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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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(a) Structures of BODIPY analogues 9, 10, and 12a. (b) One-pot synthesis of MayaFluor analogues 12a–e. Isolated yield after purificationis given in parentheses. (c) Synthesis of MayaFluor 14 and (d) tetrazine-functionalized MayaFluor 15. HaloTag-ligandconjugated BODIPY 16 and MayaFluor 17.
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fig2: (a) Structures of BODIPY analogues 9, 10, and 12a. (b) One-pot synthesis of MayaFluor analogues 12a–e. Isolated yield after purificationis given in parentheses. (c) Synthesis of MayaFluor 14 and (d) tetrazine-functionalized MayaFluor 15. HaloTag-ligandconjugated BODIPY 16 and MayaFluor 17.

Mentions: We selected BODIPY (9) asa model substrate since it is well established and provides directaccess to dimethoxy BODIPY (10) as a reference compound(Figure 2a).18,20,22 To selectively substitute only one fluorine, we applieda two-step one-pot strategy, inspired by our previous work on 19F/18F exchange on BODIPYs for hybrid optical/positronemission tomography imaging.21 The synthesisrelies on abstraction of a single fluoride from the BF2-core to generate a borenium intermediate (11).25,26 We found this intermediate readily reacts with suitable alcoholsto yield the desired monoalkoxy-BODIPY (12) in high yieldswithout the formation of dialkoxy BODIPY (Figure 2b).


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)

(a) Structures of BODIPY analogues 9, 10, and 12a. (b) One-pot synthesis of MayaFluor analogues 12a–e. Isolated yield after purificationis given in parentheses. (c) Synthesis of MayaFluor 14 and (d) tetrazine-functionalized MayaFluor 15. HaloTag-ligandconjugated BODIPY 16 and MayaFluor 17.
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Related In: Results  -  Collection

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Show All Figures
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fig2: (a) Structures of BODIPY analogues 9, 10, and 12a. (b) One-pot synthesis of MayaFluor analogues 12a–e. Isolated yield after purificationis given in parentheses. (c) Synthesis of MayaFluor 14 and (d) tetrazine-functionalized MayaFluor 15. HaloTag-ligandconjugated BODIPY 16 and MayaFluor 17.
Mentions: We selected BODIPY (9) asa model substrate since it is well established and provides directaccess to dimethoxy BODIPY (10) as a reference compound(Figure 2a).18,20,22 To selectively substitute only one fluorine, we applieda two-step one-pot strategy, inspired by our previous work on 19F/18F exchange on BODIPYs for hybrid optical/positronemission tomography imaging.21 The synthesisrelies on abstraction of a single fluoride from the BF2-core to generate a borenium intermediate (11).25,26 We found this intermediate readily reacts with suitable alcoholsto yield the desired monoalkoxy-BODIPY (12) in high yieldswithout the formation of dialkoxy BODIPY (Figure 2b).

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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