N-Phenacylthiazolium Salts as Inhibitors of Cholinesterases

Inhibition of acetylcholinesterase is considered as a promising approach for treatment of neurodegenerative disorders including Alzheimer's disease. In this study, we demonstrated that 5-substituted N-phenacylthiazolium derivatives are capable of inhibiting acetylcholinesterase and butyrylcholi...

Full description

Saved in:
Bibliographic Details
Published inFrench-Ukrainian journal of chemistry Vol. 5; no. 2; pp. 1 - 14
Main Authors Ocheretniuk, Alla, Kobzar, Oleksandr, Mischenko, Iryna, Vovk, Andriy
Format Journal Article
LanguageEnglish
Published 2017
Online AccessGet full text

Cover

Abstract Inhibition of acetylcholinesterase is considered as a promising approach for treatment of neurodegenerative disorders including Alzheimer's disease. In this study, we demonstrated that 5-substituted N-phenacylthiazolium derivatives are capable of inhibiting acetylcholinesterase and butyrylcholinesterase activities with IC50 values in the micromolar range. Some of the new thiazolium-based inhibitiors showed more than 10-fold selectivity for butyrylcholinesterase. Kinetic experiments and molecular docking were performed for understanding the inhibition mechanisms.
AbstractList Inhibition of acetylcholinesterase is considered as a promising approach for treatment of neurodegenerative disorders including Alzheimer's disease. In this study, we demonstrated that 5-substituted N-phenacylthiazolium derivatives are capable of inhibiting acetylcholinesterase and butyrylcholinesterase activities with IC50 values in the micromolar range. Some of the new thiazolium-based inhibitiors showed more than 10-fold selectivity for butyrylcholinesterase. Kinetic experiments and molecular docking were performed for understanding the inhibition mechanisms.
Author Mischenko, Iryna
Vovk, Andriy
Ocheretniuk, Alla
Kobzar, Oleksandr
Author_xml – sequence: 1
  givenname: Alla
  surname: Ocheretniuk
  fullname: Ocheretniuk, Alla
  organization: Institute of Bioorganic Chemistry and Petrochemistry of National Academy of Sciences of Ukraine
– sequence: 2
  givenname: Oleksandr
  surname: Kobzar
  fullname: Kobzar, Oleksandr
  organization: Institute of Bioorganic Chemistry and Petrochemistry of National Academy of Sciences of Ukraine
– sequence: 3
  givenname: Iryna
  surname: Mischenko
  fullname: Mischenko, Iryna
  organization: Institute of Bioorganic Chemistry and Petrochemistry of National Academy of Sciences of Ukraine
– sequence: 4
  givenname: Andriy
  surname: Vovk
  fullname: Vovk, Andriy
  organization: Institute of Bioorganic Chemistry and Petrochemistry of National Academy of Sciences of Ukraine
BookMark eNpNj81Kw0AURgepYK3dus4LTJ17Z5JJcCVBbaBowZ9tmFzvkJQ0kZl0UZ9eUUFX54MDH5xzMRvGgYW4BLUCaxGu_GFHr2mFW5BgTsQcNaDUiDj7t8_EMsadUgrBKIt6Lq4f5LblwdGxn9rOfYx9d9gnT66fYuJiUg1t13TTGGIy-qRsv_TAceLgIscLcepdH3n5y4V4ubt9Ltdy83hflTcbSZAVkzSMylFOWWqzNGdVOIN5UdCb0UVDGhq2lGIGxmDDbH3GhJhqa9ATAlq9EKufXwpjjIF9_R66vQvHGlT9XV__1ddg9CeVl099
CitedBy_id crossref_primary_10_15407_visn2018_08_048
Cites_doi 10.1021/bi00773a018
10.1021/jm00211a035
10.1021/ja01467a041
10.1016/s0165-3806(02)00367-x
10.1248/yakushi1947.71.2_69
10.1016/j.bmc.2016.02.033
10.2174/1567205054367838
10.1016/j.phrs.2003.11.017
10.1185/03007990152673800
