IP Library › Granted Patent US 10,111,842
Granted Patent B2
US 10,111,842 · App. 15/540,688 · Granted Oct 30, 2018

Eutectic solvents and uses thereof

Inventors: Hanne Hjorth Tønnesen (Oslo, NO); Kristine Opsvik Wikene (Oslo, NO)
Assignee: University of Oslo
A61K31/14A01N33/12A01N37/36A01N43/16A61K31/20A61K31/409A61K31/661A61K31/047H05K999/99
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Quick Facts
Patent No.
US 10,111,842
App. No.
15/540,688
Granted
Oct 30, 2018
Kind
B2
Abstract

Provided herein are photosensitizer compounds for use in a variety of clinical, industrial, and research applications. In particular, provided are deep eutectic solvents and natural deep eutectic solvents for use in killing of bacteria.

Claims (20)

1. A method of killing or inhibiting the growth of a bacterial cell, fungal cell, or cancer cell, comprising:

contacting said cell with a composition comprising a eutectic solvent and a photosensitizer selected from the group consisting of a porphyrin compround, a chlorin compound, a bacteriochlorin compound , a phthalocyanine compound, a texaphyrin comppund, a sapphyrin compound a porphycene compound, a curcuminoid compound, and a flavin compound.

2. A composition comprising a eutectic solvent and a photosensitizer selected from the group consisting of a porphyrin compround, a chlorin compound, a bacteriochlorin compound, a phthalocyanine compound a texaphyrin compound, a sapphyrin compound, a porphycene compound, a curcuminoid compound, and a flavin compound.

3. The composition of claim 2 , wherein said eutectic solvent is selected from the group consisting of a deep eutectic solvent (DES) and a natural deep eutectic solvent (NADES).

4. The composition of claim 2 , wherein said eutectic solvent comprises at least two components selected from the group consisting of an organic acid, a salt, a sugar, a sugar alcohol, an amino acid, a di or tri alkanol, and a choline derivative.

5. The composition of claim 4 , wherein said choline derivative is choline or phosphatidylcholine.

6. The composition of claim 4 , wherein said sugar or sugar alcohol is selected from the group consisting of sucrose, glucose, fructose, lactose, maltose, cellobiose, arabinose, ribose, ribulose, galactose, rhamnose, raffinose, xylose, sucrose, mannose, trehalose, mannitol, sorbitol, inositol, ribitol, galactitol, erythritol, xylitol and adonitol, and a phosphate thereof.

7. The composition of claim 4 , wherein said organic acid is selected from malic acid, maleic acid, citric acid, lactic acid, pyruvic acid, fumaric acid, succinic acid, lactic acid, acetic acid, aconitic acid, tartaric acid, malonic acid, ascorbic acid, glucuronic acid, oxalic acid, neuraminic acid and sialic acids.

8. The composition of claim 4 , wherein the first component is selected from the group consisting of citric acid, choline chloride, D-(+)-glucose, and sucrose.

9. The composition of claim 8 , wherein the second component is selected from the group consisting of sucrose, D-(+)-trehalose, choline chloride, DL-malic acid, glycerol, sucrose, xylitol and D-(−)-fructose.

10. The composition of claim 8 , wherein said eutectic solvent comprises said first and second components at a molar ratio of 1:1, 1:2, 1:3, 1:4, 1:5, 2:1, 2:3, 2:4, 2:5, 3:1, 3:2, 3:4, 3:5, 4:1, 4:2, 4:3, 4:5, 5:1, 5:2, 5:3, or 5:4.

11. The composition of claim 2 , wherein said eutectic solvent comprises an organic acid and a sugar or sugar alcohol in a molar ratio characteristic of formation of eutectic solution by said organic acid and a sugar or sugar alcohol.

12. The composition of claim 2 , wherein said eutectic solvent comprises a choline salt and a sugar, sugar alcohol, or organic acid in a molar ratio consistent with formation of eutectic solution by said organic acid and a sugar or sugar alcohol.

13. The composition of claim 2 , wherein said eutectic solvent comprises at least two sugars or sugar alcohols in a molar ratio consistent with formation of eutectic solution by said at least two sugars or sugar alcohols.

14. The composition of claim 2 , wherein said eutectic solvent comprises at least three sugars or sugar alcohols or organic acids in a molar ratio consistent with formation of eutectic solution by said at least two sugars or sugar alcohols.

15. The composition of claim 2 , wherein said eutectic solvent is selected from the group consisting of citric acid and sucrose at a molar ratio of 1:1, choline chloride and maleic acid at a molar ratio of 1:1, choline chloride and glycerol at a molar ration of 1:1, D-(+)-glucose and DL-malic acid at a molar ratio of 1:1, choline chloride and citric acid at a molar ratio of 2:1, citric acid and xylitol at a molar ratio of 1:1, choline chloride and xylitol at a molar ratio of 5:2, choline chloride and D-(−)-fructose at a molar ratio of 5:2, choline chloride and maleic acid 2:1, choline chloride and maleic acid 1:3, and glucose and sucrose 1:1.

16. The composition of claim 2 , wherein said eutectic solvent comprises sucrose, glucose, and fructose at a ratio of 1:1:1, or DL-malic acid and D-(−)-fructose and D-(+)-glucose at a molar ratio 1:1:1.

17. The composition of claim 2 , wherein said eutectic solvent is provided in a solution comprising a 1:1 to 1:1000 dilution of said eutectic solvent in water or an aqueous buffer.

18. The composition of claim 2 , wherein said porphyrin is 5,10,15 ,20-tetrakis(4-hydroxyphenyl)porphyrin (THPP), tetra-(4-trimethylanilinum)-porphine tetrachloride (TMAP), or porphyrin tetra-(4-carboxyphenyl)-porphine (TCPP).

19. The composition of claim 2 , wherein said curcuminoid is curcumin.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2018
From: TØNNESEN, HANNE HJORTH; WIKENE, KRISTINE OPSVIK
To: UNIVERSITY OF OSLO
Reel/Frame 047393/0969 →
Continuity (2)
Provisional Application 62098463 · Dec 31, 2014
Related Publication 20180000753A1 · Jan 4, 2018