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Design and Synthesis of Various 5'-Deoxy-5'-(4-Substituted-1,2,3-Triazol-1-yl)-Uridine Analogues as Inhibitors of Mycobacterium tuberculosis Mur Ligases
The synthesis of hitherto unknown 5'-deoxy-5'-(4-substituted-1,2,3-triazol-1-yl)-uridine and its evaluation, through an one-pot screening assay, against MurA-F enzymes involved in (Mtb), are described. Starting from UDP- -acetylmuramic acid (UDP-MurNAc), the natural substrate involved in t...
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| Published in: | Molecules (Basel, Switzerland) Switzerland), 2020-10, Vol.25 (21), p.4953 |
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| creator | Hervin, Vincent Arora, Ritu Rani, Jyoti Ramchandran, Srinivasan Bajpai, Urmi Agrofoglio, Luigi A Roy, Vincent |
| description | The synthesis of hitherto unknown 5'-deoxy-5'-(4-substituted-1,2,3-triazol-1-yl)-uridine and its evaluation, through an one-pot screening assay, against MurA-F enzymes involved in
(Mtb), are described. Starting from UDP-
-acetylmuramic acid (UDP-MurNAc), the natural substrate involved in the peptidoglycan biosynthesis, our strategy was to substitute the diphosphate group of UDP-MurNAc by a 1,2,3-triazolo spacer under copper-catalyzed azide-alkyne cycloaddition conditions. The structure-activity relationship was discussed and among the 23 novel compounds developed,
-acetylglucosamine analogues
and
emerged as the best inhibitors against the Mtb MurA-F enzymes reconstruction pathway with an inhibitory effect of 56% and 50%, respectively, at 100 μM. Both compounds are selective inhibitors of Mtb MurE, the molecular docking and molecular dynamic simulation suggesting that
and
are occupying the active site of Mtb MurE ligase. |
| doi_str_mv | 10.3390/molecules25214953 |
| format | article |
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(Mtb), are described. Starting from UDP-
-acetylmuramic acid (UDP-MurNAc), the natural substrate involved in the peptidoglycan biosynthesis, our strategy was to substitute the diphosphate group of UDP-MurNAc by a 1,2,3-triazolo spacer under copper-catalyzed azide-alkyne cycloaddition conditions. The structure-activity relationship was discussed and among the 23 novel compounds developed,
-acetylglucosamine analogues
and
emerged as the best inhibitors against the Mtb MurA-F enzymes reconstruction pathway with an inhibitory effect of 56% and 50%, respectively, at 100 μM. Both compounds are selective inhibitors of Mtb MurE, the molecular docking and molecular dynamic simulation suggesting that
and
are occupying the active site of Mtb MurE ligase.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules25214953</identifier><identifier>PMID: 33114668</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Alcohol ; Alkynes ; Amino acids ; antibacterial agents ; Antibiotics ; Binding sites ; Biological activity ; Biosynthesis ; Catalytic Domain ; Chemistry Techniques, Synthetic ; copper-catalyzed azide-alkyne cycloaddition ; Cycloaddition ; Drug Design ; Drug resistance ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Enzymes ; Hydrogen bonds ; Inhibitors ; Ligands ; Molecular docking ; Molecular Docking Simulation ; Molecular dynamics ; molecular modelling ; Mur ligase ; Mycobacterium tuberculosis ; Mycobacterium tuberculosis - enzymology ; N-Acetylglucosamine ; nucleoside analogues ; Peptide Synthases - antagonists & inhibitors ; Peptide Synthases - chemistry ; Peptide Synthases - metabolism ; Peptidoglycans ; Proteins ; Simulation ; Substitutes ; Triazoles - chemistry ; Tuberculosis ; Uridine ; Uridine - chemical synthesis ; Uridine - chemistry ; Uridine - pharmacology</subject><ispartof>Molecules (Basel, Switzerland), 2020-10, Vol.25 (21), p.4953</ispartof><rights>2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2020 by the authors. 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c493t-e48dcd7f90afc1c4c54e8cebf406e8033587289a5242bcc888165f672aedb6ea3</citedby><cites>FETCH-LOGICAL-c493t-e48dcd7f90afc1c4c54e8cebf406e8033587289a5242bcc888165f672aedb6ea3</cites><orcidid>0000-0002-6083-0810 ; 0000-0002-2491-6019</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2550233335/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2550233335?