# US 8,784,866 B2 · Water-soluble carbon nanotube compositions for drug delivery and medicinal applications

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- Number: US 8,784,866 B2
- Document ID: US8784866B2
- Status: Granted
- Kind: B2
- Application number: 12/245,438
- Filed: 2008-10-03
- Published: 2009-07-02
- Granted: 2014-07-22
- Earliest claimed: 2007-03-26
- Assignees: William Marsh Rice University; Board of Regents, The University of Texas System
- Applicants: James M. Tour; Rebecca Lucente-Schultz; Ashley Leonard; Dmitry V. Kosynkin; Brandi Katherine Price; Jared L. Hudson; Jodie L. Conyers, Jr.; Valerie C. Moore; S. Ward Casscells; Jeffrey N. Myers; Zvonimir L. Milas; Kathy A. Mason; Luka Milas
- Inventors: James M. Tour; Rebecca Lucente-Schultz; Ashley Leonard; Dmitry V. Kosynkin; Brandi Katherine Price; Jared L. Hudson; Jodie L. Conyers, Jr.; Valerie C. Moore; S. Ward Casscells; Jeffrey N. Myers; Zvonimir L. Milas; Kathy A. Mason; Luka Milas
- Web page: https://patentgrep.com/patent/US8784866B2

## CPC

- A61K 31/337: having four-membered rings, e.g. taxol
- A61K 38/1808: {Epidermal growth factor [EGF] urogastrone}
- A61K 47/60: the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
- A61K 47/6925: {the form being a microcapsule, nanocapsule, microbubble or nanobubble}
- A61K 47/6929: {the form being a nanoparticle, e.g. an immuno-nanoparticle}
- B82Y 5/00: Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
- 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)
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES

## Abstract

Compositions comprising a plurality of functionalized carbon nanotubes and at least one type of payload molecule are provided herein. The compositions are soluble in water and PBS in some embodiments. In certain embodiments, the payload molecules are insoluble in water. Methods are described for making the compositions and administering the compositions. An extended release formulation for paclitaxel utilizing functionalized carbon nanotubes is also described.

## Claims

### Claim 1

A composition comprising:
a plurality of functionalized single-wall carbon nanotubes;
wherein the functionalized single-wall carbon nanotubes are water-soluble; and
wherein the functionalized single-wall carbon nanotubes are covalently functionalized with a plurality of PEG moieties; and
a drug molecule comprising paclitaxel;
wherein the paclitaxel is insoluble in water;
wherein the paclitaxel is non-covalently associated with the functionalized single-wall carbon nanotubes; and
wherein the paclitaxel is sequestered from its surrounding environment by the non-covalent association with the functionalized single-wall carbon nanotubes.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the composition is soluble in aqueous PBS buffer.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the non-covalent association does not comprise π-stacking of the paclitaxel with the functionalized single-wall carbon nanotubes.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the PEG moieties have an average molecular weight greater than about 400.

### Claim 5 (depends on 4)

The composition of claim 4, wherein the PEG moieties have an average molecular weight greater than about 2000.

### Claim 6 (depends on 5)

The composition of claim 5, wherein the PEG moieties have an average molecular weight greater than about 5000.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the functionalized single-wall carbon nanotubes comprise at least one tissue-targeting moiety selected from a group consisting of aptamers, antibodies, antibody fragments, saccharides, peptides, proteins, hormones, and receptor ligands.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the functionalized single-wall carbon nanotubes comprise at least one folate moiety.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the composition provides an extended in vivo release of paclitaxel;
wherein the extended in vivo release comprises a greater in vivo residence time of paclitaxel compared to that of paclitaxel alone.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the composition provides intracellular delivery of paclitaxel.

### Claim 11

A paclitaxel extended release formulation comprising:
a solution of functionalized single-wall carbon nanotubes;
wherein the functionalized single-wall carbon nanotubes are water-soluble;
wherein the functionalized single-wall carbon nanotubes are covalently functionalized with a plurality of PEG moieties; and
wherein the solution comprises water; and
a quantity of paclitaxel, wherein the paclitaxel is non-covalently associated with the functionalized single-wall carbon nanotubes and sequestered from its surrounding environment by the non-covalent association with the functionalized single-wall carbon nanotubes.

### Claim 12 (depends on 11)

The extended release formulation of claim 11, wherein the solution is a PBS buffer.

### Claim 13 (depends on 11)

The extended release formulation of claim 11, wherein the PEG moieties have an average molecular weight greater than about 400.

### Claim 14 (depends on 13)

The extended release formulation of claim 13, wherein the PEG moieties have an average molecular weight greater than about 2000.

### Claim 15 (depends on 14)

The extended release formulation of claim 14, wherein the PEG moieties have an average molecular weight greater than about 5000.

### Claim 16 (depends on 11)

The extended release formulation of claim 11, wherein the quantity of paclitaxel is at least 1 mg of paclitaxel per 1 mL of the solution.

### Claim 17 (depends on 11)

The extended release formulation of claim 11, wherein an in vivo paclitaxel residence time is greater than that of paclitaxel alone.

### Claim 18 (depends on 11)

The extended release formulation of claim 11, wherein the paclitaxel is delivered intracellularly.