Loading…
Design, synthesis and SAR studies of NAD analogues as potent inhibitors towards CD38 NADase
Nicotinamide adenine dinucleotide (NAD), one of the most important coenzymes in the cells, is a substrate of the signaling enzyme CD38, by which NAD is converted to a second messenger, cyclic ADP-ribose, which releases calcium from intracellular calcium stores. Starting with 2'-deoxy-2'-fl...
Saved in:
| Published in: | Molecules (Basel, Switzerland) Switzerland), 2014-09, Vol.19 (10), p.15754-15767 |
|---|---|
| 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-c496t-6a7760e14926104075e63d07c471eda1ca3e8afcc9127b9178f815c608209ac73 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c496t-6a7760e14926104075e63d07c471eda1ca3e8afcc9127b9178f815c608209ac73 |
| container_end_page | 15767 |
| container_issue | 10 |
| container_start_page | 15754 |
| container_title | Molecules (Basel, Switzerland) |
| container_volume | 19 |
| creator | Wang, Shengjun Zhu, Wenjie Wang, Xuan Li, Jianguo Zhang, Kehui Zhang, Liangren Zhao, Yong-Juan Lee, Hon Cheung Zhang, Lihe |
| description | Nicotinamide adenine dinucleotide (NAD), one of the most important coenzymes in the cells, is a substrate of the signaling enzyme CD38, by which NAD is converted to a second messenger, cyclic ADP-ribose, which releases calcium from intracellular calcium stores. Starting with 2'-deoxy-2'-fluoroarabinosyl-β-nicotinamide adenine dinucleotide (ara-F NAD), a series of NAD analogues were synthesized and their activities to inhibit CD38 NAD glycohydrolase (NADase) were evaluated. The adenosine-modified analogues showed potent inhibitory activities, among which 2'-deoxy-2'-fluoroarabinosyl-β-nicotinamide guanine dinucleotide (ara-F NGD) was the most effective one. The structure-activity relationship of NAD analogues was also discussed. |
| doi_str_mv | 10.3390/molecules191015754 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_ed23aa8ba80c488bb504974a84cc40d6</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_ed23aa8ba80c488bb504974a84cc40d6</doaj_id><sourcerecordid>3495017701</sourcerecordid><originalsourceid>FETCH-LOGICAL-c496t-6a7760e14926104075e63d07c471eda1ca3e8afcc9127b9178f815c608209ac73</originalsourceid><addsrcrecordid>eNplkk1vEzEQhleIipbCH-CALHHh0JTxt_eCFCUFKlVF4uPEwZr1ehNHm3Wwd0H99zikrVo4efT6nUee11NVryicc17Du23svZt6n2lNgUotxZPqhAoGMw6ifvqgPq6e57wBYFRQ-aw6ZpIpo5k8qX4sfQ6r4Yzkm2FclzoTHFrydf6F5HFqg88kduR6viwy9nE1FQEz2cXRDyMJwzo0YYwpkzH-xtRmslhys_dj9i-qow777F_enqfV9w8X3xafZlefP14u5lczJ2o1zhRqrcBTUTNFQYCWXvEWtBOa-hapQ-4Nds7VlOmmptp0hkqnwDCo0Wl-Wl0euG3Ejd2lsMV0YyMG-1eIaWUxjcH13vqWcUTToAEnjGkaWdLRAo1wTkCrCuv9gbWbmq1vXZkyYf8I-vhmCGu7ir-sYppquge8vQWk-LOkNdptyM73PQ4-TtlSqTRI4NwU65t_rJs4pRJzcSkmajAcoLjYweVSzDn57v4xFOx-D-z_e1CaXj8c477l7uP5HxzNrxI</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1624908300</pqid></control><display><type>article</type><title>Design, synthesis and SAR studies of NAD analogues as potent inhibitors towards CD38 NADase</title><source>Publicly Available Content (ProQuest)</source><source>PubMed Central</source><creator>Wang, Shengjun ; Zhu, Wenjie ; Wang, Xuan ; Li, Jianguo ; Zhang, Kehui ; Zhang, Liangren ; Zhao, Yong-Juan ; Lee, Hon Cheung ; Zhang, Lihe</creator><creatorcontrib>Wang, Shengjun ; Zhu, Wenjie ; Wang, Xuan ; Li, Jianguo ; Zhang, Kehui ; Zhang, Liangren ; Zhao, Yong-Juan ; Lee, Hon Cheung ; Zhang, Lihe</creatorcontrib><description>Nicotinamide adenine dinucleotide (NAD), one of the most important coenzymes in the cells, is a substrate of the signaling enzyme