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Loaded latex optical molecular imaging probes

A technology of latex particles and latex materials, which is applied in the field of fluorescent probes for optical molecular images, can solve problems such as easy bleaching, non-emission, and colloidal instability, and achieve the effects of enhancing fluorescence effects, resisting adhesion, and good dispersion

Inactive Publication Date: 2009-04-29
CARESTREAM HEALTH INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First, the dye is usually highly aggregated and thus non-emissive
Second, aggregate fluorescers for dye-nanoparticles are often ineffective in aqueous environments
Third, the dyes used in such aggregates are unstable to light and oxygen and are prone to bleaching, which creates difficulties in handling and management
Fourth, such administration is often colloidally unstable and cytotoxic

Method used

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  • Loaded latex optical molecular imaging probes
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  • Loaded latex optical molecular imaging probes

Examples

Experimental program
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Effect test

preparation example Construction

[0238] Dye Synthesis Example 1 - Preparation of Dye 1

[0239] Using 2,3,3-trimethyl-1-octadecyl-3H-indolium perchlorate (4.28g, 10mmol) and dianiline (1.4g, 5mmol) in 40ml containing triethylamine ( 1.5 g, 15 mmoles) of acetic anhydride, the dye was prepared according to the general procedure above. The reaction time was 5 minutes. The reaction was cooled to 25°C and poured into 2 liters of ice water with vigorous stirring. The water layer was separated, and the oil layer was dissolved in 100 mL of 80 / 20 dichloromethane-methanol solution. The material was chromatographed on a silica gel column eluting with 80 / 20 dichloromethane-methanol solution. After drying over anhydrous magnesium sulfate the solution was evaporated to give pure dye (4 g, 32% yield). λmax in methanol = 747 nm, extinction coefficient = 220,020.

[0240] Dye Synthesis Example 2-Preparation of Dye 5

[0241] Using 2,3,3-trimethyl-1-butyl-3H-indolium perchlorate (12g, 38mmol) and dianiline (5.4g, 19mmol)...

Embodiment 10

[0260] Embodiment 10. Preparation of amine-terminated polyethylene glycol macromonomer

[0261]

[0262] Poly(ethylene glycol dimethacrylate) (Aldrich, Mn=875, 335 g) was mixed with 100 mL of methanol and treated with cysteamine (Aldrich, 5.8 g) and diisopropylethylamine (Hunigs base), then at room temperature After stirring for 2 days, it was concentrated on a rotary evaporator. The resulting residue was dissolved in 1 L of ethyl acetate and extracted with 10% aqueous hydrochloric acid. The aqueous layer was collected and made alkaline by adding 50% aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The resulting residue was dissolved in anhydrous diethyl ether and treated with gaseous hydrogen chloride and stood. The ether was decanted leaving a dark blue oil. It was rinsed with fresh diethyl ether and the diethyl ether was poured off. The dark blue oil was concentrated on...

Embodiment 11

[0264] Example 11. Contains methoxyethyl methacrylate (45% w / w), divinylbenzene (4%), ethylstyrene (1%) and polyethylene glycol monomethyl ether methyl Preparation of Nanolatex 1 of Acrylate (50%)

[0265] A 500ml three-neck flask was bottomed with an Ace #15 glass line and a series of adapters to allow it to be connected to 1 / 16 inch size teflon tubing. The flask (hereinafter referred to as the "header" flask) was equipped with a mechanical stirrer, a rubber septum with a needle syringe nitrogen inlet. In the Header flask, methoxyethyl methacrylate (5.63 g), divinylbenzene (0.63 g, containing a mixture of isomers with a purity of 80% of ethyl styrene isomers), poly Ethylene glycol monomethyl ether methacrylate (6.25g, Mn=1100), cetylpyridinium chloride (0.31g), 2,2'-azobis(N,N'-dimethylene isobutylamidine) dihydrochloride (0.06g), sodium bicarbonate (0.06g) and distilled water (159.13g). Into a 1 L three-neck round bottom flask equipped with a mechanical stirrer, reflux co...

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Abstract

The present invention relates to a loaded latex particle comprising a latex material made from a mixture represented by formula (X)m-(Y)n-(Z)o-(W)p, wherein Y is at least one monomer with at least two ethylenically unsaturated chemical functionalities; Z is at least one polyethylene glycol macromonomer with an average molecular weight of between 300 and 10,000; W is an ethylenic monomer different from X, Y, or Z; and X is at least one water insoluble, alkoxethyl containing monomer; and m, n, o, and p are the respective weight percentages of each monomer. The particle may be loaded with a fluorescent dye.

Description

field of invention [0001] The invention relates to the application of fluorescent particles in biological analysis, especially fluorescent probes for optical molecular images. Background technique [0002] Dyes have been incorporated into silica particles (Ow, H.; Larson, D.R.; Srivastava, M.; Baird, B.A.; Webb, W.W.; Wiesner, U. "Bright and Stable Core-Shell Fluorescent Nanoparticles" Nano Letters 2005, 5, 113-117 / Verhaegh, N.A.M.; Blaaderen, A.v. "Dispersions of Rhodamine-Labeled Silica Spheres: Synthesis, Characterization, and Fluorescence Confocal Scanning Laser Microscopy" Langmuir 1994, 10, 1427-1438. / Imhof, A.; Megens, M .; Engelberts, J.J.; Lang, D.T.N.d.; Sprik, R.; Vos, W.L. "Spectroscopy of Fluorescein (FITC) Dyed Colloidal Silica Spheres" J. Phys. Chem. B 1999, 103, 1408-1415.). [0003] Latexes loaded with IR dyes are known for imaging and photographic applications (US 2002 / 0113854, US 6,706,460). Latexes loaded with non-IR dyes are known for biological an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/28A61B5/00A61K49/00G01N33/58
CPCA61K49/0032C08F212/36A61K49/0036A61K49/0093A61K49/0058C08F220/26C08F222/1006C08F220/28A61K49/0021B82Y5/00Y10T436/143333C08F220/286C08F222/102C08F212/08C08F212/12
Inventor J·W·莱昂W·J·哈里森B·J·凯利J·R·贝内特D·A·斯特格曼R·王J·W·哈德
Owner CARESTREAM HEALTH INC
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