Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Chemical aftertreatment – e.g. – acylation – methylation – etc.
Reexamination Certificate
2007-12-20
2011-12-06
Audet, Maury (Department: 1654)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Chemical aftertreatment, e.g., acylation, methylation, etc.
C514S001100, C424S001690
Reexamination Certificate
active
08071718
ABSTRACT:
Provided herein are methods for introducing fluorine atom onto a biomolecule comprising: (i) providing a linker comprising a thiol-reactive terminus and an azido/alkyne-reactive terminus; (ii) reacting the thiol-reactive terminus of the linker with a biomolecule comprising at least one thiol group or a reactive derivative thereof; and (iii) subsequently reacting the azido/alkyne-reactive terminus of the linker with a fluorine-substituted azide or alkyne respectively. Also provided are compositions and method of synthesis of bifunctional linkers and bioconjugates as well as radio-diagnostic agents comprising fluorine-labeled biomolecules.
REFERENCES:
patent: 7902332 (2011-03-01), De Jesus et al.
patent: 2008/0139787 (2008-06-01), De Jesus et al.
patent: WO9935499 (1999-07-01), None
patent: WO03101972 (2003-12-01), None
patent: WO2005087818 (2005-09-01), None
patent: WO2006005046 (2006-01-01), None
patent: WO2006012569 (2006-02-01), None
patent: WO2006067376 (2006-06-01), None
patent: WO2006116629 (2006-11-01), None
patent: WO2006116736 (2006-11-01), None
patent: WO2007011696 (2007-01-01), None
Young Soo Chang, et al; Bioconjugate Chem., vol. 16, No. 5, pp. 1329-1333, 2005.
Tatsushi Toyokuni, et al, Synthesis of a new heterobifunctional linker, N-[4-(aminooxy)butyl]maleimide, for facile access to a thiol-reactive 18F-labeling agent; Bioconjugate Chem., vol. 14, p. 1253-1259, 2003.
Ramenda et al., Synthesis of 18F-labeled Neurotensin(8-13) via Copper-Mediated 1,3-Dipolar [3+2}Cycloaddition Reaction, Letters in Drug Design & Discovery, vol. 4, pp. 279-285, 2007.
Burley, G.A., “Directed DNA Metallization”, JACS Communications, J. Am. Chem. Soc, 2006, 128, 1398-1399.
Link, James et al., “Non-canonical Amino Acids in Protein Engineering”, Current Opinion in Biotechology (2003), 14: 603-609.
Torne, C.W. et al., “Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Catalyzed 1.3-Dipolar Cycloadditions of Terminal Alkynes to Azides”, American Chemical Society, J. Org. Chem., 2002, 67, 3057-3064.
Manetsch, Roman et al., “In Situ Click Chemistry: Enzyme Inhibitors Made to Their Own Specifications”, J. Amer. Chem. Soc.,, 2004, 126, 12809-1281i.
Speers, Anna et al., “Activity-Based Protein Profiing in Vivo Using a Copper(1)-Catalyzed Azide-Alkyne [3+2] Cycloaddition”, J. Am. Chem. Soc., 2003, 125, 4686-4687.
Link, A. James et al., “Cell Surface Labeling ofEscherichia coliVia Copper(1)-Catalyzed [3+2] Cycloaddition”, Am. Chem Soc., 2003, 11164-11165.
Fazio, F. et al, “Synthesis of Sugar Arrays in Microtiter Plate”, J. Am. Chem. Soc., 2002, 124, 14397-14402.
Mindt, Thomas et al., “Click to Chelate”: Synthesis and Installation of Metal Chelates Into Biomolecules in a Single Step, J. Am. Chem. Soc., 2006, 128, 15096-15097.
Gupta, Sayan et al., “Accelerated Bioorthogonal Conjugation: A Practical Method for the Ligation of Diverse Functional Molecules to a Polyvalent Virus Scaffold”, Bioconjigate Chem., 2005, 1572-1579.
Lewis, Warren et al., “Discovery and Characterization of Catalysts for Azide—Alkyne Cycloaddition by Fluorescence Quenching”, J. Am. Chem. Soc., 2004, 126, 9152-9153.
Wang, Q. et al., “Bioconjugation by Copper(1)-Catalyzed Azide-Alkyne [3+2] Cycloaddition”, J. Am. Soc., 2003, 125, 3192-3193.
Marik, Jan et al., “Click for PET: Rapid Preparation of [ 18F]fluoropeptides Using Cu Catalyzed 1,3-dipolar Cycloadditon”, Tetrahedron Letters, 47, 2006, 6681-6684.
Hassane, Fatouma et al., “Targeted Liposomes: Convenient Coupling of Ligands to Preformed Vesicles Using ‘Click Chemistry’”, Bioconjugate Chem., 2006, 17, 849-854.
Agard, Nicholas et al., “A Comparative Study of Bioorthogonal Reactions with Azides”, ACS Chemical Biology, 2006, vol. 1, No. 10, 644-648.
Hatzakis, Nikos et al., “Synthesis and Single Enzyme Activity of a Clicked Lipase-BSA Hetero-Dimer”, Chem. Communications, 2006, 2012-2014.
Fukukawa, K. et al., “Synthesis of PEGylated Star Microgel With Core Functionality for Click Chemistry by Nitroxide-Mediated Radical Polymerization”, The 231st ACS National Meeting—Mar. 26-30, 2006, Abstract.
Kolb, H. et al., Application of Click Chemistry to the Development of COX-2 and CA-II Inhibitors, The 231st ACS National Meeting, Mar. 26-30, 2006, Abstract.
Li et al., “Click Chemistry for 18F-Labeling of RGD Peptides and microPET Imaging of Tumor Integrin αvβ3 Expression”, Bioconjugate Chem., vol. 18, No. 6, pp. 1987-1994, Noveber 1, 2007.
Hermanson et al., Bioconjugate Techniques, Academic Press, San Diego, US, pp. 146-152, section “Thiol-Reactive Chemical Reactions”, XP002523340, 1996.
Cai et al., “A Thiol-Reactive 18F-Labeling Agent, N-[2-(4-18F-Fluorobenzamido)Ethyl]Maleimide, and Synthesis of RGD Peptide-Based Tracer for PET Imaging of αvβ3 Integrin Expression”, Journal of Nuclear Medicine, vol. 47, No. 7, pp. 1172-1180, Jul. 1, 2006, XP002470156.
PCT International Search Report dated May 6, 2009.
Arstad Erik
Glaser Matthias Eberhard
Kovacs Ernest William
Padilla De Jesus Omayra Liz
Syud Faisal Ahmed
Audet Maury
Gallagher Eileen B.
General Electric Company
LandOfFree
Selective radiolabeling of biomolecules does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Selective radiolabeling of biomolecules, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Selective radiolabeling of biomolecules will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4301723