Abstract

Ultrafast Reversible DNA Photo Cross-Linker 3-Cyanovinylcarbazole Modified Nucleosides from Nicca

Takahiro Inatsugi, Assistant Director, Specialty Chemicals Division, Nicca Chemical Co.,Ltd.

Photo cross-linking reactions toward DNA/RNA have great potential for regulating the structures, functions and characters of nucleic acids. Various photo cross-linkers e.g., psoralen, coumarin, and diazirine, have been developed and applied for regulating gene expression in cells and for constructing DNA nanostructures. As another class of DNA/RNA photo cross-linker, 3-cyanovinylcarbazole nucleoside (CNV-K) was reported by Prof. Fujimoto’s team of Japan Advanced Institute of Science and Technology (JAIST) in 2008. A cyanovinylcarbazole nucleoside analogue is one of the most promising analogue in cross-linking. According to recent developments, photo-reactive triplex forming oligonucleotide, photo-reactive antisense oligonucleotide, photo-reactive detection probe for DNA/RNA, and thermally stable DNA nanostructure have been developed by using oligonucleotide containing CNV-K. 2nd generation of photo cross-linker called as CNV-D was developed last year and its photo-reactivity was 1.8- to 8-fold greater than CNV-K. Through close cooperation works between Nicca Chemical and Prof. Fujimoto’s team of JAIST under the joint research agreement, Nicca Chemical has successfully materialized these patented or patent-pending ultrafast reversible photo cross-linkers (CNV-K and CNV-D) which are now in commercial production. The high photo-reactivity of CNV-D opens further possibilities of applicability of the DNA/RNA photo cross-linking reaction in nanotechnology and biotechnology because the photo-damage on nucleic acids or cells is reduced. Manufacturing and selling of CNV-K and CNV-D by Nicca Chemical are authorized by Japan Science and Technology Agency.