Potential New H1N1 Neuraminidase Inhibitors from Ferulic Acid and Vanillin: Molecular Modelling, Synthesis and in Vitro Assay
We report the computational and experimental efforts in the design and synthesis of novel neuraminidase (NA) inhibitors from ferulic acid and vanillin. Two proposed ferulic acid analogues, MY7 and MY8 were predicted to inhibit H1N1 NA using molecular docking. From these two analogues, we designed, s...
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| Veröffentlicht in: | Scientific reports 2016-12, Vol.6 (1), p.38692, Article 38692 |
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| creator | Hariono, Maywan Abdullah, Nurshariza Damodaran, K.V. Kamarulzaman, Ezatul E. Mohamed, Nornisah Hassan, Sharifah Syed Shamsuddin, Shaharum Wahab, Habibah A. |
| description | We report the computational and experimental efforts in the design and synthesis of novel neuraminidase (NA) inhibitors from ferulic acid and vanillin. Two proposed ferulic acid analogues,
MY7
and
MY8
were predicted to inhibit H1N1 NA using molecular docking. From these two analogues, we designed, synthesised and evaluated the biological activities of a series of ferulic acid and vanillin derivatives. The enzymatic H1N1 NA inhibition assay showed
MY21
(a vanillin derivative) has the lowest IC
50
of 50 μM. In contrast, the virus inhibition assay showed
MY15
, a ferulic acid derivative has the best activity with the EC
50
of ~0.95 μM. Modelling studies further suggest that these predicted activities might be due to the interactions with conserved and essential residues of NA with ΔG
bind
values comparable to those of oseltamivir and zanamivir, the two commercial NA inhibitors. |
| doi_str_mv | 10.1038/srep38692 |
| format | Article |
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MY7
and
MY8
were predicted to inhibit H1N1 NA using molecular docking. From these two analogues, we designed, synthesised and evaluated the biological activities of a series of ferulic acid and vanillin derivatives. The enzymatic H1N1 NA inhibition assay showed
MY21
(a vanillin derivative) has the lowest IC
50
of 50 μM. In contrast, the virus inhibition assay showed
MY15
, a ferulic acid derivative has the best activity with the EC
50
of ~0.95 μM. Modelling studies further suggest that these predicted activities might be due to the interactions with conserved and essential residues of NA with ΔG
bind
values comparable to those of oseltamivir and zanamivir, the two commercial NA inhibitors.</description><identifier>ISSN: 2045-2322</identifier><identifier>EISSN: 2045-2322</identifier><identifier>DOI: 10.1038/srep38692</identifier><identifier>PMID: 27995961</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>101/58 ; 119/118 ; 140/131 ; 631/154/309/2420 ; 631/92/2783 ; Acids ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Benzaldehydes - chemical synthesis ; Benzaldehydes - chemistry ; Benzaldehydes - pharmacology ; Binding Sites ; Biological Assay ; Computer applications ; Coumaric Acids - chemical synthesis ; Coumaric Acids - chemistry ; Coumaric Acids - pharmacology ; Crystallography, X-Ray ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Exo-a-sialidase ; Ferulic acid ; Humanities and Social Sciences ; Influenza A Virus, H1N1 Subtype - drug effects ; Influenza A Virus, H1N1 Subtype - enzymology ; Inhibitors ; Inhibitory Concentration 50 ; Models, Molecular ; Molecular Docking Simulation ; Molecular modelling ; multidisciplinary ; Neuraminidase - antagonists & inhibitors ; Neuraminidase - chemistry ; Neuraminidase - metabolism ; Oseltamivir ; Science ; Vanillin ; Zanamivir</subject><ispartof>Scientific reports, 2016-12, Vol.6 (1), p.38692, Article 38692</ispartof><rights>The Author(s) 2016</rights><rights>Copyright Nature Publishing Group Dec 2016</rights><rights>Copyright © 2016, The Author(s) 2016 The Author(s)</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-f9aa877770a3c81fec8b6038a0011a0360cfd582f7469d7aac04031040b9c3583</citedby><cites>FETCH-LOGICAL-c438t-f9aa877770a3c81fec8b6038a0011a0360cfd582f7469d7aac04031040b9c3583</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5171792/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5171792/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,725,778,782,862,883,27907,27908,41103,42172,51559,53774,53776</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27995961$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hariono, Maywan</creatorcontrib><creatorcontrib>Abdullah, Nurshariza</creatorcontrib><creatorcontrib>Damodaran, K.V.</creatorcontrib><creatorcontrib>Kamarulzaman, Ezatul E.</creatorcontrib><creatorcontrib>Mohamed, Nornisah</creatorcontrib><creatorcontrib>Hassan, Sharifah Syed</creatorcontrib><creatorcontrib>Shamsuddin, Shaharum</creatorcontrib><creatorcontrib>Wahab, Habibah A.</creatorcontrib><title>Potential New H1N1 Neuraminidase Inhibitors from Ferulic Acid and Vanillin: Molecular Modelling, Synthesis and in Vitro Assay</title><title>Scientific reports</title><addtitle>Sci Rep</addtitle><addtitle>Sci Rep</addtitle><description>We report the computational and experimental efforts in the design and synthesis of novel neuraminidase (NA) inhibitors from ferulic acid and vanillin. Two proposed ferulic acid analogues,
