Peptide nucleic acid conjugates
View Patent ↗A novel class of peptide nucleic acids are described which include a conjugate attached thereto. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.
1. A peptide nucleic acid of the formula:
wherein:
m is an integer from 1 to about 50;
L and L m independently are naturally occurring nucleobases;
C and C m are (CR 6 R 7 ) y ; wherein:
R 6 and R 7 are hydrogen;
R 3 is hydrogen;
D and D m are (CR 6 R 7 ) z ;
y is 1 and z is 2;
G m is —NR 3 CO— in either orientation;
each pair of A-A m and B-B m are >N—C(O)—CH 2 —;
I is —NR 8 R 9 or —NR 10 C(O)R 11 ; wherein:
R 8 , R 9 , R 10 and R 11 independently are hydrogen, alkyl, an amino protecting group, a reporter ligand, an intercalator, a chelator, a peptide, a protein, a carbohydrate, a lipid, a steroid, a nucleoside, a nucleotide, a nucleotide diphosphate, a nucleotide triphosphate, an oligonucleotide, an oligonucleoside, a soluble polymer, a non-soluble polymer, a reporter enzyme, a reporter molecule, a terpene, a phospholipid, a cell receptor binding molecule, a water soluble vitamin, a lipid soluble vitamin, an RNA/DNA cleaving complex, a porphyrin, or a polymeric compound selected from polymeric amines, polymeric glycols and polyethers; and
Q is —CO 2 H, —CO 2 R 8 , or —CONR 8 R 9 .
2. The peptide nucleic acid of claim 1 wherein R 8 , R 9 , R 10 and R 11 independently are hydrogen, alkyl, a peptide, a protein, a carbohydrate, a nucleoside, a nucleotide, a nucleotide diphosphate, a nucleotide triphosphate, an oligonucleotide, or an oligonucleoside.
3. The peptide nucleic acid of claim 1 wherein R 8 , R 9 , R 10 and R 11 independently are a nucleoside, a nucleotide, an oligonucleotide, or an oligonucleoside.