Nucleic Acid‐Templated Synthesis of Cationic Styryl Dyes in Vitro and in Living Cells

Author:

Faikhruea Kriangsak1,Supabowornsathit Kotchakorn1,Angsujinda Kitipong2,Aonbangkhen Chanat3,Chaikeeratisak Vorrapon4,Palaga Tanapat5,Assavalapsakul Wanchai5,Wagenknecht Hans‐Achim6,Vilaivan Tirayut1ORCID

Affiliation:

1. Organic Synthesis Research Unit (OSRU), Department of Chemistry, Faculty of Science Chulalongkorn University Phayathai Road, Patumwan Bangkok 10330 Thailand

2. Aquatic Resources Research Institute Chulalongkorn University Phayathai Road, Patumwan Bangkok 10330 Thailand

3. Center of Excellence in Natural Products Chemistry (CENP), Department of Chemistry, Faculty of Science Chulalongkorn University Phayathai Road, Patumwan Bangkok 10330 Thailand

4. Department of Biochemistry, Faculty of Science Chulalongkorn University Phayathai Road, Patumwan Bangkok 10330 Thailand

5. Department of Microbiology, Faculty of Science Chulalongkorn University Phayathai Road, Patumwan Bangkok 10330 Thailand

6. Institute of Organic Chemistry Karlsruhe Institute of Technology (KIT) Fritz-Haber-Weg 6 76131 Karlsruhe Germany

Abstract

AbstractA novel method for synthesizing cationic styryl dyes through a nucleic acid‐templated reaction has been developed. This approach overcomes issues associated with traditional synthesis methods, such as harsh conditions, low throughput, and wasteful chemicals. The presence of a nucleic acid template accelerated the styryl dye formation from quaternized heteroaromatic and cationic aldehyde substrates. These styryl dyes show remarkable optical properties change when bound to nucleic acids, hence the success of the synthesis could be readily monitored in situ by UV‐Vis and fluorescence spectroscopy and the optical properties data were also observable at the same time. This method provides the desired products from a broad range of coupling partners. By employing different substrates and templates, it is possible to identify new dyes that can bind to a specific type of nucleic acid such as a G‐quadruplex. The templated dye synthesis is also successfully demonstrated in live HeLa cells. This approach is a powerful tool for the rapid synthesis and screening of dyes specific for diverse types of nucleic acids or cellular organelles, facilitating new biological discoveries.

Funder

Thailand Science Research and Innovation

Chulalongkorn University

Office of the Permanent Secretary, Ministry of Higher Education, Science, Research and Innovation, Thailand

Thailand Toray Science Foundation

Publisher

Wiley

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