CA2762277C - Specific analysis of ketone and aldehyde analytes using reagent compounds, labeling strategies, and mass spectrometry workflow - Google Patents
Specific analysis of ketone and aldehyde analytes using reagent compounds, labeling strategies, and mass spectrometry workflow Download PDFInfo
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- CA2762277C CA2762277C CA2762277A CA2762277A CA2762277C CA 2762277 C CA2762277 C CA 2762277C CA 2762277 A CA2762277 A CA 2762277A CA 2762277 A CA2762277 A CA 2762277A CA 2762277 C CA2762277 C CA 2762277C
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- ion
- analyte
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- ions
- testosterone
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 168
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 105
- 150000002576 ketones Chemical class 0.000 title claims abstract description 82
- 238000002372 labelling Methods 0.000 title claims abstract description 68
- 238000004458 analytical method Methods 0.000 title claims description 55
- 150000001299 aldehydes Chemical class 0.000 title claims description 45
- 238000004949 mass spectrometry Methods 0.000 title abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 103
- 150000002500 ions Chemical class 0.000 claims description 310
- 239000012491 analyte Substances 0.000 claims description 138
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- 239000012634 fragment Substances 0.000 claims description 46
- 229960003604 testosterone Drugs 0.000 claims description 44
- 230000007704 transition Effects 0.000 claims description 41
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- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000006853 reporter group Chemical group 0.000 claims description 30
- 238000013467 fragmentation Methods 0.000 claims description 27
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- XQZVQQZZOVBNLU-QDTBLXIISA-N 4-hydroxyestrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O XQZVQQZZOVBNLU-QDTBLXIISA-N 0.000 claims description 3
- QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 claims description 3
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 3
- OXHNQTSIKGHVBH-ANULTFPQSA-N Tetrahydrogestrinone Chemical compound C1CC2=CC(=O)CCC2=C2[C@@H]1[C@@H]1CC[C@](CC)(O)[C@@]1(CC)C=C2 OXHNQTSIKGHVBH-ANULTFPQSA-N 0.000 claims description 3
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- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 3
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- 150000003515 testosterones Chemical class 0.000 claims 3
- JERGUCIJOXJXHF-UHFFFAOYSA-N 17alpha-Hydroxypregnenolone Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(=O)C)(O)C1(C)CC2 JERGUCIJOXJXHF-UHFFFAOYSA-N 0.000 claims 1
- JERGUCIJOXJXHF-TVWVXWENSA-N 17alpha-hydroxypregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 JERGUCIJOXJXHF-TVWVXWENSA-N 0.000 claims 1
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- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 44
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- 238000004885 tandem mass spectrometry Methods 0.000 description 24
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- G—PHYSICS
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/64—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving ketones
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/74—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving hormones or other non-cytokine intercellular protein regulatory factors such as growth factors, including receptors to hormones and growth factors
- G01N33/743—Steroid hormones
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- G—PHYSICS
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- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N2030/042—Standards
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- G—PHYSICS
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- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/884—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample organic compounds
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J49/00—Particle spectrometers or separator tubes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J49/00—Particle spectrometers or separator tubes
- H01J49/004—Combinations of spectrometers, tandem spectrometers, e.g. MS/MS, MSn
- H01J49/0045—Combinations of spectrometers, tandem spectrometers, e.g. MS/MS, MSn characterised by the fragmentation or other specific reaction
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J49/00—Particle spectrometers or separator tubes
- H01J49/02—Details
- H01J49/10—Ion sources; Ion guns
- H01J49/16—Ion sources; Ion guns using surface ionisation, e.g. field-, thermionic- or photo-emission
- H01J49/161—Ion sources; Ion guns using surface ionisation, e.g. field-, thermionic- or photo-emission using photoionisation, e.g. by laser
- H01J49/164—Laser desorption/ionisation, e.g. matrix-assisted laser desorption/ionisation [MALDI]
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
- Y10T436/147777—Plural nitrogen in the same ring [e.g., barbituates, creatinine, etc.]
