US 8,148,322 B2Granted

Method and carrier complexes for delivering molecules to cells

AssigneeCornell Research Foundation, Inc.

InventorsHazel Szeto, Kesheng Zhao, Hugh Robertson, Alex Birk

Life of this patent

Estimating the term…

Abstract

The invention relates to carrier complexes and methods for delivering molecules to cells. The carrier complexes comprises a molecule and an aromatic cationic peptide in accordance with the invention. In one embodiment, the method for delivering a molecule to a cell comprises contacting the cell with a carrier complex. In another embodiment, the method for delivering a molecule to a cell comprises contacting the cell with a molecule and an aromatic cationic peptide.

Claims20

Dependent claims

A carrier complex comprising a biological molecule conjugated to an aromatic cationic peptide, wherein the aromatic cationic peptide is selected from the group consisting of:

Lys-D-Arg-Tyr-NH2,
Phe-D-Arg-His,
D-Tyr-Trp-Lys-NH2,
Trp-D-Lys-Tyr-Arg-NH2,
Tyr-His-D-Gly-Met,
Phe-Arg-D-His-Asp,
Tyr-D-Arg-Phe-Lys-Glu-NH2 (SEQ ID NO:
3),
Met-Tyr-D-Lys-Phe-Arg (SEQ ID NO:
4),
D-His-Glu-Lys-Tyr-D-Phe-Arg (SEQ ID NO:
5),
Lys-D-Gln-Tyr-Arg-D-Phe-Trp-NH2 (SEQ ID NO:
6),
Phe-D-Arg-Lys-Trp-Tyr-D-Arg-His (SEQ ID NO:
7),
Gly-D-Phe-Lys-Tyr-His-D-Arg-Tyr-NH2 (SEQ ID NO:
8),
Val-D-Lys-His-Tyr-D-Phe-Ser-Tyr-Arg-NH−2 (SEQ ID NO:
9),
Trp-Lys-Phe-D-Asp-Arg-Tyr-D-His-Lys (SEQ ID NO:
10),
Lys-Trp-D-Tyr-Arg-Asn-Phe-Tyr-D-His-NH2 (SEQ ID NO:
11),
Thr-Gly-Tyr-Arg-D-His-Phe-Trp-D-His-Lys (SEQ ID NO:
12),
Asp-D-Trp-Lys-Tyr-D-His-Phe-Arg-D-Gly-Lys-NH2 (SEQ ID NO:
13),
D-His-Lys-Tyr-D-Phe-Glu-D-Asp-D-His-D-Lys-Arg-Trp-NH2 (SEQ ID NO:
14),
Ala-D-Phe-D-Arg-Tyr-Lys-D-Trp-His-D-Tyr-Gly-Phe (SEQ ID NO:
15),
Tyr-D-Arg-Phe-Orn-NH2,
Tyr-D-Arg-Phe-Dab-NH2,
Tyr-D-Arg-Phe-Dap-NH2,
2′6′Dmt-D-Arg-Phe-Lys-Cys-NH2 (SEQ ID NO:
16),
2′6′Dmt-D-Arg-Phe-Lys-NH(CH2)2-NH-dns-NH2,
2′6′Dmt-D-Arg-Phe-Lys-NH(CH2)2-NH-atn-NH2,
2′6′Dmt-D-Arg-Phe-dnsLys-NH2,
2′6′Dmt-D-Cit-Phe-Lys-NH2,
2′6′Dmt-D-Cit-Phe-Ahp-NH2,
2′6′Dmt-D-Arg-Phe-Orn-NH2,
2′6′Dmt-D-Arg-Phe-Dab-NH2,
2′6′Dmt-D-Arg-Phe-Dap-NH2,
2′6′Dmt-D-Arg-Phe-Ahp(2-aminoheptanoic acid)-NH2,
3′5′Dmt-D-Arg-Phe-Lys-NH2,
3′5′Dmt-D-Arg-Phe-Orn-NH2,
3′5′Dmt-D-Arg-Phe-Dab-NH2,
3′5′Dmt-D-Arg-Phe-Dap-NH2,
Tyr-D-Arg-Tyr-Lys-NH2,
Tyr-D-Arg-Tyr-Orn-NH2,
Tyr-D-Arg-Tyr-Dab-NH2,
Tyr-D-Arg-Tyr-Dap-NH2,
2′6′Dmt-D-Arg-Tyr-Lys-NH2,
2′6′Dmt-D-Arg-Tyr-Orn-NH2,
2′6′Dmt-D-Arg-Tyr-Dab-NH2,
2′6′Dmt-D-Arg-Tyr-Dap-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Lys-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Orn-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Dab-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Pap-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Arg-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Lys-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Orn-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Dab-NH2,
Tyr-D-Lys-Phe-Dap-NH2,
Tyr-D-Lys-Phe-Arg-NH2,
Tyr-D-Lys-Phe-Lys-NH2,
Tyr-D-Lys-Phe-Orn-NH2,
2′6′Dmt-D-Lys-Phe-Dab-NH2,
2′6′Dmt-D-Lys-Phe-Dap-NH2,
2′6′Dmt-D-Lys-Phe-Arg-NH2,
2′6′Dmt-D-Lys-Phe-Lys-NH2,
3′5′Dmt-D-Lys-Phe-Orn-NH2,
3′5′Dmt-D-Lys-Phe-Dab-NH2,
3′5′Dmt-D-Lys-Phe-Dap-NH2,
3′5′Dmt-D-Lys-Phe-Arg-NH2,
Tyr-D-Lys-Tyr-Lys-NH2,
Tyr-D-Lys-Tyr-Orn-NH2,
Tyr-D-Lys-Tyr-Dab-NH2,
Tyr-D-Lys-Tyr-Dap-NH2,
2′6′Dmt-D-Lys-Tyr-Lys-NH2,
2′6′Dmt-D-Lys-Tyr-Orn-NH2,
2′6′Dmt-D-Lys-Tyr-Dab-NH2,
