CA2873650A1 - Analysis of a panel of cerebrotendinous xanthomatosis biomarkers using site specific derivation and lc/ms/ms workflow - Google Patents
Analysis of a panel of cerebrotendinous xanthomatosis biomarkers using site specific derivation and lc/ms/ms workflow Download PDFInfo
- Publication number
- CA2873650A1 CA2873650A1 CA2873650A CA2873650A CA2873650A1 CA 2873650 A1 CA2873650 A1 CA 2873650A1 CA 2873650 A CA2873650 A CA 2873650A CA 2873650 A CA2873650 A CA 2873650A CA 2873650 A1 CA2873650 A1 CA 2873650A1
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- ketosterol
- cholesten
- bile acid
- ion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000004458 analytical method Methods 0.000 title claims abstract description 70
- 102100036325 Sterol 26-hydroxylase, mitochondrial Human genes 0.000 title claims abstract description 49
- 208000001088 cerebrotendinous xanthomatosis Diseases 0.000 title claims abstract description 41
- 239000000090 biomarker Substances 0.000 title abstract description 33
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 title description 19
- 238000009795 derivation Methods 0.000 title description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 145
- 239000002243 precursor Substances 0.000 claims abstract description 132
- 238000000034 method Methods 0.000 claims abstract description 131
- 239000003613 bile acid Substances 0.000 claims abstract description 127
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims abstract description 126
- 238000002372 labelling Methods 0.000 claims abstract description 73
- 210000002966 serum Anatomy 0.000 claims abstract description 32
- 238000012216 screening Methods 0.000 claims abstract description 23
- 210000004369 blood Anatomy 0.000 claims abstract description 21
- 239000008280 blood Substances 0.000 claims abstract description 21
- 150000002500 ions Chemical group 0.000 claims description 266
- 150000001875 compounds Chemical class 0.000 claims description 121
- 239000012491 analyte Substances 0.000 claims description 90
- 239000012634 fragment Substances 0.000 claims description 52
- 210000002381 plasma Anatomy 0.000 claims description 27
- 150000003839 salts Chemical group 0.000 claims description 22
- 230000007812 deficiency Effects 0.000 claims description 17
- NYOXRYYXRWJDKP-GYKMGIIDSA-N cholest-4-en-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 NYOXRYYXRWJDKP-GYKMGIIDSA-N 0.000 claims description 16
- NYOXRYYXRWJDKP-UHFFFAOYSA-N cholestenone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 NYOXRYYXRWJDKP-UHFFFAOYSA-N 0.000 claims description 16
- 230000007935 neutral effect Effects 0.000 claims description 14
- 239000011159 matrix material Substances 0.000 claims description 10
- 101000875401 Homo sapiens Sterol 26-hydroxylase, mitochondrial Proteins 0.000 claims description 9
- 238000003556 assay Methods 0.000 claims description 7
- PESKGJQREUXSRR-UHFFFAOYSA-N 10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 PESKGJQREUXSRR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- 150000001450 anions Chemical group 0.000 claims description 4
- 108090000854 Oxidoreductases Proteins 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- 238000004949 mass spectrometry Methods 0.000 abstract description 46
- 239000000523 sample Substances 0.000 description 133
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 50
- 230000007704 transition Effects 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 238000012544 monitoring process Methods 0.000 description 26
- 239000003795 chemical substances by application Substances 0.000 description 23
- 238000002552 multiple reaction monitoring Methods 0.000 description 23
- 238000001212 derivatisation Methods 0.000 description 22
- 238000001514 detection method Methods 0.000 description 22
- 238000013467 fragmentation Methods 0.000 description 21
- 238000006062 fragmentation reaction Methods 0.000 description 21
- PESKGJQREUXSRR-UXIWKSIVSA-N 5alpha-cholestan-3-one Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 PESKGJQREUXSRR-UXIWKSIVSA-N 0.000 description 16
- 238000004885 tandem mass spectrometry Methods 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 13
- 230000035945 sensitivity Effects 0.000 description 13
- 238000010494 dissociation reaction Methods 0.000 description 12
- 230000005593 dissociations Effects 0.000 description 12
- 238000000605 extraction Methods 0.000 description 12
- 238000004811 liquid chromatography Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000003745 diagnosis Methods 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 238000005040 ion trap Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001360 collision-induced dissociation Methods 0.000 description 9
- 230000000155 isotopic effect Effects 0.000 description 9
- 150000003431 steroids Chemical class 0.000 description 9
- UQPYXHJTHPHOMM-NIBOIBLTSA-N 7alpha,12alpha-dihydroxycholest-4-en-3-one Chemical compound C([C@H]1O)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C2 UQPYXHJTHPHOMM-NIBOIBLTSA-N 0.000 description 8
- 208000002551 irritable bowel syndrome Diseases 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000012472 biological sample Substances 0.000 description 6
- 238000013375 chromatographic separation Methods 0.000 description 6
- 238000000132 electrospray ionisation Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000011002 quantification Methods 0.000 description 6
