Thiadiazole Derivatives: Highly Potent and Selective Inhibitors of Human Immunodeficiency Virus Type 1 (HIV-1) Replications In Vitro
We have recently reported that thiadiazole (TDA) derivatives are highly potent inhibitors of human immunodeficiency virus type 1 (HIV-1) replication. These compounds belong to the family of nonnucleoside reverse transcriptase inhibitors (NNRTIs). In an attempt to develop more effective and pharmacol...
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| Veröffentlicht in: | MICROBIOLOGY and IMMUNOLOGY 1997, Vol.41(4), pp.301-308 |
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| creator | Fujiwara, Masatoshi Ijichi, Katsushi Hanasaki, Yasuaki Ide, Teruhiko Katsuura, Kimio Takayama, Hiromitsu Aimi, Norio Shigeta, Shiro Konno, Kenji Yokota, Tomoyuki Baba, Masanori |
| description | We have recently reported that thiadiazole (TDA) derivatives are highly potent inhibitors of human immunodeficiency virus type 1 (HIV-1) replication. These compounds belong to the family of nonnucleoside reverse transcriptase inhibitors (NNRTIs). In an attempt to develop more effective and pharmacologically favorable compounds, novel TDA derivatives have been synthesized and examined for their anti-HIV-1 activity in vitro. Among them, RD4-2217 was found to be the most potent inhibitor of HIV-1 replication. It inhibited replication of the HTLV-IIIB strain in MT-4 cells at a concentration of 6nM. RD4-2217 was also inhibitory to clinical isolates and zidovudine-resistant mutants of HIV-1. The combination of RD4-2217 with zidovudine or the protease inhibitor A-75925 synergistically inhibited HIV-1 replication. Studies on the emergence of drug-resistant mutants revealed that, although much higher concentrations (1-10μM) were required, RD4-2217 completely suppressed the breakthrough of HIV-1 in the supernatants during long-term culturing of infected cells. Furthermore, RD4-2217 at low concentrations (10 or 100nM), in combination with zidovudine, also completely inhibited viral breakthrough. In addition, RD4-2217 had lower lipophilicity and improved protein binding as compared to its congener RD4-2024 and loviride. These results suggest that RD4-2217, one of the TDA derivatives, is worth pursuing as a candidate drug for the treatment of HIV-1 infections. |
| doi_str_mv | 10.1111/j.1348-0421.1997.tb01205.x |
| format | Article |
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These compounds belong to the family of nonnucleoside reverse transcriptase inhibitors (NNRTIs). In an attempt to develop more effective and pharmacologically favorable compounds, novel TDA derivatives have been synthesized and examined for their anti-HIV-1 activity in vitro. Among them, RD4-2217 was found to be the most potent inhibitor of HIV-1 replication. It inhibited replication of the HTLV-IIIB strain in MT-4 cells at a concentration of 6nM. RD4-2217 was also inhibitory to clinical isolates and zidovudine-resistant mutants of HIV-1. The combination of RD4-2217 with zidovudine or the protease inhibitor A-75925 synergistically inhibited HIV-1 replication. Studies on the emergence of drug-resistant mutants revealed that, although much higher concentrations (1-10μM) were required, RD4-2217 completely suppressed the breakthrough of HIV-1 in the supernatants during long-term culturing of infected cells. Furthermore, RD4-2217 at low concentrations (10 or 100nM), in combination with zidovudine, also completely inhibited viral breakthrough. In addition, RD4-2217 had lower lipophilicity and improved protein binding as compared to its congener RD4-2024 and loviride. These results suggest that RD4-2217, one of the TDA derivatives, is worth pursuing as a candidate drug for the treatment of HIV-1 infections.</description><identifier>ISSN: 0385-5600</identifier><identifier>EISSN: 1348-0421</identifier><identifier>DOI: 10.1111/j.1348-0421.1997.tb01205.x</identifier><identifier>PMID: 9159403</identifier><identifier>CODEN: MIIMDV</identifier><language>eng</language><publisher>Tokyo: Blackwell Publishing Ltd</publisher><subject>AIDS/HIV ; Anti-HIV Agents - therapeutic use ; Anti-HIV-1 activity ; Antibiotics. Antiinfectious agents. 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Drug treatments ; Protein Binding ; Reverse Transcriptase Inhibitors - pharmacokinetics ; Reverse Transcriptase Inhibitors - therapeutic use ; Thiadiazole derivatives ; Thiadiazoles - pharmacokinetics ; Thiadiazoles - therapeutic use ; Zidovudine - therapeutic use</subject><ispartof>MICROBIOLOGY and IMMUNOLOGY, 1997, Vol.41(4), pp.301-308</ispartof><rights>Center for Academic Publications Japan</rights><rights>owned by Center for Academic Publications Japan (Publisher)</rights><rights>1997 