CA2720124C - Analysis of antibody drug conjugates by bead-based affinity capture and mass spectrometry - Google Patents

Analysis of antibody drug conjugates by bead-based affinity capture and mass spectrometry Download PDF

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Publication number
CA2720124C
CA2720124C CA2720124A CA2720124A CA2720124C CA 2720124 C CA2720124 C CA 2720124C CA 2720124 A CA2720124 A CA 2720124A CA 2720124 A CA2720124 A CA 2720124A CA 2720124 C CA2720124 C CA 2720124C
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antibody
sample
drug
adc
mmae
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French (fr)
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CA2720124A1 (en
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Surinder Kaur
Ola Saad
Keyang Xu
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Genentech Inc
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Genentech Inc
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    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/543Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
    • G01N33/54313Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being characterised by its particulate form
    • G01N33/54326Magnetic particles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/531Production of immunochemical test materials
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803General methods of protein analysis not limited to specific proteins or families of proteins
    • G01N33/6848Methods of protein analysis involving mass spectrometry
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6854Immunoglobulins
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/94Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving narcotics or drugs or pharmaceuticals, neurotransmitters or associated receptors

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Chemical & Material Sciences (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pathology (AREA)
  • Cell Biology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Food Science & Technology (AREA)
  • Analytical Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Bioinformatics & Computational Biology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biophysics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
CA2720124A 2008-05-13 2009-05-12 Analysis of antibody drug conjugates by bead-based affinity capture and mass spectrometry Active CA2720124C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US5272708P 2008-05-13 2008-05-13
US61/052,727 2008-05-13
PCT/US2009/043560 WO2009140242A1 (en) 2008-05-13 2009-05-12 Analysis of antibody drug conjugates by bead-based affinity capture and mass spectrometry

Publications (2)

Publication Number Publication Date
CA2720124A1 CA2720124A1 (en) 2009-11-19
CA2720124C true CA2720124C (en) 2015-07-21

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CA2720124A Active CA2720124C (en) 2008-05-13 2009-05-12 Analysis of antibody drug conjugates by bead-based affinity capture and mass spectrometry

Country Status (7)

