Atom Efficient Synthesis of Trimethine Cyanines Using Formaldehyde as a Single Carbon Source.
Angew Chem Int Ed Engl
; : e202413121, 2024 Sep 18.
Article
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| MEDLINE
| ID: mdl-39291296
ABSTRACT
In this work, 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 with low atom economy and substantial side-product formation. Through systematic investigation, we have developed a practical and efficient synthetic pathway for both symmetric and asymmetric Cy3 derivatives, significantly minimizing resource utilization. Notably, this approach yields water as the byproduct, 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 the endogenous FA in the intestinal tissues. We observed a significant decrease of FA in the small intestine of the inflammatory bowel disease (IBD) mice compared to the healthy mice. This methodological advancement not only enhances the scope of fluorescent dye synthesis but also contributes to the sustainable practices within chemical manufacturing, offering a significant leap forward in the development of environmentally friendly synthetic strategies.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2024
Tipo del documento:
Article
Pais de publicación:
Alemania