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Analyte detection using near-infrared fluorophores

A fluorophore and compound technology, applied in the field of using near-infrared fluorophores to detect analytes, can solve the problem of undisclosed homocysteine ​​colorimetric selectivity and the like

Inactive Publication Date: 2014-04-23
由俄勒冈州高等教育委员会代表的波特兰州立大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These references do not disclose any appreciable colorimetric selectivity between homocysteine, cysteine ​​and glutathione

Method used

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  • Analyte detection using near-infrared fluorophores
  • Analyte detection using near-infrared fluorophores
  • Analyte detection using near-infrared fluorophores

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0251] Synthesis and Characterization of Near Infrared Fluorophores

[0252] Such as reaction scheme 1 ( Figure 5 ) by acid condensation of 1,8-dihydroxynaphthalene with phthalic anhydride in methanesulfonic acid or by 1,8-dihydroxynaphthalene with the corresponding aldehyde in 85% H 3 PO 4 Condensation at 125°C / 24h to synthesize analogs with the structure of general formula IV. Naphthofluorescein methyl ester 22 was obtained from 21 via a typical Fischer esterification scheme (Scheme 4). Via hydroxybenzophenone and corresponding naphthol in CH 3 SO 3 Asymmetric semi-naphthofluorescein, rhodol and rhodamine analogues of general formula III were synthesized by acid condensation in a 1:1 mixture of H:TFA at 80°C for 16-24 h (Schemes 2 and 3). The desired hydroxybenzophenone and 1,8-naphthalene derivatives were synthesized following described or modified literature protocols. Methyl ester derivatives were prepared by H in MeOH 2 SO 4 or HCl-catalyzed esterification; by i...

Embodiment 2

[0301] Synthesis of para-, ortho-, and meta-bridged diviologens

[0302] Synthesize para-bridged viologen according to Scheme 13:

[0303] Scheme 13

[0304]

[0305] Bipyridine (16.66 g, 106.65 mmol) was dissolved in 125 mL of acetonitrile, and the solution was refluxed. Next, p-bis(bromomethyl)benzene (5 g, 18.94 mmol) was dissolved in 300 mL of acetonitrile. This solution was added to the refluxing solution of bipyridine over 1 hour. After complete addition of the p-bis(bromomethyl)benzene solution, the mixture was continued to reflux for 24 hours. The formed precipitate was filtered, washed with acetonitrile (2x50 mL) and air dried. Single bridged viologen 103 was obtained as a light yellow solid. Yield 10.5g, 96%. 1 H NMR (DMSO-d 6 ,400MHz): δ(ppm)9.4-9.41(4H,d),8.85-8.86(4H,d),8.65-8.67(4H,d),8.00-8.01(4H,d),7.74(4H,s) ,5.94(4H,s).

[0306] Compound 103 (3 g, 5.3 mmol) was suspended in 30 mL of water, and the mixture was heated until the precipitate was compl...

Embodiment 3

[0323] Emissions in the blood

[0324] Compound 15d (Table 1) was diluted to 40 μM in 50% DMSO:50% 25 mM pH 9 phosphate buffer. Such as Figure 30 As shown in , diluted compounds produce fluorescence whose λ max ex =~690nm and λ max em =~790nm (Stokes shift=~100nm, 1834cm -1 ). Whole blood (pig blood in Na-EDTA, Lampire Biological Laboratories) was included in the aqueous portion of the solvent to yield a final blood concentration of 5% by volume, causing only minimal loss of fluorescence due to hemoglobin absorption and Scattering from blood components. The emission remained stable for at least 1 hour. The absorption curve matches the output of the laser pointer (635-670nm; max output 90% at >750nm), it is possible to NIR emission (80 μM) is clearly visible. Similar results were observed with 5% whole blood, but an increase in scattered excitation light was clearly visible in both the visible and NIR images, which was easily overcome using a second filter.

[0325] H...

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Abstract

Embodiments of compounds for selectively detecting an analyte are disclosed, along with methods and kits for detecting analytes with the compounds. The compounds are bridged viologen conjugates including at least one fluorophore according to the general structure. At least one of R1 / R2, R2 / R3, R3 / R4, R5 / R6, R6 / R7, and / or R7 / R8 together form a substituted or unsubstituted cycloalkyl or aryl.

Description

[0001] Cross references to related applications [0002] This application claims the entirety of U.S. Provisional Application No. 61 / 505,029, filed July 6, 2011, and U.S. Provisional Application No. 61 / 502,795, filed June 29, 2011, each of which is incorporated by reference in its entirety This article. technical field [0003] Embodiments of compounds, methods and kits comprising near-infrared fluorophores for detecting analytes are disclosed herein. [0004] Statement of Government Support [0005] This application was made with Government support No. R01EB002044 awarded by the National Institutes of Health. The US Government has certain rights in this invention. Background technique [0006] An obstacle to simplified diagnostic tests is that current clinical chemistry techniques require significant sample preparation and handling to analyze complex biological samples. Sample preparation is a major bottleneck in diagnostics. Indicator fluorophores for specific biomark...

Claims

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Application Information

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IPC IPC(8): C07D405/14C07D409/14G01N33/48G01N33/50
CPCC09K2211/1007C09K2211/1029C09K11/06G01N33/52G01N33/582C07D405/14C09K9/02C09K2211/1088G01N33/6815C07D493/10C09B11/24Y10T436/143333G01N2800/28
Inventor 罗伯特·迈克尔·斯特龙金马莎·萨伯瑞恩-巴斯克斯若热·奥马尔·埃斯科韦多科多瓦马克·艾伦·劳里
Owner 由俄勒冈州高等教育委员会代表的波特兰州立大学
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