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Last Updated: October 13, 2019

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Claims for Patent: 10,338,039

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Summary for Patent: 10,338,039
Title:Method for detecting monoclonal antibody using mass spectrometry
Abstract: A method is provided for more easily detecting and quantifying a protein by regioselectively digesting a variable region of an Fab domain of a monoclonal antibody while suppressing proteolysis of an Fc domain. In the method, a porous body in which a monoclonal antibody is immobilized in pores and nanoparticles on which a protease is immobilized are brought into contact with each other in a liquid to perform selective proteolysis of the monoclonal antibody, and a resulting peptide fragment is detected using liquid chromatography-mass spectrometry (LC-MS), and a peptide having an amino acid sequence that includes an amino acid derived from a CDR2 region of a heavy chain or a light chain of the monoclonal antibody is detected.
Inventor(s): Shimada; Takashi (Kyoto, JP), Iwamoto; Noriko (Kyoto, JP)
Assignee: SHIMADZU CORPORATION (Kyoto-shi, JP)
Application Number:15/556,018
Patent Claims:1. A method of detecting a monoclonal antibody, comprising: bringing into contact in a liquid a porous body having pores in which a monoclonal antibody is immobilized and nanoparticles on which a protease is immobilized such that a selective proteolysis of the monoclonal antibody occurs; and detecting a peptide fragment by multiple reaction monitoring under conditions described below using liquid chromatography-mass spectrometry, TABLE-US-00009 Trastuzumab or trastuzumab-DM1 quantitation peptide and its mass spectrometry information Reten- Q1 Colli- Q3 Parent Frag- tion Pre sion Pre ion ment time Bias Energy Bias Peptide Sequence m/z ion m/z [minutes] [V] [V] [V] IYPTNGYTR 542.8 808.4 3.405 -40 -18 -30 (SEQ ID NO. 1) IYPTNGYTR 542.8 711.3 3.405 -40 -26 -38 (SEQ ID NO. 1) IYPTNGYTR 542.8 610.3 3.405 -40 -24 -22 (SEQ ID NO. 1) IYPTNGYTR 542.8 404.7 3.405 -20 -18 -15 (SEQ ID NO. 1) IYPTNGYTR 542.8 277.2 3.405 -20 -16 -30 (SEQ ID NO. 1) FTISADTSK 485.2 822.4 3.635 -18 -18 -32 (SEQ ID NO. 3) FTISADTSK 485.2 721.4 3.635 -11 -18 -26 (SEQ ID NO. 3) FTISADTSK 485.2 608.3 3.635 -18 -19 -32 (SEQ ID NO. 3) FTISADTSK 485.2 521.3 3.635 -18 -19 -38 (SEQ ID NO. 3) FTISADTSK 485.2 335.2 3.635 -18 -24 -24 (SEQ ID NO. 3) GLEWVAR 415.7 660.3 4.077 -30 -15 -24 (SEQ ID NO. 6) GLEWVAR 415.7 531.3 4.077 -30 -16 -40 (SEQ ID NO. 6) GLEWVAR 415.7 345.2 4.077 -16 -17 -24 (SEQ ID NO. 6) GLEWVAR 415.7 246.2 4.077 -30 -18 -17 (SEQ ID NO. 6) NTAYLQMNSLR 655.8 1095.6 4.144 -24 -23 -42 (SEQ ID NO. 7) NTAYLQMNSLR 655.8 1024.5 4.144 -24 -22 -40 (SEQ ID NO. 7) NTAYLQMNSLR 655.8 861.5 4.144 -24 -22 -32 (SEQ ID NO. 7) NTAYLQMNSLR 655.8 748.4 4.144 -24 -23 -28 (SEQ ID NO. 7) NTAYLQMNSLR 655.8 620.3 4.144 -24 -23 -32 (SEQ ID NO. 7) NTAYLQMNSLR 655.8 489.3 4.144 -24 -23 -25 (SEQ ID NO. 7) NTAYLQMNSLR 655.8 375.2 4.144 -24 -22 -19 (SEQ ID NO. 7)

wherein the porous body has an average pore diameter in a range of 10 nm-200 nm, the nanoparticles have an average particle size in a range of 50 nm-500 nm, provided that the average particle size of the nanoparticles is larger than the average pore diameter of the porous body, the monoclonal antibody is trastuzumab or trastuzumab-DM1, and the peptide fragment includes the amino acid sequence of SEQ ID No: 1, 3, 6 and/or 7.

