Hydrogel-based decontamination of aqueous samples containing nanoparticles

1. A process for subtracting nanoparticles from a liquid medium containing the same, comprising a step

(a) of adding a supramolecular system to said liquid medium at a temperature of between 2 and 95° C., wherein the supramolecular system comprises:

at least one low-molecular-weight molecule,

wherein said low-molecular-weight molecule being of formula (I), said supramolecular system forming a gel on contact with the liquid medium, said gel capturing the nanoparticles contained in said liquid medium, and a step (b) of separating said liquid medium and said gel having captured said nanoparticles,

wherein said low-molecular-weight molecule being of formula (I) below:

wherein:

X represents an oxygen atom;

B represents a natural or unnatural puric or pyrimidic base, optionally substituted with an R 3 ′ group as defined below;

substituents L 1 and L 2 :

are identical or different and represent:

(i) a hydrogen atom,

(ii) a hydroxyl group,

(iii) a heteroaryl group comprising 1 to 4 nitrogen atoms, unsubstituted or substituted with a saturated or unsaturated, linear or branched C 2 -C 30 hydrocarbon-based chain,

(iv) a group chosen from an oxycarbonyl group —O—C(O)—, a thiocarbamate group —O—C(S)—NH—, a carbonate group —O—C(O)—O—, a carbamate group —O—C(O)—NH—, an ether group —O—, a phosphate group or a phosphonate group, knowing that said L 1 group is substituted with an R 1 group and said L 2 group is substituted with an R 2 group, where R 1 and R 2 , which may be identical or different, represent:

a linear or branched, saturated or unsaturated, partially fluorinated or perfluorinated, C 2 -C 30 , hydrocarbon-based chain,

a C 2 -C 30 acyl radical, or

an acylglycerol group,

or

form a ketal group of formula (II) below:

formula (II) in which K 1 and K 2 are identical or different and represent a saturated or unsaturated C 1 -C 19 hydrocarbon-based chain,

R 3 and R 3 ′

represent, independently of one another:

(i) a hydroxyl, amino, phosphate, phosphonate, phosphocholine, O-alkyl phosphocholine, thiophosphate or phosphonium group,

(ii) a linear or branched C 2 -C 30 alkyl chain optionally substituted with at least one hydroxyl group,

(iii) a —(CH 2 ) n —V—R 8 group, wherein V represents an —O—, —S— or —NH— group, R 8 represents a C 2 -C 30 alkyl, and n is an integer from 1 to 50,

(iv) a —V—C(O)—R 8 group, wherein V represents an —O—, —S— or —NH— group, and R 8 represents a C 2 -C 30 alkyl,

or

(v) a heteroaryl group containing from 1 to 4 nitrogen atoms, said heteroaryl group being unsubstituted or substituted with a C 2 -C 30 alkyl, or with a (CH 2 ) m —O—(CH 2 ) p —R 9 group, or with a —(CH 2 ) 0-1 —Y—C(═O)—R″ group, or with a monosaccharide or polysaccharide, or with a group:

or with a group:

wherein:

m is an integer from 1 to 6,

p is an integer from 0 to 10 and

R 9 represents a C 1 to C 10 alkyl group, or a cyclic ketal group containing 5 to 7 carbon atoms, said cyclic ketal group being unsubstituted or substituted with at least one linear or branched C 2 -C 30 alkyl, a sterol group, a diacyl glycerol, a hydrofluorocarbon-based chain or at least one monosaccharide or polysaccharide,

Y is an oxygen atom, an NH group or a sulfur atom,

and R″ is a hydrocarbon-based chain or a fluorocarbon-based chain,

R′ is a hydrocarbon-based chain.

2. The process according to claim 1 , also comprising, before step (b), when the temperature of the liquid medium obtained in step (a) is below 50° C., the following intermediate steps:

(a1) heating the medium obtained in step (a) to a temperature of between 50 and 95° C., and

(a2) cooling the medium obtained in step (a1) to a temperature of between 2 and 50° C.

3. The process according to claim 1 , wherein the concentration of supramolecular system used is between 0.001 mg·ml −1 and 100 mg·ml −1 of aqueous medium.

4. The process according to claim 1 , wherein the nanoparticles have a size of between 5 nm and 100 nm.

5. The process according to claim 1 , wherein the liquid medium is chosen from the group comprising water, an organic solvent and a polyphase medium.

6. The process according to claim 1 , wherein said low-molecular-weight molecule is an amphiphilic fluorinated glycosyl nucleoside.

