Inhibitory effects of various 5-halogenated derivatives of 1-.beta.-D-arabinofuranosyluracil 5'-triphosphate on DNA polymerases from murine cells and oncornavirus: substituent effects on inhibitory action
The effects of four 5-halogenated derivatives of 1- beta -D-arabinofuranosyluracil 5'-triphosphate (aUTP) on the activity of DNA polymerases from mouse cells and oncornavirus were examined. The newly synthesized and tested compounds in this study were 1- beta -D-arabinofuranosyl-5-fluorouracil...
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| Veröffentlicht in: | Biochemistry (Easton) 1982-03, Vol.21 (5), p.1019-1024 |
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| container_title | Biochemistry (Easton) |
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| creator | Ono, Katsuhiko Ogasawara, Masako Ohashi, Atsuko Matsukage, Akio Takahashi, Taijo Nakayama, Chikao Saneyoshi, Mineo |
| description | The effects of four 5-halogenated derivatives of 1- beta -D-arabinofuranosyluracil 5'-triphosphate (aUTP) on the activity of DNA polymerases from mouse cells and oncornavirus were examined. The newly synthesized and tested compounds in this study were 1- beta -D-arabinofuranosyl-5-fluorouracil 5'-triphosphate (aFUTP), 1- beta -D-arabinofuranosyl-5-chlorouracil 5'-triphosphate (aClUTP), 1- beta -D-arabinofuranosyl-5-bromouracil 5'-triphosphate (aBrUTP), and 1- beta --D-atabinofuranosyl-5-iodouracil 5'-triphosphate (aIUTP). It was concluded that both steric and hydrophobic effects of the halogen substituents were important for the inhibition of all DNA polymerases and that the effect of halogen atoms was clearly observed for DNA polymerase beta with activated DNA and for RLV DNA polymerase with (rA) sub(n) multiplied by (dT) sub(12-18). |
| doi_str_mv | 10.1021/bi00534a029 |
| format | Article |
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The newly synthesized and tested compounds in this study were 1- beta -D-arabinofuranosyl-5-fluorouracil 5'-triphosphate (aFUTP), 1- beta -D-arabinofuranosyl-5-chlorouracil 5'-triphosphate (aClUTP), 1- beta -D-arabinofuranosyl-5-bromouracil 5'-triphosphate (aBrUTP), and 1- beta --D-atabinofuranosyl-5-iodouracil 5'-triphosphate (aIUTP). It was concluded that both steric and hydrophobic effects of the halogen substituents were important for the inhibition of all DNA polymerases and that the effect of halogen atoms was clearly observed for DNA polymerase beta with activated DNA and for RLV DNA polymerase with (rA) sub(n) multiplied by (dT) sub(12-18).</description><identifier>ISSN: 0006-2960</identifier><identifier>EISSN: 1520-4995</identifier><identifier>DOI: 10.1021/bi00534a029</identifier><identifier>PMID: 6176266</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>1- beta -D-arabinofuranosyluracil 5'-triphosphate ; Animals ; Arabinofuranosyluracil - pharmacology ; Arabinonucleotides - pharmacology ; cell lines ; DNA polymerase ; Kinetics ; Mice ; Nucleic Acid Synthesis Inhibitors ; oncornavirus ; Reverse Transcriptase Inhibitors ; Structure-Activity Relationship ; Uridine - analogs & derivatives ; Uridine Triphosphate - analogs & derivatives</subject><ispartof>Biochemistry (Easton), 1982-03, Vol.21 (5), p.1019-1024</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a385t-1cd085e0b6c21e6fe581701b7a6375625b6fc430f11257978ae49f626d02ed253</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bi00534a029$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bi00534a029$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6176266$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ono, Katsuhiko</creatorcontrib><creatorcontrib>Ogasawara, Masako</creatorcontrib><creatorcontrib>Ohashi, Atsuko</creatorcontrib><creatorcontrib>Matsukage, Akio</creatorcontrib><creatorcontrib>Takahashi, Taijo</creatorcontrib><creatorcontrib>Nakayama, Chikao</creatorcontrib><creatorcontrib>Saneyoshi, Mineo</creatorcontrib><title>Inhibitory effects of various 5-halogenated derivatives of 1-.beta.