Title:
FLUORESCENT SUGAR DERIVATIVE COMPOUND AND SENSOR USING SAME
Document Type and Number:
WIPO Patent Application WO/2010/027108
Kind Code:
A1
Abstract:
Disclosed are a method for sensing saccharide-binding protein easily, quickly, and with high sensitivity, and a fluorescent compound necessary for this sensing. Specifically, disclosed is a method for sensing saccharide-binding protein that utilizes the fact that when a saccharide-binding protein acts on a molecule having a conjugate structure whereby a sugar chain is joined directly or via an appropriate linker, the fluorescent intensity is significantly greater than when there is no saccharide-binding protein.
Inventors:
TANAKA MASATO (JP)
SANJI TAKANOBU (JP)
SHIRAISHI KENTARO (JP)
SANJI TAKANOBU (JP)
SHIRAISHI KENTARO (JP)
Application Number:
PCT/JP2009/065974
Publication Date:
March 11, 2010
Filing Date:
September 07, 2009
Export Citation:
Assignee:
TOKYO INST TECH (JP)
TANAKA MASATO (JP)
SANJI TAKANOBU (JP)
SHIRAISHI KENTARO (JP)
TANAKA MASATO (JP)
SANJI TAKANOBU (JP)
SHIRAISHI KENTARO (JP)
International Classes:
C07H15/18; C07H15/203; C07H17/00; G01N33/53; G01N33/58
Domestic Patent References:
| WO2006061101A2 | 2006-06-15 | |||
| WO2004028475A2 | 2004-04-08 |
Foreign References:
| JP2007022987A | 2007-02-01 | |||
| JP2006111618A | 2006-04-27 |
Other References:
DISNEY, M.D. ET AL.: "Detection of Bacteria with Carbohydrate-Functionalized Fluorescent Polymers", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 126, no. 41, 2004, pages 13343 - 13346
KIM, I.-B. ET AL.: "Mannose-substituted PPEs detect lectins: A model for Ricin sensing", CHEMICAL COMMUNICATIONS (CAMBRIDGE, UNITED KINGDOM), no. 10, 2005, pages 1273 - 1275
KELLY, T.L. ET AL.: "Carbohydrate-labeled fluorescent microparticles and their binding to lectins", BIOCONJUGATE CHEMISTRY, vol. 17, no. 3, 2006, pages 575 - 578
XUE, C. ET AL.: "Synthesis of Highly Water- Soluble Fluorescent Conjugated Glycopoly (p-phenylene)s for Lectin and Escherichia coli", BIOMACROMOLECULES, vol. 7, no. 9, 2006, pages 2470 - 2474
PHILLIPS, R.L. ET AL.: "Fluorescence self- quenching of a mannosylated poly (p-phenyleneethynylene) induced by concanavalin A", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 130, no. 22, 4 July 2008 (2008-07-04), pages 6952 - 6954
ARENA, A. ET AL.: "2/4-Substituted-9-fluorenones and their 0-glucosides as potential immunomodulators and anti-herpes simplex virus -2 agents. Part 5", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 43, no. 12, 14 February 2008 (2008-02-14), pages 2656 - 2664
TRAMICE, A. ET AL.: "Facile biocatalytic access to 9-fluorenylmethyl polyglycosides: evaluation of antiviral activity on immunocompetent cells", CHEMMEDCHEM, vol. 3, no. 9, 23 June 2008 (2008-06-23), pages 1419 - 1426
NARUCHI, K. ET AL.: "Construction and Structural Characterization of Versatile Lactosaminoglycan- Related Compound Library for the Synthesis of Complex Glycopeptides and Glycosphingolipids", JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 26, 2006, pages 9609 - 9621
ENDO, T. ET AL.: "0-mannosylation in mammalian cells", METHODS IN MOLECULAR BIOLOGY(TOTOWA, NJ, UNITED STATES), vol. 347, 2006, pages 43 - 56
BIONDI, B. ET AL.: "Novel nociceptin analogs: synthesis and biological activity", INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, vol. 12, no. 2, 2006, pages 139 - 144
