Amphipathic squarylium cyanine dyes, its preparation method and use thereof

A technology of squaraine and dyes, applied in squaraine dyes, azo dyes, organic dyes, etc., which can solve the problems of low fluorescence quantum yield and limited application

Inactive Publication Date: 2009-01-14
COUNCIL OF SCI & IND RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these heavy-atom substituted dyes have very low fluorescence quantum yields in aqueous media (Φ F ≤0.0003), thus limiting its application in the detection of tumors (diagnostics) through the fluorescence emission of dyes that selectively localize to tumor tissue

Method used

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  • Amphipathic squarylium cyanine dyes, its preparation method and use thereof
  • Amphipathic squarylium cyanine dyes, its preparation method and use thereof
  • Amphipathic squarylium cyanine dyes, its preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Formula 1 (wherein R 1 =-(CH 2 -CH 2 -O) n -CH 3 , n=4 and R 2 =-CH 3 ) preparation of squaraine dyes. N-methyl-N-(3,6,9,12-tetraoxatridecyl)aniline (400 mg, 1.35 mmol) and squaric acid (77 mg) in a mixture of n-butanol and benzene (1:3) , 0.67mmol) solution was refluxed by azeotropic distillation of water for 18h. The solvent was distilled off under reduced pressure, and the residue obtained was chromatographed on silica gel. Carry out column elution with the mixture (1:49) of methanol and chloroform to obtain 100mg (15%) general formula 1 (wherein R 1 =-(CH 2 -CH 2 -O) n -CH 3 , n=4 and R 2 =-CH 3 ) squarylium dye, mp 100-102°C; 1 H NMR (300MHz, CDCl 3 , 30°C, TMS): δ=3.21(s, 6H, -NCH 3 ), 3.37(s, 6H, -OCH 3 ), 3.72-3.52 (m, 32H, -OCH 2 ), 6.81 (d, 4H, J=8.96, Ar-H), 8.39 (d, 4H, J=8.95Hz, Ar-H); 13 C NMR (75MHz, CDCl 3 , 30°C, TMS): δ=39.68, 52.29, 58.97, 68.53, 70.42, 70.52, 70.56, 70.81, 71.83, 112.43, 119.90, 133.17, 154.41, 183.32, 188.58; IR...

Embodiment 2

[0045] Formula 2 (wherein R 1 , R 2 =-(CH 2 -CH 2 -O) n -CH 3 , n=4) preparation of squaraine dyes. Bis-(N,N-(3,6,9,12-tetraoxatridecyl))aniline (350 mg, 0.74 mmol) and squaric acid ( 42mg, 0.37mmol) solution was refluxed by azeotropic distillation of water for 18h. The solvent was distilled off under reduced pressure, and the residue obtained was chromatographed on silica gel. Carry out column elution with the mixture (1:99) of methanol and chloroform to obtain 40mg (5%) general formula 2 (wherein R 1 , R 2 =-(CH 2 -CH 2 -O) n -CH 3 , n=4) squaraine dye, mp 78-80°C; 1 H NMR (300MHz, CDCl 3 , 30°C, TMS): δ=3.37(s, 12H, -OCH 3 ), 3.37-3.55 (m, 64H, -OCH 2 ), 6.84 (d, 4H, J=8.96, Ar-H), 8.37 (d, 4H, J=8.95Hz, Ar-H); 13 C NMR (75MHz, CDCl 3 , 30°C, TMS): δ=50.73, 58.91, 68.31, 70.38, 70.49, 70.53, 71.80, 111.54, 115.85, 129.15, 147.60, 183.32, 188.58; IR (Neat): v max2918, 2867, 1610, 1584, 1114cm -1 ;Elemental analysis (%), C 52 h 84 N 2 o 18 Calcd for: C...

Embodiment 3

[0047] Formula 3 (wherein R 1 =-(CH 2 ) n -CO 2 X, n=3, X=H and R 2 =-CH 3 ) preparation of squaraine dyes. N-methyl-N-(carboxypropyl)aniline (319 mg, 1.74 mmol) and squaric acid (100 mg, 0.87 mmol) in a mixture of n-butanol and benzene (1:3) were refluxed by azeotropic distillation of water for 24 h . The solvent was distilled off under reduced pressure, and the residue obtained was chromatographed on silica gel. Column elution with a mixture of methanol and chloroform (1:9) afforded 100 mg (13%) of general formula 3 (where R 1 =-(CH 2 ) n -CO 2 X, n=3, X=H and R 2 =-CH 3 ) squaraine dye, mp 238-240°C (d); 1 H NMR (300MHz, [D 6 ]DMSO, 30°C, TMS): δ=1.91 (p, 4H, -CH 2 ), 2.40(t, 4H, J=7.2Hz, -CH 2 ), 2.91 (s, 6H, -NH 3 ), 3.35(t, 4H, J=7.3Hz, -CH 2 ), 6.99(d, 4H, J=9.07Hz, Ar-H), 8.05(d, 4H, J=8.97Hz, Ar-H); 13 C NMR (75MHz, [D 6 ]DMSO, 30° C., TMS): δ=21.82, 31.41, 38.46, 52.03, 112.64, 116.73, 129.17, 149.13, 179.23; IR (KBr): v max 3420, 2924, 1729, 15...

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Abstract

The present invention relates to amphiphilic squaraine dyes of the general formula (1) as shown below Formula (1) wherein, R<1> = -(CH2-CH2-O)n-CH3, n = 4-8, or -(CH2)n-CO2X, n = 3-6, X = H, succinamide and R<2> = -CH3 or -(CH2-CH2-O)n-CH3, n = 4-8 and pharmaceutically acceptable derivatives thereof, for use as near infrared fluorescence probes in photodynamic diagnostic and biological, biochemical and industrial applications.

Description

technical field [0001] The present invention relates to the amphiphilic squaraine (squaraine) dye with the general formula of following formula (1) as near-infrared fluorescent probe in photodynamic diagnosis, biology, biochemistry and industrial application and its medicinal properties accepted derivatives, [0002] [0003] Formula 1 [0004] where R 1 =-(CH 2 -CH 2 -O) n -CH 3 , n=4-8, or -(CH 2 ) n -CO 2 X, n=3-6, X=H, succinamide, and R 2 =-CH 3 or -(CH 2 -CH 2 -O) n -CH 3 , n=4-8. [0005] The present invention also relates to a method for preparing the squarylium dye of general formula 1 and the use of this sensitizer as a near-infrared fluorescent probe in photodynamics, diagnosis and biology, biochemistry and industrial applications. [0006] The present invention also relates to squaraine dyes of general formula 1 or pharmaceutically acceptable derivatives thereof, which are used as near-infrared fluorescent probes in photodynamic applications for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00A61K41/00
CPCC09B57/007C09B69/00A61K49/0021B82Y5/00A61K47/48969A61K41/0057A61K47/6951
Inventor R·达纳博伊纳T·A·卡尔利阿特K·约蒂施
Owner COUNCIL OF SCI & IND RES
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