- 238000004445 quantitative analysis Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 125000000468 ketone group Chemical group 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000003172 aldehyde group Chemical group 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 238000001211 electron capture detection Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 238000001972 liquid chromatography-electrospray ionisation mass spectrometry Methods 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 241000894007 species Species 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000002068 genetic effect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000622 liquid--liquid extraction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 230000006920 protein precipitation Effects 0.000 description 3
- 238000003127 radioimmunoassay Methods 0.000 description 3
- 210000003296 saliva Anatomy 0.000 description 3
- 238000000956 solid--liquid extraction Methods 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- 238000010200 validation analysis Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 206010069703 Bile acid malabsorption Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 102000004316 Oxidoreductases Human genes 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 208000035896 Twin-reversed arterial perfusion sequence Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- -1 aldehyde compounds Chemical class 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical group OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 238000007837 multiplex assay Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 238000004451 qualitative analysis Methods 0.000 description 2
- 125000006853 reporter group Chemical group 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- UQPYXHJTHPHOMM-XSDVZAHJSA-N (8r,9s,10r,13r,14s,17r)-7,12-dihydroxy-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound OC1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)C(O)C2 UQPYXHJTHPHOMM-XSDVZAHJSA-N 0.000 description 1
- JAOINXWEFKZYIL-UHFFFAOYSA-N 4-(1-methyl-2-oxoquinolin-4-yl)oxy-n-(4-methylpyridin-2-yl)butanamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=NC(NC(=O)CCCOC=2C3=CC=CC=C3N(C)C(=O)C=2)=C1 JAOINXWEFKZYIL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000005676 Adrenogenital syndrome Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 108010022102 Cholestanetriol 26-monooxygenase Proteins 0.000 description 1
- 208000008448 Congenital adrenal hyperplasia Diseases 0.000 description 1
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000036626 Mental retardation Diseases 0.000 description 1
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 1
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 201000007410 Smith-Lemli-Opitz syndrome Diseases 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 210000003567 ascitic fluid Anatomy 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 210000003756 cervix mucus Anatomy 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000002101 electrospray ionisation tandem mass spectrometry Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 210000000416 exudates and transudate Anatomy 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 230000005405 multipole Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 238000010206 sensitivity analysis Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012421 spiking Methods 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000001138 tear Anatomy 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
Classifications
-
- 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
- G01N33/92—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving lipids, e.g. cholesterol, lipoproteins, or their receptors
-
- 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
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
-
- 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
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
-
- 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
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6893—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids related to diseases not provided for elsewhere
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J49/00—Particle spectrometers or separator tubes
- H01J49/0027—Methods for using particle spectrometers
- H01J49/0031—Step by step routines describing the use of the apparatus
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/902—Oxidoreductases (1.)
- G01N2333/90245—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14)
- G01N2333/90248—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14) with NADH or NADPH as one of the donors, and incorporation of one atom of oxygen 1.14.13
- G01N2333/90251—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14) with NADH or NADPH as one of the donors, and incorporation of one atom of oxygen 1.14.13 with a definite EC number (1.14.13.-)
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2400/00—Assays, e.g. immunoassays or enzyme assays, involving carbohydrates
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2800/00—Detection or diagnosis of diseases
- G01N2800/04—Endocrine or metabolic disorders
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2800/00—Detection or diagnosis of diseases
- G01N2800/06—Gastro-intestinal diseases