SHAO, N. ET AL.: "Solution-Phase Synthesis with Solid-State Workup of an O-Glycopeptide with a Cluster of Cancer-Related T Antigens", ORGANIC LETTERS, vol. 7, no. 16, 2005, pages 3589 - 3592
ALCARO, S. ET AL.: "Biocatalysed synthesis of beta-0-glucosides from 9-fluorenon-2- carbohydroxyesters. Part 3: IFN-inducing and anti-HSV-2 properties", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 13, no. 10, 2005, pages 3371 - 3378
ELMAGBARI, N.O. ET AL.: "Antinociceptive structure-activity studies with enkephalin- based opioid glycopeptides", JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 311, no. 1, 2004, pages 290 - 297
KARTHA, K.P.R. ET AL.: "Practical de-O-acylation reactions promoted by molecular sieves", CARBOHYDRATE RESEARCH, vol. 339, no. 3, 2004, pages 729 - 732
MIZUNO, M. ET AL.: "Synthesis of a mannosyl peptide as an acceptor substrate for a new N-acetylglucosaminyltransferase", PEPTIDES 2002, PROCEEDINGS OF THE EUROPEAN PEPTIDE SYMPOSIUM 27TH, 31 August 2002 (2002-08-31), pages 228 - 229
TAKEMURA, T. ET AL.: "Application of Fmoc-amino acid carrying an unmasked carbohydrate to the synthesis of the epidermal growth factor-like domain of bovine blood coagulation factor IX", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 2, no. 1, 2004, pages 133 - 136
TAKANO, Y. ET AL.: "Solid-phase synthesis of core 2 O-linked glycopeptide and its enzymatic sialylation", TETRAHEDRON, vol. 59, no. 42, 2003, pages 8415 - 8427
INAZU, T. ET AL.: "Synthesis of mucin-type glycopeptide", PEPTIDES 2000, PROCEEDINGS OF THE EUROPEAN PEPTIDE SYMPOSIUM, 26TH, 10 September 2000 (2000-09-10) - 15 September 2000 (2000-09-15), pages 315 - 316
VINOGRADOV, S. ET AL.: "Synthesis and Binding Properties of Oligo-2'-deoxyribonucleotides Conjugated with Triple-Helix-Specific Intercalators: Benzo[e] and Benzo[g] Pyridoindoles", BIOCONJUGATE CHEMISTRY, vol. 14, no. 1, 2003, pages 120 - 135
GOBBO, M. ET AL.: "Antimicrobial Peptides: Synthesis and Antibacterial Activity of Linear and Cyclic Drosocin and Apidaecin 1b Analogues", JOURNAL OF MEDICINAL CHEMISTRY, vol. 45, no. 20, 2002, pages 4494 - 4504
MIZUNO, M. ET AL.: "Synthesis of a mannosyl peptide as an acceptor substrate for a new N-acetylglucosaminyltransferase", PEPTIDE SCIENCE 2001, vol. 38TH, 2001, pages 85 - 88
SCOLARO, B. ET AL.: "Semisynthetic glycoproteins: preparation of glycosylated ribonuclease S' analogs", REACTIVE POLYMERS, vol. 22, no. 3, 1994, pages 195 - 201
FILIRA, F. ET AL.: "Synthesis of 0-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety", INTERNATIONAL JOURNAL OF PEPTIDE & PROTEIN RESEARCH, vol. 36, no. 1, 1990, pages 86 - 96
KOH, D. ET AL.: "Synthesis of stilbene glycosides and their anti-allergic effects", JOURNAL OF THE KOREAN SOCIETY OF AGRICULTURAL CHEMISTRY AND BIOTECHNOLOGY, vol. 44, no. 2, 2001, pages 133 - 135
ROY, R. ET AL.: "Effects of linker rigidity and orientation of mannoside clusters for multivalent interactions with proteins", ACS SYMPOSIUM SERIES, vol. 896, 2005, pages 137 - 150
DAM, T.K. ET AL.: "Thermodynamic, Kinetic, and Electron Microscopy Studies of Concanavalin A and Dioclea grandiflora Lectin Cross-linked with Synthetic Divalent Carbohydrates", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 280, no. 10, 2005, pages 8640 - 8646
