Structural analysis of 2-arylidene-1-indanone derivatives by electrospray ionization tandem mass spectrometry
RATIONALE 2‐arylidene‐4‐methoxy (or hydroxy)‐7‐methyl‐1‐indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's disease as inhibitor of acetylcholinesterase (AChE), were studied for the first time by electrospray ionization mass spectrometry (ESI‐MS)...
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Published in | Rapid communications in mass spectrometry Vol. 27; no. 21; pp. 2461 - 2471 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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England
Blackwell Publishing Ltd
15.11.2013
Wiley Subscription Services, Inc |
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Abstract | RATIONALE
2‐arylidene‐4‐methoxy (or hydroxy)‐7‐methyl‐1‐indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's disease as inhibitor of acetylcholinesterase (AChE), were studied for the first time by electrospray ionization mass spectrometry (ESI‐MS) and tandem mass spectrometry (MS/MS). Structurally, these arylidene‐indanone compounds are considered as cyclic analogues of chalcones.
METHODS
ESI‐MS and tandem mass spectra were acquired using a Q‐TOF 2 instrument. Fragmentation patterns were analyzed by CID‐MS2–3 spectra acquired in a Q‐TOF and in LXQ linear ion trap mass spectrometers using standard isolation and excitation procedures.
RESULTS
All the 2‐arylidene indanones have shown a common fragmentation pathway leading to a (21, 1')A+ product ion at m/z 187 and the retro‐aldol product ion [(2, 21)B+] that allow to establish the substitution in the B ring. The effect of electron‐donating and ‐withdrawing substituents on these fragmentation pathways was noticed. The presence of the OCH3, OH, NO2 and Br substituents gave typical fragmentation processes that allowed their unequivocal fingerprinting. The combined loss of the ortho substituent in the B‐ring plus hydrogen (H, OCH3, Br and F) is proposed to form a stable cyclic ring product.
CONCLUSIONS
Arylidene indanones with different substituents on the B ring are associated with a specific fragmentation pattern. In addition, differentiation between isomers with substituents in B ring at ortho and para positions were achieved using ESI‐MS/MS. These fragmentation pathways can be used to further identify and determine the fate of these molecules in all stages of drug discovery. Copyright © 2013 John Wiley & Sons, Ltd. |
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AbstractList | RATIONALE 2-arylidene-4-methoxy (or hydroxy)-7-methyl-1-indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's disease as inhibitor of acetylcholinesterase (AChE), were studied for the first time by electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). Structurally, these arylidene-indanone compounds are considered as cyclic analogues of chalcones. METHODS ESI-MS and tandem mass spectra were acquired using a Q-TOF 2 instrument. Fragmentation patterns were analyzed by CID-MS super(2-3) spectra acquired in a Q-TOF and in LXQ linear ion trap mass spectrometers using standard isolation and excitation procedures. RESULTS All the 2-arylidene indanones have shown a common fragmentation pathway leading to a (2 super(1), 1')A super(+) product ion at m/z 187 and the retro-aldol product ion [(2, 2 super(1))B super(+)] that allow to establish the substitution in the B ring. The effect of electron-donating and -withdrawing substituents on these fragmentation pathways was noticed. The presence of the OCH sub(3), OH, NO sub(2) and Br substituents gave typical fragmentation processes that allowed their unequivocal fingerprinting. The combined loss of the ortho substituent in the B-ring plus hydrogen (H, OCH sub(3), Br and F) is proposed to form a stable cyclic ring product. CONCLUSIONS Arylidene indanones with different substituents on the B ring are associated with a specific fragmentation pattern. In addition, differentiation between isomers with substituents in B ring at ortho and para positions were achieved using ESI-MS/MS. These fragmentation pathways can be used to further identify and determine the fate of these molecules in all stages of drug discovery. Copyright [copy 2013 John Wiley & Sons, Ltd. RATIONALE 2‐arylidene‐4‐methoxy (or hydroxy)‐7‐methyl‐1‐indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's disease as inhibitor of acetylcholinesterase (AChE), were studied for the first time by electrospray ionization mass spectrometry (ESI‐MS) and tandem mass spectrometry (MS/MS). Structurally, these arylidene‐indanone compounds are considered as cyclic analogues of chalcones. METHODS ESI‐MS and tandem mass spectra were acquired using a