Chemical switches for detecting reactive chemical agents

摘要

Certain embodiments of the present invention relate to the preparation of microbeads that exhibit a “turn on” fluorescence response within seconds of exposure to an analyte vapor (e.g., a chemical warfare agent or a reactive stimulant). This sensing approach is modeled after the mechanism for inhibition of acetylcholinesterase enzyme activity, and utilizes a specific and irreversible reaction between phosphonyl halides and a fluorescent indicator. The present invention also relates to a sensor and a method for sensing an analyte through detection of changes in the fluorescing properties of the inventive microbeads.

主权项

1. A coated microbead, comprising a microbead and a coating, wherein said coating comprises a fluorescent compound represented by I or a salt thereof: wherein, independently for each occurrence, W is O, S, or NRA; Y is O, S, or NRA; Z is O or NRA; RA is hydrogen, alkyl, acyl, or aralkyl; R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, and R12 are independently selected from the group consisting of hydrogen, halide, pseudohalide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, heteroaralkyl, carboxyl, acyl, carbamoyl, hydroxyl, alkoxy, aryloxy, aralkoxy, acyloxy, thio, sulfonyl, sulfhydryl, sulfamoyl, sulfonamido, sulfate, sulfonate, sulfoxido, seleno, nitro, amino, imino, amido, phosphonate, phosphinate, silyl, trifluoroalkyl, cyano, and —(CH2)mRB; RB is hydrogen, halide, pseudohalide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, heteroaralkyl, carboxyl, acyl, carbamoyl, hydroxyl, alkoxy, aryloxy, aralkoxy, acyloxy, thio, sulfonyl, sulfhydryl, sulfamoyl, sulfonamido, sulfate, sulfonate, sulfoxido, seleno, nitro, amino, imino, amido, phosphonate, phosphinate, silyl, trifluoroalkyl, or cyano; and m is 1-10 inclusive; provided that at least one of R1, R2, R3 and R4 iswherein M is O; E2 is hydroxyl, alkoxy, aralkoxy, sulfhydryl, amino, trifluoroalkyl, —O(CH2)nRB, —NH(CH2)nRB, or —S(CH2)nRB; E3 is alkyl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaralkyl, hydroxyl, alkoxy, aralkoxy, sulfhydryl, amino, or trifluoroalkyl; and n is 0-10 inclusive.