Novel antiviral agent tetraglycylated nordihydroguaiaretic acid hydrochloride as a host-dependent viral inhibitor
A water soluble derivative of nordihydroguaiaretic acid (NDGA), G 4N ( 2), synthesized by reaction of NDGA ( 1) with N,N-dimethylglycine in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine and then with HCl(g) (Scheme 1), competes effectively with the DNA binding domain of recombin...
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| Veröffentlicht in: | Antiviral research 2003-03, Vol.58 (1), p.57-64 |
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| creator | Huang, Ru Chih C. Li, Yen Giza, Paul E. Gnabre, John N. Abd-Elazem, Ibrahim S. King, Ke Yung Hwu, Jih Ru |
| description | A water soluble derivative of nordihydroguaiaretic acid (NDGA), G
4N (
2), synthesized by reaction of NDGA (
1) with
N,N-dimethylglycine in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine and then with HCl(g) (Scheme 1), competes effectively with the DNA binding domain of recombinant Sp1 protein for binding to the human immunodeficiency virus (HIV) LTR as demonstrated by an electrophoretic mobility-shift assay (EMSA). By blocking Sp1 binding to the HIV LTR, G
4N suppresses Sp1-regulated HIV Tat transactivation and replication in cultured cells with an IC
50 of 12
μM similar to that of 3′-
O-methyl-NDGA as we have previously reported. In addition simian immunodeficiency virus (SIV) replication was completely inhibited by G
4N at 5.0
μM. G
4N showed no toxic effect to 174×CEM cells and H9 cells at 100
μM. |
| doi_str_mv | 10.1016/S0166-3542(02)00189-4 |
| format | Article |
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4N (
2), synthesized by reaction of NDGA (
1) with
N,N-dimethylglycine in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine and then with HCl(g) (Scheme 1), competes effectively with the DNA binding domain of recombinant Sp1 protein for binding to the human immunodeficiency virus (HIV) LTR as demonstrated by an electrophoretic mobility-shift assay (EMSA). By blocking Sp1 binding to the HIV LTR, G
4N suppresses Sp1-regulated HIV Tat transactivation and replication in cultured cells with an IC
50 of 12
μM similar to that of 3′-
O-methyl-NDGA as we have previously reported. In addition simian immunodeficiency virus (SIV) replication was completely inhibited by G
4N at 5.0
μM. G
4N showed no toxic effect to 174×CEM cells and H9 cells at 100
μM.</description><identifier>ISSN: 0166-3542</identifier><identifier>EISSN: 1872-9096</identifier><identifier>DOI: 10.1016/S0166-3542(02)00189-4</identifier><identifier>PMID: 12719007</identifier><identifier>CODEN: ARSRDR</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Animals ; Anti-HIV Agents - chemical synthesis ; Anti-HIV Agents - pharmacology ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Biological and medical sciences ; Cercopithecus aethiops ; COS Cells ; Cytopathogenic Effect, Viral - drug effects ; Electrophoretic Mobility Shift Assay ; G 4N ; Gene Products, tat - metabolism ; HIV Long Terminal Repeat - drug effects ; HIV-1 - drug effects ; HIV-1 - metabolism ; HIV-1 - physiology ; Human immunodeficiency virus ; Humans ; Masoprocol - analogs & derivatives ; Masoprocol - chemical synthesis ; Masoprocol - pharmacology ; Medical sciences ; Pharmacology. Drug treatments ; Simian immunodeficiency virus ; Simian Immunodeficiency Virus - drug effects ; Simian Immunodeficiency Virus - metabolism ; Simian Immunodeficiency Virus - physiology ; Sp1 ; Sp1 Transcription Factor - metabolism ; tat Gene Products, Human Immunodeficiency Virus ; Tetra- O-glycyl-nordihydroguaiaretic acid</subject><ispartof>Antiviral research, 2003-03, Vol.58 (1), p.57-64</ispartof><rights>2002 Elsevier Science B.V.</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c422t-9fa0ae28f3fd56247f307af04f559d9dbdfaf176b655782a92ad00d7923d5b883</citedby><cites>FETCH-LOGICAL-c422t-9fa0ae28f3fd56247f307af04f559d9dbdfaf176b655782a92ad00d7923d5b883</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0166354202001894$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14731475$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12719007$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huang, Ru Chih C.</creatorcontrib><creatorcontrib>Li, Yen</creatorcontrib><creatorcontrib>Giza, Paul E.</creatorcontrib><creatorcontrib>Gnabre, John N.</creatorcontrib><creatorcontrib>Abd-Elazem, Ibrahim S.</creatorcontrib><creatorcontrib>King, Ke Yung</creatorcontrib><creatorcontrib>Hwu, Jih Ru</creatorcontrib><title>Novel antiviral agent tetraglycylated nordihydroguaiaretic acid hydrochloride as a host-dependent viral inhibitor</title><title>Antiviral research</title><addtitle>Antiviral Res</addtitle><description>A water soluble derivative of nordihydroguaiaretic acid (NDGA), G
