Class of near infrared molecular probes for biological applications

摘要

Methods for preparing 2,5-Bis(benzoxazol-2′-yl)benzene-1,4-diol derivatives (Zinhbo derivatives) are provided. Zinhbo derivatives are used to detect zinc ions and have particular application in vivo and in vitro. Zinhbo derivatives upon excitation give a florescence response emission that can be used to determine the presence of zinc cation in solution. Zinhbo derivatives complexed with zinc cations upon excitation can produce a florescence response emission in the visible and near infrared range. Zinhbo derivatives complexed with zinc cations exhibit a large stoke shift between the excitation and emission wavelengths.

主权项

1. A process of preparing a Zinhbo derivative comprising:
(i) reacting a protected compound defined by the formula: where Y is an oxygen atom, a sulfur atom, a nitrogen atom with a pendant hydrogen atom, or a nitrogen atom with a pendant alkyl group; each Pr is individually a protecting group and R1, R2, R3, and R4 are each individually selected from the group consisting of a hydrogen atom, an electron withdrawing group, and an electron donating group; with a the 2-aminophenol derivative defined by the formula where R5 is a chelating group attached through a nitrogen atom, via a process that includes an oxidation reaction; and (ii) deprotecting the protecting groups to form a Zinhbo derivation defined by the following formula: where R1, R2, R3, and R4 are each individually selected from the group consisting of a hydrogen atom, an electron withdrawing group, and an electron donating group; Y is an oxygen atom, a sulfur atom, a nitrogen atom with a pendant hydrogen atom, or a nitrogen atom with a pendant alkyl group; and R5 is a chelating group attached through a nitrogen atom.