Calibration aid for optical imaging applications

1 . A calibration device for optical imaging applications, comprising a body forming at least two separate areas and a material arranged on said areas, wherein:

said material comprises at least one hydrophobic polymer and at least one dye visible in a spectral range of wave-lengths comprised between 500 nm and 2000 nm included;

said at least one hydrophobic polymer forms a continued matrix;

said at least one dye selected from luminescent dyes and is homogeneously distributed within said polymer matrix, in a predetermined weight percentage by weight of the hydrophobic polymer in said material; and

the weight percentage of said at least one dye is different in each of said areas.

2 . The calibration device according to claim 1 , wherein the body comprises at least two recesses respectively forming said at least two separate areas.

3 . The calibration device according to claim 1 , wherein said material is in the form of a coating.

4 . The calibration device according to claim 1 , wherein said hydrophobic polymer is chosen from poly(methyl methacrylate), poly(ethyl methacrylate), poly(propyl methacrylate), poly(butyl methacrylate), poly(methyl methacrylate-co-methacrylic acid), poly(lactide-co-glycolide), polylactic acid, polyglycolic acid, polycaprolacton, cellulose triacetate, nitrocellulose, polydimethylsiloxane, poly(ethylene terephthalate), polycarbonate, polyethylene, ethylene vinyl acetate copolymer, polyurethane, polystyrene, and copolymers thereof with poly(ethylene glycol).

5 . The calibration device according to claim 1 , wherein said luminescent dyes include fluorescent dyes, phosphorescent dyes and chemiluminescent dyes.

6 . The calibration device according to claim 1 , wherein said at least one dye is chosen in the group comprising:

i) cyanine dyes of the following formula (I) below:

wherein:

n is an integer equal to 1, 2, 3 or 4;

X − is a counterion,

W is a heteroatom selected from the group comprising S, N and O or a carbon atom bearing two methyl substituents (C(CH 3 ) 2 );

R 1 , R 2 and R 3 , which may be identical or different, represent a hydrogen atom, a hydrocarbon chain having from 1 to 24 carbon atoms;

R 4 and R 5 , which may be identical or different, represent a hydrogen atom or a hydrocarbon chain having from 1 to 24 carbon atoms;

R 6 and R 7 are identical and represent a hydrogen atom, or form together and with the carbon atoms to which they are respectively bonded, a fused benzene ring,

ii) a dye of following formula (II) below:

and

iii) dyes of following formula (III) below:

wherein:

A and B are independently selected from the group consisting of:

X and Y are each independently selected from the group consisting of S and Se,

Z is independently one of N and P; and

R 9 , R 10 , R 11 and R 12 are each independently of the formula-alkyl-linker wherein “alkyl” is —(CH 2 ) n —, further wherein n is between 1 and 14, inclusive, and further wherein “linker” is selected form the group consisting of sulfonic, phosphonic, carboxyl, hydroxyl, NETS-ester, maleimide, amine, —SH, sulfonic acid and hydrazide.

7 . The calibration device according to claim 1 , wherein said at least one dye is a fluorescent dye chosen among 7.5 cyanines of following formula (IV):

wherein:

R 13 and R 14 are the same or different and independently selected from a group consisting of:

a hydrogen,

a group chosen from a (C 1 -C 20 )alkyl, a cyclo(C 3 -C 20 )alkyl, a (C 2 -C 20 )alkenyl, a (C 2 -C 20 )alkynyl, a heterocyclic group, a cyclo(C 3 -C 20 )alkenyl, a heterocyclo(C 2 -C 20 )alkenyl, an aryl, a heteroaryl, a hetero(C 1 -C 20 )alkyl, a (C 1 -C 20 )alkylaryl, and a (C 1 -C 20 )alkylheteroaryl, said group being unsubstituted or substituted by one or two substituents chosen from a (C 1 -C 5 )alkyl, an aryl, and —COOR 11 , R 11 being a (C 1 -C 20 )alkyl, and

a group of formula E-R 15 , wherein E is chosen from —O—, —S—, —Se—, —NH—, —CH 2 —; R 15 is chosen from a (C 1 -C 20 )alkyl, a cyclo(C 3 -C 20 )alkyl, a (C 2 -C 20 )alkenyl, a (C 2 -C 20 )alkynyl, a heterocyclic group, a cyclo(C 3 -C 20 )alkenyl, a heterocyclo(C 2 -C 20 )alkenyl, an aryl, a heteroaryl, a hetero(C 1 -C 20 )alkyl, a (C 1 -C 20 )alkylaryl, a (C 1 -C 20 )alkylheteroaryl, R 15 being unsubstituted or substituted by one to three substituents chosen from a (C 1 -C 5 )alkyl, an aryl, or —COOR 16 , R 16 being a (C 1 -C 20 )alkyl,