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33114668$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hervin, Vincent</creatorcontrib><creatorcontrib>Arora, Ritu</creatorcontrib><creatorcontrib>Rani, Jyoti</creatorcontrib><creatorcontrib>Ramchandran, Srinivasan</creatorcontrib><creatorcontrib>Bajpai, Urmi</creatorcontrib><creatorcontrib>Agrofoglio, Luigi A</creatorcontrib><creatorcontrib>Roy, Vincent</creatorcontrib><title>Design and Synthesis of Various 5'-Deoxy-5'-(4-Substituted-1,2,3-Triazol-1-yl)-Uridine Analogues as Inhibitors of Mycobacterium tuberculosis Mur Ligases</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>The synthesis of hitherto unknown 5'-deoxy-5'-(4-substituted-1,2,3-triazol-1-yl)-uridine and its evaluation, through an one-pot screening assay, against MurA-F enzymes involved in
(Mtb), are described. Starting from UDP-
-acetylmuramic acid (UDP-MurNAc), the natural substrate involved in the peptidoglycan biosynthesis, our strategy was to substitute the diphosphate group of UDP-MurNAc by a 1,2,3-triazolo spacer under copper-catalyzed azide-alkyne cycloaddition conditions. The structure-activity relationship was discussed and among the 23 novel compounds developed,
-acetylglucosamine analogues
and
emerged as the best inhibitors against the Mtb MurA-F enzymes reconstruction pathway with an inhibitory effect of 56% and 50%, respectively, at 100 μM. Both compounds are selective inhibitors of Mtb MurE, the molecular docking and molecular dynamic simulation suggesting that
and
are occupying the active site of Mtb MurE ligase.</description><subject>Alcohol</subject><subject>Alkynes</subject><subject>Amino acids</subject><subject>antibacterial agents</subject><subject>Antibiotics</subject><subject>Binding sites</subject><subject>Biological activity</subject><subject>Biosynthesis</subject><subject>Catalytic Domain</subject><subject>Chemistry Techniques, Synthetic</subject><subject>copper-catalyzed azide-alkyne cycloaddition</subject><subject>Cycloaddition</subject><subject>Drug Design</subject><subject>Drug resistance</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Enzymes</subject><subject>Hydrogen bonds</subject><subject>Inhibitors</subject><subject>Ligands</subject><subject>Molecular docking</subject><subject>Molecular Docking Simulation</subject><subject>Molecular dynamics</subject><subject>molecular modelling</subject><subject>Mur ligase</subject><subject>Mycobacterium tuberculosis</subject><subject>Mycobacterium tuberculosis - enzymology</subject><subject>N-Acetylglucosamine</subject><subject>nucleoside analogues</subject><subject>Peptide Synthases - antagonists & inhibitors</subject><subject>Peptide Synthases - chemistry</subject><subject>Peptide Synthases - metabolism</subject><subject>Peptidoglycans</subject><subject>Proteins</subject><subject>Simulation</subject><subject>Substitutes</subject><subject>Triazoles - chemistry</subject><subject>Tuberculosis</subject><subject>Uridine</subject><subject>Uridine - chemical synthesis</subject><subject>Uridine - chemistry</subject><subject>Uridine - pharmacology</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplkstu1DAUhiMEohd4ADYoEguKVIOvib1BqlouI03Foi1by3FOMh5l4mI7qOFJeFw8nVK14I2P7f989jn-i-IVwe8ZU_jDxg9gpwEiFZRwJdiTYp9wihHDXD19EO8VBzGuMc4qIp4Xe4wRwqtK7he_zyC6fizN2JYX85hWeRlL35XfTXB-iqV4i87A38woB0ccXUxNTC5NCVpEjukxQ5fBmV9-QATNwzt0FVzrRihPRjP4foJYmlguxpVrXPLhlnw-W98YmyC4aVOmqYGQi_Dbe8-nUC5dbyLEF8WzzgwRXt7Nh8XV50-Xp1_R8tuXxenJElmuWELAZWvbulPYdJZYbgUHaaHpOK5AYsaErKlURlBOG2ullKQSXVVTA21TgWGHxWLHbb1Z6-vgNibM2hunbzd86LUJydkBdIuNqWgtWScUzwTVMWhFU3dcNZgpnlkfd6zrqdlAa2FMwQyPoI9PRrfSvf-p66pilaoz4OgOEPyP3LykNy5aGAYzQv4MTbkQMivpVvrmH-naTyF3PauEwJTlIbKK7FQ2-BgDdPePIVhvPaT_81DOef2wivuMv6ZhfwArMMWR</recordid><startdate>20201026</startdate><enddate>20201026</enddate><creator>Hervin, Vincent</creator><creator>Arora, Ritu</creator><creator>Rani, Jyoti</creator><creator>Ramchandran, Srinivasan</creator><creator>Bajpai, Urmi</creator><creator>Agrofoglio, Luigi A</creator><creator>Roy, Vincent</creator><general>MDPI AG</general><general>MDPI</general><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>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-6083-0810</orcidid><orcidid>https://orcid.org/0000-0002-2491-6019</orcidid></search><sort><creationdate>20201026</creationdate><title>Design and Synthesis of Various 5'-Deoxy-5'-(4-Substituted-1,2,3-Triazol-1-yl)-Uridine Analogues as Inhibitors of Mycobacterium tuberculosis Mur Ligases</title><author>Hervin, Vincent ; Arora, Ritu ; Rani, Jyoti ; Ramchandran, Srinivasan ; Bajpai, Urmi ; Agrofoglio, Luigi A ; Roy, Vincent</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c493t-e48dcd7f90afc1c4c54e8cebf406e8033587289a5242bcc888165f672aedb6ea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alcohol</topic><topic>Alkynes</topic><topic>Amino acids</topic><topic>antibacterial agents</topic><topic>Antibiotics</topic><topic>Binding sites</topic><topic>Biological activity</topic><topic>Biosynthesis</topic><topic>Catalytic Domain</topic><topic>Chemistry Techniques, Synthetic</topic><topic>copper-catalyzed azide-alkyne cycloaddition</topic><topic>Cycloaddition</topic><topic>Drug Design</topic><topic>Drug resistance</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Enzymes</topic><topic>Hydrogen bonds</topic><topic>Inhibitors</topic><topic>Ligands</topic><topic>Molecular docking</topic><topic>Molecular Docking Simulation</topic><topic>Molecular dynamics</topic><topic>molecular modelling</topic><topic>Mur ligase</topic><topic>Mycobacterium tuberculosis</topic><topic>Mycobacterium tuberculosis - enzymology</topic><topic>N-Acetylglucosamine</topic><topic>nucleoside analogues</topic><topic>Peptide Synthases - antagonists & inhibitors</topic><topic>Peptide Synthases - chemistry</topic><topic>Peptide Synthases - metabolism</topic><topic>Peptidoglycans</topic><topic>Proteins</topic><topic>Simulation</topic><topic>Substitutes</topic><topic>Triazoles - chemistry</topic><topic>Tuberculosis</topic><topic>Uridine</topic><topic>Uridine - chemical synthesis</topic><topic>Uridine - chemistry</topic><topic>Uridine - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hervin, Vincent</creatorcontrib><creatorcontrib>Arora, Ritu</creatorcontrib><creatorcontrib>Rani, Jyoti</creatorcontrib><creatorcontrib>Ramchandran, Srinivasan</creatorcontrib><creatorcontrib>Bajpai, Urmi</creatorcontrib><creatorcontrib>Agrofoglio, Luigi A</creatorcontrib><creatorcontrib>Roy, Vincent</creatorcontrib><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>Medical Database (Alumni Edition)</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)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</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 Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>ProQuest - 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(Mtb), are described. Starting from UDP-
-acetylmuramic acid (UDP-MurNAc), the natural substrate involved in the peptidoglycan biosynthesis, our strategy was to substitute the diphosphate group of UDP-MurNAc by a 1,2,3-triazolo spacer under copper-catalyzed azide-alkyne cycloaddition conditions. The structure-activity relationship was discussed and among the 23 novel compounds developed,
-acetylglucosamine analogues
and
emerged as the best inhibitors against the Mtb MurA-F enzymes reconstruction pathway with an inhibitory effect of 56% and 50%, respectively, at 100 μM. Both compounds are selective inhibitors of Mtb MurE, the molecular docking and molecular dynamic simulation suggesting that
and
are occupying the active site of Mtb MurE ligase.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>33114668</pmid><doi>10.3390/molecules25214953</doi><orcidid>https://orcid.org/0000-0002-6083-0810</orcidid><orcidid>https://orcid.org/0000-0002-2491-6019</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Alcohol Alkynes Amino acids antibacterial agents Antibiotics Binding sites Biological activity Biosynthesis Catalytic Domain Chemistry Techniques, Synthetic copper-catalyzed azide-alkyne cycloaddition Cycloaddition Drug Design Drug resistance Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Enzymes Hydrogen bonds Inhibitors Ligands Molecular docking Molecular Docking Simulation Molecular dynamics molecular modelling Mur ligase Mycobacterium tuberculosis Mycobacterium tuberculosis - enzymology N-Acetylglucosamine nucleoside analogues Peptide Synthases - antagonists & inhibitors Peptide Synthases - chemistry Peptide Synthases - metabolism Peptidoglycans Proteins Simulation Substitutes Triazoles - chemistry Tuberculosis Uridine Uridine - chemical synthesis Uridine - chemistry Uridine - pharmacology |
| title | Design and Synthesis of Various 5'-Deoxy-5'-(4-Substituted-1,2,3-Triazol-1-yl)-Uridine Analogues as Inhibitors of Mycobacterium tuberculosis Mur Ligases |
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