Country Link
US (1) US8541178B2 (https=)
EP (1) EP2277044B1 (https=)
JP (1) JP5539971B2 (https=)
AU (1) AU2009246516B2 (https=)
CA (1) CA2720124C (https=)
ES (1) ES2544971T3 (https=)
WO (1) WO2009140242A1 (https=)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6136311A (en) 1996-05-06 2000-10-24 Cornell Research Foundation, Inc. Treatment and diagnosis of cancer
WO2007109321A2 (en) 2006-03-20 2007-09-27 The Regents Of The University Of California Engineered anti-prostate stem cell antigen (psca) antibodies for cancer targeting
US8940298B2 (en) 2007-09-04 2015-01-27 The Regents Of The University Of California High affinity anti-prostate stem cell antigen (PSCA) antibodies for cancer targeting and detection
EP2398504B1 (en) 2009-02-17 2018-11-28 Cornell Research Foundation, Inc. Methods and kits for diagnosis of cancer and prediction of therapeutic value
CA2782333C (en) 2009-12-02 2019-06-04 Imaginab, Inc. J591 minibodies and cys-diabodies for targeting human prostate specific membrane antigen (psma) and methods for their use
KR102023496B1 (ko) * 2011-04-21 2019-09-20 시애틀 지네틱스, 인크. 신규 결합제-약물 콘주게이트 (adc) 및 그의 용도
KR101992502B1 (ko) 2011-05-12 2019-06-24 제넨테크, 인크. 프레임워크 시그너처 펩티드를 사용하여 동물 샘플에서 치료 항체를 검출하기 위한 다중 반응 모니터링 lc-ms/ms 방법
CA2848520C (en) * 2011-09-29 2019-11-26 Seattle Genetics, Inc. Intact mass determination of protein conjugated agent compounds
RU2638812C2 (ru) * 2012-03-08 2017-12-15 Ф. Хоффманн-Ля Рош Аг Мультиплексный иммунохроматографический способ определения циркулирующих иммунокомплексов
CN104540518A (zh) 2012-04-27 2015-04-22 西托姆克斯治疗公司 结合表皮生长因子受体的可活化的抗体其使用方法
EP3795215A1 (en) 2012-05-30 2021-03-24 Chugai Seiyaku Kabushiki Kaisha Target tissue-specific antigen-binding molecule
TWI693073B (zh) 2012-12-21 2020-05-11 日商中外製藥股份有限公司 對gpc3標的治療劑療法為有效之患者投與的gpc3標的治療劑
EP4119947A1 (en) 2012-12-21 2023-01-18 Chugai Seiyaku Kabushiki Kaisha Gpc3-targeting drug which is administered to patient responsive to gpc3-targeting drug therapy
EP2777714A1 (en) * 2013-03-15 2014-09-17 NBE-Therapeutics LLC Method of producing an immunoligand/payload conjugate by means of a sequence-specific transpeptidase enzyme
EP3933384A1 (en) 2013-03-15 2022-01-05 Hycor Biomedical, LLC Device and associated method for performing luminescence and fluorescence measurements of a sample
GB2513405A (en) 2013-04-26 2014-10-29 Adc Biotechnology Ltd Method of synthesising ADCs using affinity resins
US9758588B2 (en) 2013-09-30 2017-09-12 Becton, Dickinson And Company Blocking reagent compositions and methods of making and using the same
WO2015066279A2 (en) 2013-10-30 2015-05-07 Cytomx Therapeutics, Inc. Activatable antibodies that bind epidermal growth factor receptor and methods of use thereof
TWI853985B (zh) 2013-12-04 2024-09-01 日商中外製藥股份有限公司 因應化合物濃度使抗原結合能力變化的抗原結合分子及其資料庫
US9737623B2 (en) 2013-12-11 2017-08-22 Cytomx Therapeutics, Inc. Antibodies that bind activatable antibodies and methods of use thereof
LT3424955T (lt) 2013-12-25 2025-06-25 Daiichi Sankyo Company, Limited Anti-trop2 antikūno ir vaisto konjugato gamybos būdas
SI3466976T1 (sl) * 2014-01-31 2021-12-31 Daiichi Sankyo Company, Limited Anti-her2 konjugat protitelesa-zdravila
CN104974252B (zh) * 2014-04-01 2020-04-24 三生国健药业(上海)股份有限公司 一种抑制肿瘤生长的抗体-小分子药物偶联物及其制备方法和用途
JP6612738B2 (ja) 2014-04-10 2019-11-27 第一三共株式会社 抗her2抗体−薬物コンジュゲート
CN113933504A (zh) 2014-05-08 2022-01-14 中外制药株式会社 对gpc3靶向治疗剂疗法有效的患者施用的gpc3靶向治疗剂
BR112017004810A2 (pt) * 2014-11-05 2017-12-12 Hoffmann La Roche imunoensaio
EP4180455A1 (en) 2015-06-29 2023-05-17 Daiichi Sankyo Company, Limited Method for selectively manufacturing antibody-drug conjugate
HRP20210547T1 (hr) 2015-07-10 2021-05-14 Byondis B.V. Sastavi koji sadrže konjugate lijeka antitijela-duocarmycin
WO2017027325A1 (en) 2015-08-07 2017-02-16 Imaginab, Inc. Antigen binding constructs to target molecules
CN106467575B (zh) * 2015-08-18 2020-07-31 四川百利药业有限责任公司 半胱氨酸改造的抗体-毒素偶联物
EP3423831B1 (en) 2016-03-02 2022-05-25 Waters Technologies Corporation Identification and quantification of conjugated peptides in antibody drug conjugates by mass spectrometry
US11340233B2 (en) * 2016-03-07 2022-05-24 Pierre Fabre Medicament Universal method to capture and analyze ADCs for characterization of drug distribution and the drug-to-antibody ratio in biological samples
CN116196412A (zh) 2016-03-15 2023-06-02 中外制药株式会社 使用pd-1轴结合拮抗剂和抗gpc3抗体治疗癌症的方法
US20170315132A1 (en) 2016-03-25 2017-11-02 Genentech, Inc. Multiplexed total antibody and antibody-conjugated drug quantification assay
EP3465221B1 (en) * 2016-05-27 2020-07-22 H. Hoffnabb-La Roche Ag Bioanalytical method for the characterization of site-specific antibody-drug conjugates
BR112019011794A2 (pt) 2016-12-12 2019-10-29 Daiichi Sankyo Co Ltd composição farmacêutica, e, método terapêutico.
CA3050668C (en) 2017-01-17 2023-08-15 Daiichi Sankyo Company, Limited Anti-gpr20 antibody and anti-gpr20 antibody-drug conjugate
WO2018147960A1 (en) 2017-02-08 2018-08-16 Imaginab, Inc. Extension sequences for diabodies
US11092597B2 (en) * 2017-02-28 2021-08-17 Waters Technoligies Corporation Devices and methods for analyzing intact proteins, antibodies, antibody subunits, and antibody drug conjugates
TW202532102A (zh) 2017-05-15 2025-08-16 日商第一三共股份有限公司 抗體-藥物結合物及其用途
JP2020526584A (ja) 2017-06-28 2020-08-31 ザ ロックフェラー ユニバーシティー 抗mertkアゴニスト抗体−薬物コンジュゲートおよびその使用
BR112020003466B1 (pt) 2017-08-31 2023-12-12 Daiichi Sankyo Company, Limited Métodos de produção de composto, e, composto
ES3057444T3 (en) 2017-08-31 2026-03-02 Daiichi Sankyo Co Ltd Improved method for producing antibody-drug conjugate
BR112020000978A2 (pt) * 2017-09-08 2020-07-14 Regeneron Pharmaceuticals, Inc. método para determinar uma razão de fármaco para anticorpo em uma amostra compreendendo um conjugado anticorpo-fármaco.
WO2019059411A1 (en) 2017-09-20 2019-03-28 Chugai Seiyaku Kabushiki Kaisha DOSAGE FOR POLYTHERAPY USING PD-1 AXIS BINDING ANTAGONISTS AND GPC3 TARGETING AGENT
HUE067382T2 (hu) 2018-05-18 2024-10-28 Daiichi Sankyo Co Ltd Anti-MUC1-exatecan antitest-hatóanyag konjugátum
JP7165210B2 (ja) 2018-05-24 2022-11-02 シグマ-アルドリッチ・カンパニー・リミテッド・ライアビリティ・カンパニー タンパク質の定量分析
TWI846717B (zh) 2018-07-27 2024-07-01 日商第一三共股份有限公司 辨識抗體-藥物結合物之藥物部位的蛋白質
TW202537643A (zh) 2018-07-31 2025-10-01 日商第一三共股份有限公司 抗體-藥物結合物之用途
WO2020157381A1 (en) * 2019-01-29 2020-08-06 Teknologian Tutkimuskeskus Vtt Oy Methods for screening polypeptides capable of binding specific target molecules and tools related thereto
MA55080A (fr) 2019-02-26 2022-01-05 Inspirna Inc Anticorps anti-mertk à affinité élevée et utilisations associées
CN113613676A (zh) 2019-03-19 2021-11-05 中外制药株式会社 包含对抗原的结合活性因mta而变化的抗原结合结构域的抗原结合分子及用于获得该抗原结合结构域的文库
WO2021016138A1 (en) 2019-07-19 2021-01-28 Adeptrix Corp. Multiplexed bead-based analytical assays
WO2021055306A1 (en) 2019-09-16 2021-03-25 Bristol-Myers Squibb Company Dual capture method for analysis of antibody-drug conjugates
WO2021080008A1 (ja) * 2019-10-24 2021-04-29 国立大学法人 鹿児島大学 1価ccap生成物の製造方法
CN111366655A (zh) * 2020-04-01 2020-07-03 上海中科新生命生物科技有限公司 一种基于免疫亲和的贝伐珠单抗生物分析的质谱检测方法
GB202007047D0 (en) * 2020-05-13 2020-06-24 Binding Site Group Ltd Mass spectrometry controls
EP4229393A4 (en) * 2020-10-13 2024-11-06 University of Maryland, Baltimore County Rapid and low-cost sampling for detection of airborne sars-cov-2 in dehumidifier condensate
CN120202411A (zh) 2022-11-18 2025-06-24 基因泰克公司 使用质量标签进行基于ia-lc-ms/ms的测定的信号放大和多重化