LIU, B. ET AL.: "Comparative studies of galactoside-containing clusters", METHODS IN ENZYMOLOGY, vol. 362, 2003, pages 226 - 239
ANDRE, S. ET AL.: "First demonstration of differential inhibition of lectin binding by synthetic tri- and tetravalent glycoclusters from cross-coupling of rigidified 2-propynyl lactoside", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 1, no. 22, 2003, pages 3909 - 3916
ROY, R. ET AL.: "Palladium-mediated oxidative homocoupling of prop-2-ynyl glycosides: application toward the synthesis of symmetrical conjugated sugar diynes", SYNTHESIS, no. 7, 2001, pages 1049 - 1052
ROY, R. ET AL.: "Synthesis of "sugar-rods" with phytohemagglutinin cross-linking properties by using the palladium-catalyzed Sonogashira reaction", CHEMISTRY--A EUROPEAN JOURNAL, vol. 6, no. 10, 2000, pages 1757 - 1762
DAM, T.K. ET AL.: "Binding of multivalent carbohydrates to concanavalin A and Dioclea grandiflora lectin. Thermodynamic analysis of the "multivalency effect"", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 275, no. 19, 2000, pages 14223 - 14230
SANJI, T. ET AL.: "Synthesis and Photophysical Properties of Phosphole-Cored Dendrimers", ORGANIC LETTERS, vol. 9, no. 18, 2007, pages 3611 - 3614
SCHUDDEBOOM, W. ET AL.: "Sudden polarization in the twisted, phantom state of tetraphenylethylene detected by time-resolved microwave conductivity", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 115, no. 8, 1993, pages 3286 - 90
LEIGH, W.J. ET AL.: "Merostabilization in radical ions, triplets, and biradicals. 6. The excited state behavior of para-substituted tetraphenylethylenes", CANADIAN JOURNAL OF CHEMISTRY, vol. 59, no. 21, 1981, pages 3061 - 75
SANJI, T. ET AL.: "Sugar-Phosphole Oxide Conjugates as "Turn-on" Luminescent Sensors for Lectins", ACS APPLIED MATERIALS & INTERFACES, vol. 1, no. 2, 2009, pages 270 - 273
OCHIAI, H. ET AL.: "Endo-beta-N- acetylglucosaminidase-catalyzed polymerization of beta-Glcp-(1-4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation", CARBOHYDRATE RESEARCH, vol. 344, no. 5, 31 March 2009 (2009-03-31), pages 592 - 598
ZHU, J. ET AL.: "Synthesis of biotinylated tumor- associated carbohydrate antigens for immunological studies", TETRAHEDRON LETTERS, vol. 50, no. 6, 2009, pages 712 - 714
KIM, I.-B. ET AL.: "Mannose-substituted PPEs detect lectins: A model for Ricin sensing", CHEMICAL COMMUNICATIONS (CAMBRIDGE, UNITED KINGDOM), no. 10, 2005, pages 1273 - 1275
KELLY, T.L. ET AL.: "Carbohydrate-labeled fluorescent microparticles and their binding to lectins", BIOCONJUGATE CHEMISTRY, vol. 17, no. 3, 2006, pages 575 - 578
XUE, C. ET AL.: "Synthesis of Highly Water- Soluble Fluorescent Conjugated Glycopoly (p-phenylene)s for Lectin and Escherichia coli", BIOMACROMOLECULES, vol. 7, no. 9, 2006, pages 2470 - 2474
PHILLIPS, R.L. ET AL.: "Fluorescence self- quenching of a mannosylated poly (p-phenyleneethynylene) induced by concanavalin A", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 130, no. 22, 4 July 2008 (2008-07-04), pages 6952 - 6954
ARENA, A. ET AL.: "2/4-Substituted-9-fluorenones and their 0-glucosides as potential immunomodulators and anti-herpes simplex virus -2 agents. Part 5", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 43, no. 12, 14 February 2008 (2008-02-14), pages 2656 - 2664
