6,7-methylenedioxy-3-(3,4-methylenedioxy-6-phenylethanol)-isoquinoline; precursor sensor molecule
Inventors
McElhanon, James R. • Shepodd, Timothy J.
Assignees
National Technology and Engineering Solutions of Sandia LLC • Sandia National Laboratories
Publication Number
US-7449579-B1
Publication Date
2008-11-11
Expiration Date
2026-05-02
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Abstract
A “real time” method for detecting electrophilic and nucleophilic species generally by employing tunable, precursor sensor materials that mimic the physiological interaction of these agents to form highly florescent berberine-type alkaloids that can be easily and rapidly detected. These novel precursor sensor materials can be tuned for reaction with both electrophilic (chemical species, toxins) and nucleophilic (proteins and other biological molecules) species.
Core Innovation
This invention provides a "real time" method for detecting electrophilic and nucleophilic species by using tunable precursor sensor materials. These precursor sensor materials mimic the physiological interaction of chemical and biological warfare agents to form highly fluorescent berberine-type alkaloids that are easily and rapidly detectable. The precursor sensors can be adjusted for reactions with both chemical species, including toxins, and biological molecules such as proteins.
The problem addressed by the invention is the lack of rapid, sensitive, and specific detection methods for chemical warfare agents and biological agents. Existing detection methods, such as ion mobility spectroscopy, surface acoustic wave devices, microcantilevers, and interferometric devices, often lack sufficient specificity and discrimination among chemical threat agents. Other fluorescent chemical sensors suffer from limitations including low detection sensitivity due to low Stokes shifts, slow kinetics, difficulty of chemical modification, and background fluorescence interference. Additionally, no long-wavelength fluorogenic chemical sensors exist that are reactively activated by biological agents.
The invention overcomes these issues by exploiting the well-characterized optical properties of berberine-type alkaloids, which exhibit high fluorescence intensity and large Stokes shifts. The precursor sensor materials react with target species to transform from weakly conjugated, short-wavelength sensor molecules into a rigid, planar, conjugated chromophore with strong long-wavelength fluorescence (530-560 nm) and a large Stokes shift (100-180 nm). These optical properties, along with fluorescence intensity and reactivity, can be tuned by altering substituents on the precursor molecule, enabling sensitive and specific detection of chemical and biological warfare agents.
Claims Coverage
The patent contains one independent claim defining a novel precursor sensor molecule with specific structural features.
Generic precursor sensor molecule structure
A precursor sensor molecule having a generic formula in which the substituent R is a functionality or group that reacts with biological or chemical warfare materials. This functionality may include thio-, hydroxy-, protected ethers such as t-butyldimethylether, or isourea derived from carbonyldiimidizole. The molecule is designed to transform upon reaction with target agents into a highly fluorescent berberine-type alkaloid.
Tunability of fluorescence properties
The fluorescence intensity, wavelength, and Stokes shift of the berberine alkaloid reaction product can be tuned by altering the composition and positions of substituents on the precursor molecule, specifically on rings A and D, with preferred substituents including methoxy and methylenedioxy groups.
The independent claim focuses on the design of a tunable precursor sensor molecule capable of reacting with chemical and biological agents to form a fluorescent berberine-type adduct, wherein fluorescence properties can be precisely controlled through molecular substituents.
Stated Advantages
Allows for rapid and sensitive detection of chemical and biological warfare agents in real time.
Enables tuning of fluorescence characteristics such as intensity, wavelength, and Stokes shift to optimize detection sensitivity and selectivity.
Produces reaction products with high fluorescence intensity and large Stokes shifts (100-180 nm), reducing background interference and increasing detection clarity.
Applicable to detection of both electrophilic chemical species and nucleophilic biological molecules.
Can be integrated into multiple analytical platforms, including polymers, fiber optic systems, and handheld devices for field detection.
Documented Applications
Detection of chemical warfare agents in fluid samples, including sewage or industrial discharges, by bonding precursor sensor materials to clear amorphous polymer substrates.
Incorporation of precursor sensor materials into flexible fiber optic systems for optical detection of chemical and biological agents.
Use of precursor chemical sensor materials in handheld platforms for field detection of chemical warfare and biological agents.
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