Synthesis of nitrated oligo-N-methylpyrrole carboxamide derivatives and their photochemical DNA cleaving activities

Sequence-Specific DNA Minor Groove Binders. Design and Synthesis of Netropsin and Distamycin Analogues

“…The same conclusion was drawn for simple oligopeptides such as 57 and 58, which do not possess special side chains sensitive to UV light but which, nevertheless, can induce DNA cleavage under UV-A irradiation (209). Conversely, for nitrated oligopyrrolecarboxamide derivatives such as 59 and 60, the DNA photocleavage efficiency is higher for the monopyrrole compounds than for the bis-and tris(peptide)s (210).…”

“…These two sensitizers only react only weakly with DNA, presumably via an electron-seeking radical (203,204). Targeting of a nitroarene moiety to DNA via a minor groove binder is expected to increase the sensitizer concentrations at defined sites on DNA (205)(206)(207). The affinity of the 2-nitroimidazole-netropsin conjugate (55) for DNA is ∼200-fold superior to that of misonidazole, but despite the improved interaction with DNA and improved cellular uptake capacity, the radiosenzitization efficiency remains relatively poor and not better than that of misonidazole (206).…”

An Intercalating Isoxazole

“…The minor-groove binding lexitropsins (polyamidopyrroles) can be prepared by existing methodology (Bialer, Yagen & Mechoulam, 1978;Turchin, Grokhovskii, Zhuze & Gottikh, 1978;Nishiwaki et al, 1990). These compounds could be linked to isoxazole tethers via existing methodology (Niou & Natale, 1986).…”

6‐Nitro‐Quinazolin−4(3H)−one Exhibits Photodynamic Effects and Photodegrades Human Melanoma Cell Lines. A Study on the Photoreactivity of Simple Quinazolin−4(3H)−ones

“…However, due to the diversity of those substrates (naphthalimides, nitrobenzamidoacridines and N ‐methyl‐pyrrole‐carboxamides) a prediction of the role of the position may lead to uncertain conclusions and, thus, for the moment this seems to be a case study for each class of compounds. (41,42,60) As far as the halogenated compounds concerns, we observed that 6−fluoro quinazolinone 16 has a negligible activity, which was slightly improved when fluorine was replaced by chlorine ( 17 ) and this trend reached the top of activity almost equally for 6−bromo ( 18 ) and 6−iodo−quinozalinone ( 19 ), Fig. 2 (Lanes 7, 8, 9 and 10, respectively).…”

“…Several organic compounds, bearing quite diverse structures, have been identified as DNA photocleavaging agents. These include [1,2,4]−triazolo−[4,3−a]quinoxalines (33), quinoxalin−4(5 H )−ones (34), enediynes (35,36), pyrrolecarboxamide conjugated 4′−bromo−acetophenones (37), halophenyl sulfonamide derivatives of poly N −methylimidazoles (38), naphthalimides, (39–41) nitrobenzamido amino‐acridine derivatives (42,43), benzo[ b ][1,8]naphthyridines (44) and quinolones (45–47), N −phenylhydroxylamine derivatives (48), O −acyl (49–53), O −sulphonyl (54,55) and O ‐carbamoyl (56) oximes, β−carbolines (57,58), pyrazole derivatives (59,60), azido carbonyl compounds (61), etc.…”