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6815-63ede3abe2add346629ea43a2624cfbfa22d134d206f9402707a88cbe018e1e73</citedby><cites>FETCH-LOGICAL-c6815-63ede3abe2add346629ea43a2624cfbfa22d134d206f9402707a88cbe018e1e73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fj.1348-0421.1997.tb01205.x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fj.1348-0421.1997.tb01205.x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,1427,1877,27901,27902,45550,45551,46384,46808</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2687308$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9159403$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fujiwara, Masatoshi</creatorcontrib><creatorcontrib>Ijichi, Katsushi</creatorcontrib><creatorcontrib>Hanasaki, Yasuaki</creatorcontrib><creatorcontrib>Ide, Teruhiko</creatorcontrib><creatorcontrib>Katsuura, Kimio</creatorcontrib><creatorcontrib>Takayama, Hiromitsu</creatorcontrib><creatorcontrib>Aimi, Norio</creatorcontrib><creatorcontrib>Shigeta, Shiro</creatorcontrib><creatorcontrib>Konno, Kenji</creatorcontrib><creatorcontrib>Yokota, Tomoyuki</creatorcontrib><creatorcontrib>Baba, Masanori</creatorcontrib><title>Thiadiazole Derivatives: Highly Potent and Selective Inhibitors of Human Immunodeficiency Virus Type 1 (HIV-1) Replications In Vitro</title><title>MICROBIOLOGY and IMMUNOLOGY</title><addtitle>Microbiology and Immunology</addtitle><description>We have recently reported that thiadiazole (TDA) derivatives are highly potent inhibitors of human immunodeficiency virus type 1 (HIV-1) replication. 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Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Biological and medical sciences</topic><topic>Cells, Cultured</topic><topic>Drug Resistance, Microbial - genetics</topic><topic>Drug Therapy, Combination</topic><topic>HIV Infections - drug therapy</topic><topic>HIV Protease Inhibitors - therapeutic use</topic><topic>HIV-1 - drug effects</topic><topic>HIV-1 - genetics</topic><topic>HIV-1 - growth & development</topic><topic>Human immunodeficiency virus 1</topic><topic>Humans</topic><topic>Leukocytes, Mononuclear</topic><topic>Medical sciences</topic><topic>Nonnucleoside reverse transcriptase inhibitor</topic><topic>Oligopeptides - therapeutic use</topic><topic>Pharmacology. 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These compounds belong to the family of nonnucleoside reverse transcriptase inhibitors (NNRTIs). In an attempt to develop more effective and pharmacologically favorable compounds, novel TDA derivatives have been synthesized and examined for their anti-HIV-1 activity in vitro. Among them, RD4-2217 was found to be the most potent inhibitor of HIV-1 replication. It inhibited replication of the HTLV-IIIB strain in MT-4 cells at a concentration of 6nM. RD4-2217 was also inhibitory to clinical isolates and zidovudine-resistant mutants of HIV-1. The combination of RD4-2217 with zidovudine or the protease inhibitor A-75925 synergistically inhibited HIV-1 replication. Studies on the emergence of drug-resistant mutants revealed that, although much higher concentrations (1-10μM) were required, RD4-2217 completely suppressed the breakthrough of HIV-1 in the supernatants during long-term culturing of infected cells. Furthermore, RD4-2217 at low concentrations (10 or 100nM), in combination with zidovudine, also completely inhibited viral breakthrough. In addition, RD4-2217 had lower lipophilicity and improved protein binding as compared to its congener RD4-2024 and loviride. These results suggest that RD4-2217, one of the TDA derivatives, is worth pursuing as a candidate drug for the treatment of HIV-1 infections.</abstract><cop>Tokyo</cop><pub>Blackwell Publishing Ltd</pub><pmid>9159403</pmid><doi>10.1111/j.1348-0421.1997.tb01205.x</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0385-5600 |
| ispartof | MICROBIOLOGY and IMMUNOLOGY, 1997, Vol.41(4), pp.301-308 |
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| recordid | cdi_proquest_miscellaneous_79002031 |
| source | J-STAGE Free; Wiley Free Content; MEDLINE; Wiley Online Library Journals Frontfile Complete; Open Access Titles of Japan; Alma/SFX Local Collection |
| subjects | AIDS/HIV Anti-HIV Agents - therapeutic use Anti-HIV-1 activity Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences Cells, Cultured Drug Resistance, Microbial - genetics Drug Therapy, Combination HIV Infections - drug therapy HIV Protease Inhibitors - therapeutic use HIV-1 - drug effects HIV-1 - genetics HIV-1 - growth & development Human immunodeficiency virus 1 Humans Leukocytes, Mononuclear Medical sciences Nonnucleoside reverse transcriptase inhibitor Oligopeptides - therapeutic use Pharmacology. Drug treatments Protein Binding Reverse Transcriptase Inhibitors - pharmacokinetics Reverse Transcriptase Inhibitors - therapeutic use Thiadiazole derivatives Thiadiazoles - pharmacokinetics Thiadiazoles - therapeutic use Zidovudine - therapeutic use |
| title | Thiadiazole Derivatives: Highly Potent and Selective Inhibitors of Human Immunodeficiency Virus Type 1 (HIV-1) Replications In Vitro |
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