7. The process according to claim 1 , wherein

X represents an oxygen atom, and/or

B represents a thymine, adenine, guanine, cytosine, 6-methoxypurine or hypoxanthine or an unnatural puric or pyrimidic base, which can encompass the base:

wherein:

R 3 ′ is as defined below,

and/or

L 1 represents a hydroxyl group, L 2 represents a hydrogen atom, or L 1 and L 2 together form a ketal group of formula (II) below:

wherein K 1 and K 2 are identical or different and represent a saturated or unsaturated C 1 -C 19 hydrocarbon-based chain and/or

R 3 and R 3 ′

represent:

(i) a hydroxyl, amino, phosphate, phosphonate, phosphocholine, O-alkyl phosphocholine, thiophosphate or phosphonium group,

(ii) a linear or branched C 2 -C 30 alkyl chain, optionally substituted with at least one hydroxyl group,

(iii) a —(CH 2 ) n —V—R 8 group, wherein V represents an —O—, —S— or —NH— group, R 8 represents a C 2 -C 30 alkyl, and n is an integer from 1 to 50,

(iv) a —V—C(O)—R 8 group, wherein V represents an —O—, —S— or —NH— group, and R 8 represents a C 2 -C 30 alkyl,

or

(v) a heteroaryl group containing from 1 to 4 nitrogen atoms, said heteroaryl group being unsubstituted or substituted with a C 2 -C 30 alkyl, or with a (CH 2 ) m —O—(CH 2 ) p —R 9 group, or with a —(CH 2 ) 0-1 —Y—C(═O)—R″ group, or with a monosaccharide or polysaccharide, or with a group:

or with a group:

wherein:

m is an integer from 1 to 6,

p is an integer from 0 to 10 and

R 9 represents a C 1 to C 10 alkyl group, or a cyclic ketal group containing 5 to 7 carbon atoms, said cyclic ketal group being unsubstituted or substituted with at least one linear or branched C 2 -C 30 alkyl, a sterol group, a diacyl glycerol, a hydrofluorocarbon-based chain or at least one monosaccharide or polysaccharide,

Y is an oxygen atom, an NH group or a sulfur atom,

and R″ is a hydrocarbon-based chain or a fluorocarbon-based chain,

R′ is a hydrocarbon-based chain.

8. The process according to claim 1 , wherein:

X represents an oxygen atom,

B represents an unnatural pyrimidic base substituted with a heteroaryl group containing three nitrogen atoms, said heteroaryl group being substituted with a group:

substituents L 1 and L 2 are identical or different and represent:

(i) a hydrogen atom,

(ii) a hydroxyl group,

R 3

represents a heteroaryl group comprising three nitrogen atoms, said heteroaryl group being substituted with a group:

wherein:

R′ is a hydrocarbon-based chain;

Y is an oxygen atom, an NH group or a sulfur atom,

and R″ is a hydrocarbon-based chain or a fluorocarbon-based chain.

9. The process according to claim 1 , wherein

X represents an oxygen atom;

B represents a puric or pyrimidic base;

substituents L 1 and L 2 form a ketal group of formula (II) below:

formula (II) in which K 1 and K 2 are identical or different and represent a saturated or unsaturated C 1 -C 19 hydrocarbon-based chain,

R 3

represents a phosphocholine group.

10. The process according to claim 1 , wherein said low-molecular-weight molecule is chosen from:

the group defined by formula (III) below, wherein R′ is a hydrocarbon-based chain:

the group defined by formula (IV) below, wherein Y is an oxygen atom, an NH group or a sulfur atom, and R″ is a hydrocarbon-based chain or a fluorocarbon-based chain:

the group defined by formula (V) below, wherein n is an integer between 0 and 19:

or

the group defined by formula (VI) below, wherein n is an integer between 0 and 19:

11. The process according to claim 1 , wherein said low-molecular-weight molecule is chosen from the group comprising:

5′-(4-((2H,2H,3H,3H-perfluoroundecanamide)methyl)-1H-1,2,3-triazol-1-yl)-N3-(1-((β-D-glucopyranoside)-1H-1,2,3,-triazol-4-yl)methyl)thymidine,

5′-(4-((1H, 1H,2H, 2H-perfluoroundecanamide)methyl)-1H-1,2,3-triazol-1-yl)-N3-(1-((β-D-glucopyranoside)-1H-1,2,3-triazol-4-yl)methyl)thymidine,

5′-(4-((oleamide)methyl)-1H-1,2,3-triazol-1-yl)-N3-(1-((β-D-glucopyranoside)-1H-1,2,3-triazol-4-yl)methyl)thymidine,

5′-(4-((stearamide)methyl)-1H-1,2,3-triazol-1-yl)-N3-(1-((β-D-glucopyranoside)-1H-1,2,3-triazol-4-yl)methyl)thymidine,

5′-(4-((octadecyloxy)methyl)-1H-1,2,3-triazol-1-yl)-N3-(1-((β-D-glucopyranoside)-1H-1,2,3-triazol-4-yl)methyl)thymidine, and

5′-(4-((cholesteryloxy)methyl)-1H-1,2,3-triazol-1-yl)-N3-(1-((β-D-glucopyranoside)-1H-1,2,3-triazol-4-yl)methyl)thymidine,

2′,3′-O-18-pentatriacontanylidenuridine-5′-phosphocholine,

2′,3′-O-18-pentatriacontanylidenadenosine-5′-phosphocholine, and

a mixture of at least two of these compounds.