Loading…
Antiplasmodial Drugs in the Gas Phase: A CID and DFT Study of Quinolon-4(1H)-Imine Derivatives
The gas-phase behavior of 12 quinolon-4( 1H )-imine derivatives with antiplasmodial activity was investigated using electrospray ionization tandem mass spectrometry together with collision induced dissociation and density functional theory (DFT) calculations. The most probable protonation site was p...
Saved in:
| Published in: | Journal of the American Society for Mass Spectrometry 2014-09, Vol.25 (9), p.1650-1661 |
|---|---|
| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c372t-10331ad511795aa58bed56870bf8ebc48928666750e10f3652213e9cd6ccd7533 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c372t-10331ad511795aa58bed56870bf8ebc48928666750e10f3652213e9cd6ccd7533 |
| container_end_page | 1661 |
| container_issue | 9 |
| container_start_page | 1650 |
| container_title | Journal of the American Society for Mass Spectrometry |
| container_volume | 25 |
| creator | Amorim Madeira, Paulo J. Sitoe, Ana Raquel Fernandes Gonçalves, Daniel Rodrigues, Tiago Guedes, Rita C. Lopes, Francisca Moreira, Rui Bronze, M. Rosário |
| description | The gas-phase behavior of 12 quinolon-4(
1H
)-imine derivatives with antiplasmodial activity was investigated using electrospray ionization tandem mass spectrometry together with collision induced dissociation and density functional theory (DFT) calculations. The most probable protonation site was predicted by calculating the proton affinity (PA) values for each possible protonation site and it was found to be the imine nitrogen for all compounds under study. Fragmentation pathways of the protonated molecules were proposed and the assignment of product ion structures was performed taking into account theoretical calculations. The nature of the quinoline substituent was found to influence the gas-phase behavior of the compounds under study. The data acquired allowed to bracket the proton affinity of the quinolin-4-imine scaffold, which can be a useful starting point to choose appropriate references for determining PA values of this scaffold.
Figure
ᅟ |
| doi_str_mv | 10.1007/s13361-014-0940-x |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1552367561</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1552367561</sourcerecordid><originalsourceid>FETCH-LOGICAL-c372t-10331ad511795aa58bed56870bf8ebc48928666750e10f3652213e9cd6ccd7533</originalsourceid><addsrcrecordid>eNp1kF1LHDEUhoNU_Ko_oDcl0Bu9iD1nMvmY3i27VRcEW2pvDdmZjEZmMttkRvTfG1kVKXiVA-d53xweQr4gnCCA-p6Qc4kMsGRQlcAetsgealUxxIJ_yjOUecNB7JL9lO4AUEGldshuIfLMNeyR61kY_bqzqR8abzu6iNNNoj7Q8dbRM5vor1ub3A86o_PlgtrQ0MXpFf0zTs0jHVr6e_Jh6IbAyiM8P2bL3gdHFy76ezv6e5c-k-3WdskdvrwH5O_pz6v5Obu4PFvOZxes5qoYGQLnaBuBqCphrdAr1wipFaxa7VZ1qatCSymVAIfQcimKArmr6kbWdaME5wfkaNO7jsO_yaXR9D7VrutscMOUDApR8JyXmNFv_6F3wxRDvs5gJUDLErXIFG6oOg4pRdeadfS9jY8GwTzLNxv5Jss3z_LNQ858fWmeVr1r3hKvtjNQbICUV-HGxXdff9j6BLI-i2c</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1950864185</pqid></control><display><type>article</type><title>Antiplasmodial Drugs in the Gas Phase: A CID and DFT Study of Quinolon-4(1H)-Imine Derivatives</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><creator>Amorim Madeira, Paulo J. ; Sitoe, Ana Raquel Fernandes ; Gonçalves, Daniel ; Rodrigues, Tiago ; Guedes, Rita C. ; Lopes, Francisca ; Moreira, Rui ; Bronze, M. Rosário</creator><creatorcontrib>Amorim Madeira, Paulo J. ; Sitoe, Ana Raquel Fernandes ; Gonçalves, Daniel ; Rodrigues, Tiago ; Guedes, Rita C. ; Lopes, Francisca ; Moreira, Rui ; Bronze, M. Rosário</creatorcontrib><description>The gas-phase behavior of 12 quinolon-4(
1H
)-imine derivatives with antiplasmodial activity was investigated using electrospray ionization tandem mass spectrometry together with collision induced dissociation and density functional theory (DFT) calculations. The most probable protonation site was predicted by calculating the proton affinity (PA) values for each possible protonation site and it was found to be the imine nitrogen for all compounds under study. Fragmentation pathways of the protonated molecules were proposed and the assignment of product ion structures was performed taking into account theoretical calculations. The nature of the quinoline substituent was found to influence the gas-phase behavior of the compounds under study. The data acquired allowed to bracket the proton affinity of the quinolin-4-imine scaffold, which can be a useful starting point to choose appropriate references for determining PA values of this scaffold.