TRAMICE, A. ET AL.: "Facile biocatalytic access to 9-fluorenylmethyl polyglycosides: evaluation of antiviral activity on immunocompetent cells", CHEMMEDCHEM, vol. 3, no. 9, 23 June 2008 (2008-06-23), pages 1419 - 1426
NARUCHI, K. ET AL.: "Construction and Structural Characterization of Versatile Lactosaminoglycan- Related Compound Library for the Synthesis of Complex Glycopeptides and Glycosphingolipids", JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 26, 2006, pages 9609 - 9621
ENDO, T. ET AL.: "0-mannosylation in mammalian cells", METHODS IN MOLECULAR BIOLOGY(TOTOWA, NJ, UNITED STATES), vol. 347, 2006, pages 43 - 56
BIONDI, B. ET AL.: "Novel nociceptin analogs: synthesis and biological activity", INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, vol. 12, no. 2, 2006, pages 139 - 144
SHAO, N. ET AL.: "Solution-Phase Synthesis with Solid-State Workup of an O-Glycopeptide with a Cluster of Cancer-Related T Antigens", ORGANIC LETTERS, vol. 7, no. 16, 2005, pages 3589 - 3592
ALCARO, S. ET AL.: "Biocatalysed synthesis of beta-0-glucosides from 9-fluorenon-2- carbohydroxyesters. Part 3: IFN-inducing and anti-HSV-2 properties", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 13, no. 10, 2005, pages 3371 - 3378
ELMAGBARI, N.O. ET AL.: "Antinociceptive structure-activity studies with enkephalin- based opioid glycopeptides", JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 311, no. 1, 2004, pages 290 - 297
KARTHA, K.P.R. ET AL.: "Practical de-O-acylation reactions promoted by molecular sieves", CARBOHYDRATE RESEARCH, vol. 339, no. 3, 2004, pages 729 - 732
MIZUNO, M. ET AL.: "Synthesis of a mannosyl peptide as an acceptor substrate for a new N-acetylglucosaminyltransferase", PEPTIDES 2002, PROCEEDINGS OF THE EUROPEAN PEPTIDE SYMPOSIUM 27TH, 31 August 2002 (2002-08-31), pages 228 - 229
TAKEMURA, T. ET AL.: "Application of Fmoc-amino acid carrying an unmasked carbohydrate to the synthesis of the epidermal growth factor-like domain of bovine blood coagulation factor IX", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 2, no. 1, 2004, pages 133 - 136
TAKANO, Y. ET AL.: "Solid-phase synthesis of core 2 O-linked glycopeptide and its enzymatic sialylation", TETRAHEDRON, vol. 59, no. 42, 2003, pages 8415 - 8427
INAZU, T. ET AL.: "Synthesis of mucin-type glycopeptide", PEPTIDES 2000, PROCEEDINGS OF THE EUROPEAN PEPTIDE SYMPOSIUM, 26TH, 10 September 2000 (2000-09-10) - 15 September 2000 (2000-09-15), pages 315 - 316
VINOGRADOV, S. ET AL.: "Synthesis and Binding Properties of Oligo-2'-deoxyribonucleotides Conjugated with Triple-Helix-Specific Intercalators: Benzo[e] and Benzo[g] Pyridoindoles", BIOCONJUGATE CHEMISTRY, vol. 14, no. 1, 2003, pages 120 - 135
GOBBO, M. ET AL.: "Antimicrobial Peptides: Synthesis and Antibacterial Activity of Linear and Cyclic Drosocin and Apidaecin 1b Analogues", JOURNAL OF MEDICINAL CHEMISTRY, vol. 45, no. 20, 2002, pages 4494 - 4504
MIZUNO, M. ET AL.: "Synthesis of a mannosyl peptide as an acceptor substrate for a new N-acetylglucosaminyltransferase", PEPTIDE SCIENCE 2001, vol. 38TH, 2001, pages 85 - 88
SCOLARO, B. ET AL.: "Semisynthetic glycoproteins: preparation of glycosylated ribonuclease S' analogs", REACTIVE POLYMERS, vol. 22, no. 3, 1994, pages 195 - 201
