WO2006095181A3 - Biosensor labelling groups - Google Patents

Biosensor labelling groups Download PDF

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Publication number
WO2006095181A3
WO2006095181A3 PCT/GB2006/000849 GB2006000849W WO2006095181A3 WO 2006095181 A3 WO2006095181 A3 WO 2006095181A3 GB 2006000849 W GB2006000849 W GB 2006000849W WO 2006095181 A3 WO2006095181 A3 WO 2006095181A3
Authority
WO
WIPO (PCT)
Prior art keywords
label
raman spectroscopy
resonance raman
halogen
labels
Prior art date
Application number
PCT/GB2006/000849
Other languages
French (fr)
Other versions
WO2006095181A2 (en
Inventor
Richard Gilbert
Original Assignee
E2V Biosensors Ltd
Richard Gilbert
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by E2V Biosensors Ltd, Richard Gilbert filed Critical E2V Biosensors Ltd
Priority to US11/817,945 priority Critical patent/US20090027667A1/en
Priority to AU2006221782A priority patent/AU2006221782A1/en
Priority to EP06710061A priority patent/EP1861717A2/en
Priority to JP2008500269A priority patent/JP2008533462A/en
Publication of WO2006095181A2 publication Critical patent/WO2006095181A2/en
Publication of WO2006095181A3 publication Critical patent/WO2006095181A3/en

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Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/583—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with non-fluorescent dye label
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Immunology (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Analytical Chemistry (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Physics & Mathematics (AREA)
  • Cell Biology (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Pathology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biophysics (AREA)
  • General Engineering & Computer Science (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Abstract

A class of compounds specifically designed to act as resonance Raman spectroscopy labels, particularly surface-enhanced resonance Raman spectroscopy (SERRS) labels, for analytes such as proteins, peptides, nucleic acids, and related molecules is described. A resonance Raman spectroscopy label of the invention comprises a metallocene covalently attached to: a reactive group for covalent attachment of the label to an analyte; a SERRS surface binding group; and a halogen, wherein attachment of the halogen to the metallocene is such that the halogen causes a characteristic Raman peak to be produced when the label is subjected to resonance Raman spectroscopy. In a preferred aspect the label also has redox properties suitable for a second use as a label for electrochemical sensing.
PCT/GB2006/000849 2005-03-09 2006-03-09 Biosensor labelling groups WO2006095181A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US11/817,945 US20090027667A1 (en) 2005-03-09 2006-03-09 Biosensor labelling groups
AU2006221782A AU2006221782A1 (en) 2005-03-09 2006-03-09 Biosensor labelling groups
EP06710061A EP1861717A2 (en) 2005-03-09 2006-03-09 Biosensor labelling groups
JP2008500269A JP2008533462A (en) 2005-03-09 2006-03-09 Biosensor labeling group

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0504851.7 2005-03-09
GBGB0504851.7A GB0504851D0 (en) 2005-03-09 2005-03-09 Biosensor labelling groups

Publications (2)

Publication Number Publication Date
WO2006095181A2 WO2006095181A2 (en) 2006-09-14
WO2006095181A3 true WO2006095181A3 (en) 2006-12-14

Family

ID=34452076

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2006/000849 WO2006095181A2 (en) 2005-03-09 2006-03-09 Biosensor labelling groups

Country Status (7)

Country Link
US (1) US20090027667A1 (en)
EP (1) EP1861717A2 (en)
JP (1) JP2008533462A (en)
CN (1) CN101189521A (en)
AU (1) AU2006221782A1 (en)
GB (2) GB0504851D0 (en)
WO (1) WO2006095181A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0603355D0 (en) * 2006-02-20 2006-03-29 E2V Biosensors Ltd Novel serrs chromophores
GB0620200D0 (en) * 2006-10-11 2006-11-22 E2V Biosensors Ltd Conjugates for use in analyte detection
GB201021896D0 (en) 2010-12-22 2011-02-02 Atlas Genetics Ltd Novel compounds and their use in analytical methods
CN103159801B (en) * 2011-12-08 2016-09-07 天承南运(天津)科技有限公司 N-ferrocenyl-N '-aryl ureas compound and application thereof
EP2948771B8 (en) * 2013-01-25 2019-06-19 Hewlett-Packard Development Company, L.P. Chemical sensing device
CN112574619B (en) * 2020-12-01 2022-08-09 德莱森(北京)医疗科技有限公司 Conductive ink functional material and preparation method thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3678088A (en) * 1971-02-24 1972-07-18 Us Air Force Polychlorinated metallocenes and their synthesis
US5079359A (en) * 1989-03-09 1992-01-07 Tosoh Corporation Chiral amino-methyl ferrocene derivatives
WO1992019968A1 (en) * 1991-05-09 1992-11-12 British Technology Group Ltd. Spectroscopic investigation using organometallic compounds
EP0795542A1 (en) * 1995-06-29 1997-09-17 Mitsui Petrochemical Industries, Ltd. Process for the production of acrylonitrile dimers
WO2001040239A2 (en) * 1999-12-03 2001-06-07 Yale University Transition metal-cyclopentadienyl-tropane conjugates
WO2005019812A1 (en) * 2003-08-26 2005-03-03 University Of Strathclyde Nucleic acid sequence identification
WO2006006196A2 (en) * 2004-07-15 2006-01-19 Universita' Degli Studi Di Milano Synthesis of organometallic molecules that can be used as markers of organic substances

