ANALYTE DETECTION USING NEAR-INFRARED FLUOROPHORES

摘要

Embodiments of compounds for selectively detecting an analyte are disclosed, along with methods and kits for detecting analytes with the compounds. The compounds are bridged viologen conjugates including at least one fluorophore according to the general structure;;At least one of R1/R2, R2/R3, R3/R4, R5/R6, R6/R7, and/or R7/R8 together form a substituted or unsubstituted cycloalkyl or aryl.

主权项

1. A compound according to Formula I, Formula II, or Formula III comprising a bridged viologen backbone and substituents RA and RBwhere X− is any counteranion, RA and RB independently are substituted or unsubstituted aliphatic, or substituted or unsubstituted aryl or heteroaryl comprising one or more substituted or unsubstituted aromatic rings and/or heteroaromatic rings, and at least one of RA and RB is a fluorophore having a structure according to general formula (i)where each bond depicted as “” is a single or double bond as needed to satisfy valence requirements;
X1 is O, S, Se, Si(CH3)2, Ge(CH3)2, Sn(CH3)2, CH2, C(CH3)2, or NH; R1, R2, R4 independently are hydrogen, hydroxyl, oxygen, thiol, lower alkyl, carboxyalkyl, amino, substituted amino, alkoxy, halogen, or —NHRc where Rc is R5, R7, and R8 independently are hydrogen, hydroxyl, thiol, lower alkyl, carboxyalkyl, amino, substituted amino, alkoxy, or halogen; R3 and R6 independently are hydrogen, hydroxyl, halogen, oxygen, sulfur, thiol, amino, alkyl amino, imino, iminium, alkyl imino, alkyl iminium, cycloalkyl imino or —NHRc; at least one of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, and/or R7 and R8 together form a substituted or unsubstituted cycloalkyl or aryl; R9-R12 independently are hydrogen, alkyl, acyl, carboxyl, nitro, amino, alkyl amino, or —SO3H; R13 is hydrogen, hydroxyl, lower alkyl, lower alkoxy, —SO3H or —COOR14 where R14 is hydrogen or lower alkyl and the bond depicted as “” in ring B is a double bond, or R13 is one or more atoms forming a ring system with rings B and D and the bond depicted as “” in ring B is a single bond; and at least one of R1-R13 is a linker covalently binding the fluorophore to the bridged viologen backbone, wherein if R3 and R4 together form a substituted or unsubstituted cycloalkyl or aryl, then at least one of R1 and R8 is other than hydrogen, or R13 is not —COOR14, or at least one additional substituted or unsubstituted cycloalkyl or aryl is formed by R1 and R2, R2 and R3, R5 and R6, R6 and R7, and/or R7 and R8.