Molecular fluorophores and preparation method thereof and use for short wavelength infrared imaging

An intermolecular, electron-accepting technology, applied in pharmaceutical formulations, preparations for in vivo experiments, organic chemistry, etc., can solve the problems of large size and low real-time imaging

Active Publication Date: 2019-04-16
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the emission quantum yield of such dyes is too low (below 0.2%) for real-time imaging, the size (molecular weight 9.7k Da) is relatively large and the fluorescence is limited below ~1200nm

Method used

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  • Molecular fluorophores and preparation method thereof and use for short wavelength infrared imaging
  • Molecular fluorophores and preparation method thereof and use for short wavelength infrared imaging
  • Molecular fluorophores and preparation method thereof and use for short wavelength infrared imaging

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0191] Example 1: Synthesis of IRETBN-PEG1700 and IRETBN-PEG600

[0192]

[0193] (1) 5-(5-(2,6-bis((6-bromohexyl)oxy)phenyl)thiophen-2-yl)-2,3-dihydro-thieno[3,4-b] Synthesis of [1,4]dioxine (compound 2):

[0194] Under Ar atmosphere, tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane (860mg, 2.0mmol) and To a solution of compound 1 (720mg, 1.2mmol) in 10mL of toluene, Pd(PPh 3 ) 4 (71 mg, 0.061 mol). The mixture was stirred at 110 °C for 24 h. After cooling to room temperature, the mixture was poured into water and extracted twice with ethyl acetate, and the organic phase was washed with MgSO 4 Dry and evaporate in vacuo. The crude product was subjected to column chromatography on silica gel with PE / DCM 1:1 to afford compound 2 as a pale yellow oil (590 mg, 45%).

[0195] 1 H NMR (400MHz, CDCl 3 ): δ7.45(d, J=3.9Hz, 1H), 7.24(d, J=3.9Hz, 1H), 7.17(t, J=8.3Hz, 1H), 6.61(d, J=8.4Hz, 2H ),6.21(s,1H),4.37–4.32(m,2H),4.28–4.23(m,2H),4.01(t,J=6.2Hz,4H),3.38(t,...

Embodiment 2

[0207] Example 2: Synthesis of IREF-PEG600 and IREFN-PEG600.

[0208]

[0209] (1) Synthesis of 5-(9H-fluoren-2-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxine (compound 6):

[0210] Under a protective gas atmosphere, 2-bromo-9H-fluorene (compound 5) (5.0 g, 20.4 mmol) and tributyl (2,3-dihydrothieno[3,4-b][1,4] Dioxin-5-yl) stannane (9.2 g, 21.4 mmol) was dissolved in 40 mL of toluene, then Pd(PPh 3 ) 4 (200mg). After refluxing for 6 h, the crude product was subjected to column chromatography on silica gel to afford compound 6 as a pale yellow solid (5.8 g, 94%).

[0211] 1 H NMR (500MHz, chloroform-d) δ7.94 (dd, J = 3.8, 1.7Hz, 1H), 7.82–7.74 (m, 3H), 7.56 (dd, J = 7.3, 2.0Hz, 1H), 7.40 ( td,J=7.5,2.7Hz,1H),7.36–7.29(m,1H),6.41–6.26(m,1H),4.37–4.31(m,2H),4.29–4.23(m,2H),3.95( s, 2H). 13C NMR (126MHz, chloroform-d) δ37.60, 65.10, 65.41, 98.00, 118.68, 120.45, 120.62, 123.15, 125.43, 125.64, 127.22, 127.41, 132.37, 138.60, 140.84, 142.401, 40.1, 40.1

[0212] HRMS (ESI) fo...

Embodiment 3

[0226] Example 3: Synthesis of IREFNS

[0227]

[0228] Compound 8 (100 mg, 0.069 mmol) was dissolved in 10 mL THF and dimethylamine (2.0 M in THF, 2 mL), then stirred at 50 °C for 6 h. Afterwards, the solvent was evaporated in vacuo. The dark green solid and 1,2-oxathiolane 2,2-dioxide 122 mg (1 mmol) were dissolved in 5 mL THF, and the solution was stirred overnight. Afterwards, the solution was filtered, washed several times with acetone and ethyl acetate. IREFNS (110 mg) was obtained as a green solid.

[0229] HRMS (ESI) for C 88 h 120 N 8 o 16 S 8 , ([M+H + ]) The calculated value is 1800.6588, and the measured value is 1800.6545.

[0230] IREFNS in H 2 Optical parameters in O: absorption peak λ=795nm, emission peak λ em =1047nm, the absorption coefficient K=6.2L / g.cm at 808nm, the quantum yield is 0.46% (using 808nm excitation)

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Abstract

Provided is the design, synthesis and applications of molecular fluorophores for bioimaging in the short wavelength infrared window (1000-1700 nm). The molecular fluorophores compound comprise structures with electron accepting aromatic units, electron donating aromatic units, and an shielding units which shield the conjugated backbones from intermolecular interactions.

Description

technical field [0001] Embodiments of the present disclosure generally relate to biomedical imaging using molecular fluorophores. Background technique [0002] The development of biomedical imaging requires higher imaging resolution and deeper penetration depth, which is limited by photon scattering, autofluorescence of biological tissue and optical absorption of water. It is known that at longer wavelengths photon scattering is reduced and biological tissue autofluorescence is reduced. At the same time, the optical absorption of water is low in the near-infrared region. Thus, for in vivo optical imaging, the short-wave infrared (SWIR, SWIR 1.0-1.7 μm) has recently shown promise relative to the traditional near-infrared window (750-1000 nm). [0003] Inorganic nanomaterials (such as carbon nanotubes, PbS and Ag 2 S quantum dots) and rare earth nanoparticles have been used as SWIR fluorophores due to their low band gap, high quantum yield and good stability. However, thes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04C07D487/04C07D498/04C07D517/04A61K49/00
CPCC07D487/04C07D498/04C07D513/04C07D517/04A61K49/0021A61K49/0054A61K49/0058C07D519/00
Inventor 梁永晔王华森杨晴来唐梅杰赵星瀚
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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