NDLI: Synthesis and Spectroscopic Characterization of Fluorescent Boron Dipyrromethene-Derived Hydrazones

Content Provider	Springer Nature Link
Author	Dilek, Ozlem Bane, Susan L.
Copyright Year	2010
Abstract	Derivatives of 4,4-difluoro-4-bora-3a,4a,diaza-s-indacene (BODIPY® or BDP) that possess a hydrazine substituent on position 5 are potential “turn-on” fluorophores for labeling aldehydes The unnatural amino acid L-3-formyltyrosine can be incorporated into a protein or peptide; thus, these hydrazines are potentially site specific labels for such polymers. In this work, model compounds were synthesized to assess whether the photochemical properties of the BDP-hydrazone would be suitable for protein labeling. Hydrazones were synthesized from the fluorophore 3-chloro-5-hydrazino-BDP and different aldehydes, and the absorption and emission spectra of the products were compared. The hydrazone of an unsubstituted aromatic aldehyde displays absorption and emission maxima (531 nm and 559 nm, respectively in dioxane) that are red shifted relative to those of a hydrazone from an aliphatic aldehyde (513 nm and 543 nm, respectively, in dioxane) and an increased quantum yield (0.21 vs. 0.11, respectively, in dioxane). The presence of a hydroxyl group ortho- to the aldehyde produces a hydrazone in which the absorption and emission maxima are slightly red shifted (528 nm and 564 nm, respectively in dioxane) from the unsubstituted aromatic hydrazone, but the quantum yields of the two hydrazones are equivalent. Thus, an ortho-hydroxy substituted aromatic aldehyde is a suitable electrophile for “turn on” protein labeling using the hydrazino-BDP. The specificity of this labeling reaction for the unnatural amino acid was demonstrated through fluorescent labeling of just the 3-formyltyrosine-containing α-subunit of α,β-tubulin.
Starting Page	347
Ending Page	354
Page Count	8
File Format	PDF
ISSN	10530509
Journal	Journal of Fluorescence
Volume Number	21
Issue Number	1
e-ISSN	15734994
Language	English
Publisher	Springer US
Publisher Date	2010-10-01
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	BODIPY Hydrazones Bioorthogonal labeling Fluorescent probes Unnatural amino acids Analytical Chemistry Biochemistry Biotechnology Biophysics and Biological Physics Biomedicine general
Content Type	Text
Resource Type	Article
Subject	Sociology and Political Science Spectroscopy Law Biochemistry Clinical Biochemistry Clinical Psychology

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