Methods for the selective detection of alkyne-presenting molecules and related compositions and systems

Valdez, Carlos A.; Vu, Alexander K.

Methods for the selective detection of alkyne-presenting molecules and related compositions and systems

Patent · 17 October 2017

OSTI ID:1400219

Valdez, Carlos A.; Vu, Alexander K.

Provided herein are methods for selectively detecting an alkyne-presenting molecule in a sample and related detection reagents, compositions, methods and systems. The methods include contacting a detection reagent with the sample for a time and under a condition to allow binding of the detection reagent to the one or more alkyne-presenting molecules possibly present in the matrix to the detection reagent. The detection reagent includes an organic label moiety presenting an azide group. The binding of the azide group to the alkyne-presenting molecules results in emission of a signal from the organic label moiety.

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Research Organization:: Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC52-07NA27344

Assignee:: Lawrence Livermore National Security, LLC

Patent Number(s):: 9,791,463

Application Number:: 14/201,530

OSTI ID:: 1400219

Country of Publication:: United States

Language:: English

References (31)

ClickFerrophos: New Chiral Ferrocenyl Phosphine Ligands Synthesized by Click Chemistry and the Use of Their Metal Complexes as Catalysts for Asymmetric Hydrogenation and Allylic Substitution Fukuzawa, Shin-ichi; Oki, Hiroshi; Hosaka, Mitsuteru Organic Letters, Vol. 9, Issue 26, p. 5557-5560 https://doi.org/10.1021/ol702519f	journal	December 2007
Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo Sawa, M.; Hsu, T.-L.; Itoh, T. Proceedings of the National Academy of Sciences, Vol. 103, Issue 33, p. 12371-12376 https://doi.org/10.1073/pnas.0605418103	journal	August 2006
Determination of Estrogens in Sludge and Sediments by Liquid Extraction and GC/MS/MS Ternes, Thomas A.; Andersen, Henrik; Gilberg, Daniel Analytical Chemistry, Vol. 74, Issue 14, p. 3498-3504 https://doi.org/10.1021/ac015717z	journal	July 2002
Synthesis of steroid–ferrocene conjugates of steroidal 17-carboxamides via a palladium-catalyzed aminocarbonylation – Copper-catalyzed azide–alkyne cycloaddition reaction sequence Szánti-Pintér, Eszter; Balogh, János; Csók, Zsolt Steroids, Vol. 76, Issue 12, p. 1377-1382 https://doi.org/10.1016/j.steroids.2011.07.006	journal	July 2011
Micelle-induced multiple performance improvement of fluorescent probes for H₂S detection Tian, Haiyu; Qian, Junhong; Bai, Hongyan Analytica Chimica Acta, Vol. 768, p. 136-142 https://doi.org/10.1016/j.aca.2013.01.030	journal	March 2013
Ruthenium-Catalyzed Cycloaddition of Alkynes and Organic Azides Zhang, Li; Chen, Xinguo; Xue, Peng Journal of the American Chemical Society, Vol. 127, Issue 46, p. 15998-15999 https://doi.org/10.1021/ja054114s	journal	November 2005
Exposure assessment of 17α‐ethinylestradiol in surface waters of the United States and Europe Hannah, Robert; D'Aco, Vincent J.; Anderson, Paul D. Environmental Toxicology and Chemistry, Vol. 28, Issue 12, p, 2725-2732 https://doi.org/10.1897/08-622.1	journal	July 2009
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V. Angewandte Chemie, Vol. 114, Issue 14, p. 2708-2711 https://doi.org/10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO;2-0	journal	July 2002
Copper-free click chemistry for dynamic in vivo imaging Baskin, J. M.; Prescher, J. A.; Laughlin, S. T. Proceedings of the National Academy of Sciences, Vol. 104, Issue 43, p. 16793-16797 https://doi.org/10.1073/pnas.0707090104	journal	October 2007
Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality Sletten, Ellen M.; Bertozzi, Carolyn R. Angewandte Chemie International Edition, Vol. 48, Issue 38, p. 6974-6998 https://doi.org/10.1002/anie.200900942	journal	September 2009
Design and Synthesis of a Highly Sensitive Off-On Fluorescent Chemosensor for Zinc Ions Utilizing Internal Charge Transfer Hanaoka, Kenjiro; Muramatsu, Yasuaki; Urano, Yasuteru Chemistry - A European Journal, Vol. 16, Issue 2, p. 568-572 https://doi.org/10.1002/chem.200901591	journal	January 2010
Building scientific consensus on endocrine disruptors Colborn, Theo Environmental Toxicology and Chemistry, Vol. 17, Issue 1, p. 1-2 https://doi.org/10.1002/etc.5620170101	journal	January 1998
Chemical remodelling of cell surfaces in living animals Prescher, Jennifer A.; Dube, Danielle H.; Bertozzi, Carolyn R. Nature, Vol. 430, Issue 7002, p. 873-877 https://doi.org/10.1038/nature02791	journal	August 2004
A fluorescent water-soluble naphthalimide-based receptor for saccharides with highest sensitivity in the physiological pH range Trupp, Sabine; Schweitzer, Annika; Mohr, Gerhard J. Organic & Biomolecular Chemistry, Vol. 4, Issue 15, p. 2965-2968 https://doi.org/10.1039/B604716E	journal	January 2006