2. A method of detecting a monoclonal antibody, comprising: bringing into contact in a liquid a porous body having pores in which the monoclonal antibody is immobilized and nanoparticles on which a protease is immobilized such that a selective proteolysis of the monoclonal antibody occurs; and detecting a peptide fragment by multiple reaction monitoring under conditions described below using liquid chromatography-mass spectrometry, TABLE-US-00010 Bevacizumab quantitation peptide and its mass spectrometry information Parent Retention Q1 Pre Collision Q3 Pre ion Fragment time Bias Energy Bias Peptide Sequence m/z ion m/z [minutes] [V] [V] [V] STAYLQMNSLR 642.3 1024.5 4.147 -24 -25 -40 (SEQ ID NO. 9) STAYLQMNSLR 642.3 861.5 4.147 -24 -25 -20 (SEQ ID NO. 9) STAYLQMNSLR 642.3 748.4 4.147 -24 -22 -28 (SEQ ID NO. 9) STAYLQMNSLR 642.3 620.3 4.147 -24 -24 -32 (SEQ ID NO. 9) STAYLQMNSLR 642.3 489.3 4.147 -24 -22 -25 (SEQ ID NO. 9) STAYLQMNSLR 642.3 375.2 4.147 -24 -22 -27 (SEQ ID NO. 9) FTFSLDTSK 523.3 898.5 4.432 -38 -20 -34 (SEQ ID NO. 10) FTFSLDTSK 523.3 797.4 4.432 -38 -18 -30 (SEQ ID NO. 10) FTFSLDTSK 523.3 650.3 4.432 -38 -19 -34 (SEQ ID NO. 10) FTFSLDTSK 523.3 563.3 4.432 -38 -22 -40 (SEQ ID NO. 10) FTFSLDTSK 523.3 450.2 4.432 -20 -23 -30 (SEQ ID NO. 10) FTFSLDTSK 523.3 335.2 4.432 -20 -25 -24 (SEQ ID NO. 10) FTFSLDTSK 523.3 399.2 4.432 -38 -17 -11 (SEQ ID NO. 10) FTFSLDTSK 523.3 249.1 4.432 -38 -17 -17 (SEQ ID NO. 10) VLIYFTSSLHSGVPSR 588.3 832.4 4.515 -22 -19 -30 (SEQ ID NO. 11) VLIYFTSSLHSGVPSR 588.3 775.9 4.515 -22 -18 -28 (SEQ ID NO. 11) VLIYFTSSLHSGVPSR 588.3 719.4 4.515 -22 -18 -26 (SEQ ID NO. 11) VLIYFTSSLHSGVPSR 588.3 637.8 4.515 -22 -18 -24 (SEQ ID NO. 11) VLIYFTSSLHSGVPSR 588.3 564.3 4.515 -22 -22 -20 (SEQ ID NO. 11) VLIYFTSSLHSGVPSR 588.3 602.3 4.515 -22 -28 -22 (SEQ ID NO. 11) VLIYFTSSLHSGVPSR 588.3 359.2 4.515 -22 -26 -26 (SEQ ID NO. 11) VLIYFTSSLHSGVPSR 588.3 213.2 4.515 -22 -20 -23 (SEQ ID NO. 11)

wherein the porous body has an average pore diameter in a range of 10 nm-200 nm, the nanoparticles have an average particle size in a range of 50 nm-500 nm, provided that the average particle size of the nanoparticles is larger than the average pore diameter of the porous body, the monoclonal antibody is bevacizumab, and the peptide fragment includes the amino acid sequence of at least one of SEQ ID No: 9-11.

