JP2009543069A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009543069A5 JP2009543069A5 JP2009518574A JP2009518574A JP2009543069A5 JP 2009543069 A5 JP2009543069 A5 JP 2009543069A5 JP 2009518574 A JP2009518574 A JP 2009518574A JP 2009518574 A JP2009518574 A JP 2009518574A JP 2009543069 A5 JP2009543069 A5 JP 2009543069A5
- Authority
- JP
- Japan
- Prior art keywords
- independently
- hydrogen
- formula
- analyte
- group
- 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.)
- Granted
Links
- 239000012491 analyte Substances 0.000 claims description 315
- 239000003153 chemical reaction reagent Substances 0.000 claims description 295
- 238000002372 labelling Methods 0.000 claims description 282
- 150000002500 ions Chemical class 0.000 claims description 238
- 239000000203 mixture Substances 0.000 claims description 229
- 150000001875 compounds Chemical class 0.000 claims description 208
- 229910052739 hydrogen Inorganic materials 0.000 claims description 131
- 239000001257 hydrogen Substances 0.000 claims description 131
- 238000000034 method Methods 0.000 claims description 113
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 100
- 150000003839 salts Chemical class 0.000 claims description 91
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 87
- 229910052805 deuterium Inorganic materials 0.000 claims description 87
- 150000002431 hydrogen Chemical class 0.000 claims description 84
- 125000005647 linker group Chemical group 0.000 claims description 83
- 239000012634 fragment Substances 0.000 claims description 82
- 102000004169 proteins and genes Human genes 0.000 claims description 76
- 108090000623 proteins and genes Proteins 0.000 claims description 76
- 125000004429 atom Chemical group 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 229910052757 nitrogen Inorganic materials 0.000 claims description 58
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 125000003342 alkenyl group Chemical group 0.000 claims description 45
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
- 125000000304 alkynyl group Chemical group 0.000 claims description 43
- 239000000460 chlorine Substances 0.000 claims description 39
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 38
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 38
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 38
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 38
- 229910052794 bromium Inorganic materials 0.000 claims description 38
- 229910052801 chlorine Inorganic materials 0.000 claims description 38
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 239000011737 fluorine Substances 0.000 claims description 38
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 37
- 125000002947 alkylene group Chemical group 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000004450 alkenylene group Chemical group 0.000 claims description 32
- 125000004419 alkynylene group Chemical group 0.000 claims description 32
- 125000000732 arylene group Chemical group 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 150000001413 amino acids Chemical class 0.000 claims description 17
- 150000002632 lipids Chemical class 0.000 claims description 10
- 150000003180 prostaglandins Chemical class 0.000 claims description 10
- 150000003431 steroids Chemical class 0.000 claims description 10
- 150000001720 carbohydrates Chemical class 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims description 6
- 229960004203 carnitine Drugs 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 235000013343 vitamin Nutrition 0.000 claims description 6
- 239000011782 vitamin Substances 0.000 claims description 6
- 229930003231 vitamin Natural products 0.000 claims description 6
- 229940088594 vitamin Drugs 0.000 claims description 6
- MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 4
- 102100025342 Voltage-dependent N-type calcium channel subunit alpha-1B Human genes 0.000 claims description 2
- 101710088658 Voltage-dependent N-type calcium channel subunit alpha-1B Proteins 0.000 claims description 2
- 238000004458 analytical method Methods 0.000 description 110
- 235000018102 proteins Nutrition 0.000 description 73
- 238000004949 mass spectrometry Methods 0.000 description 68
- 102000004196 processed proteins & peptides Human genes 0.000 description 41
- 238000000926 separation method Methods 0.000 description 39
- 238000013467 fragmentation Methods 0.000 description 32
- 238000006062 fragmentation reaction Methods 0.000 description 32
- 238000010494 dissociation reaction Methods 0.000 description 31