A 1 is a group of following formula:

and A 2 is a group of following formula:

or A 1 is a group of following formula:

and A 2 is a group of following formula:

wherein:

R 18 and R 20 are independently selected from the group consisting of hydrogen, halogen, (C 1 -C 10 )alkyl, —OR 21 , —NR 21 R 22 , —NO 2 , —CF 3 , —CN, —S R 21 , —N 3 , —C(═O) R 21 , —OC(═)OR 21 , —C(═O) NR 21 R 22 , —NR 21 C(═O) R 22 , wherein R 21 and R 22 are independently selected from hydrogen, unsubstituted (C 1 -C 10 )alkyl, unsubstituted (C 2 -C 10 )alkenyl, unsubstituted (C 2 -C 10 )alkynyl, cyclo(C 3 -C 10 )alkyl, heterocyclic group, cyclo(C 3 -C 10 )alkenyl, heterocyclo(C 2 -C 10 )alkenyl, aryl, heteroaryl, aryl(C 1 -C 10 )alkyl, hetero(C 1 -C 10 )alkyl, (C 1 -C 10 )alkylaryl, (C 1 -C 10 )alkylheteroaryl;

R 17 and R 19 are independently selected from the group consisting of a (C 1 -C 20 )alkyl eventually substituted by a hydrophobic group, a cyclo(C 3 -C 20 )alkyl eventually substituted by a hydrophobic group, a (C 2 -C 20 )alkenyl eventually substituted by a hydrophobic group, a (C 2 -C 20 )alkynyl, a heterocyclic group eventually substituted by a hydrophobic group, a cyclo(C 3 -C 20 )alkenyl eventually substituted by a hydrophobic group, a heterocyclo(C 2 -C 20 )alkenyl eventually substituted by a hydrophobic group, an aryl eventually substituted by a hydrophobic group, a heteroaryl eventually substituted by a hydrophobic group, a hetero(C 1 -C 20 )alkyl eventually substituted by a hydrophobic group, a (C 1 -C 20 )alkylaryl eventually substituted by a hydrophobic group, a (C 1 -C 20 )alkylheteroaryl eventually substituted by a hydrophobic group, said hydrophobic group being selected from methyl, ethyl, methoxy, ethyloxy;

X − is a counterion,

and their analogues.

8 . The calibration device according to claim 7 , wherein said at least one dye of formula (I) is a fluorescent dye and is a 5.5, cyanine of following formula:

9 . The calibration device according to claim 5 , wherein the counterion X − is chosen from:

an inorganic counterion,

an organic counterion, or

a bulky organic counterion chosen from tetraphenylborate, tetrakis(pentafluorophenyl) borate, tetrakis(4-fluorophenyl) borate, tetraphenylborate, tetrakis[3,5-bis-(trifluoromethyl)phenyl]borate, tetrakis[3,5-bis-(1,1,1,3,3,3-hexafluoro-2-methoxy-2-propyl)phenyl]borate and tetrakis[perfluoro-tert-butoxy]aluminate.

10 . The calibration device according to claim 1 , wherein the weight percentage of the at least one dye in each area is from 0.001 to 30% by weight of the hydrophobic polymer in said material.

11 . A method for manufacturing a calibration device according to claim 1 , comprising a step of disposing said material on said areas of the body of the calibration device.

12 . A method for imaging an object and/or for calibrating an imaging apparatus, characterized in that it comprises a step of illuminating a calibration device according to claim 1 and a step of acquiring an optical signal from this calibration device.

13 . The method according to claim 12 , wherein the step of acquiring the optical signal is carried out using an imaging device comprising a near-infrared camera or a multispectral or hyperspectral imaging system.

14 . The method according to claim 13 , comprising a step of quantifying a distance between the imaging device and the calibration device on the basis of the acquired optical signal.

15 . A method for analyzing an object, comprising a step of acquiring an optical signal from said object and a step of constructing an image of said object using the optical signal thus acquired, characterized in that it comprises a step of correcting this image on the basis of an optical signal acquired using a method according to claim 12 .