Figure
ᅟ</description><identifier>ISSN: 1044-0305</identifier><identifier>EISSN: 1879-1123</identifier><identifier>DOI: 10.1007/s13361-014-0940-x</identifier><identifier>PMID: 25001380</identifier><language>eng</language><publisher>Boston: Springer US</publisher><subject>Affinity ; Analytical Chemistry ; Bioinformatics ; Biotechnology ; Chemistry ; Chemistry and Materials Science ; Collision dynamics ; Data acquisition ; Density functional theory ; Derivatives ; Ionization ; Ions ; Mass spectrometry ; Mathematical analysis ; Organic Chemistry ; Proteomics ; Protonation ; Quinoline ; Research Article</subject><ispartof>Journal of the American Society for Mass Spectrometry, 2014-09, Vol.25 (9), p.1650-1661</ispartof><rights>American Society for Mass Spectrometry 2014</rights><rights>Journal of The American Society for Mass Spectrometry is a copyright of Springer, 2014.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c372t-10331ad511795aa58bed56870bf8ebc48928666750e10f3652213e9cd6ccd7533</citedby><cites>FETCH-LOGICAL-c372t-10331ad511795aa58bed56870bf8ebc48928666750e10f3652213e9cd6ccd7533</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25001380$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Amorim Madeira, Paulo J.</creatorcontrib><creatorcontrib>Sitoe, Ana Raquel Fernandes</creatorcontrib><creatorcontrib>Gonçalves, Daniel</creatorcontrib><creatorcontrib>Rodrigues, Tiago</creatorcontrib><creatorcontrib>Guedes, Rita C.</creatorcontrib><creatorcontrib>Lopes, Francisca</creatorcontrib><creatorcontrib>Moreira, Rui</creatorcontrib><creatorcontrib>Bronze, M. Rosário</creatorcontrib><title>Antiplasmodial Drugs in the Gas Phase: A CID and DFT Study of Quinolon-4(1H)-Imine Derivatives</title><title>Journal of the American Society for Mass Spectrometry</title><addtitle>J. Am. Soc. Mass Spectrom</addtitle><addtitle>J Am Soc Mass Spectrom</addtitle><description>The gas-phase behavior of 12 quinolon-4(
1H
)-imine derivatives with antiplasmodial activity was investigated using electrospray ionization tandem mass spectrometry together with collision induced dissociation and density functional theory (DFT) calculations. The most probable protonation site was predicted by calculating the proton affinity (PA) values for each possible protonation site and it was found to be the imine nitrogen for all compounds under study. Fragmentation pathways of the protonated molecules were proposed and the assignment of product ion structures was performed taking into account theoretical calculations. The nature of the quinoline substituent was found to influence the gas-phase behavior of the compounds under study. The data acquired allowed to bracket the proton affinity of the quinolin-4-imine scaffold, which can be a useful starting point to choose appropriate references for determining PA values of this scaffold.