- 230000005593 dissociations Effects 0.000 description 31
- -1 carboxylic acid compounds Chemical class 0.000 description 30
- 0 CCC*(CON)*C(C)C(CC(C)=*)*CC Chemical compound CCC*(CON)*C(C)C(CC(C)=*)*CC 0.000 description 25
- 229910052799 carbon Inorganic materials 0.000 description 25
- 230000008569 process Effects 0.000 description 24
- 238000012545 processing Methods 0.000 description 23
- 238000001360 collision-induced dissociation Methods 0.000 description 21
- 239000002243 precursor Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000001228 spectrum Methods 0.000 description 20
- 238000009739 binding Methods 0.000 description 19
- 230000027455 binding Effects 0.000 description 19
- 229910052760 oxygen Inorganic materials 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 102000004190 Enzymes Human genes 0.000 description 15
- 108090000790 Enzymes Proteins 0.000 description 15
- 229940088598 enzyme Drugs 0.000 description 15
- 238000011002 quantification Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 235000001014 amino acid Nutrition 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 13
- 125000005842 heteroatom Chemical group 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 230000029087 digestion Effects 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
- 230000000269 nucleophilic effect Effects 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 102000035195 Peptidases Human genes 0.000 description 9
- 108091005804 Peptidases Proteins 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 230000000155 isotopic effect Effects 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- 108010026552 Proteome Proteins 0.000 description 8
- 108090000631 Trypsin Proteins 0.000 description 8
- 102000004142 Trypsin Human genes 0.000 description 8
- 235000014633 carbohydrates Nutrition 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000002843 carboxylic acid group Chemical group 0.000 description 7
- 239000013592 cell lysate Substances 0.000 description 7
- 230000002596 correlated effect Effects 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 235000018417 cysteine Nutrition 0.000 description 7
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 7
- 238000001962 electrophoresis Methods 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 239000012588 trypsin Substances 0.000 description 7
- 229960001322 trypsin Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 239000004365 Protease Substances 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- 239000004475 Arginine Substances 0.000 description 5
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 5
- CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 238000011088 calibration curve Methods 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000000670 limiting effect Effects 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 108020004707 nucleic acids Proteins 0.000 description 5
- 150000007523 nucleic acids Chemical class 0.000 description 5
- 102000039446 nucleic acids Human genes 0.000 description 5
- 239000012038 nucleophile Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 5
- 125000004193 piperazinyl group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- XYONNSVDNIRXKZ-UHFFFAOYSA-N S-methyl methanethiosulfonate Chemical compound CSS(C)(=O)=O XYONNSVDNIRXKZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000013375 chromatographic separation Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012039 electrophile Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000003386 piperidinyl group Chemical group 0.000 description 4
- 230000004481 post-translational protein modification Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000575 proteomic method Methods 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102000005367 Carboxypeptidases Human genes 0.000 description 3
- 108010006303 Carboxypeptidases Proteins 0.000 description 3
- 108090000317 Chymotrypsin Proteins 0.000 description 3
- 108010051815 Glutamyl endopeptidase Proteins 0.000 description 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 101710163270 Nuclease Proteins 0.000 description 3
- 108090000526 Papain Proteins 0.000 description 3
- 108090000284 Pepsin A Proteins 0.000 description 3
- 102000057297 Pepsin A Human genes 0.000 description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 3
- 108010059712 Pronase Proteins 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 210000001124 body fluid Anatomy 0.000 description 3
- 239000010839 body fluid Substances 0.000 description 3
