FRICTIONLESS MOLECULAR ROTARY MOTORS

• US 20100016610A1
• Filed: 02/06/2008
• Published: 01/21/2010
• Est. Priority Date: 02/06/2007
• Status: Active Grant

• Current Assignee: TECHNION RESEARCH AND DEVELOPMENT FOUNDATION, LTD.
• Original Assignee: TECHNION RESEARCH AND DEVELOPMENT FOUNDATION, LTD.
• Inventors: Keinan, Ehud
• Granted Patent: US 8,715,635 B2
• Time in Patent Office: Days
• US Class Current: 548/303.400
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings

Abstract

A rotaxane consisting of a cucurbituril and an uncharged guest molecule, having low or null affinity therebetween is provided as well as processes for providing the same. Various uses as energy converters (“frictionless” molecular motors), biochips and biosensors using the same are also provided.

Claims

1. A rotaxane comprising a host molecule and a guest molecule, said host molecule being a cucurbit[n]uril (CB[n]), and said guest molecule having the general Formula I:

U—

B₁-L₁-[A]_m-L₂-B₂—

Y 

 

Formula I

wherein;

n is an integer that ranges from 5 to 20;

B₁ and B₂ are each independently an uncharged stopper moiety;

L₁ and L₂ are each independently an uncharged linking moiety or absent;

[A]_m is an uncharged threading moiety;

m is an integer that ranges from 1 to 50;

U and Y are each independently selected from the group consisting of an anchoring group, an effector moiety, a detectible moiety, a biomolecule, or absent.

2. The rotaxane of claim 1, wherein n ranges from 5 to 8.

3. The rotaxane of claim 1, wherein A is selected from the group consisting of a 1,2-ethyn-di-yl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, substituted or unsubstituted cyclobuta-1,3-diene-1,3-di-yl, substituted or unsubstituted pentalene-2,5-di-yl, substituted or unsubstituted benzene-1,4-di-yl, substituted or unsubstituted pyrene-2,7-di-yl, C-substituted or unsubstituted pyridine-2,5-di-yl, C-substituted or unsubstituted pyrimidine-2,5-di-yl, C-substituted or unsubstituted pyrazine-3,6-di-yl and 1,2,4,5-tetrazine-3,6-diyl.

4. The rotaxane of claim 1, wherein said stopper moiety is selected from the group consisting of a branched alkyl moiety, a branched cycloalkyl moiety, a branched heteroalicyclic moiety, a branched polyaryl moiety, a branched polyheteroaryl moiety, an adamantly moiety, a branched organophosphorous, a branched organoboron, a branched organosilicon and a branched carboranes.

5. The rotaxane of claim 1, wherein said linking moiety is selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, heteroalicyclic, aryl, heteroaryl, ether, thioether, amide, ester, carbamate, thioamide, thiocarbamate, imine, aza, organophosphorous, organoboron and organosilicon.

6. The rotaxane of claim 1, wherein said effector moiety is selected from the group consisting of a charged moiety, a metal ion complex moiety, a magnetic moiety and a light absorbing moiety.

7. The rotaxane of claim 1, wherein said cucurbit[n]uril further comprises at least one functionality attached thereto selected from the group consisting of an anchoring group, an effector moiety, a detectible moiety and a biomolecule.

8. A composition-of-matter comprising the rotaxane of claim 1 attached to a solid support.

9. A composition-of-matter comprising a plurality of the rotaxane of claim 1 attached to a solid support.

10. A composition-of-matter comprising a plurality of the rotaxane of claim 1 attached to one another.

11. The composition of claim 8, wherein said rotaxane is attached via said anchoring group on said guest molecule.

12. The composition of claim 8, wherein said rotaxane is attached via said anchoring group on said host molecule.

13. The composition of claim 8, capable of converting energy from one form to another.

14. A process of preparing the rotaxane of claim 1, the process comprising:

providing a complex which comprises a host molecule and a guest molecule, said host molecule being a cucurbit[n]uril (CB[n]), and said guest molecule having a general formula selected from the group consisting of Formula II or Formula III;

U—

B₁-L′

₁-[A]_m-L′

₂-B₂—

Y 

 

Formula II

U—

B₁-L₁-[A]_m-L′

₂-B₂—

Y 

 

Formula III

wherein;

n is an integer that ranges from 5 to 20;

[A]_m is an uncharged threading moiety;

m is an integer that ranges from 1 to 50;

L′

₁ and L′

₂ are each independently an affinity moiety or one of L′

₁ and L′

₂ is absent and at least one of L′

₁ and L′

₂ independently comprises a positively charged group;

L₁ is an uncharged linking moiety or absent;

B₁ and B₂ are each independently an uncharged stopper moiety;

U and Y are each independently selected from the group consisting of an anchoring group, an effector moiety, a detectible moiety, a biomolecule, or absent; and

substantially neutralizing said positively charged group to thereby obtain the rotaxane.

