Conjugated 4'-desmethyl nucleoside analog compounds

Claim 2

A compound having the structure: ##STR13## wherein: R L is a group of formula: R.sub.C --[Y].sub.e --Z-- wherein: Z is O, S or HN; Y is a bivalent linker; e is 0 or 1; R C is alkyl, alkenyl, alkynyl, a polyamine, a polyether, a polythioether, a steroid molecule, a reporter molecule, an aromatic lipophilic molecule, a non-aromatic lipophilic molecule, a reporter enzyme, a peptide, a protein, a water soluble vitamin, a lipid soluble vitamin, a carbohydrate, a terpene molecule, a phospholipid, an intercalator, a cell receptor binding molecule, a crosslinking agent, or a porphyrin; B x is a nucleobase; X is H, OH, O-alkyl, O-alkoxyalkyl, O-alkylamino, or F; Q is O, S, CH 2 , CHF or CF 2 ; and R D is H, hydroxyl, an activated phosphorous group, a nucleoside, an activated nucleotide, a nucleotide, an oligonucleotide, an oligonucleoside or a protected derivative thereof.

Claim 3

The compound having the structure: ##STR14## wherein: L is a group of formula: R 7 --[W] a --[S--(CH 2 ) q ] u --[HN--(CH 2 ) n ] t --.sub.[O--(CH 2 ) m ] v --Z-- wherein: t, u and v are each independently integers from 0 to 200; m, n and q are each independently integers from 1 to 4; Z is S, O or HN; R 7 is R c , H, or a protecting group; B x is a nucleobase; X is H, OH, O-alkyl, O-alkoxylalkyl, O-alkylamino, or F; Q is O; W is the residue of a linking moiety, said linking moiety being selected from the group consisting of acid chlorides, anhydrides, cyclic anhydrides, alkyl halides, organometallics, chloroformates, isocynates, hydrazines, acids, hydroxylamines, semicarbazides, thiosemicarbazides, hydrazones, hydrazides, trityl thiol, oximes, hydrazide-hydrazones, semicarbazones and semithiocarbazones; a is 0 or 1; R D is H, hydroxyl, an activated phosphorous group, a nucleoside, an activated nucleotide, a nucleotide, an oligonucleotide, an oligonucleoside or a protected derivative thereof; R C is alkyl, alkenyl, alkynyl, a polyamine, a polyether, a polythioether, a steroid molecule, a reporter molecule, an aromatic lipophilic molecule, a non-aromatic lipophilic molecule, a reporter enzyme, a peptide, a protein, a water soluble vitamin, a lipid soluble vitamin, a carbohydrate, a terpene molecule, a phospholipid, an intercalator, a cell receptor binding molecule, a crosslinking agent, or a porphyrin; and provided that t, u and v are not all simultaneously 0.

Claim 4

The compound having the structure: ##STR14## wherein: L is a group of formula: R 7 --[W] a --[S--(CH 2 ) q ] u --[HN--(CH 2 ) n ] t --.sub.[O--(CH 2 ) m ] v --Z-- wherein: t, u and v are each independently integers from 0 to 200; m, n and q are each independently integers from 1 to 4; Z is S, O or HN; R 7 is R c , H, or a protecting group; B x is a nucleobase; X is H, OH, O-alkyl, O-alkoxylalkyl, O-alkylamino, or F; Q is O; W is the residue of a linking moiety, said linking moiety being selected from the group consisting of acid chlorides, anhydrides, cyclic anhydrides, alkyl halides, organometallics, chloroformates, isocynates, hydrazines, acids, hydroxylamines, semicarbazides, thiosemicarbazides, hydrazones, hydrazides, trityl thiol, oximes, hydrazide-hydrazones, semicarbazones and semithiocarbazones; a is 0 or 1; R D is H, hydroxyl, an activated phosphorous group, a nucleoside, an activated nucleotide, a nucleotide, an oligonucleotide, an oligonucleoside or a protected derivative thereof; R C is alkyl, alkenyl, alkynyl, a polyamine, a polyether, a polythioether, a steroid molecule, a reporter molecule, an aromatic lipophilic molecule, a non-aromatic lipophilic molecule, a reporter enzyme, a peptide, a protein, a water soluble vitamin, a lipid soluble vitamin, a carbohydrate, a terpene molecule, a phospholipid, an intercalator, a cell receptor binding molecule, a crosslinking agent, or a porphyrin; and provided that t, u and v are not all simultaneously 0.

Claim 5

The compound of claim 2 wherein t and u are 0.

Claim 6

The compound of claim 2 wherein t and u are 0, and m is 2.

Claim 7

The compound of claim 2 wherein u and v are 0.

Claim 8

The compound of claim 2 wherein u and v are 0 and n is 2.

Claim 9

The compound of claim 2 wherein X is H or OH.

Claim 10

The compound of claim 2 wherein R D is H or OH.

Claim 11

The compound of claim 2 wherein R D is an activated phosphorous group.

Claim 12

A compound of claim 2 wherein R D is an oligonucleotide.

Claim 13

The compound of claim 2 wherein t and v are 0.

Claim 14

The compound of claim 2 wherein t and v are 0 and q is 2.

