# US 2008/0187998 A1 · Sulfonamide-based oligomers and polymers for destabilization of biological membranes

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- Number: US 2008/0187998 A1
- Document ID: US20080187998A1
- Status: Published application
- Kind: A1
- Application number: 11/701,975
- Filed: 2007-02-01
- Published: 2008-08-07
- Earliest claimed: 2007-02-01
- Assignees: University of Utah Research Foundation
- Inventors: Han Chang Kang; You Han Bae
- Web page: https://patentgrep.com/patent/US20080187998A1

## CPC

- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- A61K 48/0008: {characterised by an aspect of the 'non-active' part of the composition delivered, e.g. wherein such 'non-active' part is not delivered simultaneously with the 'active' part of the composition}
- A61K 48/0041: {the non-active part being polymeric}
- C07D 239/52: Two oxygen atoms
- C07D 285/12: 1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)

## Abstract

Oligomeric sulfonamides for use as endosomolytic reagents for transfection with polymeric or lipid-based vectors are described. A mixture of an oligomeric sulfonamide with a polymeric or lipid-based gene carrier and a nucleic acid results in a polyplex that exhibits 6-12-fold better gene expression than controls. A method of transfecting cells in vitro is carried out by contacting cultured mammalian cells with an effective amount of a polyplex.

## Claims

### Claim 1

An oligomeric sulfonamide represented by the formula:
wherein X is (CH3)3—C— or H2N—CH2—CH2-S—; R is a sulfonamide or N-substituted sulfonamide having a pKa of about 3 to 10; and n is about 2 to 300.

### Claim 2 (depends on 1)

The oligomeric sulfonamide of claim 1 wherein R is sulfamethizole.

### Claim 3 (depends on 1)

The oligomeric sulfonamide of claim 1 wherein R is sulfadimethoxine.

### Claim 4 (depends on 1)

The oligomeric sulfonamide of claim 1 wherein R is sulfadiazine.

### Claim 5 (depends on 1)

The oligomeric sulfonamide of claim 1 wherein R is sulfamerazine.

### Claim 6

A polyplex comprising a mixture of a nucleic acid, a polymeric or lipid-based gene carrier, and an oligomeric sulfonamide represented by the formula:
wherein X is (CH3)3—C— or H2N—CH2—CH2—S—; R is a sulfonamide or N-substituted sulfonamide having a pKa of about 3 to 10; and n is about 2 to 300.

### Claim 7 (depends on 6)

The polyplex of claim 6 wherein R is sulfamethizole.

### Claim 8 (depends on 6)

The polyplex of claim 6 wherein R is sulfadimethoxine.

### Claim 9 (depends on 6)

The polyplex of claim 6 wherein R is sulfadiazine.

### Claim 10 (depends on 6)

The polyplex of claim 6 wherein R is sulfamerazine.

### Claim 11 (depends on 6)

The polyplex of claim 6 wherein the nucleic acid comprises a plasmid, a small interfering RNA, or an oligonucleotide.

### Claim 12 (depends on 6)

The polyplex of claim 6 wherein the polymeric or lipid-based gene carrier comprises a polycation or liposome.

### Claim 13 (depends on 6)

The polyplex of claim 6 wherein the polyplex has a charge ratio of about 0.0001 to 10,000.

### Claim 14 (depends on 13)

The polyplex of claim 13 wherein the polyplex has a charge ratio of about 3.

### Claim 15

A method for transfecting mammalian cells in vitro, the method comprising:
(a) culturing the mammalian cells in a selected growth medium; and
(b) contacting the cultured mammalian cells with an effective amount of a polyplex comprising a mixture of a nucleic acid, a positively charged polymer or lipid-based gene carrier, and an oligomeric sulfonamide represented by the formula:
wherein X is (CH3)3—C— or H2N—CH2—CH2—S—; R is a sulfonamide or N-substituted sulfonamide having a pKa of about 3 to 10; and n is about 2 to 300.

### Claim 16 (depends on 15)

The method of claim 15 wherein R is sulfamethizole.

### Claim 17 (depends on 15)

The method of claim 15 wherein R is sulfadimethoxine.

### Claim 18 (depends on 15)

The method of claim 15 wherein R is sulfadiazine.

### Claim 19 (depends on 15)

The method of claim 15 wherein R is sulfamerazine.

### Claim 20 (depends on 15)

The method of claim 15 wherein the nucleic acid comprises a plasmid, a small interfering RNA, or an oligonucleotide.