2′6′Dmt-D-Lys-Tyr-Dap-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Lys-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Orn-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Dab-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Dap-NH2,
2′6′Dmt-D-Arg-Phe-dnsDap-NH2,
2′6′Dmt-D-Arg-Phe-atnDap-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Lys-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Orn-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Dab-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Dap-NH2,
Tyr-D-Lys-Phe-Arg-NH2,
Tyr-D-Orn-Phe-Arg-NH2,
Tyr-D-Dap-Phe-Arg-Tyr-NH2,
2′6′Dmt-D-Arg-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Lys-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Orn-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Dab-Phe-Arg-2′6′Dmt-NH2,
3′5′Dmt-D-Dap-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Arg-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Lys-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Orn-Phe-Arg-3′5′Dmt-NH2,
Tyr-D-Lys-Tyr-Arg-Tyr-NH2,
Tyr-D-Orn-Tyr-Arg-Tyr-NH2,
Tyr-D-Dab-Tyr-Arg-Tyr-NH2,
Tyr-D-Dap-Tyr-Arg-Tyr-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Arg-2′6′Dmt-NH2,
2′6′Drnt-D-Lys-2′6′Dmt-Arg-2′6′Drnt-NH2,
2′6′Dmt-D-Orn-2′6′Dmt-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Dab-2′6′Dmt-Arg-2′6′Dmt-NH2,
3′5′Dmt-D-Dap-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Orn-3′5′Dmt-Arg-3′5′Dmt-NH2,
Mmt-D-Arg-Phe-Lys-Mmt-NH2,
Mmt-D-Arg-Phe-Orn-Mmt-NH2,
Mmt-D-Arg-Phe-Dab-Mmt-NH2,
Mmt-D-Arg-Phe-Dap-Mmt-NH2,
Tmt-D-Arg-Phe-Lys-Tmt-NH2,
Tmt-D-Arg-Phe-Orn-Tmt-NH2,
Tmt-D-Arg-Phe-Dab-Tmt-NH2,
Tmt-D-Arg-Phe-Dap-Tmt-NH2,
Hmt-D-Arg-Phe-Lys-Hmt-NH2,
Hmt-D-Arg-Phe-Orn-Hmt-NH2,
Hmt-D-Arg-Phe-Dab-Hmt-NH2,
Hmt-D-Arg-Phe-Dap-Hmt-NH2,
Mmt-D-Lys-Phe-Lys-Mmt-NH2,
Mmt-D-Lys-Phe-Orn-Mmt-NH2,
Mmt-D-Lys-Phe-Dab-Mmt-NH2,
Mmt-D-Lys-Phe-Dap-Mmt-NH2,
Mmt-D-Lys-Phe-Arg-Mmt-NH2,
Tmt-D-Lys-Phe-Lys-Tmt-NH2,
Tmt-D-Lys-Phe-Om-Tmt-NH2,
Tmt-D-Lys-Phe-Dab-Tmt-NH2,
Tmt-D-Lys-Phe-Dap-Tmt-NH2,
Tmt-D-Lys-Phe-Arg-Tmt-NH2,
Hmt-D-Lys-Phe-Lys-Hmt-NH2,
Hmt-D-Lys-Phe-Orn-Hmt-NH2,
Hmt-D-Lys-Phe-Dab-Hmt-NH2,
Hmt-D-Lys-Phe-Dap-Hmt-NH2,
Hmt-D-Lys-Phe-Arg-Hmt-NH2,
Mmt-D-Lys-Phe-Arg-Mmt-NH2,
Mmt-D-Orn-Phe-Arg-NH2,
Mmt-D-Dab-Phe-Arg-NH2,
Mmt-D-Dap-Phe-Arg-NH2,
Mmt-D-Arg-Phe-Arg-NH2,
Tmt-D-Lys-Phe-Arg-NH2,
Tmt-D-Orn-Phe-Arg-NH2,
Tmt-D-Dab-Phe-Arg-NH2,
Tmt-D-Dap-Phe-Arg-NH2,
Tmt-D-Arg-Phe-Arg-NH2,
Hmt-D-Lys-Phe-Arg-NH2,
Hmt-D-Orn-Phe-Arg-NH2,
Hmt-D-Dab-Phe-Arg-NH2,
Hmt-D-Dap-Phe-Arg-NH2,
Hmt-D-Arg-Phe-Arg-NH2,
D-Arg-Dmt-Lys-Phe-NH2,
D-Arg-Dmt-Phe-Lys-NH2,
D-Arg-Phe-Lys-Dmt-NH2,
D-Arg-Phe-Dmt-Lys-NH2,
D-Arg-Lys-Drnt-Phe-NH2,
D-Arg-Lys-Phe-Dmt-NH2,
Phe-Lys-Dmt-D-Arg-NH2,
Phe-Lys-D-Arg-Dmt-NH2,
Phe-D-Arg-Dmt-Lys-NH2,
Phe-D-Arg-Lys-Dmt-NH2,
Phe-Dmt-D-Arg-Lys-NH2,
Phe-Dmt-Lys-D-Arg-NH2,
Lys-Phe-D-Arg-Dmt-NH2,
Lys-Phe-Dmt-D-Arg-NH2,
Lys-Dmt-D-Arg-Phe-NH2,
Lys-Dmt-Phe-D-Arg-NH2,
Lys-D-Arg-Phe-Dmt-NH2,
Lys-D-Arg-Dmt-Phe-NH2,
D-Arg-Dmt-D-Arg-Phe-NH2,
D-Arg-Dmt-D-Arg-Dmt-NH2,
D-Arg-Dmt-D-Arg-Tyr-NH2,
D-Arg-Dmt-D-Arg-Trp-NH2,
Trp-D-Arg-Phe-Lys-NH2,
Trp-D-Arg-Tyr-Lys-NH2,
Trp-D-Arg-Trp-Lys-NH2,
Trp-D-Arg-Dmt-Lys-NH2,
D-Arg-Trp-Lys-Phe-NH2,
D-Arg-Trp-Phe-Lys-NH2,
D-Arg-Trp-Lys-Dmt-NH2,
D-Arg-Trp-Dmt-Lys-NH2,
D-Arg-Lys-Trp-Phe-NH2,
D-Arg-Lys-Trp-Dmt-NH2, and
Cha-D-Arg-Phe-Lys-NH2,
and wherein the molecule is selected from the group consisting of:
a polynucleotide, a polyamino acid, a cytotoxic agent, an antibiotic, an antioxidant, a growth factor, and a cytokine.

