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Angew. Chem.-Int. Edit., Sep 18 2024, | https://doi.org/10.1002/anie.202413121
Atom-Efficient Synthesis of Trimethine Cyanines Using Formaldehyde as a Single-Carbon Source
Sun Hyeok Lee 1, Taek-Jun Lee 2, Sourav Sarkar 3, Heewon Cho 2, Quynh Pham Nguyen Nhu 4, Young-Tae Chang 2
1Basic Science Research Institute (BSRI), Pohang University of Science and Technology (POSTECH), Pohang, 37673, Republic of Korea.
2Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673, Republic of Korea.
3Senpro Co., Ltd., Pohang, 37673, Republic of Korea.
4Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.
Corresponding Author : Prof. Young-Tae Chang
1Basic Science Research Institute (BSRI), Pohang University of Science and Technology (POSTECH), Pohang, 37673, Republic of Korea.
2Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, 37673, Republic of Korea.
3Senpro Co., Ltd., Pohang, 37673, Republic of Korea.
4Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.
Corresponding Author : Prof. Young-Tae Chang
Abstract
Herein, we present an innovative and atom-efficient synthesis of trimethine cyanines (Cy3) using formaldehyde (FA) as a single-carbon reagent. The widespread application of Cy3 dyes in bioimaging and genomics/proteomics is often limited by synthetic routes plagued by low atom economy and substantial side-product formation. Through systematic investigation, we have developed a practical and efficient synthetic pathway for both symmetrical and unsymmetrical Cy3 derivatives, significantly minimizing resource utilization. Notably, this approach yields water as the by-product, in alignment with sustainable chemistry principles. Moreover, the efficient one-pot synthesis facilitates the detection of intracellular FA levels, utilizing the fluorescence signal of Cy3 in live cells. It is also possible to detect endogenous FA in the intestinal tissues. We observed a significant decrease in FA in the small intestine of inflammatory bowel disease (IBD) mice as compared to healthy mice. This methodological advancement not only enhances the scope of fluorescent dye synthesis but also contributes to sustainable practices within chemical manufacturing, offering a significant leap forward in the development of environmentally friendly synthetic strategies.
논문정보
- Research article
- 2024년 09월 (BRIC 등록일 2024-12-18)
- 국내(교신)+국외 연구진
- 바이오·의료융합 > 바이오센싱 및 나노바이오물질
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