About: Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides

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About: Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides Goto Sponge NotDistinct Permalink

An Entity of Type : schema:ScholarlyArticle, within Data Space : wasabi.inria.fr associated with source document(s)

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type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
has title	Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides
Creator	Balzarini, Jan Derudas, Marco Pertusati, Fabrizio Serpi, Michaela Bourdin, Claire Chamberlain, Stanley Hamon, Nadège Hinsinger, Karen Introini, Andrea Kandil, Sahar Kolykhalov, Alexander Madela, Karolina Margolis, Leonid Meneghesso, Silvia Slusarczyk, Magdalena Vanpouille, Christophe Vernachio, John Mcguigan, Christopher
Source	Elsevier; Medline; PMC
abstract	We herein report the application of the phosphorodiamidate phosphate prodrug approach to a series of thirteen nucleoside analogs with antiviral or anticancer activity. Twenty-five symmetrical phosphorodiamidates were synthesized, bearing esterified l-Alanine (and in one case d-alanine) in the prodrug moiety, each as single stereoisomer. The presence of an achiral phosphorus represents a potential advantage over the phosphoramidate ProTide approach, where diastereoisomeric mixtures are routinely obtained, and different biological profiles may be expected from the diastereoisomers. Optimization of the synthetic pathway allowed us to identify two general methods depending on the particular nucleoside analogs. All the compounds were biologically evaluated in antiviral and anticancer assays and several showed improvement of activity compared to their parent nucleosides, as in the case of ddA, d4T, abacavir and acyclovir against HIV-1 and/or HIV-2. The biological results were supported by metabolism studies with carboxypeptidase Y monitored by (31)P NMR to investigate their bioactivation. This work further validates the phosphorodiamidate approach as a monophosphate prodrug motif with broad application in the antiviral and anticancer fields.
has issue date	2013-12-01(xsd:dateTime)
bibo:doi	10.1016/j.ejmech.2013.09.047
bibo:pmid	24177359
has license	green-oa
sha1sum (hex)	e9017314d5ca5cb633bc57077761da73a0bae324
schema:url	https://doi.org/10.1016/j.ejmech.2013.09.047
resource representing a document's title	Design, synthesis and biological evaluation of phosphorodiamidate prodrugs of antiviral and anticancer nucleosides
has PubMed Central identifier	PMC4358806
has PubMed identifier	24177359
schema:publication	European Journal of Medicinal Chemistry
resource representing a document's body	covid:e9017314d5ca5cb633bc57077761da73a0bae324#body_text
is schema:about of	named entity 'nucleoside' named entity 'antiviral' named entity 'antiviral' named entity 'D-Alanine' named entity 'antiviral' named entity 'DESIGN' named entity 'BIOLOGICAL EVALUATION' named entity 'PRESENCE OF' named entity 'MOIETY' named entity 'MEDIATED' named entity 'DIFFERENT' named entity 'MIXTURES' named entity 'ANTICANCER' named entity 'BOND' named entity 'ACHIRAL' named entity 'WORK' named entity 'DISPLACEMENT' named entity 'PROTIDE' named entity 'BEARING' named entity 'CASE' named entity 'ABACAVIR' named entity 'ESTERIFIED' named entity 'CARBOXYPEPTIDASE' named entity 'HIV-1' named entity 'PARENT' named entity 'NUCLEOSIDES' named entity 'RESULTS' named entity 'TWENTY-FIVE' named entity 'ALLOWED' named entity 'ANTIVIRAL' named entity 'IMPROVEMENT' named entity 'PARTICULAR' named entity 'CLEAVAGE' named entity 'APPROACH' named entity 'DDA' named entity 'PHOSPHORAMIDATE' named entity 'PRODRUGS' named entity 'SYNTHESIS' named entity 'GENERAL METHODS' named entity 'SINGLE' named entity 'COMPARED' named entity 'L-ALANINE' named entity 'ESTER' named entity 'D-ALANINE' named entity 'NMR' named entity 'SCHEME' named entity 'SPONTANEOUS' named entity 'MONITORED' named entity 'POTENTIAL' named entity 'THIRTEEN' named entity 'INTRACELLULAR' named entity 'ADVANTAGE' named entity 'ANTIVIRAL' named entity 'STEREOISOMER' named entity 'PHOSPHATE' named entity 'SUPPORTED' named entity 'SERIES' named entity 'TO INVESTIGATE' named entity 'NUCLEOSIDES' named entity 'OPTIMIZATION' named entity 'D4T' named entity 'HYDROLYSIS' named entity 'OBTAINED' named entity 'EVALUATED'

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