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Substituted silaxanthenium red to near-infrared fluorochromes for in vitro and in vivo imaging and detection

一种取代基、杂环基的技术，应用在体内试验用的配制品、二苯氧杂芑胺/氧杂蒽酮/噻吨酮/硒代呫吨酮/碲杂呫吨酮染料、有机染料等方向，能够解决体积大、限制应用、低细胞膜通透性等问题

Active Publication Date: 2015-11-18
VISEN MEDICAL INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, current molecular constructs that fluoresce in the NIR region, including the indocyanine family, tend to be bulky (>750 Da) and poorly soluble in water, requiring the incorporation of solubilizing groups such as multiple sulfonic acid groups
Consequently, the resulting dyes exhibit very low cell membrane permeability, limiting their utility for targeting intracellular structures

Method used

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  • Substituted silaxanthenium red to near-infrared fluorochromes for in vitro and in vivo imaging and detection
  • Substituted silaxanthenium red to near-infrared fluorochromes for in vitro and in vivo imaging and detection
  • Substituted silaxanthenium red to near-infrared fluorochromes for in vitro and in vivo imaging and detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0355] Example 1-Compound 22 (3,6-bis(dimethylamino)-9-(2-carboxy-4-methyl-thiophen-5-yl)-10,10-dimethyl-10-sila Anthracene cation chloride) synthesis

[0356] Compound 22 was synthesized according to the following scheme:

[0357]

[0358] To a solution of compound N,N-dimethyl-3-bromoaniline (10.0 g, 50.0 mmol) in AcOH (250 mL) was added 12.16 mL of 37% aqueous formaldehyde (4.5 g, 150.0 mmol), and the mixture was stirred at 60° C. for 115 minute. After cooling to room temperature, a portion of the acetic acid was removed by vacuum. Then, with saturated NaHCO 3 (aq.) and NaOH (aq.) to neutralize the reaction mixture, and CH 2 Cl 2 extract. The organic layer was washed with concentrated saline solution (brine), in Na 2 SO 4and evaporated to dryness. The residue was purified by flash chromatography (silica gel) to yield pure 4,4'-methylenebis(3-bromo-N,N-dimethylaniline) (5.24 g, 12.7 mmol, 51% yield).

[0359]

[0360] To a nitrogen-purged flask was added 4,4'...

Embodiment 2

[0363] Example 2-Compound 65 (3,6-bis(dimethylamino)-9-(2-carboxy-thiophen-5-yl)-10,10-dimethyl-10-siloxanthene cation chloride) Synthesis

[0364]

[0365] In a nitrogen-purged flask, 3,6-bis(dimethylamino)-10,10-dimethyl-10-siloxanthone (50.0 mg, 0.16 mmol) was dissolved in anhydrous THF (10 mL) . The solution was cooled to -78°C. At the same temperature, tert-butyl 4-bromo-3-methyl-2-thiophenecarboxylic acid (136 mg, 0.81 mmol) and anhydrous THF (5 mL) were added to the flask, and 1M sec-butyllithium (1.16 mL, 1.62 mmol), and the mixture was stirred for 30 minutes. The lithiation solution was added slowly, and the mixture was warmed to room temperature, then stirred for 2 hours. The reaction was blocked by the addition of 2N HCl, and the mixture was stirred at room temperature for 10 minutes. Add saturated NaHCO 3 , and with CH 2 Cl 2 Extract it all. The organic layer was in Na 2 SO 4 Dry under , and evaporate the solvent. The crude mixture was purified by HP...

Embodiment 3

[0366] Example 3-Compound 18 (3,6-bis(dimethylamino)-9-(2-carboxy-3-methyl-thiophen-4-yl)-10,10-dimethyl-10-sila Anthracene cation chloride) synthesis

[0367]

[0368] In a nitrogen-purged flask, 3,6-bis(dimethylamino)-10,10-dimethyl-10-siloxanthone (50.0 mg, 0.16 mmol) was dissolved in anhydrous THF (10 mL) . The solution was cooled to -78°C. At the same temperature, 3-methyl-4-bromo-2-thiophenecarboxylic acid (136 mg, 0.81 mmol) and anhydrous THF (5 mL) were added to the flask, and 1M sec-butyllithium (1.16 mL, 1.62 mmol) was added , and the mixture was stirred for 30 minutes. The lithiation solution was added slowly, and the mixture was warmed to room temperature, then stirred for 2 hours. The reaction was blocked by the addition of 2N HCl, and the mixture was stirred at room temperature for 10 minutes. Add saturated NaHCO 3 , and with CH 2 Cl 2 Extract it all. The organic layer was in Na 2 SO 4 Dry under , and evaporate the solvent. The crude mixture was pu...

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Abstract

The invention provides a family of fluorescent compounds. The compounds are substituted silaxanthenium compounds that can be chemically linked to one or more biomolecules, such as a protein, nucleic acid, and therapeutic small molecule. The compounds can be used for imaging in a variety of medical, biological and diagnostic applications. The dyes are particularly useful for in vitro, in vivo and ex vivo imaging applications.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of US Provisional Application Serial No. 61 / 794,188, filed March 15, 2013, which is hereby incorporated by reference in its entirety. technical field [0003] This application relates to compositions and methods for using fluorescent dyes (fluorochromes). The compositions typically comprise silaxanthenium fluorescent dyes, which can be used in a variety of medical, diagnostic and biological applications. Fluorescent dyes enable fluorescence detection in in vitro, ex vivo, and in vivo imaging applications. Background technique [0004] Optical imaging and detection methods offer several advantages over other imaging and detection methods. Imaging of tissues, organs, or whole objects typically uses light in the red and near-infrared (NIR) range (600-1200nm) to maximize tissue penetration and minimize absorption from natural bioabsorbents such as hemoglobin and water as well as biolog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08A61K47/10A61K47/48C07K7/00C08L71/02
CPCA61K47/48023A61K47/48092A61K47/48384A61K49/0021A61K49/0054C07F7/0816C09B11/28C09B69/008G01N33/56966A61K49/0052A61K49/0019
Inventor 凯文·格罗夫斯莱恩·巴福
Owner VISEN MEDICAL INC
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