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- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/20—Oxygen containing
- Y10T436/200833—Carbonyl, ether, aldehyde or ketone containing
Landscapes
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- Medicinal Chemistry (AREA)
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| US18274809P | 2009-05-31 | 2009-05-31 | |
| US61/182,748 | 2009-05-31 | ||
| PCT/US2010/001598 WO2010141075A1 (en) | 2009-05-31 | 2010-06-01 | Specific analysis of ketone and aldehyde analytes using reagent compounds labeling strategies, and mass spectrometry workflow |
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| CA2762277A1 CA2762277A1 (en) | 2010-12-09 |
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| WO (1) | WO2010141075A1 (enExample) |
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| EP1868616A2 (en) * | 2005-03-29 | 2007-12-26 | The University of Maryland, Baltimore | Inhibitors for extracellular signal-regulated kinase docking domains and uses therefor |
| GB0916881D0 (en) * | 2009-09-25 | 2009-11-11 | Electrophoretics Ltd | Mass labels |
| US8309359B2 (en) * | 2010-01-15 | 2012-11-13 | California Institute Of Technology | Isobaric tags for analyte detection and quantification |
| US8372653B2 (en) * | 2010-01-22 | 2013-02-12 | Dh Technologies Development Pte. Ltd. | Mass tag reagents for simultaneous quantitation and identification of small molecules |
| US8617898B2 (en) | 2010-01-25 | 2013-12-31 | Dh Technologies Development Pte. Ltd. | Quantitative analysis of vitamin D3, vitamin D2, and metabolites thereof |
| US9834578B2 (en) * | 2010-05-27 | 2017-12-05 | University Of Utah Research Foundation | Enhanced sensitivity for analysis of ketosteroid compounds using mass spectrometry |
| EP3702774B1 (en) * | 2011-02-07 | 2025-10-01 | Laboratory Corporation of America Holdings | Method for determining the presence or amount of testosterone in a sample |
| CN103782166B (zh) * | 2011-06-06 | 2018-01-16 | 沃特世科技公司 | 用于定量样品中目标分析物的组合物、方法和试剂盒 |
| CN104040343A (zh) * | 2012-01-05 | 2014-09-10 | Dh科技发展私人贸易有限公司 | 增强含有酮类固醇和酮基或醛的分析物的灵敏度和特异性 |
| CN104040332B (zh) | 2012-01-20 | 2017-10-20 | Dh科技发展私人贸易有限公司 | 使用标记化学和lc‑msms工作流分析具有酚系oh的雌二醇和分析物 |
| EP2850430B1 (en) * | 2012-05-18 | 2017-04-19 | Dh Technologies Development Pte. Ltd. | Analysis of a panel of cerebrotendinous xanthomatosis biomarkers using site specific derivation and lc/ms/ms workflow |
| GB201215924D0 (en) | 2012-09-06 | 2012-10-24 | Univ Swansea | Kit and method for quantitative detection of steroids |
| TW201619606A (zh) | 2014-06-27 | 2016-06-01 | 脈動健康有限責任公司 | 用於羰基之偵測及定量之方法及裝置 |
| WO2017087852A1 (en) * | 2015-11-19 | 2017-05-26 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Stress biomarkers and related non-invasive detection methods |
| GB201521903D0 (en) * | 2015-12-11 | 2016-01-27 | Electrophoretics Ltd | Isorbaric mass labels |
| CN107014846A (zh) * | 2016-01-27 | 2017-08-04 | 沈阳药科大学 | 一种检测植物油过热处理的方法及其用途 |