MY7
and
MY8
were predicted to inhibit H1N1 NA using molecular docking. From these two analogues, we designed, synthesised and evaluated the biological activities of a series of ferulic acid and vanillin derivatives. The enzymatic H1N1 NA inhibition assay showed
MY21
(a vanillin derivative) has the lowest IC
50
of 50 μM. In contrast, the virus inhibition assay showed
MY15
, a ferulic acid derivative has the best activity with the EC
50
of ~0.95 μM. Modelling studies further suggest that these predicted activities might be due to the interactions with conserved and essential residues of NA with ΔG
bind
values comparable to those of oseltamivir and zanamivir, the two commercial NA inhibitors.</description><subject>101/58</subject><subject>119/118</subject><subject>140/131</subject><subject>631/154/309/2420</subject><subject>631/92/2783</subject><subject>Acids</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Benzaldehydes - chemical synthesis</subject><subject>Benzaldehydes - chemistry</subject><subject>Benzaldehydes - pharmacology</subject><subject>Binding Sites</subject><subject>Biological Assay</subject><subject>Computer applications</subject><subject>Coumaric Acids - chemical synthesis</subject><subject>Coumaric Acids - chemistry</subject><subject>Coumaric Acids - pharmacology</subject><subject>Crystallography, X-Ray</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Exo-a-sialidase</subject><subject>Ferulic acid</subject><subject>Humanities and Social Sciences</subject><subject>Influenza A Virus, H1N1 Subtype - drug effects</subject><subject>Influenza A Virus, H1N1 Subtype - enzymology</subject><subject>Inhibitors</subject><subject>Inhibitory Concentration 50</subject><subject>Models, Molecular</subject><subject>Molecular Docking Simulation</subject><subject>Molecular modelling</subject><subject>multidisciplinary</subject><subject>Neuraminidase - antagonists & inhibitors</subject><subject>Neuraminidase - chemistry</subject><subject>Neuraminidase - metabolism</subject><subject>Oseltamivir</subject><subject>Science</subject><subject>Vanillin</subject><subject>Zanamivir</subject><issn>2045-2322</issn><issn>2045-2322</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>C6C</sourceid><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNplkUtLAzEQx4MoKurBLyABT4rVPPaReBCK-AJf4OMaptlsG9kmNdlVevC7G62WinNIhpkf_5nhj9A2JYeUcHEUg5lwUUi2hNYZyfIe44wtL-RraCvGF5IiZzKjchWtsVLKXBZ0HX3c-9a41kKDb807vqS3NCVdgLF1toJo8JUb2YFtfYi4Dn6Mz03oGqtxX9sKg6vwMzjbNNYd4xvfGN01EFJWma_a8AA_TF07MtHGb9g6_Gzb4HE_RphuopUammi2fv4N9HR-9nh62bu-u7g67V_3dMZF26slgChTEOBa0NpoMSjS7UAIpUB4QXRd5YLVZVbIqgTQJCOcpmcgNc8F30AnM91JNxibSqeLAzRqEuwYwlR5sOpvx9mRGvo3ldOSlpIlgd0fgeBfOxNb9eK74NLOigopM05IWSZqb0bp4GPypZ5PoER9maXmZiV2Z3GlOflrTQL2Z0BMLTc0YWHkP7VPus2e2g</recordid><startdate>20161220</startdate><enddate>20161220</enddate><creator>Hariono, Maywan</creator><creator>Abdullah, Nurshariza</creator><creator>Damodaran, K.V.</creator><creator>Kamarulzaman, Ezatul E.</creator><creator>Mohamed, Nornisah</creator><creator>Hassan, Sharifah Syed</creator><creator>Shamsuddin, Shaharum</creator><creator>Wahab, Habibah A.</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><scope>C6C</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>5PM</scope></search><sort><creationdate>20161220</creationdate><title>Potential New H1N1 Neuraminidase Inhibitors from Ferulic Acid and Vanillin: Molecular Modelling, Synthesis and in Vitro Assay</title><author>Hariono, Maywan ; Abdullah, Nurshariza ; Damodaran, K.V. ; Kamarulzaman, Ezatul E. ; Mohamed, Nornisah ; Hassan, Sharifah Syed ; Shamsuddin, Shaharum ; Wahab, Habibah A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-f9aa877770a3c81fec8b6038a0011a0360cfd582f7469d7aac04031040b9c3583</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>101/58</topic><topic>119/118</topic><topic>140/131</topic><topic>631/154/309/2420</topic><topic>631/92/2783</topic><topic>Acids</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Benzaldehydes - chemical synthesis</topic><topic>Benzaldehydes - chemistry</topic><topic>Benzaldehydes - pharmacology</topic><topic>Binding Sites</topic><topic>Biological Assay</topic><topic>Computer