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Nuclease resistant, pyrimidine modified oligonucleotides that detect and modulate gene expression

  • US 5,614,617 A
  • Filed: 02/18/1993
  • Issued: 03/25/1997
  • Est. Priority Date: 07/27/1990
  • Status: Expired due to Term
First Claim
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1. An oligonucleotide or an oligonucleotide analog comprising at least five covalently bound nucleoside units connected together by phosphate linkages, which nucleoside units individually comprise a ribose or deoxyribose sugar portion covalently bound to a base portion, wherein a plurality of base portions are pyrimidine bases;

  • and at least one of said pyrimidine bases is a modified pyrimidine base having the structure;

    ##STR2## wherein;

    X=OH or NH2 ;

    B is selected from the group consisting of;

    C-lower alkyl, N, C--CF3, C--F, C--Cl, C--Br, C--I, C-halocarbon, C--NO2, C--CF3, C--SH, C--SCH3, C--OH, C--O-lower alkyl, C--CH2 OH, C--CH2 SH, C--CH2 SCH3, C--CH2 OCH3, C--NH2, C--CH2 NH2, C--alkyl-NH2, C-benzyl, C-aryl, C-substituted aryl or benzyl wherein said substituents are selected from the group consisting of methyl, hydroxyl, alkoxy, alcohol, benzyl, phenyl, nitro, thiol, and halogen;

    provided that when B is N, then said sugar portion to which said modified pyrimidine base is bound is deoxyribose; and

    A is selected from the group consisting of;

    C--H, N, C--CF3, C-halocarbon, C--NO2, C--OCF3, C--SH, C--SCH3, C--OH, C--O-lower alkyl, C--CH2 OH, C--CH2 SH, C--CH2 SCH3, C--CH2 OCH3, C--NH2, C--CH2 NH2, C-benzyl, C-aryl, C-substituted aryl or benzyl wherein said substituents are selected from the group consisting of methyl, hydroxyl, alkoxy, alcohol, benzyl, phenyl, nitro, thiol, and halogen.

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