# US 7,608,271 B2 · Modified human immunodeficiency virus anti-fusogenic GP41 peptides comprising a maleimide-containing group

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- Number: US 7,608,271 B2
- Document ID: US7608271B2
- Status: Granted
- Kind: B2
- Application number: 10/950,010
- Filed: 2004-09-24
- Published: 2005-03-31
- Granted: 2009-10-27
- Earliest claimed: 1999-05-17
- Assignees: ConjuChem Biotechnologies Inc.
- Inventors: Dominique P. Bridon; Robert S. Dufresne; Nisssab Boudjellab; Martin Robitaille; Peter G. Milner
- Web page: https://patentgrep.com/patent/US7608271B2

## CPC

- C07K 14/005: from viruses
- A61P 31/12: Antivirals
- A61P 31/16: for influenza or rhinoviruses
- A61P 31/18: for HIV
- A61P 37/00: Drugs for immunological or allergic disorders
- A61K 38/00: Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00)
- C12N 2740/16122: New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)

## Abstract

Peptides exhibiting anti-viral and anti-fusogenic activity are modified to provide greater stability and improved half-life in vivo. The selected peptides include fusion inhibitors DP178 and DP107 and related peptides and analogs thereof. The modified peptides are capable of forming covalent bonds with one or more blood components, preferably a mobile blood component.

## Claims

### Claim 1

A modified anti-fusogenic peptide comprising a peptide that has been modified to have a maleimide containing group coupled thereto which is reactive with a thiol group at cysteine 34 of albumin, said peptide comprising an amino acid sequence selected from the group consisting of SEQ ID NO:1. SEQ ID NO: 3, SEQ ID NO: 4, SEQ ID NO: 5, SEQ ID NO: 117, SEQ ID NO: 118, SEQ ID NO: 119, SEQ ID NO: 534, SEQ ID NO: 535, SEQ ID NO: 536, SEQ ID NO: 537, SEQ ID NO: 538, SEQ ID NO: 539, SEQ ID NO: 540, and SEQ ID NO: 541, wherein said maleimide containing group is attached to said peptide without a linker or via a (2-amino)ethoxy acetic acid (AEA) or a [2-(2-amino) ethoxy] acetic acid (AEEA) linker and said modified anti-fusogenic peptide exhibits an anti-viral and anti-fusogenic activity against human immunodeficiency virus (HIV).

### Claim 2 (depends on 1)

The modified anti-fusogenic peptide of claim 1, wherein cm said peptide is DP 178, the amino acid sequence of which is SEQ ID NO:1.

### Claim 3 (depends on 1)

The modified anti-fusogenic peptide of claim 1, wherein said peptide has an amino acid sequence selected from the group consisting of SEQ ID NO: 3, SEQ ID NO: 4, SEQ ID NO: 5, SEQ ID NO: 117, SEQ ID NO: 118, SEQ ID NO: 119, SEQ ID NO: 534, SEQ ID NO: 535, SEQ ID NO: 536, SEQ ID NO: 537, SEQ ID NO: 538, SEQ ID NO: 539, SEQ ID NO: 540, and SEQ ID NO: 541.

### Claim 4 (depends on 1)

The modified anti-fusogenic peptide of claim 1, having the formula

### Claim 5 (depends on 1)

The modified anti-fusogenic peptide of claim 1, wherein the maleimide containing group is maleimidopropionic acid (MPA) or gamma-maleimide-butyralamide (GMBA).

### Claim 6 (depends on 1)

The modified anti-fusogenic peptide of claim 1, wherein the peptide exhibits anti-viral and anti-fusogenic activity by modulation of a viral-cellular fusion process involving a coiled-coil peptide structure.

### Claim 7 (depends on 5)

The modified anti-fusogenic peptide of claim 5, wherein the peptide exhibits anti-viral and anti-fusogenic activity by modulation of a viral-cellular fusion process involving a coiled-coil peptide structure.

### Claim 8 (depends on 1)

The modified anti-fusogenic peptide of claim 1, wherein said maleimide containing group is attached to said peptide without a linker.

### Claim 9 (depends on 1)

The modified anti-fusogenic peptide of claim 1, wherein said maleimide containing group is attached to said peptide via a (2-amino)ethoxy acetic acid (AEA) or a [2-(2-amino) ethoxy] acetic acid (AEEA) linker.

### Claim 10 (depends on 1)

The modified anti-fusogenic peptide of claim 1, wherein the maleimido-containing group is coupled to the thiol group at cysteine 34 of albumin and the conjugate formed has a 1:1 molar ratio of the modified peptide to albumin.