193 more elements

A method for delivering a molecule to a cell, the method comprising contacting the cell with a carrier complex, wherein the carrier complex comprises the molecule conjugated to an aromatic-cationic peptide, wherein the aromatic-cationic peptide is selected from the group consisting of:

Lys-D-Arg-Tyr-NH2,
Phe-D-Arg-His,
D-Tyr-Trp-Lys-NH2,
Trp-D-Lys-Tyr-Arg-NH2,
Tyr-His-D-Gly-Met,
Phe-Arg-D-His-Asp,
Tyr-D-Arg-Phe-Lys-Glu-NH2 (SEQ ID NO:
3),
Met-Tyr-D-Lys-Phe-Arg (SEQ ID NO:
4),
D-His-Glu-Lys-Tyr-D-Phe-Arg (SEQ ID NO:
5),
Lys-D-Gln-Tyr-Arg-D-Phe-Trp-NH2 (SEQ ID NO:
6),
Phe-D-Arg-Lys-Trp-Tyr-D-Arg-His (SEQ ID NO:
7),
Gly-D-Phe-Lys-Tyr-His-D-Arg-Tyr-NH2 (SEQ ID NO:
8),
Val-D-Lys-His-Tyr-D-Phe-Ser-Tyr-Arg-NH−2 (SEQ ID NO:
9),
Trp-Lys-Phe-D-Asp-Arg-Tyr-D-His-Lys (SEQ ID NO:
10),
Lys-Trp-D-Tyr-Arg-Asn-Phe-Tyr-D-His-NH2 (SEQ ID NO:
11),
Thr-Gly-Tyr-Arg-D-His-Phe-Trp-D-His-Lys (SEQ ID NO:
12),
Asp-D-Trp-Lys-Tyr-D-His-Phe-Arg-D-Gly-Lys-NH2 (SEQ ID NO:
13),
D-His-Lys-Tyr-D-Phe-Glu-D-Asp-D-His-D-Lys-Arg-Trp-NH2 (SEQ ID NO:
14),
Ala-D-Phe-D-Arg-Tyr-Lys-D-Trp-His-D-Tyr-Gly-Phe (SEQ ID NO:
15),
Tyr-D-Arg-Phe-Orn-NH2,
Tyr-D-Arg-Phe-Dab-NH2,
Tyr-D-Arg-Phe-Dap-NH2,
2′6′Dmt-D-Arg-Phe-Lys-Cys-NH2 (SEQ ID NO:
16),
2′6′Dmt-D-Arg-Phe-Lys-NH(CH2)2-NH-dns-NH2,
2′6′Dmt-D-Arg-Phe-Lys-NH(CH2)2-NH-atn-NH2,
2′6′Dmt-D-Arg-Phe-dnsLys-NH2,
2′6′Dmt-D-Cit-Phe-Lys-NH2,
2′6′Dmt-D-Cit-Phe-Ahp-NH2,
2′6′Dmt-D-Arg-Phe-Orn-NH2,
2′6′Dmt-D-Arg-Phe-Dab-NH2,
2′6′Dmt-D-Arg-Phe-Dap-NH2,
2′6′Dmt-D-Arg-Phe-Ahp(2-aminoheptanoic acid)-NH2,
3′5′Dmt-D-Arg-Phe-Lys-NH2,
3′5′Dmt-D-Arg-Phe-Orn-NH2,
3′5′Dmt-D-Arg-Phe-Dab-NH2,
3′5′Dmt-D-Arg-Phe-Dap-NH2,
Tyr-D-Arg-Tyr-Lys-NH2,
Tyr-D-Arg-Tyr-Orn-NH2,
Tyr-D-Arg-Tyr-Dab-NH2,
Tyr-D-Arg-Tyr-Dap-NH2,
2′6′Dmt-D-Arg-Tyr-Lys-NH2,
2′6′Dmt-D-Arg-Tyr-Orn-NH2,
2′6′Dmt-D-Arg-Tyr-Dab-NH2,
2′6′Dmt-D-Arg-Tyr-Dap-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Lys-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Orn-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Dab-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Pap-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Arg-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Lys-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Orn-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Dab-NH2,
Tyr-D-Lys-Phe-Dap-NH2,
Tyr-D-Lys-Phe-Arg-NH2,
Tyr-D-Lys-Phe-Lys-NH2,
Tyr-D-Lys-Phe-Orn-NH2,
2′6′Dmt-D-Lys-Phe-Dab-NH2,
2′6′Dmt-D-Lys-Phe-Dap-NH2,
2′6′Dmt-D-Lys-Phe-Arg-NH2,
2′6′Dmt-D-Lys-Phe-Lys-NH2,
3′5′Dmt-D-Lys-Phe-Orn-NH2,
3′5′Dmt-D-Lys-Phe-Dab-NH2,
3′5′Dmt-D-Lys-Phe-Dap-NH2,
3′5′Dmt-D-Lys-Phe-Arg-NH2,
Tyr-D-Lys-Tyr-Lys-NH2,
Tyr-D-Lys-Tyr-Orn-NH2,
Tyr-D-Lys-Tyr-Dab-NH2,
Tyr-D-Lys-Tyr-Dap-NH2,
2′6′Dmt-D-Lys-Tyr-Lys-NH2,
2′6′Dmt-D-Lys-Tyr-Orn-NH2,
2′6′Dmt-D-Lys-Tyr-Dab-NH2,
2′6′Dmt-D-Lys-Tyr-Dap-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Lys-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Orn-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Dab-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Dap-NH2,
2′6′Dmt-D-Arg-Phe-dnsDap-NH2,
