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 (I):
wherein
Y is O or NH;
Z is alkynyl, —N 3 , a label, or a therapeutic; and
n is 0 to 50,
wherein C 1-n alkylene is optionally substituted.
2. The compound of claim 1 having formula (I-a):
wherein
Z is alkynyl, —N 3 , a label, or a therapeutic; and
n is 0 to 50,
wherein C 1-n alkylene is optionally substituted.
3. The compound of claim 1 having formula (I-b):
wherein
Z is alkynyl, —N 3 , a label, or a therapeutic; and
n is 0 to 50,
wherein C 1-n alkylene is optionally substituted.
4. The compound of claim 1 , wherein
Z is alkynyl, —N 3 , or a label; and
n is 2to 10.
5. The compound of claim 1 , wherein Z is a therapeutic.
6. The compound of claim 3 , wherein Z is a therapeutic.
7. The compound of claim 2 of formula (I-b-10)
wherein p is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
8. The compound of claim 7 , wherein p is 1, 2, 4, or 9.
9. The compound of claim 5 , wherein the therapeutic comprises an antibody-recruiting small molecule.
10. The compound of claim 9 , wherein the antibody-recruiting small molecule is a 2,4-dinitrophenyl.
11. The compound of claim 7 , wherein the therapeutic comprises an antibody-recruiting small molecule.
12. The compound of claim 11 , wherein the antibody-recruiting small molecule is a 2,4-dinitrophenyl.
13. A compound according to formula (II):
wherein
Y 1 is O or NH;
Y 2 is alkynyl, —N 3 , OC(O)Ci 1-n alkylene-Z 2 , or NHC(O)C 1-n alkylene-Z 2 ;
Z 1 and Z 2 are each independently selected from the group consisting of alkynyl, —N 3 , quencher, a label, and a therapeutic; and
n is 0 to 50,
wherein C 1-n alkylene is optionally substituted.
14. The compound of claim 13 , wherein
Y 1 is O;
Y 2 is alkynyl or —N 3 ; and
Z 1 is alkynyl or —N 3 .
15. The compound of claim 13 , wherein
Y 1 is O;
Y 2 is NHC(O)C 1-n alkylene-Z 2 ; and
Z 1 is alkynyl or —N 3 .
16. A method of detecting mycobacteria comprising:
a. contacting a sample with a compound according to claim 1 , wherein Z is alkynyl or —N 3 ;
b. contacting the sample with a compound that is reactive with alkynyl or —N 3 and comprises a label to label any mycobacteria present in the sample; and
c. detecting the labeled mycobacteria.
17. A method of detecting mycobacteria comprising:
a. contacting a sample with a compound according to claim 1 , wherein Z is a label, to label any mycobacteria present in the sample;
b. detecting the labeled mycobacteria.
18. The method of claim 16 , wherein the sample is sputum, cerebrospinal fluid, pericardial fluid, synovial fluid, ascitic fluid, blood, bone marrow, urine, feces, or a cell.
19. The method of claim 16 , wherein the label comprises a fluorophore, 18 F, 64 Cu, 124 I, 14 C, 3 H, 123 I, 131 I, 13 C, 2 H, 19 F, or a combination thereof.
20. The method of claim 16 , wherein the mycobacteria is Mycobacteria tuberculosis.