Visible Light Photochemical Reactions for Nucleic Acid-Based Technologies

Abstract

The expanding scope of chemical reactions applied to nucleic acids has diversified the design of nucleic acid-based technologies that are essential to medicinal chemistry and chemical biology. Among chemical reactions, visible light photochemical reaction is considered a promising tool that can be used for the manipulations of nucleic acids owing to its advantages, such as mild reaction conditions and ease of the reaction process. Of late, inspired by the development of visible light-absorbing molecules and photocatalysts, visible light-driven photochemical reactions have been used to conduct various molecular manipulations, such as the cleavage or ligation of nucleic acids and other molecules as well as the synthesis of functional molecules. In this review, we describe the recent developments (from 2010) in visible light photochemical reactions involving nucleic acids and their applications in the design of nucleic acid-based technologies including DNA photocleaving, DNA photoligation, nucleic acid sensors, the release of functional molecules, and DNA-encoded libraries.

DNA-encoded librariesvialate-stage functionalization strategies: a review

“…This section will therefore deal with those methodologies involving the photocatalytic modification of DNA for the generation of DNA-encoded libraries. [88][89][90] In 2019, Molander and co-workers 91 reported the Ni/photoredox dual catalytic C(sp 2 )-C(sp 3 ) cross-coupling between DNAconjugated aryl bromide and iodide with DHP and N-protected amino acids for DEL synthesis. The photoredox-catalyzed radical/polar crossover defluorinative alkylation of DNA-conjugated trifluoromethyl alkenes was performed to form gem-difluoroalkenes for DEL synthesis.…”

“…This section will therefore deal with those methodologies involving the photocatalytic modification of DNA for the generation of DNA-encoded libraries. 88–90…”

Metal Complexes as DNA Synthesis and/or Repair Inhibitors: Anticancer and Antimicrobial Agents

“…56 In terms of nucleic acid cleavage, visible light-based photosensitizers (PSs), relying on metal complexes such as ruthenium(II) and iridium(III) with riboflavin as a ligand, have resulted in the design of more efficient and site-selective DNA photocleavage induced by the generation of ROS. 57 In photodynamic therapy, the drug TOOKAD Soluble, which utilizes a palladium-based PS, has been approved for use in treating low-risk prostate cancer, while the ruthenium-based PS TLD-1433 is currently undergoing clinical trials. 58 There are different mechanisms of photocatalytic action of metal complexes which can lead to cell death.…”

In situ fluorescence visualizing of a temperature-dependent photoreaction process of pyridazine N-oxide

“…Organic photochemical reactions, a type of organic reaction activated by light, have recently attracted growing attention due to their advantages such as simple/mild reaction conditions, metal-free catalysis, additive-free process, high yields as well as environmental friendliness. [24][25][26][27] However, during the photochemical reaction process, excited species with high reactivity are usually present. [28][29][30] It is necessary to monitor the reaction process in a real-time and in situ manner to avoid the generation of by-products and reduce the difficulty of separation of target products.…”