10.1111/cbdd.12362
10.1124/jpet.110.174847
10.1136/jnnp.66.2.137
10.1042/bj20130013
10.1176/ajp.157.1.4
10.3109/14756366.2014.987138
10.1126/science.7058341
10.1007/bf01081907
10.1016/0223-5234(93)90128-2
10.1016/j.bmcl.2016.01.001
10.1021/jm300871x
10.1016/j.pharmthera.2014.11.011
10.1046/j.1365-3032.2003.00314.x
10.1016/s0003-2697(02)00506-7
10.1345/aph.10192
10.1016/j.mcn.2012.09.001
10.1248/bpb.18.1145
10.1136/bmj.2.6150.1457
10.1016/0022-510x(77)90073-9
10.1055/s-0034-1375613
10.3998/ark.5550190.0009.d29
10.1016/j.bmc.2007.07.003
10.1006/bbrc.1996.0366
10.1111/j.1365-2990.1978.tb00545.x
10.1016/j.ejmech.2014.05.020
10.1038/382275a0
10.1021/ja020850+
10.1246/bcsj.19.185
10.1177/0891988704267463
10.1074/jbc.m210241200
10.1097/00002826-200203000-00009
10.1016/0163-7258(95)00019-d
10.3109/14756366.2012.709242
10.1002/ana.410420613
10.1016/0006-2952(73)90196-2
10.1007/s10571-008-9297-7
10.1016/0006-2952(61)90145-9
10.1021/ja01313a026
10.1021/bi00096a018
10.1126/science.1678899
10.1111/j.1749-6632.1991.tb00217.x
ContentType Journal Article
DBID AAYXX
CITATION
DOI 10.17721/fujcV5I2P1-14
DatabaseName CrossRef
DatabaseTitle CrossRef
DatabaseTitleList CrossRef
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 2312-3222
EndPage 14
ExternalDocumentID 10_17721_fujcV5I2P1_14
GroupedDBID AAFWJ
AAYXX
ADBBV
AFPKN
ALMA_UNASSIGNED_HOLDINGS
BCNDV
CITATION
GROUPED_DOAJ
M~E
OK1
ID FETCH-LOGICAL-c169t-4e20ac8c657658e09a42899cd439bc31be7c5261442bee7f6ec2253742fc21273
ISSN 2312-3222
IngestDate Fri Aug 23 00:53:21 EDT 2024
IsPeerReviewed true
IsScholarly true
Issue 2
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c169t-4e20ac8c657658e09a42899cd439bc31be7c5261442bee7f6ec2253742fc21273
PageCount 14
ParticipantIDs crossref_primary_10_17721_fujcV5I2P1_14
PublicationCentury 2000
PublicationDate 2017-00-00
PublicationDateYYYYMMDD 2017-01-01
PublicationDate_xml – year: 2017
  text: 2017-00-00
PublicationDecade 2010
PublicationTitle French-Ukrainian journal of chemistry
PublicationYear 2017
References ref13
ref12
ref15
ref14
ref11
ref10
ref17
ref16
ref19
ref18
ref50
ref46
ref45
ref48
ref47
ref42
ref41
ref44
ref43
ref49
ref8
ref7
ref9
ref4
ref3
ref6
ref5
ref40
ref35
ref34
ref37
ref36
ref31
ref30
ref33
ref32
ref0
ref2
ref1
ref39
ref38
ref24
ref23
ref26
ref25
ref20
ref22
ref21
ref28
ref27
ref29
References_xml – ident: ref39
  doi: 10.1021/bi00773a018
– ident: ref34
  doi: 10.1021/jm00211a035
– ident: ref38
  doi: 10.1021/ja01467a041
– ident: ref13
  doi: 10.1016/s0165-3806(02)00367-x
– ident: ref37
  doi: 10.1248/yakushi1947.71.2_69
– ident: ref23
  doi: 10.1016/j.bmc.2016.02.033
– ident: ref6
  doi: 10.2174/1567205054367838
– ident: ref0
  doi: 10.1016/j.phrs.2003.11.017
– ident: ref1
  doi: 10.1185/03007990152673800
– ident: ref26
  doi: 10.1111/cbdd.12362
– ident: ref21
  doi: 10.1124/jpet.110.174847
– ident: ref4
  doi: 10.1136/jnnp.66.2.137
– ident: ref50
  doi: 10.1042/bj20130013
– ident: ref7
  doi: 10.1176/ajp.157.1.4
– ident: ref19
  doi: 10.3109/14756366.2014.987138
– ident: ref5
  doi: 10.1126/science.7058341
– ident: ref28
  doi: 10.1007/bf01081907
– ident: ref27
  doi: 10.1016/0223-5234(93)90128-2
– ident: ref20
  doi: 10.1016/j.bmcl.2016.01.001
– ident: ref49
  doi: 10.1021/jm300871x
– ident: ref14
  doi: 10.1016/j.pharmthera.2014.11.011
