Synthesis of highly efficient pH-sensitive DNA cleaving aminomethyl N-substituted cyclic enediyne and its L-lysine conjugate

Hatial, Ishita ; Addy, Partha S. ; Ghosh, Ananta K. ; Basak, Amit (2013) Synthesis of highly efficient pH-sensitive DNA cleaving aminomethyl N-substituted cyclic enediyne and its L-lysine conjugate Tetrahedron Letters, 54 (8). pp. 854-857. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/J.Tetlet.2012.11.102

Related URL: http://dx.doi.org/10.1016/J.Tetlet.2012.11.102

Abstract

Two 10-membered benzo-fused N-substituted cyclic enediynes, one an amino methyl and the other, a C-lysine conjugated derivative 2 and 3, respectively were synthesized (as a 1.2:1 mixture of regioisomers) and their DNA-cleavage efficiency studied. Both the compounds showed much better DNA-cleavage profile than that of the parent unsubstituted enediyne 1. The lysine conjugate 3 showed an efficient pH dependent cleavage to the extent of ∼50% of linear DNA formation under ambient conditions.

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