-D-arabinofuranosyluracil 5'-triphosphate on DNA polymerases from murine cells and oncornavirus: substituent effects on inhibitory action</title><title>Biochemistry (Easton)</title><addtitle>Biochemistry</addtitle><description>The effects of four 5-halogenated derivatives of 1- beta -D-arabinofuranosyluracil 5'-triphosphate (aUTP) on the activity of DNA polymerases from mouse cells and oncornavirus were examined. The newly synthesized and tested compounds in this study were 1- beta -D-arabinofuranosyl-5-fluorouracil 5'-triphosphate (aFUTP), 1- beta -D-arabinofuranosyl-5-chlorouracil 5'-triphosphate (aClUTP), 1- beta -D-arabinofuranosyl-5-bromouracil 5'-triphosphate (aBrUTP), and 1- beta --D-atabinofuranosyl-5-iodouracil 5'-triphosphate (aIUTP). It was concluded that both steric and hydrophobic effects of the halogen substituents were important for the inhibition of all DNA polymerases and that the effect of halogen atoms was clearly observed for DNA polymerase beta with activated DNA and for RLV DNA polymerase with (rA) sub(n) multiplied by (dT) sub(12-18).</description><subject>1- beta -D-arabinofuranosyluracil 5'-triphosphate</subject><subject>Animals</subject><subject>Arabinofuranosyluracil - pharmacology</subject><subject>Arabinonucleotides - pharmacology</subject><subject>cell lines</subject><subject>DNA polymerase</subject><subject>Kinetics</subject><subject>Mice</subject><subject>Nucleic Acid Synthesis Inhibitors</subject><subject>oncornavirus</subject><subject>Reverse Transcriptase Inhibitors</subject><subject>Structure-Activity Relationship</subject><subject>Uridine - analogs & derivatives</subject><subject>Uridine Triphosphate - analogs & derivatives</subject><issn>0006-2960</issn><issn>1520-4995</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1982</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUFv1DAQhSMEKkvhxBnJJ3pAXuwktjfcqpaWogqQWCRu1iQZsy6JvbWdFfsf-6PwsquWAxKnkfU-Pc-8VxQvOZtzVvK3rWVMVDWwsnlUzLgoGa2bRjwuZowxSctGsqfFsxhv8rNmqj4qjiRXspRyVtxduZVtbfJhS9AY7FIk3pANBOunSARdweB_oIOEPekx2A0ku8E_EKfzFhPM6TmFAK113kwBnI_bIc_ODkSc0BTseuXjepUdiHfk_NMpWfthO2KAmH1M8CMZp2Adkg6HIRJwfQY7HxxsbJjiOxKnNiabJnTpYUlH7MPq0CXr3fPiiYEh4ovDPC6-Xbxfnn2g158vr85OrylUC5Eo73q2EMha2ZUcpUGx4IrxVoGslJClaKXp6ooZzkuhGrUArBuT8-pZiX0pquPi9d53HfzthDHp0cbd8uAwp6ZVnWvhtfwvyEUtqoXagW_2YBd8jAGNXgc7QthqzvSuZP1XyZl-dbCd2hH7e_bQatbpXrcx4a97GcJPLVU-US-_fNXfP16qqmZLveNP9jx0Ud_4KSc_xH_-_BuAgcFX</recordid><startdate>19820302</startdate><enddate>19820302</enddate><creator>Ono, Katsuhiko</creator><creator>Ogasawara, Masako</creator><creator>Ohashi, Atsuko</creator><creator>Matsukage, Akio</creator><creator>Takahashi, Taijo</creator><creator>Nakayama, Chikao</creator><creator>Saneyoshi, Mineo</creator><general>American Chemical Society</general><scope>BSCLL</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>7QL</scope><scope>7TM</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>19820302</creationdate><title>Inhibitory effects of various 5-halogenated derivatives of 1-.beta.-D-arabinofuranosyluracil 5'-triphosphate on DNA polymerases from murine cells and oncornavirus: substituent effects on inhibitory action</title><author>Ono, Katsuhiko ; 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The newly synthesized and tested compounds in this study were 1- beta -D-arabinofuranosyl-5-fluorouracil 5'-triphosphate (aFUTP), 1- beta -D-arabinofuranosyl-5-chlorouracil 5'-triphosphate (aClUTP), 1- beta -D-arabinofuranosyl-5-bromouracil 5'-triphosphate (aBrUTP), and 1- beta --D-atabinofuranosyl-5-iodouracil 5'-triphosphate (aIUTP). It was concluded that both steric and hydrophobic effects of the halogen substituents were important for the inhibition of all DNA polymerases and that the effect of halogen atoms was clearly observed for DNA polymerase beta with activated DNA and for RLV DNA polymerase with (rA) sub(n) multiplied by (dT) sub(12-18).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>6176266</pmid><doi>10.1021/bi00534a029</doi><tpages>6</tpages></addata></record> |
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| ispartof | Biochemistry (Easton), 1982-03, Vol.21 (5), p.1019-1024 |
| issn | 0006-2960 1520-4995 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | 1- beta -D-arabinofuranosyluracil 5'-triphosphate Animals Arabinofuranosyluracil - pharmacology Arabinonucleotides - pharmacology cell lines DNA polymerase Kinetics Mice Nucleic Acid Synthesis Inhibitors oncornavirus Reverse Transcriptase Inhibitors Structure-Activity Relationship Uridine - analogs & derivatives Uridine Triphosphate - analogs & derivatives |
| title | Inhibitory effects of various 5-halogenated derivatives of 1-.beta.-D-arabinofuranosyluracil 5'-triphosphate on DNA polymerases from murine cells and oncornavirus: substituent effects on inhibitory action |
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