WO2002008245A3 - Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation - Google Patents

Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation Download PDF

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Publication number
WO2002008245A3
WO2002008245A3 PCT/US2001/022194 US0122194W WO0208245A3 WO 2002008245 A3 WO2002008245 A3 WO 2002008245A3 US 0122194 W US0122194 W US 0122194W WO 0208245 A3 WO0208245 A3 WO 0208245A3
Authority
WO
WIPO (PCT)
Prior art keywords
biosensors
living cells
gtp
attachment
synthons
Prior art date
Application number
PCT/US2001/022194
Other languages
French (fr)
Other versions
WO2002008245A2 (en
Inventor
Klaus M Hahn
Alexei Toutchkine
Rajeev Muthyala
Vadim Kraynov
Steven J Bark
Dennis R Burton
Chester Chamberlain
Original Assignee
Scripps Research Inst
Klaus M Hahn
Alexei Toutchkine
Rajeev Muthyala
Vadim Kraynov
Steven J Bark
Dennis R Burton
Chester Chamberlain
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
Priority claimed from PCT/US2000/026821 external-priority patent/WO2002028890A1/en
Priority claimed from US09/839,577 external-priority patent/US6951947B2/en
Application filed by Scripps Research Inst, Klaus M Hahn, Alexei Toutchkine, Rajeev Muthyala, Vadim Kraynov, Steven J Bark, Dennis R Burton, Chester Chamberlain filed Critical Scripps Research Inst
Priority to EP01954689A priority Critical patent/EP1301473A2/en
Priority to AU2001276916A priority patent/AU2001276916A1/en
Priority to CA002415960A priority patent/CA2415960A1/en
Publication of WO2002008245A2 publication Critical patent/WO2002008245A2/en
Publication of WO2002008245A3 publication Critical patent/WO2002008245A3/en
Priority to US10/455,713 priority patent/US7176037B2/en
Priority to US11/673,909 priority patent/US7662644B2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
    • C07K1/1077—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/13—Labelling of peptides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Peptides Or Proteins (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Abstract

The invention provides peptide synthons having protected functional groups for attachment of desired moieties (e.g. functional molecules or probes). Also provided are peptide conjugates prepared from such synthons, and synthon and conjugate preparation methods including procedures for identifying optimum probe attachment sites. Biosensors are provided having functional molecules that can locate and bind to specific biomolecules within living cells. Biosensors can detect chemical and physiological changes in those biomolecules as living cells are moving, metabolizing and reacting to its environment. Methods are included for detecting GTP activation of a Pho GTP are protein using polypeptide biosensors. When the biosensor binds GTP-activated Rho GTPase protein, an environmentally sensitive dye emits a signal of a different lifetime, intensity or wavelength than when not bound. New fluorophores whose fluorescence responds to environmental changes are also provided that have improved detection and attachment properties, and that can be used in living cells, or in vitro.
PCT/US2001/022194 2000-07-13 2001-07-13 Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation WO2002008245A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP01954689A EP1301473A2 (en) 2000-07-13 2001-07-13 Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
AU2001276916A AU2001276916A1 (en) 2000-07-13 2001-07-13 Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
CA002415960A CA2415960A1 (en) 2000-07-13 2001-07-13 Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
US10/455,713 US7176037B2 (en) 2000-07-13 2003-06-03 Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
US11/673,909 US7662644B2 (en) 2000-07-13 2007-02-12 Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US21811300P 2000-07-13 2000-07-13
US60/218,113 2000-07-13
PCT/US2000/026821 WO2002028890A1 (en) 2000-09-29 2000-09-29 Labeled peptides, and processes and intermediates useful for their preparation
USPCT/US00/26821 2000-09-29
US27930201P 2001-03-28 2001-03-28
US60/279,302 2001-03-28
US09/839,577 US6951947B2 (en) 2000-07-13 2001-04-20 Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
US09/839,577 2001-04-20

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/455,713 Continuation US7176037B2 (en) 2000-07-13 2003-06-03 Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation

Publications (2)

Publication Number Publication Date
WO2002008245A2 WO2002008245A2 (en) 2002-01-31
WO2002008245A3 true WO2002008245A3 (en) 2003-01-30

Family

ID=56290166

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/022194 WO2002008245A2 (en) 2000-07-13 2001-07-13 Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation

Country Status (4)

Country Link
EP (1) EP1301473A2 (en)
AU (1) AU2001276916A1 (en)
CA (1) CA2415960A1 (en)
WO (1) WO2002008245A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6951947B2 (en) 2000-07-13 2005-10-04 The Scripps Research Institute Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
US7176037B2 (en) 2000-07-13 2007-02-13 The Scripps Research Institute Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation
WO2004101709A1 (en) 2003-05-09 2004-11-25 Applera Corporation Phenyl xanthene dyes
US7432298B2 (en) 2003-05-09 2008-10-07 Applied Biosystems Inc. Fluorescent polymeric materials containing lipid soluble rhodamine dyes
WO2005088308A2 (en) * 2004-03-12 2005-09-22 The Scripps Research Institute Fluorescent signal emitting live cell biosensor molecules and dyes for detection and quantification of protein activities
US7763418B2 (en) * 2005-07-05 2010-07-27 Cytoskeleton, Inc. Detection of Rho proteins
SG172321A1 (en) 2009-01-29 2011-07-28 Commw Scient Ind Res Org Measuring g protein coupled receptor activation
CN116004221B (en) * 2022-12-15 2023-12-19 湖南卓润生物科技有限公司 New application of cyclic peptide, acridine labeled complex, preparation method and detection kit

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5880270A (en) * 1995-06-07 1999-03-09 Cellpro, Incorporated Aminooxy-containing linker compounds for formation of stably-linked conjugates and methods related thereto

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5880270A (en) * 1995-06-07 1999-03-09 Cellpro, Incorporated Aminooxy-containing linker compounds for formation of stably-linked conjugates and methods related thereto

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BARK S J ET AL: "A HIGHLY EFFICIENT METHOD FOR SITE-SPECIFIC MODIFICATION OF UNPROTECTED PEPTIDES AFTER CHEMICAL SYNTHESIS", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 122, no. 15, 19 April 2000 (2000-04-19), pages 3567 - 3573, XP002946035, ISSN: 0002-7863 *
CHAMBERLAIN, C AND HAHN, K M: "Watching proteins in the wild: Fluorescence methods to study protein dynamics in living cells", TRAFFIC, vol. 1, 2000, MUNKSGAARD,, DK, pages 755 - 762, XP002207592, ISSN: 1398-9219 *

Also Published As

Publication number Publication date
AU2001276916A1 (en) 2002-02-05
CA2415960A1 (en) 2002-01-31
WO2002008245A2 (en) 2002-01-31
EP1301473A2 (en) 2003-04-16

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