Figure
ᅟ</description><subject>Affinity</subject><subject>Analytical Chemistry</subject><subject>Bioinformatics</subject><subject>Biotechnology</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Collision dynamics</subject><subject>Data acquisition</subject><subject>Density functional theory</subject><subject>Derivatives</subject><subject>Ionization</subject><subject>Ions</subject><subject>Mass spectrometry</subject><subject>Mathematical analysis</subject><subject>Organic Chemistry</subject><subject>Proteomics</subject><subject>Protonation</subject><subject>Quinoline</subject><subject>Research Article</subject><issn>1044-0305</issn><issn>1879-1123</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp1kF1LHDEUhoNU_Ko_oDcl0Bu9iD1nMvmY3i27VRcEW2pvDdmZjEZmMttkRvTfG1kVKXiVA-d53xweQr4gnCCA-p6Qc4kMsGRQlcAetsgealUxxIJ_yjOUecNB7JL9lO4AUEGldshuIfLMNeyR61kY_bqzqR8abzu6iNNNoj7Q8dbRM5vor1ub3A86o_PlgtrQ0MXpFf0zTs0jHVr6e_Jh6IbAyiM8P2bL3gdHFy76ezv6e5c-k-3WdskdvrwH5O_pz6v5Obu4PFvOZxes5qoYGQLnaBuBqCphrdAr1wipFaxa7VZ1qatCSymVAIfQcimKArmr6kbWdaME5wfkaNO7jsO_yaXR9D7VrutscMOUDApR8JyXmNFv_6F3wxRDvs5gJUDLErXIFG6oOg4pRdeadfS9jY8GwTzLNxv5Jss3z_LNQ858fWmeVr1r3hKvtjNQbICUV-HGxXdff9j6BLI-i2c</recordid><startdate>20140901</startdate><enddate>20140901</enddate><creator>Amorim Madeira, Paulo J.</creator><creator>Sitoe, Ana Raquel Fernandes</creator><creator>Gonçalves, Daniel</creator><creator>Rodrigues, Tiago</creator><creator>Guedes, Rita C.</creator><creator>Lopes, Francisca</creator><creator>Moreira, Rui</creator><creator>Bronze, M. Rosário</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>MBDVC</scope><scope>P5Z</scope><scope>P62</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope></search><sort><creationdate>20140901</creationdate><title>Antiplasmodial Drugs in the Gas Phase: A CID and DFT Study of Quinolon-4(1H)-Imine Derivatives</title><author>Amorim Madeira, Paulo J. ; Sitoe, Ana Raquel Fernandes ; Gonçalves, Daniel ; Rodrigues, Tiago ; Guedes, Rita C. ; Lopes, Francisca ; Moreira, Rui ; Bronze, M. Rosário</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c372t-10331ad511795aa58bed56870bf8ebc48928666750e10f3652213e9cd6ccd7533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Affinity</topic><topic>Analytical Chemistry</topic><topic>Bioinformatics</topic><topic>Biotechnology</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Collision dynamics</topic><topic>Data acquisition</topic><topic>Density functional theory</topic><topic>Derivatives</topic><topic>Ionization</topic><topic>Ions</topic><topic>Mass spectrometry</topic><topic>Mathematical analysis</topic><topic>Organic Chemistry</topic><topic>Proteomics</topic><topic>Protonation</topic><topic>Quinoline</topic><topic>Research Article</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Amorim Madeira, Paulo J.</creatorcontrib><creatorcontrib>Sitoe, Ana Raquel Fernandes</creatorcontrib><creatorcontrib>Gonçalves, Daniel</creatorcontrib><creatorcontrib>Rodrigues, Tiago</creatorcontrib><creatorcontrib>Guedes, Rita C.</creatorcontrib><creatorcontrib>Lopes, Francisca</creatorcontrib><creatorcontrib>Moreira, Rui</creatorcontrib><creatorcontrib>Bronze, M. Rosário</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central</collection><collection>Advanced Technologies & Aerospace Collection</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>Research Library</collection><collection>Research Library (Corporate)</collection><collection>Advanced Technologies & Aerospace Database</collection><collection>ProQuest Advanced Technologies & Aerospace Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Society for Mass Spectrometry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Amorim Madeira, Paulo J.