Synthesis and Optical Properties of Excited-State Intramolecular Proton Transfer Active π-Conjugated Benzimidazole Compounds: Influence of Structural Rigidification by Ring Fusion Takagi, Koji; Ito, Kaede; Yamada, Yoshihiro The Journal of Organic Chemistry, Vol. 82, Issue 23, p. 12173-12180 https://doi.org/10.1021/acs.joc.7b01967	journal	November 2017
Modified paramagnetic beads in a microfluidic system for the determination of ethinylestradiol (EE2) in river water samples Martínez, Noelia A.; Schneider, Rudolf J.; Messina, Germán A. Biosensors and Bioelectronics, Vol. 25, Issue 6, p. 1376-1381 https://doi.org/10.1016/j.bios.2009.10.031	journal	February 2010
Direct sub-ppt detection of the endocrine disruptor ethinylestradiol in water with a chemiluminescence enzyme-linked immunosorbent assay Schneider, Christian; Schöler, Heinz F.; Schneider, Rudolf J. Analytica Chimica Acta, Vol. 551, Issue 1-2, p. 92-97 https://doi.org/10.1016/j.aca.2005.07.018	journal	October 2005
Direct conversion of activated alcohols to azides using diphenyl phosphorazidate. A practical alternative to Mitsunobu conditions Thompson, Andrew S.; Humphrey, Guy R.; DeMarco, Anthony M. The Journal of Organic Chemistry, Vol. 58, Issue 22, p. 5886-5888 https://doi.org/10.1021/jo00074a008	journal	October 1993
Kinetic Evidence for the Formation of Azene (Electron-deficient Nitrogen) Intermediates from Aryl Azides Smith, Peter A. S.; Hall, J. Herbert. Journal of the American Chemical Society, Vol. 84, Issue 3, p. 480-485 https://doi.org/10.1021/ja00862a032	journal	February 1962
Ferrocene-Based Electroactive Derivatizing Reagents for the Rapid Selective Screening of Alcohols and Phenols in Natural Product Mixtures Using Electrospray−Tandem Mass Spectrometry Quirke, J. Martin E.; Hsu, Ya-Li; Van Berkel, Gary J. Journal of Natural Products, Vol. 63, Issue 2, p. 230-237 https://doi.org/10.1021/np990407l	journal	February 2000
Fate of Alkylbenzenesulfonates and Dialkyltetralinsulfonates in Sewage-Contaminated Groundwater Field, Jennifer A.; Barber, Larry B.; Thurman, E. Michael Environmental Science & Technology, Vol. 26, Issue 6, p. 1140-1148 https://doi.org/10.1021/es50002a600	journal	June 1992
A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes Sivakumar, Krishnamoorthy; Xie, Fang; Cash, Brandon M. Organic Letters, Vol. 6, Issue 24, p. 4603-4606 https://doi.org/10.1021/ol047955x	journal	November 2004
Derivatization for Electrospray Ionization Mass Spectrometry. 3. Electrochemically Ionizable Derivatives Van Berkel, Gary J.; Quirke, J. Martin E.; Tigani, Rudolfo A. Analytical Chemistry, Vol. 70, Issue 8, p. 1544-1554 https://doi.org/10.1021/ac971348o	journal	April 1998
Synthesis of ferrocene-functionalized monomers for biodegradable polymer formation Upton, Brianna M.; Gipson, Raymond M.; Duhović, Selma Inorganic Chemistry Frontiers, Vol. 1, Issue 3, p. 271-277 https://doi.org/10.1039/C3QI00041A	journal	January 2014
Determination of Endocrine-Disrupting Phenolic Compounds and Estrogens in Surface and Drinking Water by HRGC−(NCI)−MS in the Picogram per Liter Range Kuch, Holger M.; Ballschmiter, Karlheinz Environmental Science & Technology, Vol. 35, Issue 15, p. 3201-3206 https://doi.org/10.1021/es010034m	journal	August 2001
Water Analysis: Emerging Contaminants and Current Issues Richardson, Susan D. Analytical Chemistry, Vol. 81, Issue 12, p. 4645-4677 https://doi.org/10.1021/ac9008012	journal	June 2009
Synthesis of ferrocene-labelled steroid derivatives via homogeneous catalytic methods Szánti-Pintér, Eszter; Csók, Zsolt; Kollár, László Journal of Organometallic Chemistry, Vol. 718, p. 105-107 https://doi.org/10.1016/j.jorganchem.2012.08.013	journal	November 2012
Are Fluorescence Quantum Yields So Tricky to Measure? A Demonstration Using Familiar Stationery Products Fery-Forgues, Suzanne; Lavabre, Dominique Journal of Chemical Education, Vol. 76, Issue 9, p. 1260 https://doi.org/10.1021/ed076p1260	journal	September 1999
Environmentally Relevant Concentrations of 17α-Ethinylestradiol (EE2) Interfere With the Growth Hormone (GH)/Insulin-Like Growth Factor (IGF)-I System in Developing Bony Fish Shved, Natallia; Berishvili, Giorgi; Baroiller, Jean-François Toxicological Sciences, Vol. 106, Issue 1, p. 93-102 https://doi.org/10.1093/toxsci/kfn150	journal	July 2008
Practical Synthesis of Amides from In Situ Generated Copper(I) Acetylides and Sulfonyl Azides Cassidy, Michael P.; Raushel, Jessica; Fokin, Valery V. Angewandte Chemie, Vol. 118, Issue 19, p. 3226-3229 https://doi.org/10.1002/ange.200503805	journal	May 2006
Analytical Methods for Detection of Selected Estrogenic Compounds in Aqueous Mixtures Snyder, Shane A.; Keith, Timothy L.; Verbrugge, David A. Environmental Science & Technology, Vol. 33, Issue 16, p. 2814-2820 https://doi.org/10.1021/es981294f	journal	August 1999

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