- 210000004899 c-terminal region Anatomy 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 229960002376 chymotrypsin Drugs 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000003828 downregulation Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229940055729 papain Drugs 0.000 description 3
- 235000019834 papain Nutrition 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 229940111202 pepsin Drugs 0.000 description 3
- 235000019419 proteases Nutrition 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 235000004252 protein component Nutrition 0.000 description 3
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 3
- 125000006853 reporter group Chemical group 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 3
- 230000003827 upregulation Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102000000496 Carboxypeptidases A Human genes 0.000 description 2
- 108010080937 Carboxypeptidases A Proteins 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 108091060211 Expressed sequence tag Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 102000007079 Peptide Fragments Human genes 0.000 description 2
- 108010033276 Peptide Fragments Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- PZBFGYYEXUXCOF-UHFFFAOYSA-N TCEP Chemical compound OC(=O)CCP(CCC(O)=O)CCC(O)=O PZBFGYYEXUXCOF-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical group 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 239000000090 biomarker Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000001211 electron capture detection Methods 0.000 description 2
- 238000000132 electrospray ionisation Methods 0.000 description 2
- 230000006862 enzymatic digestion Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 238000011331 genomic analysis Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 230000003100 immobilizing effect Effects 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 150000002780 morpholines Chemical class 0.000 description 2
- 238000002552 multiple reaction monitoring Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 230000017854 proteolysis Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000004885 tandem mass spectrometry Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- OBOHMJWDFPBPKD-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 OBOHMJWDFPBPKD-UHFFFAOYSA-N 0.000 description 1
- VUTZFAOGDXUYEJ-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 VUTZFAOGDXUYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- DJQYYYCQOZMCRC-UHFFFAOYSA-N 2-aminopropane-1,3-dithiol Chemical group SCC(N)CS DJQYYYCQOZMCRC-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108090001008 Avidin Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 102100031680 Beta-catenin-interacting protein 1 Human genes 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- IOZHPLALLXMKDG-UHFFFAOYSA-N CN1CCN(CC(NCCN)=O)CC1 Chemical compound CN1CCN(CC(NCCN)=O)CC1 IOZHPLALLXMKDG-UHFFFAOYSA-N 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
- 108020004414 DNA Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 101000993469 Homo sapiens Beta-catenin-interacting protein 1 Proteins 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
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- 101800005149 Peptide B Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000010847 SEQUEST Methods 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 210000004381 amniotic fluid Anatomy 0.000 description 1
- 238000005571 anion exchange chromatography Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000006177 biological buffer Substances 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005277 cation exchange chromatography Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004976 cyclobutylene group Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004980 cyclopropylene group Chemical group 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 230000005264 electron capture Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000013095 identification testing Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000004880 lymph fluid Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000013777 protein digestion Effects 0.000 description 1
- 230000007026 protein scission Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000000539 two dimensional gel electrophoresis Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81751306P | 2006-06-30 | 2006-06-30 | |
| US60/817,513 | 2006-06-30 | ||
