# US 2013/0280237 A1 · Protein transduction domains mimics

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- Number: US 2013/0280237 A1
- Document ID: US20130280237A1
- Status: Published application
- Kind: A1
- Application number: 13/703,645
- Filed: 2011-06-24
- Published: 2013-10-24
- Earliest claimed: 2010-06-25
- Assignees: University of Massachusetts
- Inventors: Gregory N. Tew; Gregory J. Gabriel; Abhigyan Som; Arife Ozgul Tezgel
- Web page: https://patentgrep.com/patent/US20130280237A1

## CPC

- A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone}
- C08F 234/02: in a ring containing oxygen (coumarone-indene polymers C08F244/00)
- C08G 61/08: of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- G01N 33/582: {with fluorescent label}
- G01N 33/588: {with semiconductor nanocrystal label, e.g. quantum dots}
- G01N 33/60: involving radioactive labelled substances
- C08G 2261/126: block
- C08G 2261/1426: containing carboxy groups (COOH) and/or -C(=O)O-moieties
- C08G 2261/143: Side-chains containing nitrogen
- C08G 2261/3324: derived from norbornene
- C08G 2261/3342: derived from cycloolefins containing heteroatoms
- C08G 2261/418: Ring opening metathesis polymerisation [ROMP]
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

The invention generally relates to synthetic mimics of cell penetrating peptides. More particularly, the invention relates to certain novel monomers, oligomers and polymers (e.g., co-polymers) that are useful for the preparation of synthetic mimics of cell penetrating peptides, their compositions, preparations and use.

## Claims

### Claim 1

A block co-polymer having the Formula of (I):
wherein
X1, X2 each is independently O, CH2 or substituted CH2;
Y11, Y12 each is independently a single bond or a linking group;
Z11, Z12 each is independently hydrogen, an —N(Rz)2, alkyl, substituted alkyl, aryl, substituted aryl group, with the proviso that at least one of Z11 and Z12 comprises N(Rz)2 or
Y21, Y22 each is independently a single bond or a linking group;
Z21, Z22 each is independently hydrogen, an —ORz, alkyl, substituted alkyl, aryl, substituted aryl group;
Rz each is independently hydrogen, an alkyl, substituted alkyl, aryl, substituted aryl, poly(ethylene oxide) group;
R is hydrogen, a C1-C6 alkyl group, or a poly(ethylene oxide) group; and
m, n each is independently an integer from about 2 to about 50.

### Claim 2 (depends on 1)

The block co-polymer of claim 1, wherein each of X1 and X2 is O; each of Y11 and Y12 is independently a linking group comprising a carbonyl group; each of Z11 and Z12 comprises
each of Y21 and Y22 is independently a linking group comprising a carbonyl group; each of Z21, Z22 is —ORz, wherein at least one —ORz comprises an aryl group; each R is hydrogen; and each of m and n is selected from an integer from about 4 to about 24.

### Claim 3 (depends on 1)

The block co-polymer of claim 1, wherein each of X1 and X2 is O; each of Y11 and Y12 is independently a linking group comprising a carbonyl group; each of Z11 and Z12 comprises N(Rz)2; each of Y21 and Y22 is independently a linking group comprising a carbonyl group; each of Z21, Z22 is —ORz, wherein at least one —ORz comprises an aryl group; each R is hydrogen; and each of m and n is selected from an integer from about 2 to about 24.

### Claim 4 (depends on 1)

The block co-polymer of claim 1, wherein each of X1 and X2 is CH2; each of Y11 and Y12 is independently a linking group comprising a carbonyl group; one of Z11 and Z12 comprises
each of Y21 and Y22 is independently a linking group comprising a carbonyl group; each of Z21, Z22 is —ORz, wherein at least one —ORz comprises an aryl group; each R is hydrogen; and each of m and n is selected from an integer from about 4 to about 24.

