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Synthesis of boron dipyrromethene fluorescent probes for bioorthogonal labeling.

ABSTRACT: Seven 5-substituted 3-hydrazinyl derivatives of 3a, 4a-diaza-4,4-difluoro-8-phenyl boron dipyrromethene (BODIPY) were prepared for use as bioorthogonal fluorescent labels of aldehydes and ketones. The absorption energies can be tuned to absorb visible light over a large span of wavelengths by changing the nature of the 5-substituent. Optical properties of the hydrazones formed with these molecules are affected by the nature of the electrophile such that aliphatic and aromatic hydrazones can be differentiated from each other and from unreacted fluorophore.

SUBMITTER: Dilek O

PROVIDER: S-EPMC6705144 | biostudies-literature | 2008 Feb

REPOSITORIES: biostudies-literature

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Synthesis of boron dipyrromethene fluorescent probes for bioorthogonal labeling.

Dilek Özlem Ö Bane Susan L SL

Tetrahedron letters 20071215 8

Seven 5-substituted 3-hydrazinyl derivatives of 3a, 4a-diaza-4,4-difluoro-8-phenyl boron dipyrromethene (BODIPY) were prepared for use as bioorthogonal fluorescent labels of aldehydes and ketones. The absorption energies can be tuned to absorb visible light over a large span of wavelengths by changing the nature of the 5-substituent. Optical properties of the hydrazones formed with these molecules are affected by the nature of the electrophile such that aliphatic and aromatic hydrazones can be d ...[more]

PMID: 31439966

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Project description:Precise control of covalent bond formation in the presence of multiple functional groups is pertinent in the development of many next-generation bioconjugates and materials. Strategies derived from bioorthogonal chemistries are contributing greatly in that regard; however, the gain of chemoselectivity is often compromised by the slow rates of many of these existing chemistries. Recent work on a variation of the classical aldehyde/ketone condensation based on ortho-carbonylphenylboronic acids has uncovered markedly accelerated rates compared to those of the simple carbonyl counterparts. The products of these reactions are distinct, often in the form of boron-nitrogen heterocycles. In particular, we have shown that 2-formylphenylboronic acid (2fPBA), when coupled with an ?-amino-hydrazide, produces a unique zwitterionic and stable 2,3,1-benzodiazaborine derivative. In this work, we apply this chemistry to generate chemically defined and functional bioconjugates, herein illustrated with immunoconjugates. We show that an antibody and a fluorophore (as payload) equipped with the relevant reactive handles undergo rapid conjugation at near-stoichiometric ratios, displaying a reaction half-life of only ?5 min with 2 equiv of the linker payload. Importantly, the reaction can be extended to multicomponent labeling by partnering with the popular strain-promoted azide-alkyne cycloaddition and tetrazine- trans-cyclooctene (Tz-TCO) ligation. The mutual orthogonality to both of these chemistries allows simultaneous triple bioorthogonal conjugations, a rare feat thus far that will widen the scope of various multilabeling applications. Further collaboration with the Tz-TCO reaction enables rapid one-pot synthesis of a site-specific dual-payload antibody conjugate. Altogether, we envision that the 2fPBA-?-amino-hydrazide ligation will facilitate efficient assembly of diverse bioconjugates and materials, enabling access to more complex modalities via partnership with other orthogonal chemistries.

Dataset Information

Synthesis of boron dipyrromethene fluorescent probes for bioorthogonal labeling.

Publications

Synthesis of boron dipyrromethene fluorescent probes for bioorthogonal labeling.

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