2′6′Dmt-D-Arg-Phe-atnDap-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Lys-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Orn-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Dab-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Dap-NH2,
Tyr-D-Lys-Phe-Arg-NH2,
Tyr-D-Orn-Phe-Arg-NH2,
Tyr-D-Dap-Phe-Arg-Tyr-NH2,
2′6′Dmt-D-Arg-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Lys-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Orn-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Dab-Phe-Arg-2′6′Dmt-NH2,
3′5′Dmt-D-Dap-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Arg-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Lys-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Orn-Phe-Arg-3′5′Dmt-NH2,
Tyr-D-Lys-Tyr-Arg-Tyr-NH2,
Tyr-D-Orn-Tyr-Arg-Tyr-NH2,
Tyr-D-Dab-Tyr-Arg-Tyr-NH2,
Tyr-D-Dap-Tyr-Arg-Tyr-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Arg-2′6′Dmt-NH2,
2′6′Drnt-D-Lys-2′6′Dmt-Arg-2′6′Drnt-NH2,
2′6′Dmt-D-Orn-2′6′Dmt-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Dab-2′6′Dmt-Arg-2′6′Dmt-NH2,
3′5′Dmt-D-Dap-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Orn-3′5′Dmt-Arg-3′5′Dmt-NH2,
Mmt-D-Arg-Phe-Lys-Mmt-NH2,
Mmt-D-Arg-Phe-Orn-Mmt-NH2,
Mmt-D-Arg-Phe-Dab-Mmt-NH2,
Mmt-D-Arg-Phe-Dap-Mmt-NH2,
Tmt-D-Arg-Phe-Lys-Tmt-NH2,
Tmt-D-Arg-Phe-Orn-Tmt-NH2,
Tmt-D-Arg-Phe-Dab-Tmt-NH2,
Tmt-D-Arg-Phe-Dap-Tmt-NH2,
Hmt-D-Arg-Phe-Lys-Hmt-NH2,
Hmt-D-Arg-Phe-Orn-Hmt-NH2,
Hmt-D-Arg-Phe-Dab-Hmt-NH2,
Hmt-D-Arg-Phe-Dap-Hmt-NH2,
Mmt-D-Lys-Phe-Lys-Mmt-NH2,
Mmt-D-Lys-Phe-Orn-Mmt-NH2,
Mmt-D-Lys-Phe-Dab-Mmt-NH2,
Mmt-D-Lys-Phe-Dap-Mmt-NH2,
Mmt-D-Lys-Phe-Arg-Mmt-NH2,
Tmt-D-Lys-Phe-Lys-Tmt-NH2,
Tmt-D-Lys-Phe-Om-Tmt-NH2,
Tmt-D-Lys-Phe-Dab-Tmt-NH2,
Tmt-D-Lys-Phe-Dap-Tmt-NH2,
Tmt-D-Lys-Phe-Arg-Tmt-NH2,
Hmt-D-Lys-Phe-Lys-Hmt-NH2,
Hmt-D-Lys-Phe-Orn-Hmt-NH2,
Hmt-D-Lys-Phe-Dab-Hmt-NH2,
Hmt-D-Lys-Phe-Dap-Hmt-NH2,
Hmt-D-Lys-Phe-Arg-Hmt-NH2,
Mmt-D-Lys-Phe-Arg-Mmt-NH2,
Mmt-D-Orn-Phe-Arg-NH2,
Mmt-D-Dab-Phe-Arg-NH2,
Mmt-D-Dap-Phe-Arg-NH2,
Mmt-D-Arg-Phe-Arg-NH2,
Tmt-D-Lys-Phe-Arg-NH2,
Tmt-D-Orn-Phe-Arg-NH2,
Tmt-D-Dab-Phe-Arg-NH2,
Tmt-D-Dap-Phe-Arg-NH2,
Tmt-D-Arg-Phe-Arg-NH2,
Hmt-D-Lys-Phe-Arg-NH2,
Hmt-D-Orn-Phe-Arg-NH2,
Hmt-D-Dab-Phe-Arg-NH2,
Hmt-D-Dap-Phe-Arg-NH2,
Hmt-D-Arg-Phe-Arg-NH2,
D-Arg-Dmt-Lys-Phe-NH2,
D-Arg-Dmt-Phe-Lys-NH2,
Arg-Phe-Lys-Dmt-NH2,
Arg-Phe-Dmt-Lys-NH2,
D-Arg-Lys-Drnt-Phe-NH2,
D-Arg-Lys-Phe-Dmt-NH2,
Phe-Lys-Dmt-D-Arg-NH2,
Phe-Lys-D-Arg-Dmt-NH2,
Phe-D-Arg-Dmt-Lys-NH2,
Phe-D-Arg-Lys-Dmt-NH2,
Phe-Dmt-D-Arg-Lys-NH2,
Phe-Dmt-Lys-D-Arg-NH2,
Lys-Phe-D-Arg-Dmt-NH2,
Lys-Phe-Dmt-D-Arg-NH2,
Lys-Dmt-D-Arg-Phe-NH2,
Lys-Dmt-Phe-D-Arg-NH2,
Lys-D-Arg-Phe-Dmt-NH2,
Lys-D-Arg-Dmt-Phe-NH2,
D-Arg-Dmt-D-Arg-Phe-NH2,
D-Arg-Dmt-D-Arg-Dmt-NH2,
D-Arg-Dmt-D-Arg-Tyr-NH2,
D-Arg-Dmt-D-Arg-Trp-NH2,
Trp-D-Arg-Phe-Lys-NH2,
Trp-D-Arg-Tyr-Lys-NH2,
Trp-D-Arg-Trp-Lys-NH2,
Trp-D-Arg-Dmt-Lys-NH2,
D-Arg-Trp-Lys-.Phe-NH2,
D-Arg-Trp-Phe-Lys-NH2,
D-Arg-Trp-Lys-Dmt-NH2,
D-Arg-Trp-Dmt-Lys-NH2,
D-Arg-Lys-Trp-Phe-NH2,
D-Arg-Lys-Trp-Dmt-NH2, and
Cha-D-Arg-Phe-Lys-NH2,
and wherein the molecule is selected from the group consisting of:
a polynucleotide, a polyamino acid, a cytotoxic agent, an antibiotic, an antioxidant, a growth factor, and a cytokine.