| CN107290459B (zh) * | 2016-03-31 | 2019-12-06 | 中国科学院大连化学物理研究所 | 一种磷酸糖类物质的富集和固相衍生预处理方法 |
| JP7153652B2 (ja) * | 2017-01-31 | 2022-10-14 | エフ．ホフマン－ラ ロシュ アーゲー | 質量分析用の試薬 |
| US20190041332A1 (en) | 2017-08-01 | 2019-02-07 | Pulse Health Llc | Methods and Systems for Aldehyde Detection |
| CN108931603A (zh) * | 2018-04-23 | 2018-12-04 | 国家烟草质量监督检验中心 | 一种基于稳定同位素标记质谱联用技术检测血浆中羧酸类代谢物的方法 |
| JP7547313B2 (ja) | 2018-07-24 | 2024-09-09 | エフ． ホフマン－ラ ロシュ アーゲー | 質量分析のための試薬 |
| CN112449636A (zh) | 2018-07-24 | 2021-03-05 | 豪夫迈·罗氏有限公司 | 用于质谱分析的试剂 |
| EP3826994A1 (en) * | 2018-07-24 | 2021-06-02 | F. Hoffmann-La Roche AG | Reagent for mass spectrometry |
| EP4623304A1 (en) * | 2022-11-21 | 2025-10-01 | F. Hoffmann-La Roche AG | Derivatisation agent for laser desorption ionization mass spectrometry |
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| WO1996040662A2 (en) * | 1995-06-07 | 1996-12-19 | Cellpro, Incorporated | Aminooxy-containing linker compounds and their application in conjugates |
| US7799576B2 (en) | 2003-01-30 | 2010-09-21 | Dh Technologies Development Pte. Ltd. | Isobaric labels for mass spectrometric analysis of peptides and method thereof |
| WO2004097372A2 (en) * | 2003-04-28 | 2004-11-11 | The Regents Of The University Of California | Element-coded affinity tags |
| US7369712B2 (en) | 2003-09-30 | 2008-05-06 | Fotonation Vision Limited | Automated statistical self-calibrating detection and removal of blemishes in digital images based on multiple occurrences of dust in images |
| US7309608B2 (en) * | 2003-09-30 | 2007-12-18 | Hoa Duc Nguyen | Method of analysis of aldehyde and ketone by mass spectrometry |
| US20050148771A1 (en) * | 2004-01-05 | 2005-07-07 | Applera Corporation. | Active esters of N-substituted piperazine acetic acids, including isotopically enriched versions thereof |
| JP4832312B2 (ja) * | 2004-01-05 | 2011-12-07 | ディーエイチ テクノロジーズ デベロップメント プライベート リミテッド | 標識試薬および標識化分析物の混合物を含む、標識試薬、標識化分析物、およびそれらに由来するフラグメントイオン、ならびにそれらの分析方法 |
| JP4566604B2 (ja) * | 2004-03-31 | 2010-10-20 | 塩野義製薬株式会社 | 糖鎖標識試薬 |
| US20060183238A1 (en) | 2005-02-09 | 2006-08-17 | Applera Corporation | Amine-containing compound analysis methods |
| GB0518585D0 (en) * | 2005-09-12 | 2005-10-19 | Electrophoretics Ltd | Mass labels |
| JP2009520949A (ja) * | 2005-11-16 | 2009-05-28 | アンブルックス，インコーポレイテッド | 非天然アミノ酸を含んでいる組成物および方法 |
| EP2054540B1 (en) * | 2006-05-26 | 2014-11-26 | DH Technologies Development Pte. Ltd. | Tagging reagents and methods for hydroxylated compounds |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2438448B1 (en) | 2020-05-20 |
| US20140004616A1 (en) | 2014-01-02 |
| CA2762277A1 (en) | 2010-12-09 |
| JP2012529010A (ja) | 2012-11-15 |
| EP2438448A1 (en) | 2012-04-11 |
| US20170115258A1 (en) | 2017-04-27 |
| US10094809B2 (en) | 2018-10-09 |
| JP5849045B2 (ja) | 2016-01-27 |
| EP2438448A4 (en) | 2015-05-06 |
| US9500622B2 (en) | 2016-11-22 |
| WO2010141075A8 (en) | 2011-10-27 |
| US20110003395A1 (en) | 2011-01-06 |
| WO2010141075A1 (en) | 2010-12-09 |
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