqueous solution was neutralized with 5% HCl, extracted with CH 2 Cl 2 (10 mL), dried (MgSO 4 ) and evaporated to give benzoic acid (8,17.4 mg, 80%).…”

Section: Photolysis Of 26-diazaanthracene-910-dione Bis-(o-benzoylomentioning

confidence: 99%

“…Recently, anthracenone-based oxime esters have been reported to display strong antiproliferative activity against K562 leukemia cells [16]. N,O-Diacyl-4-benzoyl-N-phenylhydroxylamines, also having a weak N-O bond, were recently reported to produce single strand cleavage of DNA [17]. Photolysis of the carboxylic esters of N-acyl-N-phenylhydroxylamines generated the corresponding carboxylic acids by cleaving the N-O bond [18].…”

Section: Introductionmentioning

confidence: 99%

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Oxime Esters of 2,6-Diazaanthracene-9,10-dione and 4,5-Diazafluoren-9-one as Photo-induced DNA-Cleaving Agents

et al. 2012

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Two series of oxime esters containing the 2,6-diazaanthracene-9,10-dione bis-(O-benzoyloxime) and 4,5-diazafluoren-9-one O-9-benzoyloxime moieties have been synthesized and tested as photo-induced DNA cleaving agents. All these compounds were found to cleave DNA upon irradiation with 312 nm UV light. The structure-activity relationship of these molecules for DNA cleavage was established. A plausible reaction mechanism is also proposed.

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Section: Photolysis Of 26-diazaanthracene-910-dione Bis-(o-benzoylomentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Oxime Esters of 2,6-Diazaanthracene-9,10-dione and 4,5-Diazafluoren-9-one as Photo-induced DNA-Cleaving Agents

et al. 2012

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“…Several organic compounds were found to be "DNA photocleavers", exhibiting their action at 312 nm, like [1,2,4]triazolo [4,3-a]quinoxaline [28] and quinoxalin-4(5H)one [29] derivatives, various enediyne [30][31][32], proflavine [33], N-nitroso carboxamide [34], naphazoline [35] and triazole [36] derivatives, azido carbonyl compounds [37] and N,O-diacyl-4benzoyl-N-phenylhydroxylamines [38].…”

Section: Introductionmentioning

confidence: 99%

“…Reports involve arylaminyl radicals (ArNH • ) formed from arylhydrazones through the photoinduced cleavage of N-N single bonds (along with an iminyl radical) [48] or from benzotriazole derivatives after also a N-N single bond cleavage and nitrogen elimination [36]. It has been reported that aminecentred radicals are also produced from 2-(1-naphthylmethyl)imidazoline [35], whereas acylaminyl radicals [R(COR)N • ] are formed from the photocleavage of the N-O bond of N,O-diacyl-N-phenylhydroxylamines, along with a carbonyloxyl radical [38].…”

Section: Introductionmentioning

confidence: 99%

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

Gritzapis

Varras

Andreou

et al. 2020

Beilstein J. Org. Chem.

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A number of p-pyridinyl oxime carbamate derivatives were prepared upon the reaction of the corresponding oximes with isocyanates. These novel compounds reacted photochemically in the presence of supercoiled plasmid DNA. Structure–activity relationship (SAR) studies revealed that the substituent on the imine group was not affecting the extend of the DNA damage, whereas the substituent of the carbamate group was critical, with the halogenated derivatives to be able to cause extensive single and double stranded DNA cleavages, acting as “synthetic nucleases”, independently of oxygen and pH. Calf thymus–DNA affinity studies showed a good-to-excellent affinity of selected both active and non-active derivatives. Preliminary theoretical studies were performed, in an effort to explain the reasons why some derivatives cause photocleavage and some others not, which were experimentally verified using triplet state activators and quenchers. These theoretical studies seem to allow the prediction of the activity of derivatives able to pass intersystem crossing to their triplet energy state and thus create radicals able to damage DNA. With this study, it is shown that oxime carbamate derivatives have the potential to act as novel effective photobase generating DNA-photocleavers, and are proposed as new leads for “on demand” biotechnological applications in drug discovery and medicine.

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“…15,16 Interestingly, the same group showed that when the photolysis of N,O-diacyl-N-phenylhydroxylamines was carried out in hydrogen donor solvents, fragmentation products (carboxylic acid and carboxanilide) were produced exclusively, via efficient hydrogen atom abstraction from the solvent by cage-escaped acyloxy and amido radicals. 17 The above facts concerning the efficient photoinduced homolytic N-O bond cleavage chemistry of N,O-diacyl-Nphenylhydroxylamines, together with our interest in exploring the applications of those compounds, 18 prompted us to investigate the possibility of utilizing O-alkyl-Nacyl-N-phenylhydroxylamines as alkoxy radical precursors.…”

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confidence: 99%

O-Alkyl-N-acyl-N-phenylhydroxylamines as Photochemical Alkoxy Radical Precursors

2012

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A simple and efficient technique for the photolysis of alkoxy radical precursors is developed. Irradiation of O-alkyl-Nacyl-N-phenylhydroxylamines, as representative alkoxy radical precursors, with ultraviolet light (≥254 nm) results in homolytic N-O bond cleavage to generate singlet alkoxy and acylaminyl caged radical pairs. These radicals, depending on the solvent employed, either escape from the cage to form fragmentation products, or undergo in-cage reactions to produce photorearrangement products. The homolytic cleavage of the N-O bond is analyzed using timedependent density functional theory calculations. The nature of the N-acyl substituent on the O-alkyl-N-acyl-N-phenylhydroxylamines is shown to influence their ability to generate radicals. Furthermore, identification and trapping of the alkoxy radicals is demonstrated.

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N,O-Diacyl-4-benzoyl-N-phenylhydroxylamines as photoinduced DNA cleaving agents

Cited by 12 publications

References 33 publications

Oxime Esters of 2,6-Diazaanthracene-9,10-dione and 4,5-Diazafluoren-9-one as Photo-induced DNA-Cleaving Agents

Oxime Esters of 2,6-Diazaanthracene-9,10-dione and 4,5-Diazafluoren-9-one as Photo-induced DNA-Cleaving Agents

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

O-Alkyl-N-acyl-N-phenylhydroxylamines as Photochemical Alkoxy Radical Precursors

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