4N (
2), synthesized by reaction of NDGA (
1) with
N,N-dimethylglycine in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine and then with HCl(g) (Scheme 1), competes effectively with the DNA binding domain of recombinant Sp1 protein for binding to the human immunodeficiency virus (HIV) LTR as demonstrated by an electrophoretic mobility-shift assay (EMSA). By blocking Sp1 binding to the HIV LTR, G
4N suppresses Sp1-regulated HIV Tat transactivation and replication in cultured cells with an IC
50 of 12
μM similar to that of 3′-
O-methyl-NDGA as we have previously reported. In addition simian immunodeficiency virus (SIV) replication was completely inhibited by G
4N at 5.0
μM. G
4N showed no toxic effect to 174×CEM cells and H9 cells at 100
μM.</description><subject>Animals</subject><subject>Anti-HIV Agents - chemical synthesis</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Biological and medical sciences</subject><subject>Cercopithecus aethiops</subject><subject>COS Cells</subject><subject>Cytopathogenic Effect, Viral - drug effects</subject><subject>Electrophoretic Mobility Shift Assay</subject><subject>G 4N</subject><subject>Gene Products, tat - metabolism</subject><subject>HIV Long Terminal Repeat - drug effects</subject><subject>HIV-1 - drug effects</subject><subject>HIV-1 - metabolism</subject><subject>HIV-1 - physiology</subject><subject>Human immunodeficiency virus</subject><subject>Humans</subject><subject>Masoprocol - analogs & derivatives</subject><subject>Masoprocol - chemical synthesis</subject><subject>Masoprocol - pharmacology</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Simian immunodeficiency virus</subject><subject>Simian Immunodeficiency Virus - drug effects</subject><subject>Simian Immunodeficiency Virus - metabolism</subject><subject>Simian Immunodeficiency Virus - physiology</subject><subject>Sp1</subject><subject>Sp1 Transcription Factor - metabolism</subject><subject>tat Gene Products, Human Immunodeficiency Virus</subject><subject>Tetra- O-glycyl-nordihydroguaiaretic acid</subject><issn>0166-3542</issn><issn>1872-9096</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1uEzEUhS0EomnhEUCzAZXFlGvPj8erClVAK1V0AaytO_Z1YjQZp7YTKW-P00R0ieQ_Wd85tj7G3nG44sD7zz_L0tdN14pLEJ8A-KDq9gVb8EGKWoHqX7LFP-SMnaf0BwB6qYbX7IwLyRWAXLDHH2FHU4Vz9jsfsZyWNOcqU464nPZmP2EmW80hWr_a2xiWW_QYKXtTofG2ero0qylEb6nCVGG1CinXljY020PXsdfPKz_6HOIb9srhlOjtab9gv799_XVzW98_fL-7-XJfm1aIXCuHgCQG1zjb9aKVrgGJDlrXdcoqO1qHjst-7LtODgKVQAtgpRKN7cZhaC7Yx2PvJobHLaWs1z4ZmiacKWyTLqJKjvMCdkfQxJBSJKc30a8x7jUHfXCtn1zrg0gNZRxc67bk3p8e2I5rss-pk9wCfDgBmAxOLuJsfHrmWtmU2RXu-shR0bHzFHUynmZD1kcyWdvg__OVv915nhk</recordid><startdate>20030301</startdate><enddate>20030301</enddate><creator>Huang, Ru Chih C.</creator><creator>Li, Yen</creator><creator>Giza, Paul E.</creator><creator>Gnabre, John N.</creator><creator>Abd-Elazem, Ibrahim S.</creator><creator>King, Ke Yung</creator><creator>Hwu, Jih Ru</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>IQODW</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>7QO</scope><scope>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope></search><sort><creationdate>20030301</creationdate><title>Novel antiviral agent tetraglycylated nordihydroguaiaretic acid hydrochloride as a host-dependent viral inhibitor</title><author>Huang, Ru Chih C. ; Li, Yen ; Giza, Paul E. ; Gnabre, John N. ; Abd-Elazem, Ibrahim S. ; King, Ke Yung ; Hwu, Jih Ru</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c422t-9fa0ae28f3fd56247f307af04f559d9dbdfaf176b655782a92ad00d7923d5b883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Animals</topic><topic>Anti-HIV Agents - chemical synthesis</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Biological