Q‐TOF 2 instrument. Fragmentation patterns were analyzed by CID‐MS2–3 spectra acquired in a Q‐TOF and in LXQ linear ion trap mass spectrometers using standard isolation and excitation procedures. RESULTS All the 2‐arylidene indanones have shown a common fragmentation pathway leading to a (21, 1')A+ product ion at m/z 187 and the retro‐aldol product ion [(2, 21)B+] that allow to establish the substitution in the B ring. The effect of electron‐donating and ‐withdrawing substituents on these fragmentation pathways was noticed. The presence of the OCH3, OH, NO2 and Br substituents gave typical fragmentation processes that allowed their unequivocal fingerprinting. The combined loss of the ortho substituent in the B‐ring plus hydrogen (H, OCH3, Br and F) is proposed to form a stable cyclic ring product. CONCLUSIONS Arylidene indanones with different substituents on the B ring are associated with a specific fragmentation pattern. In addition, differentiation between isomers with substituents in B ring at ortho and para positions were achieved using ESI‐MS/MS. These fragmentation pathways can be used to further identify and determine the fate of these molecules in all stages of drug discovery. Copyright © 2013 John Wiley & Sons, Ltd. RATIONALE 2‐arylidene‐4‐methoxy (or hydroxy)‐7‐methyl‐1‐indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's disease as inhibitor of acetylcholinesterase (AChE), were studied for the first time by electrospray ionization mass spectrometry (ESI‐MS) and tandem mass spectrometry (MS/MS). Structurally, these arylidene‐indanone compounds are considered as cyclic analogues of chalcones. METHODS ESI‐MS and tandem mass spectra were acquired using a Q‐TOF 2 instrument. Fragmentation patterns were analyzed by CID‐MS 2–3 spectra acquired in a Q‐TOF and in LXQ linear ion trap mass spectrometers using standard isolation and excitation procedures. RESULTS All the 2‐arylidene indanones have shown a common fragmentation pathway leading to a (2 1 , 1')A + product ion at m/z 187 and the retro‐aldol product ion [(2, 2 1 )B + ] that allow to establish the substitution in the B ring. The effect of electron‐donating and ‐withdrawing substituents on these fragmentation pathways was noticed. The presence of the OCH 3 , OH, NO 2 and Br substituents gave typical fragmentation processes that allowed their unequivocal fingerprinting. The combined loss of the ortho substituent in the B‐ring plus hydrogen (H, OCH 3 , Br and F) is proposed to form a stable cyclic ring product. CONCLUSIONS Arylidene indanones with different substituents on the B ring are associated with a specific fragmentation pattern. In addition, differentiation between isomers with substituents in B ring at ortho and para positions were achieved using ESI‐MS/MS. These fragmentation pathways can be used to further identify and determine the fate of these molecules in all stages of drug discovery. Copyright © 2013 John Wiley & Sons, Ltd. RATIONALE2-arylidene-4-methoxy (or hydroxy)-7-methyl-1-indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's disease as inhibitor of acetylcholinesterase (AChE), were studied for the first time by electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). Structurally, these arylidene-indanone compounds are considered as cyclic analogues of chalcones.METHODSESI-MS and tandem mass spectra were acquired using a Q-TOF 2 instrument. Fragmentation patterns were analyzed by CID-MS(2-3) spectra acquired in a Q-TOF and in LXQ linear ion trap mass spectrometers using standard isolation and excitation procedures.RESULTSAll the 2-arylidene indanones have shown a common fragmentation pathway leading to a (2(1), 1')A(+) product ion at m/z 187 and the retro-aldol product ion [(2, 2(1))B(+)] that allow to establish the substitution in the B ring. The effect of electron-donating and -withdrawing substituents on these fragmentation pathways was noticed. The presence of the OCH3, OH, NO2 and Br substituents gave typical fragmentation processes that allowed their unequivocal fingerprinting. The combined loss of the ortho substituent in the B-ring plus hydrogen (H, OCH3, Br and F) is proposed to form a stable cyclic ring product.CONCLUSIONSArylidene indanones with different substituents on the B ring are associated with a specific fragmentation pattern. In addition, differentiation between isomers with substituents in B ring at ortho and para positions were achieved using ESI-MS/MS. These fragmentation pathways can be used to further identify and determine the fate of these molecules in all stages of drug discovery. RATIONALE 2-arylidene-4-methoxy (or hydroxy)-7-methyl-1-indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's disease