About: A system of protein target sequences for anti-RNA-viral chemotherapy by a vitamin B6-Derived zinc-Chelating trioxa-adamantane-triol

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About: A system of protein target sequences for anti-RNA-viral chemotherapy by a vitamin B6-Derived zinc-Chelating trioxa-adamantane-triol Goto Sponge NotDistinct Permalink

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type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
has title	A system of protein target sequences for anti-RNA-viral chemotherapy by a vitamin B6-Derived zinc-Chelating trioxa-adamantane-triol
Creator	Kesel, Andreas
Source	Elsevier; Medline; PMC
abstract	Abstract The synthesis of the structurally unusual heterotricyclic compound 1-[3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinyl]-2,8,9-trioxaadamantane-3,5,7-triol (trivially named bananin, BN) from pyridoxylidenephloroglucinol and a theoretical prospect on possible biological activities of BN are presented in this report. Pyridoxylidenephloroglucinol is synthesized by Knoevenagel condensation of the vitamin B6 aldehyde pyridoxal with phloroglucinol. Pyridoxylidenephloroglucinol rearranges to light-yellow (4′RS)-1′,4′-dihydrobananin by refluxing in 5M hydrochloric acid. Air oxidation subsequently forms BN in the heat which immediately yields orange-yellow (4′RS)-4′-chloro-1′,4′-dihydrobananin by 1,4-addition of hydrogen chloride. This intermediate could be isolated but, interestingly, not a BN hydrochloride. Brown BN is finally achieved by base-catalyzed elimination of hydrogen chloride from (4′RS)-4′-chloro-1′,4′-dihydrobananin. Regarding possible biological activities, it was demonstrated that BN acts as zinc (Zn2+) chelator. Therefore, a target of interest could be the human immunodeficiency virus type 1 (HIV-1) zinc finger HIV-1 RNA-binding nucleocapsid protein p7 (NCp7). Through suggested zinc ejection from HIV-1 genomic RNA ψ-element-binding and HIV-1–RNA-duplex packaging NCp7 by BN, thus rendering NCp7 functionally obsolete, it is deduced that HIV-1 replication and effective infectious virion encapsidation could be inhibited by BN. Furthermore, theoretical and structural considerations propose that BN is converted into bananin 5′-monophosphate (BNP) by the cell type-ubiquitous human enzyme pyridoxal kinase (EC 2.7.1.35). Together with the putative antilentiviral retinoid vitamin A–vitamin B6 conjugate analogue B6RA (Kesel, A. J. Biochem. Biophys. Res. Comm. 2003, 300, 793), BNP is postulated to serve as effector in a system of protein target sequences RX(D/E) of RNA virus components. Human immunodeficiency Retroviridae (HIVs) could possibly be influenced by B6RA and BNP. In addition, candidate targets of B6RA and BNP could be adsorption, transcription and/or viral RNA replication of an interestingly wide RNA virus selection including Picornaviridae (poliovirus, human coxsackievirus, hepatitis A virus), Flaviviridae (yellow fever virus, Dengue virus, West Nile virus, Kunjin virus, St. Louis encephalitis virus, hepatitis C virus), Togaviridae (rubella virus), Coronaviridae (human coronavirus, human SARS-associated coronavirus), Rhabdoviridae (rabies virus), Paramyxoviridae (human parainfluenza virus, measles virus, human respiratory syncytial virus), Filoviridae (Marburg virus, Ebola virus), Bornaviridae (Borna disease virus), Bunyaviridae (Hantaan virus), Arenaviridae (Lassa virus), and Reoviridae (human rotavirus). The postulated scope of ‘metabolically trapped’ BNP might resemble the antiviral spectrum of the RNA-viral virustatic ribavirin.
has issue date	2003-10-15(xsd:dateTime)
bibo:doi	10.1016/s0968-0896(03)00500-5
bibo:pmid	14527557
has license	els-covid
sha1sum (hex)	5e8383ad76e29894b360169a1efe7a0565351fff
schema:url	https://doi.org/10.1016/s0968-0896%2803%2900500-5
resource representing a document's title	A system of protein target sequences for anti-RNA-viral chemotherapy by a vitamin B6-Derived zinc-Chelating trioxa-adamantane-triol
has PubMed Central identifier	PMC7157923
has PubMed identifier	14527557
schema:publication	Bioorganic & Medicinal Chemistry
resource representing a document's body	covid:5e8383ad76e29894b360169a1efe7a0565351fff#body_text
is schema:about of	named entity 'poliovirus' named entity 'replication' named entity 'The' named entity 'target' named entity 'Therefore' named entity 'virus' named entity 'yellow fever virus' named entity 'human immunodeficiency virus' named entity 'Kunjin virus' named entity 'viral' named entity 'human respiratory syncytial virus' named entity 'ribavirin' named entity 'acts' named entity 'rearranges' named entity 'Dengue virus' named entity 'Ebola virus' named entity 'CONVERTED' named entity 'HUMAN IMMUNODEFICIENCY VIRUS TYPE 1' named entity 'BANANIN' named entity 'VIRUS' named entity 'VITAMIN B 6' named entity 'EFFECTOR' named entity 'CELL TYPE' named entity '2C5' named entity '2C4' named entity 'HUMAN' named entity 'PARAINFLUENZA VIRUS' named entity 'FILOVIRIDAE' named entity 'SYNTHESIS' named entity 'YELLOW' named entity 'RNA VIRUS' named entity 'DEMONSTRATED' named entity 'EBOLA VIRUS' named entity 'SELECTION' named entity 'HETEROTRICYCLIC COMPOUND' named entity 'SYSTEM' named entity 'FLAVIVIRIDAE' named entity 'ADDITION' named entity 'BINDING' named entity 'ANTIVIRAL' named entity 'HYDROGEN CHLORIDE' named entity 'DISEASE VIRUS' named entity 'ISOLATED' named entity 'VITAMIN A' named entity 'INFECTIOUS' covid:arg/5e8383ad76e29894b360169a1efe7a0565351fff named entity 'ZINC' named entity 'RETROVIRIDAE' named entity 'RES' named entity 'CORONAVIRUS' named entity 'VITAMIN B 6' named entity 'KUNJIN VIRUS' named entity 'REPORT' named entity 'HUMAN RESPIRATORY SYNCYTIAL VIRUS' named entity 'PYRIDOXAL' named entity 'EFFECTIVE' named entity 'NAMED' named entity 'BROWN' named entity 'HIV-1 REPLICATION' named entity 'COMPONENTS' named entity 'DENGUE VIRUS' named entity 'PICORNAVIRIDAE' named entity 'HEAT' named entity 'TRAPPED' named entity 'HYDROXY' named entity 'HUMAN COXSACKIEVIRUS' named entity 'PROTEIN TARGET' named entity 'A VITAMIN' named entity 'THE CELL' named entity 'TRIOL' named entity 'BORNAVIRIDAE' named entity 'TRANSCRIPTION' named entity 'ROTAVIRUS' named entity 'ENCAPSIDATION' named entity 'SEQUENCES' named entity 'TARGETS' named entity 'RHABDOVIRIDAE' named entity 'CORONAVIRIDAE' named entity 'CHEMOTHERAPY' named entity 'SYSTEM' named entity 'TRIOL'

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