and medical sciences</topic><topic>Cercopithecus aethiops</topic><topic>COS Cells</topic><topic>Cytopathogenic Effect, Viral - drug effects</topic><topic>Electrophoretic Mobility Shift Assay</topic><topic>G 4N</topic><topic>Gene Products, tat - metabolism</topic><topic>HIV Long Terminal Repeat - drug effects</topic><topic>HIV-1 - drug effects</topic><topic>HIV-1 - metabolism</topic><topic>HIV-1 - physiology</topic><topic>Human immunodeficiency virus</topic><topic>Humans</topic><topic>Masoprocol - analogs & derivatives</topic><topic>Masoprocol - chemical synthesis</topic><topic>Masoprocol - pharmacology</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Simian immunodeficiency virus</topic><topic>Simian Immunodeficiency Virus - drug effects</topic><topic>Simian Immunodeficiency Virus - metabolism</topic><topic>Simian Immunodeficiency Virus - physiology</topic><topic>Sp1</topic><topic>Sp1 Transcription Factor - metabolism</topic><topic>tat Gene Products, Human Immunodeficiency Virus</topic><topic>Tetra- O-glycyl-nordihydroguaiaretic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Ru Chih C.</creatorcontrib><creatorcontrib>Li, Yen</creatorcontrib><creatorcontrib>Giza, Paul E.</creatorcontrib><creatorcontrib>Gnabre, John N.</creatorcontrib><creatorcontrib>Abd-Elazem, Ibrahim S.</creatorcontrib><creatorcontrib>King, Ke Yung</creatorcontrib><creatorcontrib>Hwu, Jih Ru</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Antiviral research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Ru Chih C.</au><au>Li, Yen</au><au>Giza, Paul E.</au><au>Gnabre, John N.</au><au>Abd-Elazem, Ibrahim S.</au><au>King, Ke Yung</au><au>Hwu, Jih Ru</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel antiviral agent tetraglycylated nordihydroguaiaretic acid hydrochloride as a host-dependent viral inhibitor</atitle><jtitle>Antiviral research</jtitle><addtitle>Antiviral Res</addtitle><date>2003-03-01</date><risdate>2003</risdate><volume>58</volume><issue>1</issue><spage>57</spage><epage>64</epage><pages>57-64</pages><issn>0166-3542</issn><eissn>1872-9096</eissn><coden>ARSRDR</coden><abstract>A water soluble derivative of nordihydroguaiaretic acid (NDGA), G
4N (
2), synthesized by reaction of NDGA (
1) with
N,N-dimethylglycine in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine and then with HCl(g) (Scheme 1), competes effectively with the DNA binding domain of recombinant Sp1 protein for binding to the human immunodeficiency virus (HIV) LTR as demonstrated by an electrophoretic mobility-shift assay (EMSA). By blocking Sp1 binding to the HIV LTR, G
4N suppresses Sp1-regulated HIV Tat transactivation and replication in cultured cells with an IC
50 of 12
μM similar to that of 3′-
O-methyl-NDGA as we have previously reported. In addition simian immunodeficiency virus (SIV) replication was completely inhibited by G
4N at 5.0
μM. G
4N showed no toxic effect to 174×CEM cells and H9 cells at 100
μM.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>12719007</pmid><doi>10.1016/S0166-3542(02)00189-4</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0166-3542 |
| ispartof | Antiviral research, 2003-03, Vol.58 (1), p.57-64 |
| issn | 0166-3542 1872-9096 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Animals Anti-HIV Agents - chemical synthesis Anti-HIV Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences Cercopithecus aethiops COS Cells Cytopathogenic Effect, Viral - drug effects Electrophoretic Mobility Shift Assay G 4N Gene Products, tat - metabolism HIV Long Terminal Repeat - drug effects HIV-1 - drug effects HIV-1 - metabolism HIV-1 - physiology Human immunodeficiency virus Humans Masoprocol - analogs & derivatives Masoprocol - chemical synthesis Masoprocol - pharmacology Medical sciences Pharmacology. Drug treatments Simian immunodeficiency virus Simian Immunodeficiency Virus - drug effects Simian Immunodeficiency Virus - metabolism Simian Immunodeficiency Virus - physiology Sp1 Sp1 Transcription Factor - metabolism tat Gene Products, Human Immunodeficiency Virus Tetra- O-glycyl-nordihydroguaiaretic acid |
| title | Novel antiviral agent tetraglycylated nordihydroguaiaretic acid hydrochloride as a host-dependent viral inhibitor |
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