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Original Articles

Second Generation of cycloSal‐Pronucleotides with Esterase‐Cleavable Sites: The ”Lock‐In”‐Concept

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Pages 89-115 | Received 31 Jul 2003, Accepted 19 Sep 2003, Published online: 01 Jun 2007

References

  • Meier , C. 2002 . CycloSal‐pronucleotides—design of chemical trojan horses . Mini Rev. Med. Chem. , 2 : 219 – 234 . [PUBMED] [INFOTRIEVE] [CSA]
  • Balzarini , J. , Aquaro , S. , Knispel , T. , Rampazzo , C. , Bianchi , V. , Perno , C.‐F. , De Clercq , E. and Meier , C. 2000 . Cyclosaligenyl‐2′,3′‐didehydro‐2′,3′‐dideoxythymidine monophosphate: Efficient intracellular delivery of d4TMP . Mol. Pharmacol. , 58 : 928 – 935 . [PUBMED] [INFOTRIEVE] [CSA]
  • Balzarini , J. , Naesens , L. , Aquaro , S. , Knispel , T. , Perno , C.‐F. , De Clercq , E. and Meier , C. 1999 . Intracellular Metabolism of cyclosaligenyl‐3′‐azido‐2′,3′‐dideoxythymidine monophosphate, a prodrug of 3′‐azido‐2′,3′‐dideoxythymidine (zidovudine) . Mol. Pharmacol. , 56 : 1354 – 1361 . [PUBMED] [INFOTRIEVE] [CSA]
  • Balzarini , J. , Baba , M. , Pauwels , R. , Herdewijn , P. and De Clercq , E. 1988 . Anti‐Retrovirus activity of 3′‐fluoro‐and 3′‐azido‐substituted pyrimidine 2′,3′‐dideoxynucleoside analogues . Biochem. Pharmacol. , 37 : 2847 – 2856 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Balzarini , J. and De Clercq , E. 1994 . Biochemical pharmacology of nucleoside analogs active against HIV . Biochem. Pharmacol. , 49 : 751 – 772 .
  • Meier , C. 1998 . Pronucleotides—recent advances in the design of efficient tools for the delivery of biologically active nucleoside monophosphates . Synlett , : 233 – 242 .
  • Wagner , C. R. , Iyer , V. V. and McIntee , E. J. 2000 . Pronucleotides: towards the in vivo delivery of antiviral and anticancer nucleotides . Med. Res. Rev. , 20 : 417 – 451 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Meier , C. , Renze , J. , Ducho , C. and Balzarini , J. 2002 . CycloSal‐d4TMP pronucleotides—structural variations, mechanistic insights and antiviral activity . Curr. Top. Med. Chem. , 2 : 1111 – 1121 . [CSA]
  • Meier , C. , Lorey , M. , De Clercq , E. and Balzarini , J. 1998 . CycloSal‐2′,3′‐didehydrothymidine monophosphate (cycloSal‐d4TMP): synthesis and antiviral evaluation of a new d4TMP delivery system . J. Med. Chem. , 41 : 1417 – 1427 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Meier , C. , Lorey , M. , De Clercq , E. and Balzarini , J. 1997 . Cyclic saligenyl phosphotriesters of 2′,3′‐didehydrothymidine (d4T)—a new pro‐nucleotide approach . Bioorg. Med. Chem. Lett. , 7 : 99 – 104 . [CROSSREF]
  • Meier , C. , Lomp , A. , Meerbach , A. and Wutzler , P. 2002 . CycloSal‐BVdUMP pronucleotides: How to convert an antiviral‐inactive nucleoside analogue into a bioactive compound against EBV . J. Med. Chem. , 45 : 5157 – 5172 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Meier , C. , Lomp , A. , Meerbach , A. and Wutzler , P. 2001 . CycloSaligenyl‐5‐[(E)‐2‐bromovinyl]‐2′‐deoxyuridine monophosphate (cycloSal‐BVDUMP) pronucleotides active against epstein–barr virus . ChemBioChem. , 4 : 283 – 285 . [CROSSREF]
  • Balzarini , J. , Haller‐Meier , F. , De Clercq , E. and Meier , C. 2002 . Antiviral activity of cyclosaligenyl prodrugs of acyclovir, carbovir and abacavir . Antivir. Chem. Chemother. , 12 : 301 – 306 . [CSA]
  • Meier , C. , Habel , L. , Haller‐Meier , F. , Lomp , A. , Herderich , M. , Klöcking , R. , Meerbach , A. and Wutzler , P. 1998 . Chemistry and anti‐herpes simplex virus type 1 evaluation of cycloSal‐nucleotides of acyclic nucleoside analogues . Antivir. Chem. Chemother. , 9 : 389 – 402 . [PUBMED] [INFOTRIEVE] [CSA]