as inhibitor of acetylcholinesterase (AChE), were studied for the first time by electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). Structurally, these arylidene-indanone compounds are considered as cyclic analogues of chalcones. METHODS ESI-MS and tandem mass spectra were acquired using a Q-TOF 2 instrument. Fragmentation patterns were analyzed by CID-MS2-3 spectra acquired in a Q-TOF and in LXQ linear ion trap mass spectrometers using standard isolation and excitation procedures. RESULTS All the 2-arylidene indanones have shown a common fragmentation pathway leading to a (21, 1')A+ product ion at m/z 187 and the retro-aldol product ion [(2, 21)B+] that allow to establish the substitution in the B ring. The effect of electron-donating and -withdrawing substituents on these fragmentation pathways was noticed. The presence of the OCH3, OH, NO2 and Br substituents gave typical fragmentation processes that allowed their unequivocal fingerprinting. The combined loss of the ortho substituent in the B-ring plus hydrogen (H, OCH3, Br and F) is proposed to form a stable cyclic ring product. CONCLUSIONS Arylidene indanones with different substituents on the B ring are associated with a specific fragmentation pattern. In addition, differentiation between isomers with substituents in B ring at ortho and para positions were achieved using ESI-MS/MS. These fragmentation pathways can be used to further identify and determine the fate of these molecules in all stages of drug discovery. Copyright © 2013 John Wiley & Sons, Ltd. [PUBLICATION ABSTRACT] 2-arylidene-4-methoxy (or hydroxy)-7-methyl-1-indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's disease as inhibitor of acetylcholinesterase (AChE), were studied for the first time by electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). Structurally, these arylidene-indanone compounds are considered as cyclic analogues of chalcones. ESI-MS and tandem mass spectra were acquired using a Q-TOF 2 instrument. Fragmentation patterns were analyzed by CID-MS(2-3) spectra acquired in a Q-TOF and in LXQ linear ion trap mass spectrometers using standard isolation and excitation procedures. All the 2-arylidene indanones have shown a common fragmentation pathway leading to a (2(1), 1')A(+) product ion at m/z 187 and the retro-aldol product ion [(2, 2(1))B(+)] that allow to establish the substitution in the B ring. The effect of electron-donating and -withdrawing substituents on these fragmentation pathways was noticed. The presence of the OCH3, OH, NO2 and Br substituents gave typical fragmentation processes that allowed their unequivocal fingerprinting. The combined loss of the ortho substituent in the B-ring plus hydrogen (H, OCH3, Br and F) is proposed to form a stable cyclic ring product. Arylidene indanones with different substituents on the B ring are associated with a specific fragmentation pattern. In addition, differentiation between isomers with substituents in B ring at ortho and para positions were achieved using ESI-MS/MS. These fragmentation pathways can be used to further identify and determine the fate of these molecules in all stages of drug discovery. |
Author | Menezes, José C. J. M. D. S. Domingues, M. Rosário M. Cavaleiro, José A. S. |
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Notes | European Union, QREN, FEDER and COMPETE - No. PEst-C/QUI/UI0062/2013 ark:/67375/WNG-0B67NQ4W-6 Dedicated to Dr. Shashikumar K. Paknikar on the occasion of his 78th birthday. Supporting info item istex:61B639E5BAC804D9B735B69E3AF3239021FBB6ED Network and Portuguese Mass Spectrometry Network (RNEM) - No. REDE/1504/REM/2005 ArticleID:RCM6701 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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2‐arylidene‐4‐methoxy (or hydroxy)‐7‐methyl‐1‐indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's... 2-arylidene-4-methoxy (or hydroxy)-7-methyl-1-indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's disease as... RATIONALE 2-arylidene-4-methoxy (or hydroxy)-7-methyl-1-indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's... RATIONALE2-arylidene-4-methoxy (or hydroxy)-7-methyl-1-indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer's... |
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SubjectTerms | Cholinesterase Inhibitors - chemistry Derivatives Drugs Fragmentation Indans - chemistry Inhibitors Ionization Mass spectrometry Medical services Pathways Piperidines - chemistry Spectrometry, Mass, Electrospray Ionization - methods |
Title | Structural analysis of 2-arylidene-1-indanone derivatives by electrospray ionization tandem mass spectrometry |
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