Active cores of peptide triazole HIV-1 entry inhibitors

1. A composition comprising a peptide triazole conjugate comprising a peptide component, wherein the peptide component consists essentially of the sequence X 1 X 2 X 3 NIPWX 4 (SEQ ID No. 3), wherein:

the sequence X 1 X 2 X 3 NIPWX 4 is selected from the group consisting of SEQ ID No. 7 (RINNIPW), SEQ ID No. 13 (INNIPW), SEQ ID No. 14 (NNIPWS), SEQ ID No. 15 (INIPWS) and SEQ ID No. 21 (NNIPW);

the proline in SEQ ID No. 3 is modified according to Formula I:

and

R is a bulky aromatic group.

2. The composition of claim 1 , wherein the bulky aromatic group is selected from the group consisting of a naphthyl group; a para-alkyl-substituted phenyl, wherein the alkyl is methyl or ethyl; 2-phenylethyl; and a metallocene.

3. The composition of claim 1 , wherein the bulky aromatic group is a metallocene.

4. The composition of claim 3 , wherein the metallocene is ferrocene.

5. The composition of claim 1 , further comprising at least one pharmaceutically acceptable carrier.

6. The composition of claim 1 , further comprising cyanovirin-N or a functional derivative thereof.

7. The composition of claim 6 , wherein the peptide triazole conjugate is linked to the cyanovirin-N or a functional derivative thereof.

8. The composition of claim 6 , wherein the N-terminal residue of the peptide triazole conjugate is covalently linked to the C-terminal residue of the cyanovirin-N or functional derivative thereof.

9. The composition of claim 6 , wherein the composition is formulated for topical or parenteral administration.

10. The composition of claim 6 , wherein R is ferrocene.

11. A method of treating HIV infection in an individual diagnosed therewith, the method comprising administering a therapeutically effective amount of a peptide triazole conjugate to the individual, wherein the peptide triazole conjugate comprises a peptide component, wherein the peptide component consists essentially of the sequence X 1 X 2 X 3 NIPWX 4 (SEQ ID No. 3), wherein:

the sequence X 1 X 2 X 3 NIPWX 4 is selected from the group consisting of SEQ ID No. 7 (RINNIPW), SEQ ID No. 13 (INNIPW), SEQ ID No. 14 (NNIPWS), SEQ ID No. 15 (INIPWS) and SEQ ID No. 21 (NNIPW);

the proline in SEQ ID NO. 3 is modified according to Formula I:

and

R is a bulky aromatic group.

12. The method of claim 11 , wherein the bulky aromatic group is selected from the group consisting of a naphthyl group; a para-alkyl-substituted phenyl, wherein the alkyl is methyl or ethyl; 2-phenylethyl; and a metallocene.

13. The method of claim 11 , wherein the bulky aromatic group is a metallocene.

14. The method of claim 11 , wherein the metallocene is ferrocene.

15. The method of claim 11 , wherein the peptide triazole conjugate is administered to the individual in a pharmaceutical composition comprising a pharmaceutically acceptable carrier.

16. The method of claim 11 , wherein the pharmaceutical composition further comprises cyanovirin-N or a functional derivative thereof.

17. A method of isolating a viral envelope protein gp120 from a sample, the method comprising the steps of:

contacting a solid phase matrix with a sample comprising gp120, wherein a peptide triazole conjugate is linked to the solid phase matrix,

wherein the peptide triazole conjugate comprises a peptide component, wherein the peptide component consists essentially of the sequence X 1 X 2 X 3 NIPWX 4 (SEQ ID No. 3), wherein:

the sequence X 1 X 2 X 3 NIPWX 4 is selected from the group consisting of SEQ ID No. 7 (RINNIPW), SEQ ID No. 13 (INNIPW), SEQ ID No. 14 (NNIPWS), SEQ ID No. 15 (INIPWS) and SEQ ID No. 21 (NNIPW);

the proline in SEQ ID NO. 3 is modified according to Formula I:

and

R is a bulky aromatic group,

wherein the gp120 binds to the peptide triazole conjugate, thereby partitioning the sample into a bound phase and an unbound phase; and

separating the unbound phase from the unbound phase, thereby isolating the gp 120.