Fluorescence compounds and preparation method thereof

1. A fluorescent compound represented by the following [Chemical Formula 1]:

wherein X and Y are the same or different, and each is independently selected from H, —SO 3 − and —SO 3 H;

R 1 and R 2 are the same or different, and each is selected from C 1-7 alkyl, C 8-18 alkyl, —(CH 2 ) m SO 3 − , —(CH 2 ) m SO 3 H, and

R 3 and R 4 are the same or different, and each is selected from C 1-7 alkyl, —(CH 2 ) m′ COOZ 1 and

with the proviso that both of R 3 and R 4 cannot represent any one selected from —(CH 2 ) m′ COOZ 1 and

 at the same time;

Z 1 and Z 2 are the same or different, and each is independently substituted with a substituent selected from H, N-succinimidyl, hydrazinyl, N-hydroxysuccinimidyl, N-hydrosuccinimidyloxy, sulfosuccinimidyloxy, 4-sulfo-2,3,4,5-tetrafluorophenyl, maleinimideC 0-10 alkylaminyl, vinylsulfonyl, vinylsulfonylC 0-6 alkylaminyl and aminoC 0-6 alkyl;

n is an integer of 1-6;

m is an integer of 1-7;

p is an integer of 1-10;

q is an integer of 0-6;

r is an integer of 1-10;

m′ is an integer of 1-7;

p′ is an integer of 1-10;

q′ is an integer of 1-10; and

r′ is an integer of 1-10;

wherein at least one of R 1 and R 2 is

 or each of R 3 and R 4 is

2. The fluorescent compound according to claim 1 , wherein R 1 and R 2 are the same or different, and each is selected from C 1-7 alkyl, C 8-18 alkyl, —(CH 2 ) m SO 3 − , —(CH 2 ) m SO 3 H, and

R 3 and R 4 are the same or different, and each is selected from C 1-7 alkyl, —(CH 2 ) m′ COOZ 1 and

with the proviso that both of R 3 and R 4 cannot represent any one selected from —(CH 2 ) m′ COOZ 1 and

 at the same time;

Z 1 and Z 2 are the same or different, and each independently represents H or N-succinimidyl;

n is an integer of 1-6;

m is an integer of 1-6;

p is an integer of 3-7;

q is an integer of 0-4;

r is an integer of 1-6;

m′ is an integer of 1-7;

p′ is an integer of 3-7;

q′ is an integer of 1-6; and

r′ is an integer of 1-7.

3. The fluorescent compound according to claim 1 , wherein at least one of R 1 and R 2 represents

and at least one of R 3 and R 4 represents —(CH 2 ) m′ COOZ 1 or

4. The fluorescent compound according to claim 1 , wherein the compound represented by [Chemical Formula 1] is selected from:

5. The fluorescent compound according to claim 1 , which is used for labeling a target material selected from a fiber, biomolecule, nanoparticle and an organic compound.

6. The fluorescent compound according to claim 5 , wherein the biomolecule is selected from the group consisting of proteins, peptides, carbohydrates, sugars, fats, antibodies, proteoglycans, glycoproteins and siRNA.

7. A method for preparing a fluorescent compound according to claim 1 , which comprises producing a compound represented by the following [Chemical Formula 1] from a compound represented by the following [Chemical Formula 2]:

wherein X and Y are the same or different, and each is independently selected from H, —SO 3 − and —SO 3 H;

R 1 and R 2 are the same or different, and each is selected from C 1-7 alkyl, C 8-18 alkyl, —(CH 2 ) m SO 3 − , —(CH 2 ) m SO 3 H, and

R 3 and R 4 are the same or different, and each is selected from C 1-7 alkyl, —(CH 2 ) m′ COOZ 1 and

with the proviso that both of R 3 and R 4 cannot represent any one selected from —(CH 2 ) m′ COOZ 1 and

 at the same time;

R 5 and R 6 are the same or different, and each is independently selected from C 1-7 alkyl, C 8-18 alkyl, —(CH 2 ) m SO 3 − , —(CH 2 ) m SO 3 H and

R 7 and R 8 are the same or different, and each is independently selected from C 1-7 alkyl, —(CH 2 ) m′ COOH and

n is an integer of 1-6;

m is an integer of 1-7;

p is an integer of 1-10;

q is an integer of 0-6;

r is an integer of 1-10;

m′ is an integer of 1-7;

p′ is an integer of 1-10;

q′ is an integer of 1-10; and

r′ is an integer of 1-10.

8. The method for preparing a fluorescent compound according to claim 7 , wherein the compound represented by [Chemical Formula 2] is obtained by reacting a compound represented by the following [Chemical Formula 3] with cyanuric chloride:

wherein X and Y are the same or different, and each is independently selected from H, —SO 3 − and —SO 3 H;

R 9 and R 10 are the same or different, and each is independently selected from C 1-7 alkyl, C 8-18 alkyl, —(CH 2 ) m SO 3 − , —(CH 2 ) m SO 3 H and

 and

R 11 and R 12 are the same or different, and each is independently selected from C 1-7 alkyl and

9. The method for preparing a fluorescent compound according to claim 8 , wherein the compound represented by [Chemical Formula 3] is obtained by substituting a compound represented by the following [Chemical Formula 4] with an amineC 0-6 alkylaminyl group:

wherein X and Y are the same or different, and each is independently selected from H, —SO 3 − and —SO 3 H;

R 13 and R 14 are the same or different, and each is independently selected from C 1-7 alkyl, C 8-18 alkyl, —(CH 2 ) m SO 3 − , —(CH 2 ) m SO 3 H and

 and

R 15 and R 16 are the same or different, and each is independently selected from C 1-7 alkyl and

10. The method for preparing a fluorescent compound according to claim 9 , the compound represented by [Chemical Formula 4] is obtained by refluxing a compound represented by the following [Chemical Formula 5] with a compound represented by the following [Chemical Formula 6] in the presence of a solvent containing acetic anhydride:

wherein X and Y are the same or different, and each is independently selected from H, —SO 3 − and —SO 3 H;

R 13 and R 14 are the same or different, and each is independently selected from C 1-7 alkyl, C 8-18 alkyl, —(CH 2 ) m SO 3 − , —(CH 2 ) m SO 3 H and

 and

R 15 and R 16 are the same or different, and each is independently selected from C 1-7 alkyl and

11. A contrast medium composition comprising the fluorescent compound represented by [Chemical Formula 1] as defined in claim 1 as an active ingredient.

12. A method for labeling a compound, which comprises binding the fluorescent compound represented by [Chemical Formula 1] as defined in claim 1 with a target material,

wherein the target material is at least one selected from a fiber, biomolecule, nanoparticle and an organic compound,

the target material comprises at least one functional group selected from amine, hydroxyl and thiol groups, and

the fluorescent compound as defined in claim 1 is bound with the functional group.

13. The method for labeling a compound according to claim 12 , wherein the biomolecule is selected from the group consisting of proteins, peptides, carbohydrates, sugars, fats, antibodies, proteoglycan, glycoproteins and siRNA.