CD38, by which NAD is converted to a second messenger, cyclic ADP-ribose, which releases calcium from intracellular calcium stores. Starting with 2'-deoxy-2'-fluoroarabinosyl-β-nicotinamide adenine dinucleotide (ara-F NAD), a series of NAD analogues were synthesized and their activities to inhibit CD38 NAD glycohydrolase (NADase) were evaluated. The adenosine-modified analogues showed potent inhibitory activities, among which 2'-deoxy-2'-fluoroarabinosyl-β-nicotinamide guanine dinucleotide (ara-F NGD) was the most effective one. The structure-activity relationship of NAD analogues was also discussed.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules191015754</identifier><identifier>PMID: 25268725</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Adenosine ; ADP-ribosyl Cyclase 1 - antagonists & inhibitors ; ADP-ribosyl Cyclase 1 - chemistry ; CD38 ; Chemistry Techniques, Synthetic ; Drug Design ; Enzyme Activation - drug effects ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Enzymes ; Guanine Nucleotides - chemical synthesis ; Guanine Nucleotides - chemistry ; Guanine Nucleotides - pharmacology ; inhibitors ; Molecular Structure ; NAD - analogs & derivatives ; NAD - chemical synthesis ; NAD - chemistry ; NAD - pharmacology ; NAD analogues ; Phosphates ; Physiology ; Protein Binding ; Reagents ; Substrate Specificity ; synthesis</subject><ispartof>Molecules (Basel, Switzerland), 2014-09, Vol.19 (10), p.15754-15767</ispartof><rights>Copyright MDPI AG 2014</rights><rights>2014 by the authors. 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c496t-6a7760e14926104075e63d07c471eda1ca3e8afcc9127b9178f815c608209ac73</citedby><cites>FETCH-LOGICAL-c496t-6a7760e14926104075e63d07c471eda1ca3e8afcc9127b9178f815c608209ac73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1624908300/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1624908300?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25752,27923,27924,37011,37012,44589,53790,53792,74997</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25268725$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Shengjun</creatorcontrib><creatorcontrib>Zhu, Wenjie</creatorcontrib><creatorcontrib>Wang, Xuan</creatorcontrib><creatorcontrib>Li, Jianguo</creatorcontrib><creatorcontrib>Zhang, Kehui</creatorcontrib><creatorcontrib>Zhang, Liangren</creatorcontrib><creatorcontrib>Zhao, Yong-Juan</creatorcontrib><creatorcontrib>Lee, Hon Cheung</creatorcontrib><creatorcontrib>Zhang, Lihe</creatorcontrib><title>Design, synthesis and SAR studies of NAD analogues as potent inhibitors towards CD38 NADase</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>Nicotinamide adenine dinucleotide (NAD), one of the most important coenzymes in the cells, is a substrate of the signaling enzyme CD38, by which NAD is converted to a second messenger, cyclic ADP-ribose, which releases calcium from intracellular calcium stores. Starting with 2'-deoxy-2'-fluoroarabinosyl-β-nicotinamide adenine dinucleotide (ara-F NAD), a series of NAD analogues were synthesized and their activities to inhibit CD38 NAD glycohydrolase (NADase) were evaluated. The adenosine-modified analogues showed potent inhibitory activities, among which 2'-deoxy-2'-fluoroarabinosyl-β-nicotinamide guanine dinucleotide (ara-F NGD) was the most effective one. The structure-activity relationship of NAD analogues was also discussed.