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5499296A (en) * 1995-04-11 1996-10-30 Novartis Ag Dihalogenated ferrocenes and processes for the preparation hereof
US20030143556A1 (en) * 2001-04-03 2003-07-31 Gary Blackburn Nucleic acid reactions using labels with different redox potentials
WO2003087188A1 (en) * 2001-04-26 2003-10-23 Nanosphere, Inc. Oligonucleotide-modified romp polymers and co-polymers

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3678088A (en) * 1971-02-24 1972-07-18 Us Air Force Polychlorinated metallocenes and their synthesis
US5079359A (en) * 1989-03-09 1992-01-07 Tosoh Corporation Chiral amino-methyl ferrocene derivatives
WO1992019968A1 (en) * 1991-05-09 1992-11-12 British Technology Group Ltd. Spectroscopic investigation using organometallic compounds
EP0795542A1 (en) * 1995-06-29 1997-09-17 Mitsui Petrochemical Industries, Ltd. Process for the production of acrylonitrile dimers
WO2001040239A2 (en) * 1999-12-03 2001-06-07 Yale University Transition metal-cyclopentadienyl-tropane conjugates
WO2005019812A1 (en) * 2003-08-26 2005-03-03 University Of Strathclyde Nucleic acid sequence identification
WO2006006196A2 (en) * 2004-07-15 2006-01-19 Universita' Degli Studi Di Milano Synthesis of organometallic molecules that can be used as markers of organic substances

Non-Patent Citations (31)

