Trehalose analogues
Described herein are trehalose analogues. Also described herein are methods of making the trehalose analogues and uses of the analogues. For example, the disclosed trehalose analogues may be useful in the detection of bacteria.
1. A compound according to formula (II):
wherein
Y 1 is O or NH;
Y 2 is OC(O)C 1-n alkylene-Z 2 , or NHC(O)C 1-n alkylene-Z 2 ;
Z 1 is a fluorophore;
Z 2 is a quencher of the fluorophore of Z 1 ; and
n is 0 to 50,
wherein C 1-n alkylene is optionally substituted.
2. The compound of claim 1 , wherein
Y 1 is O; and
Y 2 is OC(O)C 1-n alkylene-Z 2 .
3. The compound of claim 1 , wherein the quencher comprises a dabcyl group.
4. The compound of claim 3 , wherein the quencher is
5. The compound of claim 1 , wherein Z′ is a fluorophore selected from the group consisting of a fluorescein, xanthene, cyanine, naphthalene, coumarin, oxadiazole, pyrene, oxazine, acridine, arylmethine, tetrapyrrole, and quantum dot.
6. The compound of claim 5 , wherein Y′ is O; and Y 2 is OC(O)C 1-n alkylene-Z 2 .
7. The compound of claim 5 , wherein Z′ is a fluorescein.
8. The compound of claim 7 , wherein Z 1 is
9. The compound of claim 5 , wherein the quencher comprises a dabcyl group.
10. The compound of claim 9 , wherein the quencher is
11. The compound of claim 7 , wherein the quencher comprises a dabcyl group.
12. The compound of claim 11 , wherein the quencher is
13. The compound of claim 5 of formula
14. The compound of claim 1 , wherein each C 1-n alkylene is a branched C 1-n alkylene optionally substituted with hydroxy.
15. The compound of claim 14 , wherein the branched C 1-n alkylene has a branch at the alpha position.
16. The compound of claim 15 , wherein the optional hydroxy substituent is attached to a carbon adjacent to the branch at the alpha position in the branched C 1-n alkylene.
17. A compound according to formula (II):
wherein
Y 1 is O or NH;
Y 2 is OC(O)C 1-n alkylene-Z 2 , or NHC(O)C 1-n alkylene-Z 2 ;
Z 1 is a fluorophore;
Z 2 is a quencher; and
n is 0 to 50,
wherein C 1-n alkylene is optionally substituted and the compound acts as a fluorescence resonance energy transfer (FRET) probe that is detectable after undergoing cellular metabolism.
18. A method of detecting mycobacteria comprising:
a. contacting a sample with a compound according to claim 1 ;
b. detecting the labeled mycobacteria.
19. The method of claim 18 , wherein the sample is sputum, cerebrospinal fluid, pericardial fluid, synovial fluid, ascitic fluid, blood, bone marrow, urine, feces, or a cell.
20. The method of claim 18 , wherein the mycobacteria is Mycobacteria tuberculosis.