</description><subject>Adenosine</subject><subject>ADP-ribosyl Cyclase 1 - antagonists & inhibitors</subject><subject>ADP-ribosyl Cyclase 1 - chemistry</subject><subject>CD38</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Drug Design</subject><subject>Enzyme Activation - drug effects</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Enzymes</subject><subject>Guanine Nucleotides - chemical synthesis</subject><subject>Guanine Nucleotides - chemistry</subject><subject>Guanine Nucleotides - pharmacology</subject><subject>inhibitors</subject><subject>Molecular Structure</subject><subject>NAD - analogs & derivatives</subject><subject>NAD - chemical synthesis</subject><subject>NAD - chemistry</subject><subject>NAD - pharmacology</subject><subject>NAD analogues</subject><subject>Phosphates</subject><subject>Physiology</subject><subject>Protein Binding</subject><subject>Reagents</subject><subject>Substrate Specificity</subject><subject>synthesis</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplkk1vEzEQhleIipbCH-CALHHh0JTxt_eCFCUFKlVF4uPEwZr1ehNHm3Wwd0H99zikrVo4efT6nUee11NVryicc17Du23svZt6n2lNgUotxZPqhAoGMw6ifvqgPq6e57wBYFRQ-aw6ZpIpo5k8qX4sfQ6r4Yzkm2FclzoTHFrydf6F5HFqg88kduR6viwy9nE1FQEz2cXRDyMJwzo0YYwpkzH-xtRmslhys_dj9i-qow777F_enqfV9w8X3xafZlefP14u5lczJ2o1zhRqrcBTUTNFQYCWXvEWtBOa-hapQ-4Nds7VlOmmptp0hkqnwDCo0Wl-Wl0euG3Ejd2lsMV0YyMG-1eIaWUxjcH13vqWcUTToAEnjGkaWdLRAo1wTkCrCuv9gbWbmq1vXZkyYf8I-vhmCGu7ir-sYppquge8vQWk-LOkNdptyM73PQ4-TtlSqTRI4NwU65t_rJs4pRJzcSkmajAcoLjYweVSzDn57v4xFOx-D-z_e1CaXj8c477l7uP5HxzNrxI</recordid><startdate>20140929</startdate><enddate>20140929</enddate><creator>Wang, Shengjun</creator><creator>Zhu, Wenjie</creator><creator>Wang, Xuan</creator><creator>Li, Jianguo</creator><creator>Zhang, Kehui</creator><creator>Zhang, Liangren</creator><creator>Zhao, Yong-Juan</creator><creator>Lee, Hon Cheung</creator><creator>Zhang, Lihe</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></search><sort><creationdate>20140929</creationdate><title>Design, synthesis and SAR studies of NAD analogues as potent inhibitors towards CD38 NADase</title><author>Wang, Shengjun ; Zhu, Wenjie ; Wang, Xuan ; Li, Jianguo ; Zhang, Kehui ; Zhang, Liangren ; Zhao, Yong-Juan ; Lee, Hon Cheung ; Zhang, Lihe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c496t-6a7760e14926104075e63d07c471eda1ca3e8afcc9127b9178f815c608209ac73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Adenosine</topic><topic>ADP-ribosyl Cyclase 1 - antagonists & inhibitors</topic><topic>ADP-ribosyl Cyclase 1 - chemistry</topic><topic>CD38</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Drug Design</topic><topic>Enzyme Activation - drug effects</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Enzymes</topic><topic>Guanine Nucleotides - chemical synthesis</topic><topic>Guanine Nucleotides - chemistry</topic><topic>Guanine Nucleotides - pharmacology</topic><topic>inhibitors</topic><topic>Molecular Structure</topic><topic>NAD - analogs & derivatives</topic><topic>NAD - chemical synthesis</topic><topic>NAD - chemistry</topic><topic>NAD - pharmacology</topic><topic>NAD analogues</topic><topic>Phosphates</topic><topic>Physiology</topic><topic>Protein Binding</topic><topic>Reagents</topic><topic>Substrate Specificity</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Shengjun</creatorcontrib><creatorcontrib>Zhu, Wenjie</creatorcontrib><creatorcontrib>Wang, Xuan</creatorcontrib><creatorcontrib>Li, Jianguo</creatorcontrib><creatorcontrib>Zhang, Kehui</creatorcontrib><creatorcontrib>Zhang, Liangren</creatorcontrib><creatorcontrib>Zhao, Yong-Juan</creatorcontrib><creatorcontrib>Lee, Hon Cheung</creatorcontrib><creatorcontrib>Zhang, Lihe</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>ProQuest - Health & Medical Complete保健、医学与药学数据库</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>PML(ProQuest Medical Library)</collection><collection>Publicly Available Content (ProQuest)</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>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Shengjun</au><au>Zhu, Wenjie</au><au>Wang, Xuan</au><au>Li, Jianguo</au><au>Zhang, Kehui</au><au>Zhang, Liangren</au><au>Zhao, Yong-Juan</au><au>Lee, Hon Cheung</au><au>Zhang, Lihe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis and SAR studies of NAD analogues as potent inhibitors towards CD38 NADase</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2014-09-29</date><risdate>2014</risdate><volume>19</volume><issue>10</issue><spage>15754</spage><epage>15767</epage><pages>15754-15767</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>Nicotinamide adenine dinucleotide (NAD), one of the most important coenzymes in the cells, is a substrate of the signaling enzyme CD38, by which NAD is converted to a second messenger, cyclic ADP-ribose, which releases calcium from intracellular calcium stores. Starting with 2'-deoxy-2'-fluoroarabinosyl-β-nicotinamide adenine dinucleotide (ara-F NAD), a series of NAD analogues were synthesized and their activities to inhibit CD38 NAD glycohydrolase (NADase) were evaluated. The adenosine-modified analogues showed potent inhibitory activities, among which 2'-deoxy-2'-fluoroarabinosyl-β-nicotinamide guanine dinucleotide (ara-F NGD) was the most effective one. The structure-activity relationship of NAD analogues was also discussed.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>25268725</pmid><doi>10.3390/molecules191015754</doi><tpages>14</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1420-3049 |
| ispartof | Molecules (Basel, Switzerland), 2014-09, Vol.19 (10), p.15754-15767 |
| issn | 1420-3049 1420-3049 |
| language | eng |
| recordid | cdi_doaj_primary_oai_doaj_org_article_ed23aa8ba80c488bb504974a84cc40d6 |
| source | Publicly Available Content (ProQuest); PubMed Central |
| subjects | Adenosine ADP-ribosyl Cyclase 1 - antagonists & inhibitors ADP-ribosyl Cyclase 1 - chemistry CD38 Chemistry Techniques, Synthetic Drug Design Enzyme Activation - drug effects Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Enzymes Guanine Nucleotides - chemical synthesis Guanine Nucleotides - chemistry Guanine Nucleotides - pharmacology inhibitors Molecular Structure NAD - analogs & derivatives NAD - chemical synthesis NAD - chemistry NAD - pharmacology NAD analogues Phosphates Physiology Protein Binding Reagents Substrate Specificity synthesis |
| title | Design, synthesis and SAR studies of NAD analogues as potent inhibitors towards CD38 NADase |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T02%3A53%3A32IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Design,%20synthesis%20and%20SAR%20studies%20of%20NAD%20analogues%20as%20potent%20inhibitors%20towards%20CD38%20NADase&rft.jtitle=Molecules%20(Basel,%20Switzerland)&rft.au=Wang,%20Shengjun&rft.date=2014-09-29&rft.volume=19&rft.issue=10&rft.spage=15754&rft.epage=15767&rft.pages=15754-15767&rft.issn=1420-3049&rft.eissn=1420-3049&rft_id=info:doi/10.3390/molecules191015754&rft_dat=%3Cproquest_doaj_%3E3495017701%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c496t-6a7760e14926104075e63d07c471eda1ca3e8afcc9127b9178f815c608209ac73%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1624908300&rft_id=info:pmid/25268725&rfr_iscdi=true |