* Cited by examiner, † Cited by third party
Title
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ARATANI, T ET AL: "Asymmetric lithiation of ferrocenes", TETRAHEDRON , 26(23), 5453-64, 1970, XP002395414 *
BAUER W ET AL: "Metal Complexes of Biologically Important Ligands, CII Organometallic Complexes of Iridium, Palladium, Chromium and Iron from 2-Phenyl-5(4H)-oxazolones - Organometallc Labelled Dipeptides", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 1998, pages 485 - 493, XP002395416 *
BOEV, V I ET AL: "New permercuration reactions of ferrocene derivatives with mercury trifluoroacetate", RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 70(2), 291-297, 2000, XP008067818 *
BROSCH, O ET AL: "A two-step palladium-catalyzed coupling scheme for the synthesis of ferrocene- labeled amino acids", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY , (2), 323-330, 2000, XP002395393 *
CESATI, RR., III ET AL: "Synthesis of Cyclopentadienyltricarbonyl Rhenium Phenyltropanes by Double Ligand Transfer: Organometallic Ligands for the Dopamine Transporter", BIOCONJUGATE CHEMISTRY , 13(1), 29-39, 2002, XP002395392 *
GHOSH P ET AL: "Apoptosis-inducing vanadocene compounds against human testicular cancer.", CLINICAL CANCER RESEARCH : AN OFFICIAL JOURNAL OF THE AMERICAN ASSOCIATION FOR CANCER RESEARCH, vol. 6, no. 4, 2000, pages 1536 - 1545, XP002395418 *
GORFTI, A ET AL: "Covalent and Selective Labeling of Proteins with Heavy Metals. Synthesis, x-ray Structure, and Reactivity Studies of N-Succinimidyl and N-Sulfosuccinimidyl Ester Organotungsten Complexes", ORGANOMETALLICS , 15(1), 142-51, 1996, XP002395415 *
HEDBERG, FL ET AL: "Preparation and reactions of decachloroferrocene ad decachlororuthenocene", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 95(3), 870-5, 1973, XP002395381 *
HOFFMANNS U ET AL: "Use of the Sonogashira coupling reaction for the "two-step" labeling of phenylalanine peptide side chains with organometallic compounds", BIOCONJUGATE CHEMISTRY, vol. 17, no. 1, 23 December 2005 (2005-12-23), pages 204 - 213,195, XP002395419 *
HUFFMAN, J. W. ET AL: "Some reactions of chloroferrocene with organolithium compounds", JOURNAL OF ORGANIC CHEMISTRY , 30(5), 1600-4, 1965, XP002395410 *
HUFFMAN, JW ET AL: "Reactions of 2-methylchloroferrocene. Evidence for the ferrocyne intermediate", JOURNAL OF ORGANIC CHEMISTRY , 36(26), 4068-72, 1971, XP002395413 *
KOEPF-MAIER, P ET AL: "Antitumor activity of titanocene amino acid complexes", BIOMETALS , 9(3), 267-271, 1996, XP002395386 *
LEONE-STUMPF, D ET AL: "Synthesis of ruthenium- labelled tripeptoids with alternating amide and diaryl ether bonds", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , (10), 1853-1858, 2003, XP002395390 *
LOCKE, AJ ET AL: "Diastereoselective synthesis of enantiopure C2-symmetric dihaloferrocenes", SYNLETT , (1), 141-143, 2001, XP002395412 *
METALLINOS, C ET AL: "(-)-Sparteine-mediated directed ortho-metalation of N-cumyl-N- ethylferrocenecarboxamide. Versatile routes to functionalized planar chiral ferrocenecarboxamides, amines, esters and phosphines", ADVANCED SYNTHESIS & CATALYSIS , 345(3), 370-382, 2003, XP002395411 *
ONG, CW ET AL: "A ferrocene-intercalator conjugate with a potent cytotoxicity", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 2(9), 929-32, 1992, XP002395387 *
SCHLOTTER, KARIN ET AL: "Fancy Bioisosteres: Metallocene-Derived G- Protein -Coupled Receptor Ligands with Subnanomolar Binding Affinity and Novel Selectivity Profiles", JOURNAL OF MEDICINAL CHEMISTRY , 48(11), 3696-3699, 29 April 2005 (2005-04-29), XP002395384 *
SCHMID, A ET AL: "Modular synthesis of ruthenium- labeled diaryl ether peptoids", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION , 43(12), 1581-1583, 2004, XP002395391 *
SHEATS, JOHN E. ET AL: "Stabilization of negative charge by the cobalticinium nucleus. III. The effect of substituents on the acidities of hydroxycobalticinium and rhodicinium salts", JOURNAL OF ORGANOMETALLIC CHEMISTRY , 173(1), 107-15, 1979, XP002395380 *
SHUBINA, E. S. ET AL: "Intramolecular hydrogen bonds and conformations of ferrocenyl- and nonamethylferrocenylcarbinols", JOURNAL OF ORGANOMETALLIC CHEMISTRY , 346(1), 59-66, 1988, XP002395389 *
SUENKEL, K ET AL: "Complex chemistry of perhalogenated cyclopentadienes and alkynes. V. Preparation of additional functional derivatives of (C5Cl4R)Mn(CO)3 and (C5Cl4R)Rh(COD). Crystal structure of (C5Cl4CONH2)Mn(CO)3", JOURNAL OF ORGANOMETALLIC CHEMISTRY , 368(1), 67-76, 1989, XP002395382 *
SÜNKEL, K ET AL: "Coordination chemistry of perhalogenated cyclopentadienes and alkynes. I. Metalation of (C5Cl4Br)Mn(CO)3 and reactions with electrophiles", CHEMISCHE BERICHTE , 121(4), 799-801, 1988, XP008067826 *
SUNKEL, K. ET AL: "Coordination chemistry of perhalogenated cyclopentadienes and alkynes. XXVI. Reaction of lithiated halocymantrenes with N-electrophiles. Molecular structure of (OC)3Mn[.eta.5-C5Cl4-NH-N:C5Cl4] and (OC)3Mn[.eta.5-C5H3Cl(NH2)-1,2]", JOURNAL OF ORGANOMETALLIC CHEMISTRY , 599(2), 247-255, 2000, XP002395383 *
TAMAGNAN, G ET AL: "Cyclopentadienyltricarbonylrheniumbenzazepines: synthesis and binding affinity", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 10(10), 1113-1115, 2000, XP004204619 *
TORNIEPORTH-OETTING, IC. ET AL: "Ionic Titanocene(IV) .alpha.-Amino Acid Complexes of DL-Phenylalanine and DL-4-Fluorophenylalanine: Synthesis, Characterization, and Investigation of the Antimicrobial Behavior toward Escherichia coli", ORGANOMETALLICS , 14(4), 1632-6, 1995, XP002395388 *
VALINCIUS G ET AL: "Anion effect on mediated electron transfer through ferrocene-terminated self-assembled monolayers.", LANGMUIR : THE ACS JOURNAL OF SURFACES AND COLLOIDS. 3 AUG 2004, vol. 20, no. 16, 2004, pages 6631 - 6638, XP002395506 *
WAERN, J B ET AL: "Coordination Chemistry of the Antitumor Metallocene Molybdocene Dichloride with Biological Ligands", INORGANIC CHEMISTRY , 43(1), 206-213, 2004, XP002395417 *
WAERN, JB. ET AL: "Organometallic Anticancer Agents: Cellular Uptake and Cytotoxicity Studies on Thiol Derivatives of the Antitumor Agent Molybdocene Dichloride", JOURNAL OF MEDICINAL CHEMISTRY , 48(6), 2093-2099, 22 October 2004 (2004-10-22), XP002395385 *

Also Published As

Publication number Publication date
WO2006095181A2 (en) 2006-09-14
EP1861717A2 (en) 2007-12-05
CN101189521A (en) 2008-05-28
GB0504851D0 (en) 2005-04-13
AU2006221782A1 (en) 2006-09-14
GB2423987A (en) 2006-09-13
JP2008533462A (en) 2008-08-21
GB0604798D0 (en) 2006-04-19
US20090027667A1 (en) 2009-01-29

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