FILIRA, F. ET AL.: "Synthesis of 0-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety", INTERNATIONAL JOURNAL OF PEPTIDE & PROTEIN RESEARCH, vol. 36, no. 1, 1990, pages 86 - 96
KOH, D. ET AL.: "Synthesis of stilbene glycosides and their anti-allergic effects", JOURNAL OF THE KOREAN SOCIETY OF AGRICULTURAL CHEMISTRY AND BIOTECHNOLOGY, vol. 44, no. 2, 2001, pages 133 - 135
ROY, R. ET AL.: "Effects of linker rigidity and orientation of mannoside clusters for multivalent interactions with proteins", ACS SYMPOSIUM SERIES, vol. 896, 2005, pages 137 - 150
DAM, T.K. ET AL.: "Thermodynamic, Kinetic, and Electron Microscopy Studies of Concanavalin A and Dioclea grandiflora Lectin Cross-linked with Synthetic Divalent Carbohydrates", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 280, no. 10, 2005, pages 8640 - 8646
LIU, B. ET AL.: "Comparative studies of galactoside-containing clusters", METHODS IN ENZYMOLOGY, vol. 362, 2003, pages 226 - 239
ANDRE, S. ET AL.: "First demonstration of differential inhibition of lectin binding by synthetic tri- and tetravalent glycoclusters from cross-coupling of rigidified 2-propynyl lactoside", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 1, no. 22, 2003, pages 3909 - 3916
ROY, R. ET AL.: "Palladium-mediated oxidative homocoupling of prop-2-ynyl glycosides: application toward the synthesis of symmetrical conjugated sugar diynes", SYNTHESIS, no. 7, 2001, pages 1049 - 1052
ROY, R. ET AL.: "Synthesis of "sugar-rods" with phytohemagglutinin cross-linking properties by using the palladium-catalyzed Sonogashira reaction", CHEMISTRY--A EUROPEAN JOURNAL, vol. 6, no. 10, 2000, pages 1757 - 1762
DAM, T.K. ET AL.: "Binding of multivalent carbohydrates to concanavalin A and Dioclea grandiflora lectin. Thermodynamic analysis of the "multivalency effect"", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 275, no. 19, 2000, pages 14223 - 14230
SANJI, T. ET AL.: "Synthesis and Photophysical Properties of Phosphole-Cored Dendrimers", ORGANIC LETTERS, vol. 9, no. 18, 2007, pages 3611 - 3614
SCHUDDEBOOM, W. ET AL.: "Sudden polarization in the twisted, phantom state of tetraphenylethylene detected by time-resolved microwave conductivity", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 115, no. 8, 1993, pages 3286 - 90
LEIGH, W.J. ET AL.: "Merostabilization in radical ions, triplets, and biradicals. 6. The excited state behavior of para-substituted tetraphenylethylenes", CANADIAN JOURNAL OF CHEMISTRY, vol. 59, no. 21, 1981, pages 3061 - 75
SANJI, T. ET AL.: "Sugar-Phosphole Oxide Conjugates as "Turn-on" Luminescent Sensors for Lectins", ACS APPLIED MATERIALS & INTERFACES, vol. 1, no. 2, 2009, pages 270 - 273
OCHIAI, H. ET AL.: "Endo-beta-N- acetylglucosaminidase-catalyzed polymerization of beta-Glcp-(1-4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation", CARBOHYDRATE RESEARCH, vol. 344, no. 5, 31 March 2009 (2009-03-31), pages 592 - 598
ZHU, J. ET AL.: "Synthesis of biotinylated tumor- associated carbohydrate antigens for immunological studies", TETRAHEDRON LETTERS, vol. 50, no. 6, 2009, pages 712 - 714
Attorney, Agent or Firm:
AOKI, ATSUSHI (JP)
Atsushi Aoki (JP)
Atsushi Aoki (JP)
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