1998
DOI: 10.1055/s-1998-1637
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Pro-Nucleotides - Recent Advances in the Design of Efficient Tools for the Delivery of Biologically Active Nucleoside Monophosphates

Abstract: A summary of the most recent advances to the design of pronucleotides will be presented. Approaches that have been designed to be activated by enzymes such as carboxyesterases [bis(POM)-, bis(POC)-, bis(SATE)-, bis(AB) phosphotriesters and the arylphosphoramidates] or by reductases [bis(SDTE) approach] will be discussed as well as the amino acids phosphoramidate diester concept with its still unknown delivery mechanism and the cycloSal approach that releases the nucleotides by an induced tandem reaction.Nucleo… Show more

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Cited by 114 publications
(102 citation statements)
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“…Deprotection of the methyl esters of the amino acid part was carried out with sodium hydroxide (0.4 m) in a methanol/water solution at room temperature. An example of this type of synthesis is shown in Scheme 1 a for AspdAMP (1).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Deprotection of the methyl esters of the amino acid part was carried out with sodium hydroxide (0.4 m) in a methanol/water solution at room temperature. An example of this type of synthesis is shown in Scheme 1 a for AspdAMP (1).…”
Section: Resultsmentioning
confidence: 99%
“…[1] The important feature of most nucleotide prodrugs is that the negatively charged phosphate group remains masked outside the cell, allowing permeation through the lipophilic cell membrane, and the active nucleotide is processed in the cell by chemical and/or enzymatic degradation. [2,3] A suitable nucleotide prodrug also has to be stable in the extracellular medium so that it is not degraded outside the cell.…”
Section: Introductionmentioning
confidence: 99%
“…However, it is known that many of these analogs are poor substrates of nucleoside kinases; as such, they are slowly activated to the monophosphate form (Starnes and Cheng, 1987;Balzarini et al, 1989;Johnson and Fridland, 1989). To circumvent the need for a nucleoside kinase, membrane-permeable aryloxyalaninylphosphoramidate and cyclosaligenyl prodrugs of nucleoside 5Ј-monophosphate derivatives have been developed that result in direct intracellular delivery of free nucleoside monophosphates (reviewed in Meier, 1998). These drugs, however, might be susceptible to efflux by MRP4 or MRP5.…”
Section: Downloaded Frommentioning
confidence: 99%
“…As recently surveyed in a review by Meier (1998), a number of approaches are now emerging to the problem of the delivery of bio-active charged nucleotides into living cells. We have developed aryl phosphoramidates as an effective nucleotide delivery motif and have reported the application of this technology to potent anti-HIV drugs such as zidovudine (McGuigan et al, 1993) and stavudine (McGuigan et al, 1996a;Balzarini et al, 1996), to poorly active anti-HIV agents such as d4A (McGuigan et al, 1996b;Balzarini et al, 1997) and ddU (McGuigan et al, 1994) and to anti-herpetic agents such as netivudine (5-propynylaraU) (McGuigan et al, 1998a).…”
mentioning
confidence: 99%