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6172197B1 (en) * 1991-07-10 2001-01-09 Medical Research Council Methods for producing members of specific binding pairs
US6020208A (en) * 1994-05-27 2000-02-01 Baylor College Of Medicine Systems for surface-enhanced affinity capture for desorption and detection of analytes
US20030027216A1 (en) * 2001-07-02 2003-02-06 Kiernan Urban A. Analysis of proteins from biological fluids using mass spectrometric immunoassay
US20020197694A1 (en) * 2001-06-20 2002-12-26 Weiping Shao Conjugates of reduced antibodies and biomolecules
US7179606B2 (en) 2001-11-23 2007-02-20 Syn X Pharma, Inc. IG heavy chain, IG kappa, IG lambda biopolymer markers predictive of Alzheimer's disease
AU2002336842A1 (en) 2001-11-23 2003-06-10 Syn.X Pharma, Inc. Hp and apolipoprotein biopolymer markers predictive of alzheimers disease
WO2005073732A2 (en) * 2004-01-23 2005-08-11 Amgen Inc. Lc/ms method of analyzing high molecular weight proteins
WO2005101017A1 (en) * 2004-04-07 2005-10-27 Genentech, Inc. Mass spectrometry of antibody conjugates
AR062435A1 (es) * 2006-08-18 2008-11-05 Xoma Technology Ltd Anticuerpo especifico prlr (receptor de prolactina) y sus usos
KR20140116546A (ko) * 2006-10-27 2014-10-02 제넨테크, 인크. 항체 및 면역접합체 및 이들의 용도

Also Published As

Publication number Publication date
EP2277044A1 (en) 2011-01-26
AU2009246516A1 (en) 2009-11-19
US20090286258A1 (en) 2009-11-19
US8541178B2 (en) 2013-09-24
CA2720124A1 (en) 2009-11-19
JP2011524001A (ja) 2011-08-25
EP2277044B1 (en) 2015-06-17
JP5539971B2 (ja) 2014-07-02
ES2544971T3 (es) 2015-09-07
WO2009140242A1 (en) 2009-11-19
AU2009246516B2 (en) 2015-03-05

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