| US11/770,212 US7906341B2 (en) | 2006-06-30 | 2007-06-28 | Methods, mixtures, kits and compositions pertaining to analyte determination |
| US11/770,212 | 2007-06-28 | ||
| PCT/US2007/072503 WO2008005846A2 (en) | 2006-06-30 | 2007-06-29 | Methods, mixtures, kits and compositions pertaining to analyte determination |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010148351A Division JP2010249838A (ja) | 2006-06-30 | 2010-06-29 | 検体の決定に関する方法、混合物、キットおよび組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009543069A JP2009543069A (ja) | 2009-12-03 |
| JP2009543069A5 true JP2009543069A5 (https=) | 2010-08-19 |
| JP5548447B2 JP5548447B2 (ja) | 2014-07-16 |
Family
ID=38752488
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009518574A Expired - Fee Related JP5548447B2 (ja) | 2006-06-30 | 2007-06-29 | 検体の決定に関する方法、混合物、キットおよび組成物 |
| JP2010148351A Withdrawn JP2010249838A (ja) | 2006-06-30 | 2010-06-29 | 検体の決定に関する方法、混合物、キットおよび組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010148351A Withdrawn JP2010249838A (ja) | 2006-06-30 | 2010-06-29 | 検体の決定に関する方法、混合物、キットおよび組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7906341B2 (https=) |
| EP (1) | EP2041105A2 (https=) |
| JP (2) | JP5548447B2 (https=) |
| AU (1) | AU2007269232A1 (https=) |
| CA (1) | CA2656295A1 (https=) |
| WO (1) | WO2008005846A2 (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050148087A1 (en) * | 2004-01-05 | 2005-07-07 | Applera Corporation | Isobarically labeled analytes and fragment ions derived therefrom |
| US7972867B2 (en) * | 2005-04-06 | 2011-07-05 | Quest Diagnostics Investments Incorporated | Methods for detecting vitamin D metabolites by mass spectrometry |
| US7745226B2 (en) | 2005-04-06 | 2010-06-29 | Quest Diagnostics Investments Incorporated | Methods for detecting vitamin D metabolites |
| US7972868B2 (en) | 2007-11-28 | 2011-07-05 | Quest Diagnostics Investments Incorporated | Methods for detecting dihydroxyvitamin D metabolites by mass spectrometry |
| US20110301063A1 (en) * | 2009-02-24 | 2011-12-08 | Netzel Brian C | Multiplexing derivatized anayltes using mass spectroscopy |
| US8673267B2 (en) | 2009-03-02 | 2014-03-18 | Massachusetts Institute Of Technology | Methods and products for in vivo enzyme profiling |
| US7977117B2 (en) * | 2009-12-03 | 2011-07-12 | Quest Diagnostics Investments Incorprated | Vitamin D metabolite determination utilizing mass spectrometry following derivatization |
| US8034627B2 (en) * | 2009-12-03 | 2011-10-11 | Quest Diagnostics Investments Incorporated | Methods for detecting dihydroxyvitamin D metabolites by mass spectrometry |
| CA2783708C (en) * | 2009-12-11 | 2018-09-18 | Quest Diagnostics Investments Incorporated | Mass spectrometry of steroidal compounds in multiplex samples |
| US20110240840A1 (en) | 2009-12-11 | 2011-10-06 | Quest Diagnostics Investments Incorporated | Mass spectrometric determination of cookson-derivatized, non-metabolized vitamin d |
| EP2512639A4 (en) * | 2009-12-15 | 2013-05-08 | Dh Technologies Dev Pte Ltd | ANALYSIS OF AMINO ACIDS AND AMINOUS COMPOUNDS WITH FLAG REAGENTS AND LC-MS WORKFLOW |
| US8658355B2 (en) * | 2010-05-17 | 2014-02-25 | The Uab Research Foundation | General mass spectrometry assay using continuously eluting co-fractionating reporters of mass spectrometry detection efficiency |
| JP6245990B2 (ja) * | 2011-03-15 | 2017-12-13 | マサチューセッツ インスティテュート オブ テクノロジー | 同位体によりコード化されたレポーターによる多重検出 |
| US9388132B2 (en) | 2011-09-15 | 2016-07-12 | Wisconsin Alumni Research Foundation | Isobaric tandem mass tags for quantitative proteomics and peptidomics |
| GB2501821B (en) * | 2012-04-05 | 2016-09-14 | Univ British Columbia | MS/MS analysis using ECD or ETD fragmentation |
| CN102944604B (zh) * | 2012-07-18 | 2015-02-18 | 中国科学院上海有机化学研究所 | 哌嗪基嘧啶类同位素标记试剂的用途 |
| EP2909618B1 (en) * | 2012-10-22 | 2021-02-17 | President and Fellows of Harvard College | Accurate and interference-free multiplexed quantitative proteomics using mass spectrometry |
| US9366678B2 (en) | 2012-10-25 | 2016-06-14 | Wisconsin Alumni Research Foundation | Neutron encoded mass tags for analyte quantification |
| JP6847660B2 (ja) | 2013-06-07 | 2021-03-24 | マサチューセッツ インスティテュート オブ テクノロジー | リガンドをコードする合成バイオマーカーのアフィニティベースの検出 |
| GB201521903D0 (en) * | 2015-12-11 | 2016-01-27 | Electrophoretics Ltd | Isorbaric mass labels |
| EP3440013A4 (en) | 2016-04-08 | 2021-03-17 | Massachusetts Institute of Technology | METHOD FOR SPECIFIC PROFILING OF PROTEASE ACTIVITY ON LYMPH NODES |
| WO2017193070A1 (en) | 2016-05-05 | 2017-11-09 | Massachusetts Institute Of Technology | Methods and uses for remotely triggered protease activity measurements |
