Catch and release microwave mediated synthesis of cyanine dyes

Lopalco, Maria; Koini, Eftychia N.; Cho, Jin Ku; Bradley, Mark

doi:10.1039/b820719b

Cited by 45 publications

(48 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We note that this reaction has been used for nearly a century 121 and can now be performed using solid-phase synthesis techniques. 122 Similarly, the rhodamine–cyanine hybrid 54 is formed by condensation of chromenylium compound 57 with aldehyde 58 .…”

Section: Cyaninesmentioning

confidence: 99%

Bright Building Blocks for Chemical Biology

2014

View full text Add to dashboard Cite

Small-molecule fluorophores manifest the ability of chemistry to solve problems in biology. As we noted in a previous review (Lavis, L. D.; Raines, R. T. ACS Chem. Biol.2008, 3, 142–155), the extant collection of fluorescent probes is built on a modest set of “core” scaffolds that evolved during a century of academic and industrial research. Here, we survey traditional and modern synthetic routes to small-molecule fluorophores and highlight recent biological insights attained with customized fluorescent probes. Our intent is to inspire the design and creation of new high-precision tools that empower chemical biologists.

show abstract

Section: Cyaninesmentioning

confidence: 99%

Bright Building Blocks for Chemical Biology

2014

View full text Add to dashboard Cite

show abstract

“…The synthesis of cyanine fluorophores and their photophysical properties are well established . In general, the published procedures start with the synthesis of the terminal heterocycle.…”

Section: Figurementioning

confidence: 99%

New Polyfluorinated Cyanine Dyes for Selective NIR Staining of Mitochondria

Braun

Wehl

Schepers

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

In this communication, the synthesis of three unknown polyfluorinated cyanine dyes and their application as selective markers for mitochondria are presented. By incorporating fluorous side chains into cyanine dyes, their remarkable photophysical properties were enhanced. To investigate their biological application, several different cell lines were incubated with the synthesized cyanine dyes. It was discovered that the presented dyes can be utilized for selective near‐infrared‐light (NIR) staining of mitochondria, with very low cytotoxicity determined by MTT assay. This is the first time that polyfluorinated cyanine fluorophores are presented as selective markers for mitochondria. Due to the versatile applications of polyfluorinated fluorophores in bioimaging and materials science, it is expected that the presented fluorophores will be stimulating for the scientific community.

show abstract

“…10,21 For example, in the synthesis of 3a, reaction times decreased from 24 h (entry 1) 17d to 9 min (entry 4). In the synthesis of 3b, the yield increased from 79 19 to 94%, while reaction times decreased from 24 h to 20 min.…”

mentioning

confidence: 98%