15. The process of claim 14, further comprises, prior to said neutralizing:

contacting said cucurbit[n]uril with a compound having a general formula selected from the group consisting of Formula IV, Formula V or Formula VI;

R₁-L′

₁-[A]_m-L′

₂-R₂ 

 

Formula IV

U—

B₁-L′

₁-[A]_m-L′

₂-R₂ 

 

Formula V

U—

B₁-L₁-[A]_m-L′

₂-R₂ 

 

Formula VI

wherein;

n is an integer that ranges from 5 to 20;

[A]_m is an uncharged threading moiety;

m is an integer that ranges from 1 to 50;

L′

₁ and L′

₂ are each independently an affinity moiety or one of L′

₁ and L′

₂ is absent and at least one of L′

₁ and L′

₂ independently comprises a positively charged group;

R₁ and R₂ are each independently a reactive group;

L₁ is an uncharged linking moiety or absent;

B₁ is an uncharged stopper moiety;

U is selected from the group consisting of an anchoring group, an effector moiety, a detectible moiety, a biomolecule, or absent;

thereby forming a complex between said cucurbit[n]uril and said compound having a general formula selected from the group consisting of Formula IV, Formula V or Formula VI via at least one of said affinity moiety; and

contacting said complex with a compound having the general Formula VII and/or a compound having the general Formula VIII;

U—

B₁—

R₄ 

 

Formula VII

R₃—

B₂—

Y 

 

Formula VIII

wherein;

R₃ and R₄ are each independently a reactive group;

B₁ and B₂ are each independently an uncharged stopper moiety; and

U and Y are each independently selected from the group consisting of an anchoring group, an effector moiety, a detectible moiety, a biomolecule, or absent;

thereby forming a guest molecule within said cucurbit[n]uril, said guest molecule is having a general formula selected from the group consisting of Formula II or Formula III.

16. A process of preparing the rotaxane of claim 1, the process comprising:

contacting said cucurbit[n]uril with a compound having the general Formula VI;

U—

B₁-L₁-[A]_m-L′

₂-R₂ 

 

Formula IX

wherein;

n is an integer that ranges from 5 to 20;

[A]_m is an uncharged threading moiety;

m is an integer that ranges from 1 to 50;

L′

₂ is an affinity moiety which comprises a positively charged group;

R₂ is a reactive group;

L₁ is an uncharged linking moiety or absent;

B₁ is an uncharged stopper moiety;

U is selected from the group consisting of an anchoring group, an effector moiety, a detectible moiety, a biomolecule, or absent;

thereby forming a complex between said cucurbit[n]uril and said compound having the general Formula IV via said affinity moiety; and

contacting said complex with a compound having the general Formula X;

R₃—

B₂—

Y 

 

Formula X

wherein;

R₃ is a reactive group;

B₂ is an uncharged stopper moiety; and

Y is selected from the group consisting of an anchoring group, an effector moiety, a detectible moiety, a biomolecule, or absent;

thereby substantially neutralizing said positively charged group and forming the rotaxane.

17. The process of claim 15, wherein R₃ is an affinity moiety.

18. The process of claim 15, wherein said cucurbit[n]uril is attached to a solid support prior to said contacting.

19. The process of claim 15, wherein any one of U or Y is attached to a solid support prior to said contacting.

20. The process of claim 16, wherein R₃ is an affinity moiety.

21. The process of claim 16, wherein said cucurbit[n]uril is attached to a solid support prior to said contacting.

22. The process of claim 16, wherein any one of U or Y is attached to a solid support prior to said contacting.

23. The composition of claim 9, wherein said rotaxane is attached via said anchoring group on said guest molecule.

24. The composition of claim 9, wherein said rotaxane is attached via said anchoring group on said host molecule.

25. The composition of claim 9, capable of converting energy from one form to another.

26. The composition of claim 10, wherein said rotaxane is attached via said anchoring group on said guest molecule.

27. The composition of claim 10, wherein said rotaxane is attached via said anchoring group on said host molecule.

28. The composition of claim 10, capable of converting energy from one form to another.