Claim 15

The compound of claim 2 wherein Z is O or N.

Claim 16

The compound of claim 2 wherein R C is asteroid molecule.

Claim 17

A compound of claim 14 wherein the steroid molecule is cholic acid, deoxycholic acid, dehydrocholic acid, cortisone, digoxigenin, testosterone, cholesterol or 3-trimethylaminomethylhydrazido cortisone.

Claim 18

The compound of claim 2 wherein R C is a water soluble vitamin.

Claim 19

The compound of claim 16 wherein the water soluble vitamin is thiamine, riboflavin, nicotinic acid, pyridoxal phosphate, pyridoxine, pyridoxamine, deoxypyridoxine, pantothenic acid, biotin, folic acid, 5'-deoxyadenosylcobalamin, inositol, choline or ascorbic acid.

Claim 20

The compound of claim 2 wherein R C is a lipid soluble vitamin.

Claim 21

The compound of claim 18 wherein the lipid soluble vitamin is a retinal, a retinol, retinoic acid, β-carotene, vitamin D, cholecalciferol, a tocopherol, or a phytol.

Claim 22

The compound of claim 2 wherein R C is a protein.

Claim 23

The compound of claim 20 wherein the protein is a phosphodiesterase, a peroxidase, a phosphatase or a nuclease.

Claim 24

The compound of claim 2 wherein R C is a reporter molecule.

Claim 25

The compound of claim 22 wherein the reporter molecule is a chromaphore, a fluorophore or a radiolabel-containing moiety.

Claim 26

The compound of claim 23 wherein the fluorophore is fluorescein, chrysine, anthracene, perylene, pyrene, rhodamine.

Claim 27

The compound of claim 2 wherein X is F, O-alkyl having from one to six carbons, O-alkoxyalkyl having from 2 to 6 carbons, or O-alkylamino having from one to six carbons.

Claim 28

The compound of claim 2 wherein R D is H or OH.

Claim 29

The compound having the structure: ##STR15## wherein: R C is O-alkyl, O-alkenyl, O-alkynyl, a polyamine, a polyether, a steroid molecule, a reporter molecule, an aromatic lipophilic molecule, a non-aromatic lipophilic molecule, a reporter enzyme, a peptide, a protein, a water soluble vitamin, a lipid soluble vitamin, a carbohydrate, a terpene molecule, a phospholipid, an intercalator, a cell receptor binding molecule, a crosslinking agent, or a porphyrin; B x is a nucleobase; X is H, OH, O-alkyl, O-alkoxyalkyl, O-alkylamino, or F; Q is O, S, CH 2 , CHF or CF 2 ; and R D is H, hydroxyl, an activated phosphorous group, a nucleoside, an activated nucleotide, a nucleotide, an oligonucleotide, an oligonucleoside or a protected protected derivative thereof.

Claim 30

The compound having the structure: ##STR15## wherein: R C is O-alkyl, O-alkenyl, O-alkynyl, a polyamine, a polyether, a steroid molecule, a reporter molecule, an aromatic lipophilic molecule, a non-aromatic lipophilic molecule, a reporter enzyme, a peptide, a protein, a water soluble vitamin, a lipid soluble vitamin, a carbohydrate, a terpene molecule, a phospholipid, an intercalator, a cell receptor binding molecule, a crosslinking agent, or a porphyrin; B x is a nucleobase; X is H, OH, O-alkyl, O-alkoxyalkyl, O-alkylamino, or F; Q is O, S, CH 2 , CHF or CF 2 ; and R D is H, hydroxyl, an activated phosphorous group, a nucleoside, an activated nucleotide, a nucleotide, an oligonucleotide, an oligonucleoside or a protected protected derivative thereof.

Claim 31

The compound of claim 27 wherein R C is a polyether, a polyamine or a non-aromatic lipophilic molecule.

Claim 32

The compound having the structure: ##STR16## wherein: J is a leaving group; B x is a nucleobase; X is H, OH, O-alkyl, O-alkoxylalkyl, O-alkylamino, or F; Q is O, S, CH 2 , CHF or CF 2 ; and R D is H, hydroxyl, an activated phosphorous group, a nucleoside, an activated nucleotide, a nucleotide, an oligonucleotide, an oligonucleoside or a protected derivative thereof.

Claim 33

The compound having the structure: ##STR16## wherein: J is a leaving group; B x is a nucleobase; X is H, OH, O-alkyl, O-alkoxylalkyl, O-alkylamino, or F; Q is O, S, CH 2 , CHF or CF 2 ; and R D is H, hydroxyl, an activated phosphorous group, a nucleoside, an activated nucleotide, a nucleotide, an oligonucleotide, an oligonucleoside or a protected derivative thereof.

Claim 34

The compound of claim 29 wherein J is OH, SH, NH 2 , trifluoromethylsulfonyl, methylsulfonyl, halogen, O-trichloroacetimidate, acyloxy, dialkyl phosphite, 2,4,6-trichlorophenyl, p-toluenesulfonyl, 4-dimethylaminoazobenzenesulfonyl or 5-dimethylaminonaphthalenesulfonyl.