IP Library Granted Patent US 11,497,818
Granted Patent B2
US 11,497,818 · App. 15/987,500 · Granted Nov 15, 2022

Ultrafine nanoparticles comprising a functionalized polyorganosiloxane matrix and including metal complexes; method for obtaining same and uses thereof in medical imaging and/or therapy

Inventors: François Lux (Lyons, FR); Olivier Tillement (Fontaines Saint-Martin, FR); Maxime Saint Jean (Caluire et Cuire, FR); Pierre Mowat (Venissieux, FR); Pascal Perriat (Lyons, FR); Stéphane Roux (Cheneycey Buillon, FR); Anna Mignot (Lyons, FR)
Assignees: NANOH; UNIVERSITE LYON 1 CLAUDE BERNARD; INSTITUT NATIONAL DES SCIENCES APPLIQUEES DE LYON
A61K49/1824A61K9/14A61K41/0038A61K49/0002A61K49/0093A61K49/1857A61K49/1881A61K9/0019B82Y5/00B82Y15/00Y10T428/2982
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Quick Facts
Patent No.
US 11,497,818
App. No.
15/987,500
Granted
Nov 15, 2022
Kind
B2
Abstract

The invention relates to novel biocompatible hybrid nanoparticles of very small size, useful in particular for diagnostics and/or therapy. The purpose of the invention is to offer novel nanoparticles which are useful in particular as contrast agents in imaging (e.g. MRI) and/or in other diagnostic techniques and/or as therapeutic agents, which give better performance than the known nanoparticles of the same type and which combine both a small size (for example less than 20 nm) and a high loading with metals (e.g. rare earths), in particular so as to have, in imaging (e.g. MRI), strong intensification and a correct response (increased relaxivity) at high frequencies. Thus, the nanoparticles according to the invention, with diameter d 1 between 1 and 20 nm, each comprise a polyorganosiloxane (POS) matrix including gadolinium cations optionally associated with doping cations; a chelating graft C 1 DTPABA (diethylenetriaminepentaacetic acid bisanhydride) bound to the POS matrix by an —Si—C— covalent bond, and present in sufficient quantity to be able to complex all the gadolinium cations; and optionally another functionalizing graft Gf* bound to the POS matrix by an —Si—C— covalent bond (where Gf* can be derived from a hydrophilic compound (PEG); from a compound having an active ingredient PA1; from a targeting compound; from a luminescent compound (fluorescein). The method for the production of these nanoparticles and the applications thereof in imaging and in therapy also form part of the invention.

Claims (21)

1. A nanoparticle comprising

(i) a polyorganosiloxane (POS) matrix,

(ii) a metallic cation Gd 3+ ,

(iii) a chelating graft C 1 which is obtained by functionalizing said POS matrix of the nanoparticle with DOTAGA anhydride of the following formula:

wherein Gd 3+ is complexed to the chelating graft C 1 , wherein a diameter d 1 of said nanoparticle is from 1 to 8 nm, said nanoparticle molecular weight (in kDa) is greater than or equal to 2 and less than or equal to 200, and wherein said nanoparticle does not comprise a crystallized core of gadolinium oxide.

2. The nanoparticle of claim 1 , wherein the atom-% ratio ((Gd/Si)×100) is comprised between 10 and 60.

3. The nanoparticle of claim 1 , wherein the diameter d 1 of said nanoparticle is from 1 to 5 nm.

4. The nanoparticle according to claim 1 , wherein an atom % ratio (Gd/Si) is from 10 to 60.

5. The nanoparticle according to claim 1 , wherein said chelating graft C 1 is in excess relative to said metallic cation Gd 3+ .

6. The nanoparticle according to claim 1 , wherein the nanoparticle further comprises another functionalizing graft Gf* bound to said POS matrix by an —Si—C—covalent bond, where Gf* can be derived from:

a hydrophilic compound,

a compound having an active ingredient PA1,

a targeting compound,

a luminescent compound.

7. The nanoparticle according to claim 1 , wherein a relaxivity r 1 per Gd 3+ ion is greater than 5 mM −1 (of Gd 3+ ion)·s −1 for a frequency of 20 MHz.

8. The nanoparticle according to claim 1 , wherein a relaxivity r 1 per Gd 3+ ion at 60 MHz is greater than relaxivity r 1 per Gd 3+ ion at 20 MHz.

9. A suspension of a nanoparticle according to claim 1 .

10. A solid material obtained by removal of the liquid, optionally by lyophilization, of said suspension according to claim 9 .

11. An injectable liquid comprising a nanoparticle according claim 1 .

12. An injectable liquid comprising a suspension according to claim 9 .

13. An injectable liquid prepared from the solid material according to claim 10 .

Assignments (3)
PATENT OWNERSHIP AGREEMENT Recorded Jul 5, 2022
From: UNIVERSITE CLAUDE BERNARD LYON 1; INSTITUT NATIONAL DES SCIENCES APPLIQUEES DE LYON (NATIONAL INSTITUTE OF APPLIED SCIENCES OF LYON)
To: THE CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (FRENCH NATIONAL CENTRE FOR SCIENTIFIC RESEARCH)
Reel/Frame 060574/0302 →
CONFIRMATORY EXCLUSIVE LICENSE AGREEMENT Recorded Oct 13, 2020
From: UNIVERSITE CLAUDE BERNARD LYON I; NANO H; INSTITUT NATIONAL DES SCIENCES APPLIQUÉES DE LYON
To: PULSALYS
Reel/Frame 054054/0167 →
CONFIRMATORY SUBLICENSE AGREEMENT Recorded Oct 13, 2020
From: PULSALYS
To: NH THERAGUIX
Reel/Frame 054054/0948 →
Priority Claims (1)
FR 1053389 · Apr 30, 2010 · national
Continuity (3)
Continuation 15677167 · Aug 15, 2017
Division 13695090
Related Publication 20180264145A1 · Sep 20, 2018
Cited By (1)
US 12,533,426