193 more elements

A method for delivering a molecule to a cell, the method comprising contacting the cell with a molecule conjugated to an aromatic-cationic peptide is selected from the group consisting of:

Lys-D-Arg-Tyr-NH2,
Phe-D-Arg-His,
D-Tyr-Trp-Lys-NH2,
Trp-D-Lys-Tyr-Arg-NH2,
Tyr-His-D-Gly-Met,
Phe-Arg-D-His-Asp,
Tyr-D-Arg-Phe-Lys-Glu-NH2 (SEQ ID NO:
3),
Met-Tyr-D-Lys-Phe-Arg (SEQ ID NO:
4),
D-His-Glu-Lys-Tyr-D-Phe-Arg (SEQ ID NO:
5),
Lys-D-Gln-Tyr-Arg-D-Phe-Trp-NH2 (SEQ ID NO:
6),
Phe-D-Arg-Lys-Trp-Tyr-D-Arg-His (SEQ ID NO:
7),
Gly-D-Phe-Lys-Tyr-His-D-Arg-Tyr-NH2 (SEQ ID NO:
8),
Val-D-Lys-His-Tyr-D-Phe-Ser-Tyr-Arg-NH−2 (SEQ ID NO:
9),
Trp-Lys-Phe-D-Asp-Arg-Tyr-D-His-Lys (SEQ ID NO:
10),
Lys-Trp-D-Tyr-Arg-Asn-Phe-Tyr-D-His-NH2 (SEQ ID NO:
11),
Thr-Gly-Tyr-Arg-D-His-Phe-Trp-D-His-Lys (SEQ ID NO:
12),
Asp-D-Trp-Lys-Tyr-D-His-Phe-Arg-D-Gly-Lys-NH2 (SEQ ID NO:
13),
D-His-Lys-Tyr-D-Phe-Glu-D-Asp-D-His-D-Lys-Arg-Trp-NH2 (SEQ ID NO:
14),
Ala-D-Phe-D-Arg-Tyr-Lys-D-Trp-His-D-Tyr-Gly-Phe (SEQ ID NO:
15),
Tyr-D-Arg-Phe-Orn-NH2,
Tyr-D-Arg-Phe-Dab-NH2,
Tyr-D-Arg-Phe-Dap-NH2,
2′6′Dmt-D-Arg-Phe-Lys-Cys-NH2 (SEQ ID NO:
16),
2′6′Dmt-D-Arg-Phe-Lys-NH(CH2)2-NH-dns-NH2,
2′6′Dmt-D-Arg-Phe-Lys-NH(CH2)2-NH-atn-NH2,
2′6′Dmt-D-Arg-Phe-dnsLys-NH2,
2′6′Dmt-D-Cit-Phe-Lys-NH2,
2′6′Dmt-D-Cit-Phe-Ahp-NH2,
2′6′Dmt-D-Arg-Phe-Orn-NH2,
2′6′Dmt-D-Arg-Phe-Dab-NH2,
2′6′Dmt-D-Arg-Phe-Dap-NH2,
2′6′Dmt-D-Arg-Phe-Ahp(2-aminoheptanoic acid)-NH2,
3′5′Dmt-D-Arg-Phe-Lys-NH2,
3′5′Dmt-D-Arg-Phe-Orn-NH2,
3′5′Dmt-D-Arg-Phe-Dab-NH2,
3′5′Dmt-D-Arg-Phe-Dap-NH2,
Tyr-D-Arg-Tyr-Lys-NH2,
Tyr-D-Arg-Tyr-Orn-NH2,
Tyr-D-Arg-Tyr-Dab-NH2,
Tyr-D-Arg-Tyr-Dap-NH2,
2′6′Dmt-D-Arg-Tyr-Lys-NH2,
2′6′Dmt-D-Arg-Tyr-Orn-NH2,
2′6′Dmt-D-Arg-Tyr-Dab-NH2,
2′6′Dmt-D-Arg-Tyr-Dap-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Lys-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Orn-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Dab-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Pap-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Arg-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Lys-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Orn-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Dab-NH2,
Tyr-D-Lys-Phe-Dap-NH2,
Tyr-D-Lys-Phe-Arg-NH2,
Tyr-D-Lys-Phe-Lys-NH2,
Tyr-D-Lys-Phe-Orn-NH2,
2′6′Dmt-D-Lys-Phe-Dab-NH2,
2′6′Dmt-D-Lys-Phe-Dap-NH2,
2′6′Dmt-D-Lys-Phe-Arg-NH2,
2′6′Dmt-D-Lys-Phe-Lys-NH2,
3′5′Dmt-D-Lys-Phe-Orn-NH2,
3′5′Dmt-D-Lys-Phe-Dab-NH2,
3′5′Dmt-D-Lys-Phe-Dap-NH2,
3′5′Dmt-D-Lys-Phe-Arg-NH2,
Tyr-D-Lys-Tyr-Lys-NH2,
Tyr-D-Lys-Tyr-Orn-NH2,
Tyr-D-Lys-Tyr-Dab-NH2,
Tyr-D-Lys-Tyr-Dap-NH2,
2′6′Dmt-D-Lys-Tyr-Lys-NH2,
2′6′Dmt-D-Lys-Tyr-Orn-NH2,
2′6′Dmt-D-Lys-Tyr-Dab-NH2,
2′6′Dmt-D-Lys-Tyr-Dap-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Lys-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Orn-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Dab-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Dap-NH2,
2′6′Dmt-D-Arg-Phe-dnsDap-NH2,
