Luciferin derivatives from bicyclic reactants and aminothiol derivatives and methods of use thereof
The present disclosure features a condensation reaction and a luciferin-unmasking reaction that can be carried out under physiological conditions. In general, the condensation reaction involves reacting a bicyclic reactant with an aminothiol derivative, generating a luciferin or luciferin derivative. A luciferin can provide detectable luminescence. A luciferin derivative can be unmasked to provide detectable luminescence in a luciferin-unmasking reaction. The present disclosure provides bicyclic reactants and aminothiol derivatives suitable for use in the condensation reaction. The condensation and luciferin-unmasking reactions find use in a variety of applications, which are also provided.
1. A compound of formula:
wherein
Q 1 is a heteroatom functional group selected from —O— and —NR Q1 —;
R Q1 is selected from hydrogen, alkyl, and substituted alkyl;
PG IV is an aryl or heteroaryl boronic acid-containing protecting group for the heteroatom functional group;
R 1 is selected from hydrogen, halogen hydroxyl, alkyl, substituted alkyl, alkoxy, amino, and substituted amino; and
PG I is a protecting group for the cyano.
2. A compound having the formula:
3. The compound of claim 1 , wherein PG IV has the formula
wherein:
R 10 and R 11 are hydrogen;
A ring is selected from aryl, substituted aryl, heteroaryl and substituted heteroaryl; and
L 1 is a cleavable linker group.