Methods for the selective sequestration of alkyne-presenting molecules and related compositions and methods
View Patent ↗Provided herein are methods for sequestering an alkyne-presenting molecule in a sample and related sequestration reagents, compositions, methods and systems.
1. A method for sequestering one or more alkyne-presenting molecules possibly present in a matrix, the method comprising:
providing the matrix sample wherein the one or more alkyne presenting molecules possibly present in the matrix are dispersed;
providing a sequestration reagent comprising a support presenting one or more azide groups capable of binding the sequestration reagent to one or more alkyne-presenting molecules through click-chemistry; and
contacting the sequestration reagent with the matrix sample in absence of a treatment of the matrix sample that introduces an alkyne group into the matrix sample prior to the contacting, the contacting being performed for a time and under a condition to allow binding of the sequestration reagent to one or more alkyne-presenting molecules possibly present in the matrix sample through click-chemistry, thus sequestering the alkyne-presenting molecules, when present, from the matrix sample;
wherein the matrix sample is selected from blood, and urine.
2. The method of claim 1 , wherein the sequestration reagent has formula XXXV:
wherein: R 1 is a cross-linked organic polymer; X 1 is selected from the group consisting of O, NH, and S; and n is between 4 and 7.
3. The method of claim 1 , wherein the contacting is performed by:
dispersing the sequestration reagent in the matrix sample in combination with a copper(0), copper(I) and/or copper(II) compound to provide a mixture; and tumbling the mixture.
4. The method of claim 1 , wherein the one or more alkyne-presenting molecules possibly present in the matrix sample comprise a terminal alkyne.
5. The method of claim 4 , wherein the terminal alkyne is selected from one of 17α-ethinylestradiol, acetylene, propyne, norethynodrel, and rasagiline.
6. The method of claim 4 , wherein the terminal alkyne is 17α-ethinylestradiol.
7. The method of claim 1 , wherein the one or more alkyne-presenting molecules possibly present in the matrix sample comprise an internal alkyne group.
8. The method of claim 7 , wherein the internal alkyne is selected from one of terbinafine, cicutoxin, oenanthotoxin, falcarinol, efavirenz, calicheamicin, and tariric acid.
9. The method of claim 1 , wherein the sequestration reagent has formula XXXVI:
wherein: R 1 is a cross-linked organic polymer; X 1 is selected from the group consisting of O, NH, and S; and n is between 4 and 7; and
R1 is a Wang resin, a Rink amide resin, a trityl resin or a chloromethylphenyl polystyrene resin.
10. A method for detecting one or more alkyne-presenting molecules possibly present in a matrix, the method comprising:
providing a matrix sample wherein the one or more alkyne presenting molecules possibly present in the matrix are dispersed;
providing a sequestration reagent comprising a support presenting one or more azide groups capable of binding of the sequestration reagent to one or more alkyne-presenting molecules and a detection reagent through click chemistry; and
contacting the sequestration reagent with the matrix sample in absence of a treatment of the matrix sample that introduces an alkyne group into the matrix sample prior to the contacting, the contacting being performed for a time and under a condition to allow binding of the sequestration reagent to one or more alkyne-presenting molecules possibly present in the matrix sample through click-chemistry, thus sequestering the alkyne-presenting molecules, when present, from the matrix sample;
detecting the one or more alkyne-presenting molecules possibly present in the matrix;
wherein the sequestration reagent has formula XXXVI:
wherein: R 1 is a cross-linked organic polymer; X 1 is selected from the group consisting of O, NH, and S; and n is between 4 and 7; and
R1 is a Wang resin, a Rink amide resin, a trityl resin or a chloromethylphenyl polystyrene resin.
11. The method of claim 10 , wherein the one or more alkyne-presenting molecules possibly present in the matrix sample comprise a terminal alkyne.
12. The method of claim 11 , wherein the terminal alkyne is selected from one of 17α-ethinylestradiol, acetylene, propyne, norethynodrel, and rasagiline.
13. The method of claim 11 , wherein the terminal alkyne is 17α-ethinylestradiol.
14. The method of claim 10 , wherein the matrix sample is an aqueous or organic solution.
15. The method of claim 10 , wherein the matrix sample is selected from blood, urine, drinking water, and agricultural irrigation water.
16. The method of claim 10 , wherein the matrix sample is selected from blood, and urine.
17. The method of claim 10 , wherein the one or more alkyne-presenting molecules possibly present in the matrix sample comprise an internal alkyne group.
18. The method of claim 17 , wherein the internal alkyne is selected from one of terbinafine, cicutoxin, oenanthotoxin, falcarinol, efavirenz, calicheamicin, and tariric acid.
19. A method for sequestering one or more alkyne-presenting molecules possibly present in a matrix, the method comprising:
providing the matrix sample wherein the one or more alkyne presenting molecules possibly present in the matrix are dispersed;
providing a sequestration reagent comprising a support presenting one or more azide groups capable of binding the sequestration reagent to one or more alkyne-presenting molecules through click-chemistry; and
contacting the sequestration reagent with the matrix sample in absence of a treatment of the matrix sample that introduces an alkyne group into the matrix sample prior to the contacting, the contacting being performed for a time and under a condition to allow binding of the sequestration reagent to one or more alkyne-presenting molecules possibly present in the matrix sample through click-chemistry, thus sequestering the alkyne-presenting molecules, when present, from the matrix sample;
wherein the sequestration reagent has formula XXXVI:
wherein: R 1 is a cross-linked organic polymer; X 1 is selected from the group consisting of O, NH, and S; and n is between 4 and 7; and
R1 is a Wang resin, a Rink amide resin, a trityl resin or a chloromethylphenyl polystyrene resin.
20. The method of claim 19 , wherein the matrix sample is an aqueous or organic solution.
21. The method of claim 19 , wherein the contacting is performed by: dispersing the sequestration reagent in the matrix sample in combination with a copper(0), copper(I) and/or copper(II) compound to provide a mixture; and tumbling the mixture.
22. The method of claim 19 , wherein the matrix sample is selected from drinking water, and agricultural irrigation water.
23. The method of claim 19 , wherein the one or more alkyne-presenting molecules possibly present in the matrix sample comprise a terminal alkyne.
24. The method of claim 23 , wherein the terminal alkyne is selected from one of 17α-ethinylestradiol, acetylene, propyne, norethynodrel, and rasagiline.
25. The method of claim 23 , wherein the terminal alkyne is 17α-ethinylestradiol.
26. The method of claim 19 , wherein the one or more alkyne-presenting molecules possibly present in the matrix sample comprise an internal alkyne group.
27. The method of claim 26 , wherein the internal alkyne is selected from one of terbinafine, cicutoxin, oenanthotoxin, falcarinol, efavirenz, calicheamicin, and tariric acid.