- G01N2800/065—Bowel diseases, e.g. Crohn, ulcerative colitis, IBS
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2800/00—Detection or diagnosis of diseases
- G01N2800/38—Pediatrics
- G01N2800/385—Congenital anomalies
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Chemical & Material Sciences (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pathology (AREA)
- Food Science & Technology (AREA)
- Cell Biology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Bioinformatics & Computational Biology (AREA)
- Biophysics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Endocrinology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261649044P | 2012-05-18 | 2012-05-18 | |
| US61/649,044 | 2012-05-18 | ||
| PCT/IB2013/000961 WO2013171568A1 (en) | 2012-05-18 | 2013-05-17 | Analysis of a panel of cerebrotendinous xanthomatosis biomarkers using site specific derivation and lc/ms/ms workflow |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2873650A1 true CA2873650A1 (en) | 2013-11-21 |
Family
ID=49583216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2873650A Abandoned CA2873650A1 (en) | 2012-05-18 | 2013-05-17 | Analysis of a panel of cerebrotendinous xanthomatosis biomarkers using site specific derivation and lc/ms/ms workflow |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10078091B2 (enExample) |
| EP (1) | EP2850430B1 (enExample) |
| JP (1) | JP6272834B2 (enExample) |
| CN (1) | CN104603617B (enExample) |
| CA (1) | CA2873650A1 (enExample) |
| WO (1) | WO2013171568A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015503753A (ja) * | 2012-01-05 | 2015-02-02 | 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 | ケトステロイドとケトまたはアルデヒドを含む分析物との敏感度および特異度の強化 |
| CN105785048B (zh) * | 2016-04-15 | 2017-07-28 | 同济大学 | 基于轻同位素近同重标记的整体蛋白质定量分析方法 |
| CN105866429B (zh) * | 2016-05-06 | 2017-12-15 | 同济大学 | 基于自带电荷同位素试剂的生物分子标记和定量分析方法 |
| JP7547315B2 (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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3029907B2 (ja) * | 1991-12-20 | 2000-04-10 | 理化学研究所 | 抗肥満剤 |
| AU2004209401A1 (en) | 2003-01-30 | 2004-08-19 | Applied Biosystems, Llc. | Methods, mixtures, kits and compositions pertaining to analyte determination |
| US20050148771A1 (en) | 2004-01-05 | 2005-07-07 | Applera Corporation. | Active esters of N-substituted piperazine acetic acids, including isotopically enriched versions thereof |
| US20060183238A1 (en) | 2005-02-09 | 2006-08-17 | Applera Corporation | Amine-containing compound analysis methods |
| CN101454488A (zh) | 2006-05-26 | 2009-06-10 | 阿普里拉股份有限公司 | 用于羟基化化合物的标签试剂和方法 |
| GB0713463D0 (en) * | 2007-07-11 | 2007-08-22 | Btg Int Ltd | Modulators of hypoxia inducible factor-1 and related uses |
| WO2008137767A1 (en) | 2007-05-04 | 2008-11-13 | Oregon Health & Science University | Tandem mass spectrometry for detecting and/or screening for conditions associated with altered sterols |
| US20110003395A1 (en) * | 2009-05-31 | 2011-01-06 | Dh Technologies Development Pte. Ltd. | Specific analysis of analytes using reagent compounds, labeling strategies, and mass spectrometry workflow |
| US8372653B2 (en) * | 2010-01-22 | 2013-02-12 | Dh Technologies Development Pte. Ltd. | Mass tag reagents for simultaneous quantitation and identification of small molecules |
-
2013
- 2013-05-17 EP EP13791312.5A patent/EP2850430B1/en not_active Not-in-force
- 2013-05-17 JP JP2015512143A patent/JP6272834B2/ja not_active Expired - Fee Related
- 2013-05-17 WO PCT/IB2013/000961 patent/WO2013171568A1/en not_active Ceased
- 2013-05-17 CA CA2873650A patent/CA2873650A1/en not_active Abandoned
- 2013-05-17 US US14/401,427 patent/US10078091B2/en active Active
- 2013-05-17 CN CN201380026048.3A patent/CN104603617B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US10078091B2 (en) | 2018-09-18 |
| JP6272834B2 (ja) | 2018-01-31 |
| EP2850430A4 (en) | 2016-02-10 |
| CN104603617B (zh) | 2017-04-12 |
| CN104603617A (zh) | 2015-05-06 |
| WO2013171568A1 (en) | 2013-11-21 |
| JP2015516578A (ja) | 2015-06-11 |
| EP2850430A1 (en) | 2015-03-25 |
| US20150323554A1 (en) | 2015-11-12 |
| EP2850430B1 (en) | 2017-04-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US12196765B2 (en) | Mass spectrometry assay for congenital adrenal hyperplasia | |
| EP3511973A1 (en) | Quantitation of insulin by mass spectrometry | |
| US20140349885A1 (en) | Enhancement of sensitivity and specificity of ketosteroids and keto or aldehyde containing analytes | |
| US20110006197A1 (en) | Methods for detecting dihydrotestosterone by mass spectrometry | |
| Kamemura et al. | Sample-multiplexing by derivatization using multiple analogous reagents for enhancing throughput in LC/ESI-MS/MS assay of steroids: Plasma 17α-hydroxyprogesterone as an example | |
| EP2850430B1 (en) | Analysis of a panel of cerebrotendinous xanthomatosis biomarkers using site specific derivation and lc/ms/ms workflow | |
| US8283627B2 (en) | Methods for detecting dehydroepiandrosterone by mass spectrometry | |
| Barbosa et al. | Relative quantification of plasma N-glycans in type II congenital disorder of glycosylation patients by mass spectrometry | |
| HK40120889A (en) | Mass spectrometry assay for congenital adrenal hyperplasia |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180514 |
|
| FZDE | Discontinued |
Effective date: 20220802 |
|
| FZDE | Discontinued |
Effective date: 20220802 |