### Claim 5 (depends on 1)

The block co-polymer of claim 1, wherein each of X1 and X2 is CH2; each of Y11 and Y12 is independently a linking group comprising a carbonyl group; one of Z11 and Z12 comprises N(Rz)2; each of Y21 and Y22 is independently a linking group comprising a carbonyl group; each of Z21, Z22 is —ORz, wherein at least one —ORz comprises an aryl group; each R is hydrogen; and each of m and n is selected from an integer from about 2 to about 24.

### Claim 6 (depends on 1)

The block co-polymer of claim 1, wherein each of Y11, Y12, Y21 and Y22 is independently a linking group comprising a carbonyl group and —O(CH2)q—, wherein q is an integer from about 1 to about 6.

### Claim 7 (depends on 1)

The block co-polymer of claim 1, wherein each of m and n is an integer from about 4 to about 24.

### Claim 8 (depends on 1)

A composition comprising a block co-polymer of claim 1.

### Claim 9 (depends on 8)

The composition of claim 8, further comprising a therapeutic agent having a biological effect under physiological conditions.

### Claim 10 (depends on 9)

The composition of claim 9, wherein the therapeutic agent comprises a small molecule compound.

### Claim 11 (depends on 9)

The composition of claim 9, wherein the therapeutic agent comprises a peptide, an antibody, a protein, or a nucleic acid.

### Claim at position 12

12-14. (canceled)

### Claim 15 (depends on 8)

The composition of claim 8, further comprising a diagnostic agent capable of emitting a detectable signal.

### Claim 16 (depends on 15)

The composition of claim 15, wherein the diagnostic agent comprises a fluorescent label.

### Claim 17 (depends on 15)

The composition of claim 15, wherein the diagnostic agent comprises a radioactive label.

### Claim 18 (depends on 15)

The composition of claim 15, wherein the diagnostic agent comprises a quantum dot of label.

### Claim at position 17

19-36. (canceled)

### Claim 37

A block co-polymer having the Formula of (III):
wherein
X1, X2 each is independently O, CH2 or substituted CH2;
Y1 is a linking group;
Z1 is comprises —N(Rz)2 or
Y2 is a single bond or a linking group;
Z2 is hydrogen, an alkyl or substituted alkyl group;
Rz is hydrogen, an alkyl, substituted alkyl, aryl, substituted aryl group;
R is hydrogen or a C1-C12 alkyl group or a poly(ethylene oxide) group; and
m, n each is independently an integer from about 2 to about 300.

### Claim 38 (depends on 37)

The block co-polymer of claim 37, wherein each of X1 and X2 is O; Y1 is a linking group comprising a carbonyl group; Y2 is a single bond; Z1 comprises
Z2 is R; each R is hydrogen, an alkyl or substituted alkyl group; and each of m and n is selected from an integer from about 2 to about 24.

### Claim 39 (depends on 37)

The block co-polymer of claim 37, wherein each of X1 and X2 is O; Y1 is a linking group comprising a carbonyl group; Y2 is a single bond; Z1 comprises —N(Rz)2;
Z2 is R; each R is hydrogen, an alkyl or substituted alkyl group; and each of m and n is selected from an integer from about 2 to about 24.

### Claim 40 (depends on 37)

The block co-polymer of claim 37, wherein each of X1 and X2 is O; each of Y1 and Y2 is a linking group comprising a carbonyl group; Z1 comprises
Z2 comprises —N(Rz)2; each R is hydrogen, an alkyl or substituted alkyl group; and each of m and n is selected from an integer from about 2 to about 24.

### Claim 41 (depends on 37)

The block co-polymer of claim 37 having the formula of:
wherein R2 is a C1-C12 alkyl or substituted alkyl, aryl or substituted aryl group, or a poly(ethylene oxide) group; X is an anion.

### Claim 42

A block copolymer comprising the structural unit of the formula:
wherein X is an anion.

### Claim at position 24

43-57. (canceled)