Patent ID: 6576752
Filing Date: 2003-06-10
Classification: A61P,C07H

Abstract:
An oligonucleotide comprising a plurality of nucleotide units of the structure: wherein:Bx is a radical derived from a naturally occurring or non-naturally occurring purine or pyrimidine nucleobase; each T1 and T2 is, individually, OH, a protected hydroxyl, a nucleotide, a nucleoside or an oligonucleotide; T3 is H, OH, a protected hydroxyl or a sugar substituent group; said oligonucleotide further comprising at least one group, R, therein; said R group occurring at the 5â€²-end, the 3â€²-end, in lieu of at least one T3 or as a substituent attached to at least one Bx; said R group having one of the formulas: â€ƒwherein: each Z is, independently, a single bond, O or a phosphate diester; each Q is, independently, H, C1-C10 alkyl or a nitrogen protecting group; each T0 is, independently, a bond or a linking moiety, said linking moiety being selected from the group consisting of â€”Oâ€”, â€”NHâ€”, â€”Sâ€”, substituted or unsubstituted C1-C10 alkylenyl, substituted or unsubstituted C2-C10 alkenylenyl and substituted or unsubstituted C2-C10 alkynylenyl wherein the substituent groups are selected from hydroxyl, alkoxy, benzyl, phenyl, nitro, â€”SH, â€”Sâ€”R10, a halogen atom, alkyl, aryl, alkenyl, alkynyl, and R9â€”OH, where R9 is alkylenyl, alkenylenyl or alkynylenyl and R10 is alkyl, alkenyl, or alkynyl; each L is, independently, a chemical functional group, a conjugate group or a solid support material, wherein: said chemical functional group is selected from the group consisting of C1-C10 alkyl, substituted C1-C10 alkyl, C2-C25 alkenyl, substituted C2-C25 alkenyl, C2-C15 alkynyl, substituted C2-C15 alkynyl, C4-C7 carbocyclic alkyl, substituted carbocyclic alkyl, alkenyl carbocyclic, substituted alkenyl carbocyclic, alkynyl carbocyclic, substituted alkynyl carbocyclic, C6-C20 aryl, substituted C6-C20 aryl, heteroaryl, substituted heteroaryl, a nitrogen, oxygen, or sulfur containing heterocycle group, a substituted nitrogen, oxygen, or sulfur containing heterocycle group, a mixed heterocycle group, or a substituted mixed heterocycle group, where said substituent groups are selected from alkyl, alkenyl, alkynyl, aryl, hydroxyl, alkoxy, R9â€”OH, benzyl, nitro, â€”SH, alkoxy-SH, and a halogen atom; or L is phthalimido, an ether group having 2 to 10 carbon atoms and 1 to 4 oxygen or sulfur atoms, a metal coordination group, a halogen atom, hydroxyl, â€”SH, carboxyl, NR11R12, CONR11, C(&boxH;NH)NR12R13, NHC(&boxH;NH)NR12R13), glutamyl (R11OOCCH(NR12R13) (CH2)2C(&boxH;O), â€”NO3, â€”NO2, â€”CN, trifluoromethyl, trifluoromethoxy, â€”NH-alkyl, â€”N-dialkyl, â€”O-aralkyl, â€”S-aralkyl, â€”NH-aralkyl, â€”N3, â€”NHNH2, â€”ONH2, a nucleosidic base, an amino acid side chain, or a carbohydrate, wherein each R11 and R12 is, independently, H, haloalkyl, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, or C6-C14 aryl; and each R13 is, independently, C6-C14 aryl, substituted C6-C14 aryl, heteroaryl, substituted heteroaryl, a nitrogen, oxygen, or sulfur containing heterocycle group, a substituted nitrogen, oxygen, or sulfur containing heterocycle group, a mixed heterocycle group, or a substituted mixed heterocycle group, wherein said substituent groups are selected from hydroxyl, alkoxy, R9â€”OH, benzyl, phenyl, NO2, SH, alkoxy-SH, a halogen atom, alkyl, aryl, alkenyl, and alkynyl groups; said conjugate group is selected from the group consisting of radicals derived from an intercalator, a reporter molecule, a contrast reagent, a cleaving agent, a cell targeting agent, a polyether, a phospholipid, cholesterol, acridine, fluorescein, rhodamine, coumarin, pyrene, retinal, a cyanine dye, a polyamine or a polyamide; or Q, T0 and L, together, are a chemical functional group; each m is, independently, an integer from 1 to about 10; and each n is, independently, an integer from 1 to about 6.