Hydrogel-based decontamination of aqueous samples containing nanoparticles

Patent metadata

Field	Value
Publication number	US-10343934-B2
Application number	US-201314374676-A
Country	US
Kind code	B2
Filing date	Jan 25, 2013
Priority date	Jan 25, 2012
Publication date	Jul 9, 2019
Grant date	Jul 9, 2019

Abstract

The present invention relates to the use of a supramolecular system in order to remove particles from a liquid medium containing same. According to the invention, the supramolecular system includes at least one molecule having a low molecular weight and/or an organic compound from living organisms, preferably from jellyfish, said compound being selected from among collagen, a polysaccharide, a proteoglycan or a mixture of two of said organic compounds, and said molecule having a low molecular weight and formula (I) as defined herein. The invention also relates to a method for removing particles from a liquid medium containing same. The invention is particularly suitable for use in water decontamination and biotechnology.

First claim

The invention claimed is:

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,

Assignees

• Univ Bordeaux

Inventors

• Barthelemy Philippe
• Thiery Alain
• Patwa Amit

Classifications

• C07H19/20

  with the saccharide radical esterified by phosphoric or polyphosphoric acids · CPC title

• Y02W10/37

  using solar energy · CPC title

• C02F1/26 Primary

  by extraction · CPC title

• C07H19/10

  with the saccharide radical esterified by phosphoric or polyphosphoric acids · CPC title

• C07H19/06

  Pyrimidine radicals · CPC title