3. A method of detecting a monoclonal antibody, comprising: bringing into contact in a liquid a porous body having pores in which a monoclonal antibody is immobilized and nanoparticles on which a protease is immobilized such that a selective proteolysis of the monoclonal antibody occurs; and detecting a peptide fragment by multiple reaction monitoring under conditions described below using liquid chromatography-mass spectrometry, TABLE-US-00011 Rituximab quantitation peptide and its mass spectrometry information Retention Parent ion Fragment time Q1 Pre Collision Q3 Pre Peptide Sequence m/z ion m/z [minutes] Bias [V] Energy [V] Bias [V] ATLTADK 360.2 648.4 2.809 -26 -14 -24 (SEQ ID NO. 13) ATLTADK 360.2 547.3 2.81 -13 -13 -20 (SEQ ID NO. 13) ATLTADK 360.2 434.2 2.81 -26 -16 -22 (SEQ ID NO. 13) ATLTADK 360.2 333.2 2.81 -26 -19 -24 (SEQ ID NO. 13) ATLTADK 360.2 262.1 2.81 -13 -21 -29 (SEQ ID NO. 13) LASGVPVR 399.7 685.4 3.426 -29 -17 -34 (SEQ ID NO. 15) LASGVPVR 399.7 614.4 3.426 -30 -16 -32 (SEQ ID NO. 15) LASGVPVR 399.7 527.3 3.426 -15 -16 -38 (SEQ ID NO. 15) LASGVPVR 399.7 371.2 3.426 -15 -17 -28 (SEQ ID NO. 15) ATSNLASGVPVR 586.3 912.5 3.728 -22 -25 -34 (SEQ ID NO. 16) ATSNLASGVPVR 586.3 685.4 3.728 -22 -23 -38 (SEQ ID NO. 16) ATSNLASGVPVR 586.3 614.4 3.728 -22 -25 -24 (SEQ ID NO. 16) ATSNLASGVPVR 586.3 527.3 3.728 -22 -25 -40 (SEQ ID NO. 16) ATSNLASGVPVR 586.3 470.3 3.728 -22 -19 -17 (SEQ ID NO. 16) ATSNLASGVPVR 586.3 371.2 3.728 -22 -17 -27 (SEQ ID NO. 16)

wherein the porous body has an average pore diameter in a range of 10 nm-200 nm, the nanoparticles have an average particle size in a range of 50 nm-500 nm, provided that the average particle size of the nanoparticles is larger than the average pore diameter of the porous body, the monoclonal antibody is rituximab, and the peptide fragment includes the amino acid sequence of SEQ ID No: 13, 15 and/or 16.

4. The method according to claim 3, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 13.

5. The method according to claim 3, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 15.

6. The method according to claim 3, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 16.

7. The method according to claim 1, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 1.

8. The method according to claim 1, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 3.

9. The method according to claim 1, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 6.

10. The method according to claim 1, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 7.

11. The method according to claim 2, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 9.

12. The method according to claim 2, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 10.

13. The method according to claim 2, wherein the peptide fragment includes the amino acid sequence of SEQ ID No: 11.

Summary for Patent:   See Pricing

Foriegn Application Priority Data
Foreign Country Foreign Patent Number Foreign Patent Date
Japan2015-046059Mar 9, 2015
PCT Information
PCT FiledDecember 18, 2015PCT Application Number:PCT/JP2015/085445
PCT Publication Date:September 15, 2016PCT Publication Number:WO2016/143224

Details for Patent 10,338,039

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Genentech RITUXAN rituximab VIAL 103705 001 1997-11-26   See Pricing SHIMADZU CORPORATION (Kyoto-shi, JP) 2035-03-09 RX search
Genentech HERCEPTIN trastuzumab VIAL; INTRAVENOUS 103792 001 1998-09-25   See Pricing SHIMADZU CORPORATION (Kyoto-shi, JP) 2035-03-09 RX Orphan search
Genentech AVASTIN bevacizumab VIAL; INTRAVENOUS 125085 001 2004-02-26   See Pricing SHIMADZU CORPORATION (Kyoto-shi, JP) 2035-03-09 RX search
Genentech AVASTIN bevacizumab VIAL; INTRAVENOUS 125085 002 2004-02-26   See Pricing SHIMADZU CORPORATION (Kyoto-shi, JP) 2035-03-09 RX search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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