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Updated: May 26, 2026

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
Published on: July 6, 2016
Synthesis of directly linked diazine isosteres of pyrrole-polyamide that photochemically cleave DNA
Chi Wi Ong1, Ya-Ting Yang, Meng-Chi Liu
1Department of Chemistry, National Sun Yat Sen University, No. 70, Lienhai Rd., Kaohsiung, 804, Taiwan, R.O.C. cong@mail.nsysu.edu.tw
Abstract:
A distamycin model containing an isosteric diazine linked pyrrole has been designed and synthesized. The key steps of the synthesis involved the successful diazotization of the 4-amino-pyrrole derivatives to give the diazomium salts, which undergo coupling reactions with N-methylpyrrole to yield the directly linked diazine compounds. The amide isosteric-diazine pyrrole I demonstrated photo-induced DNA damage upon iradiation with UV light (365 nm). Spectrophotometric and mass spectrometric identification suggest that the azo-linkage in I did not dissociate during irradiation. Moreover, compound I produced DNase I footprints with the HexB DNA fragment at AT sites, as well as some other mixed sequences (5'-ATGTCG-3'), indicative of the additional role of the diazine-linkage for interaction at the duplex DNA.
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