2′6′Dmt-D-Arg-Phe-atnDap-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Lys-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Orn-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Dab-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Dap-NH2,
Tyr-D-Lys-Phe-Arg-NH2,
Tyr-D-Orn-Phe-Arg-NH2,
Tyr-D-Dap-Phe-Arg-Tyr-NH2,
2′6′Dmt-D-Arg-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Lys-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Orn-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Dab-Phe-Arg-2′6′Dmt-NH2,
3′5′Dmt-D-Dap-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Arg-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Lys-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Orn-Phe-Arg-3′5′Dmt-NH2,
Tyr-D-Lys-Tyr-Arg-Tyr-NH2,
Tyr-D-Orn-Tyr-Arg-Tyr-NH2,
Tyr-D-Dab-Tyr-Arg-Tyr-NH2,
Tyr-D-Dap-Tyr-Arg-Tyr-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Arg-2′6′Dmt-NH2,
2′6′Drnt-D-Lys-2′6′Dmt-Arg-2′6′Drnt-NH2,
2′6′Dmt-D-Orn-2′6′Dmt-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Dab-2′6′Dmt-Arg-2′6′Dmt-NH2,
3′5′Dmt-D-Dap-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Orn-3′5′Dmt-Arg-3′5′Dmt-NH2,
Mmt-D-Arg-Phe-Lys-Mmt-NH2,
Mmt-D-Arg-Phe-Orn-Mmt-NH2,
Mmt-D-Arg-Phe-Dab-Mmt-NH2,
Mmt-D-Arg-Phe-Dap-Mmt-NH2,
Tmt-D-Arg-Phe-Lys-Tmt-NH2,
Tmt-D-Arg-Phe-Orn-Tmt-NH2,
Tmt-D-Arg-Phe-Dab-Tmt-NH2,
Tmt-D-Arg-Phe-Dap-Tmt-NH2,
Hmt-D-Arg-Phe-Lys-Hmt-NH2,
Hmt-D-Arg-Phe-Orn-Hmt-NH2,
Hmt-D-Arg-Phe-Dab-Hmt-NH2,
Hmt-D-Arg-Phe-Dap-Hmt-NH2,
Mmt-D-Lys-Phe-Lys-Mmt-NH2,
Mmt-D-Lys-Phe-Orn-Mmt-NH2,
Mmt-D-Lys-Phe-Dab-Mmt-NH2,
Mmt-D-Lys-Phe-Dap-Mmt-NH2,
Mmt-D-Lys-Phe-Arg-Mmt-NH2,
Tmt-D-Lys-Phe-Lys-Tmt-NH2,
Tmt-D-Lys-Phe-Om-Tmt-NH2,
Tmt-D-Lys-Phe-Dab-Tmt-NH2,
Tmt-D-Lys-Phe-Dap-Tmt-NH2,
Tmt-D-Lys-Phe-Arg-Tmt-NH2,
Hmt-D-Lys-Phe-Lys-Hmt-NH2,
Hmt-D-Lys-Phe-Orn-Hmt-NH2,
Hmt-D-Lys-Phe-Dab-Hmt-NH2,
Hmt-D-Lys-Phe-Dap-Hmt-NH2,
Hmt-D-Lys-Phe-Arg-Hmt-NH2,
Mmt-D-Lys-Phe-Arg-Mmt-NH2,
Mmt-D-Orn-Phe-Arg-NH2,
Mmt-D-Dab-Phe-Arg-NH2,
Mmt-D-Dap-Phe-Arg-NH2,
Mmt-D-Arg-Phe-Arg-NH2,
Tmt-D-Lys-Phe-Arg-NH2,
Tmt-D-Orn-Phe-Arg-NH2,
Tmt-D-Dab-Phe-Arg-NH2,
Tmt-D-Dap-Phe-Arg-NH2,
Tmt-D-Arg-Phe-Arg-NH2,
Hmt-D-Lys-Phe-Arg-NH2,
Hmt-D-Orn-Phe-Arg-NH2,
Hmt-D-Dab-Phe-Arg-NH2,
Hmt-D-Dap-Phe-Arg-NH2,
Hmt-D-Arg-Phe-Arg-NH2,
D-Arg-Dmt-Lys-Phe-NH2,
D-Arg-Dmt-Phe-Lys-NH2,
D-Arg-Phe-Lys-Dmt-NH2,
D-Arg-Phe-Dmt-Lys-NH2,
D-Arg-Lys-Drnt-Phe-NH2,
D-Arg-Lys-Phe-Dmt-NH2,
Phe-Lys-Dmt-D-Arg-NH2,
Phe-Lys-D-Arg-Dmt-NH2,
Phe-D-Arg-Dmt-Lys-NH2,
Phe-D-Arg-Lys-Dmt-NH2,
Phe-Dmt-D-Arg-Lys-NH2,
Phe-Dmt-Lys-D-Arg-NH2,
Lys-Phe-D-Arg-Dmt-NH2,
Lys-Phe-Dmt-D-Arg-NH2,
Lys-Dmt-D-Arg-Phe-NH2,
Lys-Dmt-Phe-D-Arg-NH2,
Lys-D-Arg-Phe-Dmt-NH2,
Lys-D-Arg-Dmt-Phe-NH2,
D-Arg-Dmt-D-Arg-Phe-NH2,
D-Arg-Dmt-D-Arg-Dmt-NH2,
D-Arg-Dmt-D-Arg-Tyr-NH2,
D-Arg-Dmt-D-Arg-Trp-NH2,
Trp-D-Arg-Phe-Lys-NH2,
Trp-D-Arg-Tyr-Lys-NH2,
Trp-D-Arg-Trp-Lys-NH2,
Trp-D-Arg-Dmt-Lys-NH2,
D-Arg-Trp-Lys-.Phe-NH2,
D-Arg-Trp-Phe-Lys-NH2,
D-Arg-Trp-Lys-Dmt-NH2,
D-Arg-Trp-Dmt-Lys-NH2,
D-Arg-Lys-Trp-Phe-NH2,
D-Arg-Lys-Trp-Dmt-NH2, and
Cha-D-Arg-Phe-Lys-NH2,
and wherein the molecule is selected from the group consisting of:
a polynucleotide, a polyamino acid, a cytotoxic agent, an antibiotic, an antioxidant, a growth factor, and a cytokine.

