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Monoalkoxy BODIPYs--a fluorophore class for bioimaging.

Courtis AM, Santos SA, Guan Y, Hendricks JA, Ghosh B, Szantai-Kis DM, Reis SA, Shah JV, Mazitschek R - Bioconjug. Chem. (2014)

Bottom Line: These novel fluorescent dyes, which we term MayaFluors, are characterized by good aqueous solubility and favorable in vitro physicochemical properties.MayaFluors are readily accessible in good yields in a one-pot, two-step approach starting from well-established BODIPY dyes, and allow for facile modification with functional groups of relevance to bioconjugate chemistry and bioorthogonal labeling.Biological profiling in living cells demonstrates excellent membrane permeability, low nonspecific binding, and lack of cytotoxicity.

View Article: PubMed Central - PubMed

Affiliation: Center for Systems Biology and ∥Center for Human Genetic Research, Massachusetts General Hospital , 185 Cambridge Street, Boston, Massachusetts 02114, United States.

ABSTRACT
Small molecule fluorophores are indispensable tools for modern biomedical imaging techniques. In this report, we present the development of a new class of BODIPY dyes based on an alkoxy-fluoro-boron-dipyrromethene core. These novel fluorescent dyes, which we term MayaFluors, are characterized by good aqueous solubility and favorable in vitro physicochemical properties. MayaFluors are readily accessible in good yields in a one-pot, two-step approach starting from well-established BODIPY dyes, and allow for facile modification with functional groups of relevance to bioconjugate chemistry and bioorthogonal labeling. Biological profiling in living cells demonstrates excellent membrane permeability, low nonspecific binding, and lack of cytotoxicity.

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Structures of BODIPYdyes.
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fig1: Structures of BODIPYdyes.

Mentions: The ideal reportergroup is a chemically stable, small fluorophorethat readily trafficks through cellular compartments, maintains photostabilityin oxygenated aqueous media, and exhibits few drug-like attributes,which could interfere with a measurement of interest.6 The fluorescent tag should have high quantitative brightness,photophysical properties that are independent of the local environment,good aqueous solubility (while remaining small and uncharged), anda favorable logP. Some of the most widely employed fluorophores forbioimaging are difluoro-boron-dipyrromethene dyes (BODIPYs) (1) (Figure 1).9 BODIPY dyes fulfill most requirements for routine imaging and conjugationto small-molecule and protein targets of interest.


Monoalkoxy BODIPYs--a fluorophore class for bioimaging.

Courtis AM, Santos SA, Guan Y, Hendricks JA, Ghosh B, Szantai-Kis DM, Reis SA, Shah JV, Mazitschek R - Bioconjug. Chem. (2014)

Structures of BODIPYdyes.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4215867&req=5

fig1: Structures of BODIPYdyes.
Mentions: The ideal reportergroup is a chemically stable, small fluorophorethat readily trafficks through cellular compartments, maintains photostabilityin oxygenated aqueous media, and exhibits few drug-like attributes,which could interfere with a measurement of interest.6 The fluorescent tag should have high quantitative brightness,photophysical properties that are independent of the local environment,good aqueous solubility (while remaining small and uncharged), anda favorable logP. Some of the most widely employed fluorophores forbioimaging are difluoro-boron-dipyrromethene dyes (BODIPYs) (1) (Figure 1).9 BODIPY dyes fulfill most requirements for routine imaging and conjugationto small-molecule and protein targets of interest.

Bottom Line: These novel fluorescent dyes, which we term MayaFluors, are characterized by good aqueous solubility and favorable in vitro physicochemical properties.MayaFluors are readily accessible in good yields in a one-pot, two-step approach starting from well-established BODIPY dyes, and allow for facile modification with functional groups of relevance to bioconjugate chemistry and bioorthogonal labeling.Biological profiling in living cells demonstrates excellent membrane permeability, low nonspecific binding, and lack of cytotoxicity.

View Article: PubMed Central - PubMed

Affiliation: Center for Systems Biology and ∥Center for Human Genetic Research, Massachusetts General Hospital , 185 Cambridge Street, Boston, Massachusetts 02114, United States.

ABSTRACT
Small molecule fluorophores are indispensable tools for modern biomedical imaging techniques. In this report, we present the development of a new class of BODIPY dyes based on an alkoxy-fluoro-boron-dipyrromethene core. These novel fluorescent dyes, which we term MayaFluors, are characterized by good aqueous solubility and favorable in vitro physicochemical properties. MayaFluors are readily accessible in good yields in a one-pot, two-step approach starting from well-established BODIPY dyes, and allow for facile modification with functional groups of relevance to bioconjugate chemistry and bioorthogonal labeling. Biological profiling in living cells demonstrates excellent membrane permeability, low nonspecific binding, and lack of cytotoxicity.

Show MeSH