</au><au>Sitoe, Ana Raquel Fernandes</au><au>Gonçalves, Daniel</au><au>Rodrigues, Tiago</au><au>Guedes, Rita C.</au><au>Lopes, Francisca</au><au>Moreira, Rui</au><au>Bronze, M. Rosário</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antiplasmodial Drugs in the Gas Phase: A CID and DFT Study of Quinolon-4(1H)-Imine Derivatives</atitle><jtitle>Journal of the American Society for Mass Spectrometry</jtitle><stitle>J. Am. Soc. Mass Spectrom</stitle><addtitle>J Am Soc Mass Spectrom</addtitle><date>2014-09-01</date><risdate>2014</risdate><volume>25</volume><issue>9</issue><spage>1650</spage><epage>1661</epage><pages>1650-1661</pages><issn>1044-0305</issn><eissn>1879-1123</eissn><abstract>The gas-phase behavior of 12 quinolon-4(
1H
)-imine derivatives with antiplasmodial activity was investigated using electrospray ionization tandem mass spectrometry together with collision induced dissociation and density functional theory (DFT) calculations. The most probable protonation site was predicted by calculating the proton affinity (PA) values for each possible protonation site and it was found to be the imine nitrogen for all compounds under study. Fragmentation pathways of the protonated molecules were proposed and the assignment of product ion structures was performed taking into account theoretical calculations. The nature of the quinoline substituent was found to influence the gas-phase behavior of the compounds under study. The data acquired allowed to bracket the proton affinity of the quinolin-4-imine scaffold, which can be a useful starting point to choose appropriate references for determining PA values of this scaffold.
Figure
ᅟ</abstract><cop>Boston</cop><pub>Springer US</pub><pmid>25001380</pmid><doi>10.1007/s13361-014-0940-x</doi><tpages>12</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1044-0305 |
| ispartof | Journal of the American Society for Mass Spectrometry, 2014-09, Vol.25 (9), p.1650-1661 |
| issn | 1044-0305 1879-1123 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1552367561 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Affinity Analytical Chemistry Bioinformatics Biotechnology Chemistry Chemistry and Materials Science Collision dynamics Data acquisition Density functional theory Derivatives Ionization Ions Mass spectrometry Mathematical analysis Organic Chemistry Proteomics Protonation Quinoline Research Article |
| title | Antiplasmodial Drugs in the Gas Phase: A CID and DFT Study of Quinolon-4(1H)-Imine Derivatives |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-08T14%3A34%3A05IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Antiplasmodial%20Drugs%20in%20the%20Gas%20Phase:%20A%20CID%20and%20DFT%20Study%20of%20Quinolon-4(1H)-Imine%20Derivatives&rft.jtitle=Journal%20of%20the%20American%20Society%20for%20Mass%20Spectrometry&rft.au=Amorim%20Madeira,%20Paulo%20J.&rft.date=2014-09-01&rft.volume=25&rft.issue=9&rft.spage=1650&rft.epage=1661&rft.pages=1650-1661&rft.issn=1044-0305&rft.eissn=1879-1123&rft_id=info:doi/10.1007/s13361-014-0940-x&rft_dat=%3Cproquest_cross%3E1552367561%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c372t-10331ad511795aa58bed56870bf8ebc48928666750e10f3652213e9cd6ccd7533%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1950864185&rft_id=info:pmid/25001380&rfr_iscdi=true |