  • Meier , C. , Knispel , T. , De Clercq , E. and Balzarini , J. 1999 . CycloSal‐pro‐nucleotides (cycloSal‐NMP) of 2′,3′‐dideoxyadenosine (ddA) and 2′,3′‐dideoxy‐2′,3′‐didehydroadenosine (d4A): synthesis and antiviral evaluation of a highly efficient nucleotide delivery system . J. Med. Chem. , 42 : 1604 – 1614 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Meier , C. , Knispel , T. , Marquez , V. E. , De Clercq , E. and Balzarini , J. 1999 . CycloSal‐pro‐nucleotides of 2′‐fluoro‐ara‐and 2′‐fluoro‐ribo‐2′,3′‐dideoxyadenosine (F‐ara‐ and F‐ribo‐ddA) as a strategy to bypass a metabolic blockade . J. Med. Chem. , 42 : 1615 – 1624 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • 2003 . Part of these data have been presented at the 15th International Conference on Antiviral Research, April 2003, Savannah, USA . Antivir. Res. , 57 : A39 [CSA]
  • McGuigan , C. , Cahard , D. , Sheeka , H. M. , De Clercq , E. and Balzarini , J. 1996 . Aryl phosphoramidate derivatives of d4T have improved anti‐HIV efficacy in tissue culture and may act by the generation of a novel intracellular metabolite . J. Med. Chem. , 39 : 1748 – 1753 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Périgaud , C. , Gosselin , G. and Imbach , J.‐L. 2000 . “ Anti‐HIV phosphotriester pronucleotides: basis for the rational design of biolabile phosphate protecting groups ” . In Biomedical Chemistry: Applying Chemical Principles to the Understandimng and Treatment of Disease Edited by: Torrence , P. F. 115 – 141 . John Wiley & Sons, Inc. . Chapter 5
  • Pearson , A. J. , Zhang , P. and Lee , K. 1996 . Application of arene‐ruthenium chemistry to a formal totsl synthesis of OF 4949III . J. Org. Chem. , 61 : 6581 – 6586 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Brechbühler , H. , Büchi , H. , Hatz , E. , Schreiber , J. and Eschenmoser , A. 1965 . Die reaktion von carbonsäuren mit acetalen des N,N‐dimethylformamids: eine veresterungsmethode . Helv. Chim. Acta , 48 : 1746 – 1771 . [CROSSREF]
  • Wengatz , I. , Stoutamire , D. W. , Gee , S. J. and Hammock , B. D. 1998 . Development of an enzyme‐linked immunosorbent assay for the detection of the pyrethroid insecticide fenpropathrin . J. Agric. Food Chem. , 46 : 2211 – 2221 . [CROSSREF]
  • Garber , S. B. , Kingsbury , J. S. , Gray , B. L. and Hoveyda , A. H. 2000 . Efficient and recyclable monomeric and dentritic Ru‐based metathesis catalysts . J. Am. Chem. Soc. , 122 : 8168 – 8179 . [CROSSREF]
  • Breton , G. W. 1997 . Selective monoacetylation of unsymmetric diols catalyzed by silica gel‐supported sodium hydrogen sulfate . J. Org. Chem. , 62 : 8952 – 8954 . [CROSSREF]
  • Yamada , S. , Sugaki , T. and Matsuzaki , K. 1996 . Twisted amides as selective acylating agents for hydroxyl groups under neutral conditions: models for activated peptides during enzymatic acyl transfer reaction . J. Org. Chem. , 61 : 5932 – 5938 . [CROSSREF]
  • Nagata , W. , Okada , K. and Aoki , T. 1979 . Ortho‐Specific α‐hydroxylation of phenols with aldehydes: An efficient synthesis of saligenol derivatives . Synthesis , : 365 – 368 . [CROSSREF]
  • Meier , C. , De Clercq , E. and Balzarini , J. 1998 . CycloSal‐3′‐azido‐2′,3′‐dideoxythymidine monophosphate (cycloSal‐AZTMP) – An unexpected failure of nucleotide delivery from a proven pro‐nucleotide system . Eur. J. Org. , : 837 – 846 . [CROSSREF]
  • van Boom , J. H. and Burgers , P. M.J. 1976 . Use of levulinic acid in the protection of oligonucleotides via the modified phosphotriester method: Synthesis of decaribonucleotide U‐A‐U‐A‐U‐A‐U‐A . Tetrahedron Lett. , 52 : 4875 – 4878 . [CROSSREF]

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