Photoinduced DNA interstrand cross-linking via carbocation formation has been identified as an efficient mechanism for DNA damage. Recently, our group has discovered that the 1,1’-binaphthalene analogues induced DNA interstrand cross-link (ICL) formation via carbocation. However, most compounds showed a low ICL efficiency. Herein, we have synthesized a series of new 1,1’-binaphthalene analogues that contain a wide variety of leaving groups and/or substituents. Most of them efficiently induced DNA ICL formation upon 350nm irradiation. Among all new synthesized analogues, the compound 2j with bromo as the substituent showed the highest DNA ICL yield. Also, the compound 3c with triphenylphosphine as the leaving group had a better cross-linking efficiency than 3b and 3a. The compound 4d had a higher cross-linking yield among compounds with methoxy group as substituent. The results indicate that the DNA cross-linking efficiency depends on both substituents and the leaving groups. Next, the alkylation sites for these naphthalene analogues will be determined by heating the DNA ICL products under basic or neutral condition.

Leaving groups or substituents effects on DNA interstrand cross-link formation induced by binaphthalene analogues

2019 Fall National Meeting

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