| US11085927B2 (en) | 2016-06-03 | 2021-08-10 | President And Fellows Of Harvard College | Techniques for high throughput targeted proteomic analysis and related systems and methods |
| CN110114667B (zh) | 2016-12-23 | 2023-07-25 | 豪夫迈·罗氏有限公司 | 用于在分析系统中的过程期间标识试剂的方法 |
| WO2018115237A1 (en) | 2016-12-23 | 2018-06-28 | Roche Diagnostics Gmbh | Method for identifying a reagent during a process in an analysis system |
| CA3059358A1 (en) | 2017-04-07 | 2018-10-11 | Massachusetts Institute Of Technology | Methods to spatially profile protease activity in tissue and sections |
| WO2019173332A1 (en) | 2018-03-05 | 2019-09-12 | Massachusetts Institute Of Technology | Inhalable nanosensors with volatile reporters and uses thereof |
| US12173349B2 (en) | 2018-09-25 | 2024-12-24 | Massachusetts Institute Of Technology | Lung protease nanosensors and uses thereof |
| US11835522B2 (en) | 2019-01-17 | 2023-12-05 | Massachusetts Institute Of Technology | Sensors for detecting and imaging of cancer metastasis |
| CN118076886A (zh) * | 2021-08-06 | 2024-05-24 | 株式会社岛津制作所 | 肽分析方法及肽分析装置 |
| CN114019062B (zh) * | 2022-01-05 | 2022-03-25 | 河北欣港药业有限公司 | 一种利福平中有关物质的检测方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5800992A (en) * | 1989-06-07 | 1998-09-01 | Fodor; Stephen P.A. | Method of detecting nucleic acids |
| US5252296A (en) * | 1990-05-15 | 1993-10-12 | Chiron Corporation | Method and apparatus for biopolymer synthesis |
| US6027890A (en) * | 1996-01-23 | 2000-02-22 | Rapigene, Inc. | Methods and compositions for enhancing sensitivity in the analysis of biological-based assays |
| ES2213823T3 (es) * | 1996-04-08 | 2004-09-01 | Glaxo Group Limited | Codificacion y analisis cualitativo de bibliotecas combinatorias basadas en masa. |
| JP3884087B2 (ja) | 1997-01-15 | 2007-02-21 | イクスツィリオン ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | 質量標識結合ハイブリダイゼーションプローブ |
| GB9823646D0 (en) * | 1997-12-19 | 1998-12-23 | Brax Genomics Ltd | Compounds for mass spectrometry |
| US6270976B1 (en) * | 1998-09-15 | 2001-08-07 | Brax Group Limited | Characterizing nucleic acid by mass spectrometry |
| US7183116B2 (en) * | 2001-05-14 | 2007-02-27 | The Institute For Systems Biology | Methods for isolation and labeling of sample molecules |
| WO2003040288A2 (de) * | 2001-11-09 | 2003-05-15 | Bayer Healthcare Ag | Isotopencodierte affinitätsmarker 3 |
| US7473535B2 (en) | 2002-08-20 | 2009-01-06 | The Institute For Systems Biology | Chemical reagents and methods for detection and quantification of proteins in complex mixtures |
| US20040219685A1 (en) | 2003-01-30 | 2004-11-04 | Applera Corporation | Methods and mixtures pertaining to analyte determination using electrophilic labeling reagents |
| GB0306756D0 (en) | 2003-03-24 | 2003-04-30 | Xzillion Gmbh & Co Kg | Mass labels |
| US7307169B2 (en) | 2004-01-05 | 2007-12-11 | Applera Corporation | Isotopically enriched N-substituted piperazines and methods for the preparation thereof |
| US20070048752A1 (en) | 2004-07-12 | 2007-03-01 | Applera Corporation | Mass tags for quantitative analyses |
| WO2006017208A1 (en) | 2004-07-12 | 2006-02-16 | Applera Corporation | Mass tags for quantitative analyses |
| US8975404B2 (en) | 2006-01-24 | 2015-03-10 | Dh Technologies Development Pte. Ltd. | Labeling reagents for analyte determination and methods and compounds used in making the same |
-
2007
- 2007-06-28 US US11/770,212 patent/US7906341B2/en active Active
- 2007-06-29 CA CA002656295A patent/CA2656295A1/en not_active Abandoned
- 2007-06-29 EP EP07812488A patent/EP2041105A2/en not_active Withdrawn
- 2007-06-29 JP JP2009518574A patent/JP5548447B2/ja not_active Expired - Fee Related
- 2007-06-29 WO PCT/US2007/072503 patent/WO2008005846A2/en not_active Ceased
- 2007-06-29 AU AU2007269232A patent/AU2007269232A1/en not_active Abandoned
-
2010
- 2010-06-29 JP JP2010148351A patent/JP2010249838A/ja not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5548447B2 (ja) | 検体の決定に関する方法、混合物、キットおよび組成物 | |
| JP2009543069A5 (https=) | ||
| JP5503358B2 (ja) | 分析物分析に関する方法、混合物、キット、および組成物 | |
| CA2637959C (en) | Methods, mixtures, kits and compositions pertaining to analyte determination | |
| JP2007525639A5 (https=) | ||
| JP2009543067A (ja) | コードされていない検出可能な標識を含む質量タグ付き試薬を用いる分析物決定 | |
| JP4613320B2 (ja) | 結合特性に基づく分析物の特徴の決定 | |
| US8492163B2 (en) | Methods, mixtures, kits and compositions pertaining to analyte determination | |
| EP1798557A2 (en) | Determination of analyte characteristics based upon binding properties |