Water-soluble nanocrystals through dual-interaction ligands
View Patent ↗A dual-interaction ligand for rendering otherwise hydrophobic nanoparticles water soluble or suspendable has a hydrophilic base with a plurality of hydrophilic segments extending from a core of the base, where at least one segment or the core contains a hydrophobic groups capable of forming van der Waal interaction between hydrophobic groups of the dual-interaction ligand and other hydrophobic ligands, and at least one complexing functionality to complex a metal atom or ion of a nanoparticle. The dual-interaction ligands can be combined with hydrophobic nanoparticles, where the dual-interaction ligands can displace some or all of the hydrophobic ligands of the hydrophobic nanoparticles, to form a nanoparticle-dual interaction ligand complex that can be dissolved or dispersed readily in an aqueous solution. The dual interaction ligand can be functionalized to attach an antibody or other biomolecules such that the nanoparticle dual-interaction ligands complexes can contain biomolecules. Such biomolecules modified nanoparticle dual-interaction ligands can be used for sensing, labeling, optical imaging, magnetic resonance imaging, cell separation, and treatment of diseases.
1. A dual-interaction ligand comprising:
a hydrophilic base having a plurality of segments comprising polyethtlene glycol extending from a core of said hydrophilic base;
at least one metal coordinating functionality; and
at least one hydrophobic functionality, wherein said metal coordinating functionality is attached by a linking group to said hydrophilic base and said hydrophobic functionality is attached to said hydrophilic base.
2. The dual-interaction ligand of claim 1 , wherein said hydrophilic base and said hydrophobic functionality comprises a polyethylene glycol (PEG) sorbitan fatty-acid esters (Tween), wherein said plurality of segments comprises four polyethylene glycol chains and said hydrophobic functionality comprises a fatty-acid ester.
3. The dual-interaction ligand of claim 2 , wherein said Tween is Tween-20, Tween-40, Tween-60, or Tween-80.
4. The dual-interaction ligand of claim 1 , wherein said metal coordinating functionality comprises a dithiol.
5. The dual-interaction ligand of claim 4 , wherein said dithiol and said linking group are derived from dihydrolipoic acid.
6. The dual-interaction ligand of claim 1 , wherein said metal coordinating functionality comprises a diol.
7. The dual-interaction ligand of claim 6 , wherein said diol and said linking group are derived from a condensate of dopamine and succinic acid or succinic acid anhydride.
8. A method of preparing a water soluble or suspendable nanoparticle-dual-interaction ligand complex comprising:
providing at least one hydrophobic nanoparticle containing a plurality of hydrophobic ligands;
providing a plurality of dual-interaction ligands according to claim 1 ; and
displacing at least some of said plurality of hydrophobic ligands with a plurality of dual-interaction ligands.
9. A water soluble or suspendable nanoparticle-dual-interaction ligand complex comprising:
at least one nanoparticle; and
a plurality of dual-interaction ligands comprising:
a hydrophilic base having a plurality of segments comprising polyethylene glycol extending from a core of said hydrophilic base;
at least one metal coordinating functionality; and
at least one hydrophobic functionality, wherein said metal coordinating functionality is attached by a linking group to said base and said hydrophobic functionality is attached to said base.
10. The complex of claim 9 , wherein said hydrophilic base and said hydrophobic functionality comprises a polyethylene glycol (PEG) sorbitan fatty-acid esters (Tween), wherein said plurality of segments of said hydrophilic base comprises four polyethylene glycol chains and said hydrophobic functionality comprises a fatty-acid ester.
11. The complex of claim 10 , wherein said Tween is Tween-20, Tween-40, Tween-60, or Tween-80.
12. The complex of claim 9 , wherein said metal coordinating functionality comprises a dithiol.
13. The complex of claim 12 , wherein said dithiol and said linking group are derived from dihydrolipoic acid.
14. The complex of claim 9 , wherein said metal coordinating functionality comprises a diol.
15. The complex of claim 14 , wherein said diol and said linking group are derived from a condensate of dopamine and succinic acid or succinic acid anhydride.
16. The complex of claim 9 , wherein said nanoparticle comprises a metal, metal oxide, or semiconductor nanocrystal.
17. The complex of claim 16 , wherein said metal comprises Au, Ag, Ag/Au, Co, Pt, Pd, Cu or any combination thereof.
18. The complex of claim 16 , wherein said metal oxide comprises Fe 3 O 4 , Fe 2 O 3 , In 2 O 3 , ZnO, TiO 2 , Gd 2 O 3 , or any combination thereof.
19. The complex of claim 16 , wherein said semiconductor comprises CdSe/ZnS, CdS/ZnS, CdS, CdSe, CdTe, InAs, InP, InP/ZnS, InAs/ZnSe, PbSe, PbS, PbTe or any combination thereof.
20. The complex of claim 9 , further comprising a plurality of hydrophobic ligands.
21. The complex of claim 20 , wherein said hydrophobic ligands comprise a C4-C30thiol, a C4-C30 fatty acid, a C4-C30 amine, a C4-C30 phosphine, a C4-C30dithiol, a C4-C30 diol, a C4-C30diamine, or any combination thereof.
22. The complex of claim 21 , wherein said hydrophobic ligand comprises 1-dodecanethiol, oleic acid, or oleylamine.
23. The complex of claim 9 , further comprising an antibody or other biomolecules attached by a linking group to a segment of at least one of said dual-interaction ligands.
24. A method for preparing a dual-interaction ligand comprising the steps of:
providing a hydrophilic base having at least one hydrophilic segment comprising polyethylene glycol extending from a core of said hydrophilic base;
attaching at least one hydrophobic functionality by a linking group to said hydrophilic base; and
attaching at least one metal coordinating functionality by a linking group to said hydrophilic base.
25. The method of claim 24 , wherein said hydrophilic base and said hydrophobic functionality comprises a polyethylene glycol (PEG) sorbitan fatty-acid esters (Tween), wherein said plurality of segments comprises four polyethylene glycol chains and said hydrophobic functionality comprises a fatty-acid ester.
26. The method of claim 25 , wherein said Tween is Tween-20, Tween-40, Tween-60, or Tween-80.
27. The method of claim 24 , wherein said metal coordinating functionality comprises a dithiol.
28. The method of claim 27 , wherein said dithiol and said linking group are derived from dihydrolipoic acid.
29. The method of claim 24 , wherein said metal coordinating functionality comprises a diol.
30. The method of claim 29 , wherein said diol and said linking group are derived from a condensate of dopamine and succinic acid or succinic acid anhydride.