193 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/631,048Filed 4 Dec 2009 · continuation
Priority: 1 May 2003
Published: US 2010/0204448 A112 Aug 2010
Granted: 3 Apr 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification31 codes

C07K 17/00
Carrier-bound or immobilised peptides
A61K 31/713
Compounds having three or more nucleosides or nucleotides: double-stranded nucleic acids or oligonucleotides
A61K 38/47
Hydrolases: acting on glycosyl compounds , e.g. cellulases, lactases
A61K 47/64
The modifying agent being a protein, peptide or polyamino acid: drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying…

Family

Application60/467,516Us provisional application · filed 1 May 2003
Application10/838,135Parent of this continuation · filed 3 May 2004
US 2010/0204448 A1Pre-grant publication · published 12 Aug 2010
US 7,704,954 B2Parent of this continuation
US 2005/0158373 A1Published application
US 8,148,322 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

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Abstract

A carrier complex comprising a biological molecule conjugated to an aromatic cationic peptide, wherein the aromatic cationic peptide is selected from the group consisting of:

Lys-D-Arg-Tyr-NH2,
Phe-D-Arg-His,
D-Tyr-Trp-Lys-NH2,
Trp-D-Lys-Tyr-Arg-NH2,
Tyr-His-D-Gly-Met,
Phe-Arg-D-His-Asp,
Tyr-D-Arg-Phe-Lys-Glu-NH2 (SEQ ID NO:
3),
Met-Tyr-D-Lys-Phe-Arg (SEQ ID NO:
4),
D-His-Glu-Lys-Tyr-D-Phe-Arg (SEQ ID NO:
5),
Lys-D-Gln-Tyr-Arg-D-Phe-Trp-NH2 (SEQ ID NO:
6),
Phe-D-Arg-Lys-Trp-Tyr-D-Arg-His (SEQ ID NO:
7),
Gly-D-Phe-Lys-Tyr-His-D-Arg-Tyr-NH2 (SEQ ID NO:
8),
Val-D-Lys-His-Tyr-D-Phe-Ser-Tyr-Arg-NH−2 (SEQ ID NO:
9),
Trp-Lys-Phe-D-Asp-Arg-Tyr-D-His-Lys (SEQ ID NO:
10),
Lys-Trp-D-Tyr-Arg-Asn-Phe-Tyr-D-His-NH2 (SEQ ID NO:
11),
Thr-Gly-Tyr-Arg-D-His-Phe-Trp-D-His-Lys (SEQ ID NO:
12),
Asp-D-Trp-Lys-Tyr-D-His-Phe-Arg-D-Gly-Lys-NH2 (SEQ ID NO:
13),
D-His-Lys-Tyr-D-Phe-Glu-D-Asp-D-His-D-Lys-Arg-Trp-NH2 (SEQ ID NO:
14),
Ala-D-Phe-D-Arg-Tyr-Lys-D-Trp-His-D-Tyr-Gly-Phe (SEQ ID NO:
15),
Tyr-D-Arg-Phe-Orn-NH2,
Tyr-D-Arg-Phe-Dab-NH2,
Tyr-D-Arg-Phe-Dap-NH2,
2′6′Dmt-D-Arg-Phe-Lys-Cys-NH2 (SEQ ID NO:
16),
2′6′Dmt-D-Arg-Phe-Lys-NH(CH2)2-NH-dns-NH2,
2′6′Dmt-D-Arg-Phe-Lys-NH(CH2)2-NH-atn-NH2,
2′6′Dmt-D-Arg-Phe-dnsLys-NH2,
2′6′Dmt-D-Cit-Phe-Lys-NH2,
2′6′Dmt-D-Cit-Phe-Ahp-NH2,
2′6′Dmt-D-Arg-Phe-Orn-NH2,
2′6′Dmt-D-Arg-Phe-Dab-NH2,
2′6′Dmt-D-Arg-Phe-Dap-NH2,
2′6′Dmt-D-Arg-Phe-Ahp(2-aminoheptanoic acid)-NH2,
3′5′Dmt-D-Arg-Phe-Lys-NH2,
3′5′Dmt-D-Arg-Phe-Orn-NH2,
3′5′Dmt-D-Arg-Phe-Dab-NH2,
3′5′Dmt-D-Arg-Phe-Dap-NH2,
Tyr-D-Arg-Tyr-Lys-NH2,
Tyr-D-Arg-Tyr-Orn-NH2,
Tyr-D-Arg-Tyr-Dab-NH2,
Tyr-D-Arg-Tyr-Dap-NH2,
2′6′Dmt-D-Arg-Tyr-Lys-NH2,
2′6′Dmt-D-Arg-Tyr-Orn-NH2,
2′6′Dmt-D-Arg-Tyr-Dab-NH2,
2′6′Dmt-D-Arg-Tyr-Dap-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Lys-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Orn-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Dab-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Pap-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Arg-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Lys-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Orn-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Dab-NH2,
Tyr-D-Lys-Phe-Dap-NH2,
Tyr-D-Lys-Phe-Arg-NH2,
Tyr-D-Lys-Phe-Lys-NH2,
Tyr-D-Lys-Phe-Orn-NH2,
2′6′Dmt-D-Lys-Phe-Dab-NH2,
2′6′Dmt-D-Lys-Phe-Dap-NH2,
2′6′Dmt-D-Lys-Phe-Arg-NH2,
2′6′Dmt-D-Lys-Phe-Lys-NH2,
3′5′Dmt-D-Lys-Phe-Orn-NH2,
3′5′Dmt-D-Lys-Phe-Dab-NH2,
3′5′Dmt-D-Lys-Phe-Dap-NH2,
3′5′Dmt-D-Lys-Phe-Arg-NH2,
Tyr-D-Lys-Tyr-Lys-NH2,
Tyr-D-Lys-Tyr-Orn-NH2,
Tyr-D-Lys-Tyr-Dab-NH2,
Tyr-D-Lys-Tyr-Dap-NH2,
2′6′Dmt-D-Lys-Tyr-Lys-NH2,
2′6′Dmt-D-Lys-Tyr-Orn-NH2,
2′6′Dmt-D-Lys-Tyr-Dab-NH2,
2′6′Dmt-D-Lys-Tyr-Dap-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Lys-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Orn-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Dab-NH2,
2′6′Dmt-D-Lys-2′6′Dmt-Dap-NH2,
2′6′Dmt-D-Arg-Phe-dnsDap-NH2,
2′6′Dmt-D-Arg-Phe-atnDap-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Lys-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Orn-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Dab-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Dap-NH2,