– ident: ref44
  doi: 10.1046/j.1365-3032.2003.00314.x
– ident: ref47
  doi: 10.1016/s0003-2697(02)00506-7
– ident: ref9
  doi: 10.1345/aph.10192
– ident: ref33
  doi: 10.1016/j.mcn.2012.09.001
– ident: ref40
  doi: 10.1248/bpb.18.1145
– ident: ref16
  doi: 10.1136/bmj.2.6150.1457
– ident: ref3
  doi: 10.1016/0022-510x(77)90073-9
– ident: ref22
  doi: 10.1055/s-0034-1375613
– ident: ref24
  doi: 10.3998/ark.5550190.0009.d29
– ident: ref41
  doi: 10.1016/j.bmc.2007.07.003
– ident: ref29
  doi: 10.1006/bbrc.1996.0366
– ident: ref17
  doi: 10.1111/j.1365-2990.1978.tb00545.x
– ident: ref25
  doi: 10.1016/j.ejmech.2014.05.020
– ident: ref30
  doi: 10.1038/382275a0
– ident: ref45
  doi: 10.1021/ja020850+
– ident: ref36
  doi: 10.1246/bcsj.19.185
– ident: ref10
  doi: 10.1177/0891988704267463
– ident: ref43
  doi: 10.1074/jbc.m210241200
– ident: ref8
  doi: 10.1097/00002826-200203000-00009
– ident: ref12
  doi: 10.1016/0163-7258(95)00019-d
– ident: ref18
  doi: 10.3109/14756366.2012.709242
– ident: ref15
  doi: 10.1002/ana.410420613
– ident: ref48
  doi: 10.1016/0006-2952(73)90196-2
– ident: ref32
  doi: 10.1007/s10571-008-9297-7
– ident: ref46
  doi: 10.1016/0006-2952(61)90145-9
– ident: ref35
  doi: 10.1021/ja01313a026
– ident: ref11
  doi: 10.1021/bi00096a018
– ident: ref42
  doi: 10.1126/science.1678899
– ident: ref2
  doi: 10.1111/j.1749-6632.1991.tb00217.x
– ident: ref31
SSID ssj0002140723
Score 2.0295753
Snippet Inhibition of acetylcholinesterase is considered as a promising approach for treatment of neurodegenerative disorders including Alzheimer's disease. In this...
SourceID crossref
SourceType Aggregation Database
StartPage 1
Title N-Phenacylthiazolium Salts as Inhibitors of Cholinesterases
Volume 5
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3Na9swFBejO2yX0XUb29oVHwY7DLWxLPmDnkZpaTraFdaU3oIkS8SzK5fGKSR_ffUkx3G7HLqBEUbIwvLv8b78PhD6msZCakk11mkmMY2ZwnxAOSaaw5XrKIZs5LPz-GRET6_Z9cqZ47JLGrEnF2vzSv4HVTtncYUs2X9AttvUTth7i68dLcJ2fBbG5_hiogyX86qZFHxRV8Xs5vtvXjVTaB8zNJNCFK6bjou5gPY8ri6CFVzTvlJ6DBl_EzwqXbuI1jPfaqly2RCu88YCyqoxxaz0CTJVx9h_1mLh47V_VaqccpN3kb9nhbWilSmdY3Z4NzfdQ1f1fbmMrCzmfSeEz7b0XMrqhwTD7xovUNbMtWyW9aiJ9Fhm2JO9Pp_0L65uLQBg63r2R16xIbkIsV_4uHz2E7HWBRuCmQM7jFfPj6H1-UuSZIz2rHAQ3iSEinGRa0nYHqIt9Qlb7D96hZ4q09NJLjfRm9aYCH54yniLXiizhV4dLiF7hw7WUUjgKCTg02BFIUGtgycU8h6Njo8uD09w2y4DyzDOGkwVGXCZytiakCxVg4xTsKZlbnVOIaNQqEQyAg4AIpRKdKykZeZRQomWUOc_-oA2TG3URxRYOaATqMWoaEIFpZlMEyJVxnTOMpbkn9C35cnHt74qynj9Z_787JXb6DVQlndv7aCN5m6mvliFrxG7DqIHfr9aBg
link.rule.ids 315,786,790,870,4043,27954,27955,27956
linkProvider Directory of Open Access Journals
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=N-Phenacylthiazolium+Salts+as+Inhibitors+of+Cholinesterases&rft.jtitle=French-Ukrainian+journal+of+chemistry&rft.au=Ocheretniuk%2C+Alla&rft.au=Kobzar%2C+Oleksandr&rft.au=Mischenko%2C+Iryna&rft.au=Vovk%2C+Andriy&rft.date=2017&rft.issn=2312-3222&rft.eissn=2312-3222&rft.volume=5&rft.issue=2&rft.spage=1&rft.epage=14&rft_id=info:doi/10.17721%2FfujcV5I2P1-14&rft.externalDBID=n%2Fa&rft.externalDocID=10_17721_fujcV5I2P1_14
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2312-3222&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2312-3222&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2312-3222&client=summon