applications</topic><topic>Coumaric Acids - chemical synthesis</topic><topic>Coumaric Acids - chemistry</topic><topic>Coumaric Acids - pharmacology</topic><topic>Crystallography, X-Ray</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Exo-a-sialidase</topic><topic>Ferulic acid</topic><topic>Humanities and Social Sciences</topic><topic>Influenza A Virus, H1N1 Subtype - drug effects</topic><topic>Influenza A Virus, H1N1 Subtype - enzymology</topic><topic>Inhibitors</topic><topic>Inhibitory Concentration 50</topic><topic>Models, Molecular</topic><topic>Molecular Docking Simulation</topic><topic>Molecular modelling</topic><topic>multidisciplinary</topic><topic>Neuraminidase - antagonists & inhibitors</topic><topic>Neuraminidase - chemistry</topic><topic>Neuraminidase - metabolism</topic><topic>Oseltamivir</topic><topic>Science</topic><topic>Vanillin</topic><topic>Zanamivir</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hariono, Maywan</creatorcontrib><creatorcontrib>Abdullah, Nurshariza</creatorcontrib><creatorcontrib>Damodaran, K.V.</creatorcontrib><creatorcontrib>Kamarulzaman, Ezatul E.</creatorcontrib><creatorcontrib>Mohamed, Nornisah</creatorcontrib><creatorcontrib>Hassan, Sharifah Syed</creatorcontrib><creatorcontrib>Shamsuddin, Shaharum</creatorcontrib><creatorcontrib>Wahab, Habibah A.</creatorcontrib><collection>Springer Nature OA Free Journals</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><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>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection (ProQuest)</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database (ProQuest)</collection><collection>Biological Science Database</collection><collection>Publicly Available Content Database</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 Basic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Scientific reports</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hariono, Maywan</au><au>Abdullah, Nurshariza</au><au>Damodaran, K.V.</au><au>Kamarulzaman, Ezatul E.</au><au>Mohamed, Nornisah</au><au>Hassan, Sharifah Syed</au><au>Shamsuddin, Shaharum</au><au>Wahab, Habibah A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Potential New H1N1 Neuraminidase Inhibitors from Ferulic Acid and Vanillin: Molecular Modelling, Synthesis and in Vitro Assay</atitle><jtitle>Scientific reports</jtitle><stitle>Sci Rep</stitle><addtitle>Sci Rep</addtitle><date>2016-12-20</date><risdate>2016</risdate><volume>6</volume><issue>1</issue><spage>38692</spage><pages>38692-</pages><artnum>38692</artnum><issn>2045-2322</issn><eissn>2045-2322</eissn><abstract>We report the computational and experimental efforts in the design and synthesis of novel neuraminidase (NA) inhibitors from ferulic acid and vanillin. Two proposed ferulic acid analogues,
MY7
and
MY8
were predicted to inhibit H1N1 NA using molecular docking. From these two analogues, we designed, synthesised and evaluated the biological activities of a series of ferulic acid and vanillin derivatives. The enzymatic H1N1 NA inhibition assay showed
MY21
(a vanillin derivative) has the lowest IC
50
of 50 μM. In contrast, the virus inhibition assay showed
MY15
, a ferulic acid derivative has the best activity with the EC
50
of ~0.95 μM. Modelling studies further suggest that these predicted activities might be due to the interactions with conserved and essential residues of NA with ΔG
bind
values comparable to those of oseltamivir and zanamivir, the two commercial NA inhibitors.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>27995961</pmid><doi>10.1038/srep38692</doi><oa>free_for_read</oa></addata></record> |
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| subjects | 101/58 119/118 140/131 631/154/309/2420 631/92/2783 Acids Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Benzaldehydes - chemical synthesis Benzaldehydes - chemistry Benzaldehydes - pharmacology Binding Sites Biological Assay Computer applications Coumaric Acids - chemical synthesis Coumaric Acids - chemistry Coumaric Acids - pharmacology Crystallography, X-Ray Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Exo-a-sialidase Ferulic acid Humanities and Social Sciences Influenza A Virus, H1N1 Subtype - drug effects Influenza A Virus, H1N1 Subtype - enzymology Inhibitors Inhibitory Concentration 50 Models, Molecular Molecular Docking Simulation Molecular modelling multidisciplinary Neuraminidase - antagonists & inhibitors Neuraminidase - chemistry Neuraminidase - metabolism Oseltamivir Science Vanillin Zanamivir |
| title | Potential New H1N1 Neuraminidase Inhibitors from Ferulic Acid and Vanillin: Molecular Modelling, Synthesis and in Vitro Assay |
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