Tyr-D-Lys-Phe-Arg-NH2,
Tyr-D-Orn-Phe-Arg-NH2,
Tyr-D-Dap-Phe-Arg-Tyr-NH2,
2′6′Dmt-D-Arg-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Lys-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Orn-Phe-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Dab-Phe-Arg-2′6′Dmt-NH2,
3′5′Dmt-D-Dap-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Arg-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Lys-Phe-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Orn-Phe-Arg-3′5′Dmt-NH2,
Tyr-D-Lys-Tyr-Arg-Tyr-NH2,
Tyr-D-Orn-Tyr-Arg-Tyr-NH2,
Tyr-D-Dab-Tyr-Arg-Tyr-NH2,
Tyr-D-Dap-Tyr-Arg-Tyr-NH2,
2′6′Dmt-D-Arg-2′6′Dmt-Arg-2′6′Dmt-NH2,
2′6′Drnt-D-Lys-2′6′Dmt-Arg-2′6′Drnt-NH2,
2′6′Dmt-D-Orn-2′6′Dmt-Arg-2′6′Dmt-NH2,
2′6′Dmt-D-Dab-2′6′Dmt-Arg-2′6′Dmt-NH2,
3′5′Dmt-D-Dap-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Arg-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Lys-3′5′Dmt-Arg-3′5′Dmt-NH2,
3′5′Dmt-D-Orn-3′5′Dmt-Arg-3′5′Dmt-NH2,
Mmt-D-Arg-Phe-Lys-Mmt-NH2,
Mmt-D-Arg-Phe-Orn-Mmt-NH2,
Mmt-D-Arg-Phe-Dab-Mmt-NH2,
Mmt-D-Arg-Phe-Dap-Mmt-NH2,
Tmt-D-Arg-Phe-Lys-Tmt-NH2,
Tmt-D-Arg-Phe-Orn-Tmt-NH2,
Tmt-D-Arg-Phe-Dab-Tmt-NH2,
Tmt-D-Arg-Phe-Dap-Tmt-NH2,
Hmt-D-Arg-Phe-Lys-Hmt-NH2,
Hmt-D-Arg-Phe-Orn-Hmt-NH2,
Hmt-D-Arg-Phe-Dab-Hmt-NH2,
Hmt-D-Arg-Phe-Dap-Hmt-NH2,
Mmt-D-Lys-Phe-Lys-Mmt-NH2,
Mmt-D-Lys-Phe-Orn-Mmt-NH2,
Mmt-D-Lys-Phe-Dab-Mmt-NH2,
Mmt-D-Lys-Phe-Dap-Mmt-NH2,
Mmt-D-Lys-Phe-Arg-Mmt-NH2,
Tmt-D-Lys-Phe-Lys-Tmt-NH2,
Tmt-D-Lys-Phe-Om-Tmt-NH2,
Tmt-D-Lys-Phe-Dab-Tmt-NH2,
Tmt-D-Lys-Phe-Dap-Tmt-NH2,
Tmt-D-Lys-Phe-Arg-Tmt-NH2,
Hmt-D-Lys-Phe-Lys-Hmt-NH2,
Hmt-D-Lys-Phe-Orn-Hmt-NH2,
Hmt-D-Lys-Phe-Dab-Hmt-NH2,
Hmt-D-Lys-Phe-Dap-Hmt-NH2,
Hmt-D-Lys-Phe-Arg-Hmt-NH2,
Mmt-D-Lys-Phe-Arg-Mmt-NH2,
Mmt-D-Orn-Phe-Arg-NH2,
Mmt-D-Dab-Phe-Arg-NH2,
Mmt-D-Dap-Phe-Arg-NH2,
Mmt-D-Arg-Phe-Arg-NH2,
Tmt-D-Lys-Phe-Arg-NH2,
Tmt-D-Orn-Phe-Arg-NH2,
Tmt-D-Dab-Phe-Arg-NH2,
Tmt-D-Dap-Phe-Arg-NH2,
Tmt-D-Arg-Phe-Arg-NH2,
Hmt-D-Lys-Phe-Arg-NH2,
Hmt-D-Orn-Phe-Arg-NH2,
Hmt-D-Dab-Phe-Arg-NH2,
Hmt-D-Dap-Phe-Arg-NH2,
Hmt-D-Arg-Phe-Arg-NH2,
D-Arg-Dmt-Lys-Phe-NH2,
D-Arg-Dmt-Phe-Lys-NH2,
D-Arg-Phe-Lys-Dmt-NH2,
D-Arg-Phe-Dmt-Lys-NH2,
D-Arg-Lys-Drnt-Phe-NH2,
D-Arg-Lys-Phe-Dmt-NH2,
Phe-Lys-Dmt-D-Arg-NH2,
Phe-Lys-D-Arg-Dmt-NH2,
Phe-D-Arg-Dmt-Lys-NH2,
Phe-D-Arg-Lys-Dmt-NH2,
Phe-Dmt-D-Arg-Lys-NH2,
Phe-Dmt-Lys-D-Arg-NH2,
Lys-Phe-D-Arg-Dmt-NH2,
Lys-Phe-Dmt-D-Arg-NH2,
Lys-Dmt-D-Arg-Phe-NH2,
Lys-Dmt-Phe-D-Arg-NH2,
Lys-D-Arg-Phe-Dmt-NH2,
Lys-D-Arg-Dmt-Phe-NH2,
D-Arg-Dmt-D-Arg-Phe-NH2,
D-Arg-Dmt-D-Arg-Dmt-NH2,
D-Arg-Dmt-D-Arg-Tyr-NH2,
D-Arg-Dmt-D-Arg-Trp-NH2,
Trp-D-Arg-Phe-Lys-NH2,
Trp-D-Arg-Tyr-Lys-NH2,
Trp-D-Arg-Trp-Lys-NH2,
Trp-D-Arg-Dmt-Lys-NH2,
D-Arg-Trp-Lys-Phe-NH2,
D-Arg-Trp-Phe-Lys-NH2,
D-Arg-Trp-Lys-Dmt-NH2,
D-Arg-Trp-Dmt-Lys-NH2,
D-Arg-Lys-Trp-Phe-NH2,
D-Arg-Lys-Trp-Dmt-NH2, and
Cha-D-Arg-Phe-Lys-NH2,
and wherein the molecule is selected from the group consisting of:
a polynucleotide, a polyamino acid, a cytotoxic agent, an antibiotic, an antioxidant, a growth factor, and a cytokine.

193 more elements

Facts

Application

12/631,048Filed 4 Dec 2009 · continuation

Priority

1 May 2003

Published

US 2010/0204448 A112 Aug 2010

Granted

3 Apr 2012

Term ends

Not estimatedThe source records don’t support an estimate.

Classification31 codes

C07K 17/00
Carrier-bound or immobilised peptides
A61K 31/713
Compounds having three or more nucleosides or nucleotides: double-stranded nucleic acids or oligonucleotides
A61K 38/47
Hydrolases: acting on glycosyl compounds , e.g. cellulases, lactases
A61K 47/64
The modifying agent being a protein, peptide or polyamino acid: drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying…

Family

Application60/467,516Us provisional application · filed 1 May 2003

Application10/838,135Parent of this continuation · filed 3 May 2004

US 2010/0204448 A1Pre-grant publication · published 12 Aug 2010

US 7,704,954 B2Parent of this continuation

US 2005/0158373 A1Published application

US 8,148,322 B2This patent

From the US filing history. Foreign family members aren’t listed.