Grafted dinuclear metal complexes, and use thereof as cellular microparticle sensors

Patent metadata

Field	Value
Publication number	US-9453837-B2
Application number	US-201214006387-A
Country	US
Kind code	B2
Filing date	Mar 23, 2012
Priority date	Mar 23, 2011
Publication date	Sep 27, 2016
Grant date	Sep 27, 2016

Abstract

Novel grafted dinuclear metal complexes having formula (I) or of formula (II)

wherein M represents a metal ion,
and also the use thereof as sensors in a method for detecting and/or characterising cellular microparticles.

First claim

The invention claimed is:

1. A compound having formula (I) or formula (II):

wherein
M +i is a metal ion, and i is 1, 2 or 3;
L is an exchangeable ligand;
X is a —(CH 2 ) m —NH-A group, or a —CH 2 —NHC(O)—R—NH-A group wherein R is a C 2 -C 10 alkyl group, preferably a C 6 -C 10 alkyl group, either substituted or unsubstituted, linear or branched, and A is H or a fluorophore group;
m=1 to 12;
n=1, 2 or 3; and
Y is —(CH 2 ) p —NH 2 wherein p=0 to 12.

2. A compound having formula (I) or formula (II) according to claim 1 , characterised in that M is selected from Zn, Cu, Mn, Co, Ni and Fe.

3. A compound according to claim 1 having formula (I) or (II) wherein:
M is Zn or Cu;
X is —(CH 2 ) m —NH-A, where m=1, A is H, n=1 and p=0; or
X is —(CH 2 ) m —NH-A, where m=1, A is H, n=2 and p=0; or
X is —CH 2 —NHC(O)—R—NH-A, A is H, n=1 and p=0.

4. A compound having formula (I) or formula (II) according to claim 1 , wherein X is —(CH 2 ) m —NH-A, —CH 2 —NHC(O)—R—NH-A wherein R is a C 2 -C 10 alkyl group, preferably a C 6 -C 10 alkyl group, either substituted or unsubstituted, linear or branched, and A is a fluorophore group.

5. A compound having formula (III)

wherein
Z is NH 2 or a —(CH 2 ) m —NH-A group, or a —CH 2 —NHC(O)—R—NH-A group wherein R is a C 2 -C 10 alkyl group, preferably a C 6 -C 10 alkyl group, either substituted or unsubstituted, linear or branched, and A is H or a fluorophore group, provided that when m=2, A is not H;
m=1 to 12;
n=1, 2 or 3; and
Y is (CH 2 ) p —NH 2 wherein p=0 to 12.

6. A compound having formula (III) according to claim 5 , wherein
z is —(CH 2 ) m —NH-A, where m=1, A is H, n=1 and p=0; or
z is —(CH 2 ) m —NH-A, where m=1, A is H, n=2 and p=0; or
z is —CH 2 —NHC(O)—R—NH-A, A is H, n=1and p=0.

Assignees

• Belle Catherine
• Gellon Gisele
• Plawinski Laurent
• Doeuvre Loic
• Angles Cano Eduardo
• Centre Nat De La Rech Scient (Cnrs)
• Univ De Caen Basse-Normandie
• Univ Joseph Fourier

Inventors

• Belle Catherine
• Gellon Gisele
• Plawinski Laurent
• Doeuvre Loic
• Angles Cano Eduardo

Classifications

• C07F3/06

  Zinc compounds · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• G01N33/54353 Primary

  with ligand attached to the carrier via a chemical coupling agent (coatings G01N33/54393) · CPC title

• C07F1/08

  Copper compounds · CPC title

• C07D213/38 Primary

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title