WO2004032862A2 - Cyclodextrin-based materials, compositions and uses related thereto - Google Patents

Cyclodextrin-based materials, compositions and uses related thereto Download PDF

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Publication number
WO2004032862A2
WO2004032862A2 PCT/US2003/031991 US0331991W WO2004032862A2 WO 2004032862 A2 WO2004032862 A2 WO 2004032862A2 US 0331991 W US0331991 W US 0331991W WO 2004032862 A2 WO2004032862 A2 WO 2004032862A2
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WO
WIPO (PCT)
Prior art keywords
polymer
inclusion
cyclodextrin
matrix
polymer composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2003/031991
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English (en)
French (fr)
Other versions
WO2004032862A3 (en
Inventor
Nathalie C. Bellocq
Mark E. Davis
Suzie Hwang Pun
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Calando Pharmaceuticals Inc
Original Assignee
Insert Therapeutics Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Insert Therapeutics Inc filed Critical Insert Therapeutics Inc
Priority to AU2003295344A priority Critical patent/AU2003295344B2/en
Priority to JP2004543586A priority patent/JP4602085B2/ja
Priority to MXPA05003591A priority patent/MXPA05003591A/es
Priority to BR0315198-0A priority patent/BR0315198A/pt
Priority to EP03786526A priority patent/EP1549269A4/en
Priority to CA002501132A priority patent/CA2501132A1/en
Publication of WO2004032862A2 publication Critical patent/WO2004032862A2/en
Publication of WO2004032862A3 publication Critical patent/WO2004032862A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Definitions

  • Figure 1 schematically depicts a crosslinked polymer matrix of the present invention.
  • Figure 3 depicts molecular weights of CD-PEG 3 0 o as a function of polymerization times.
  • Figure 8 provides a dynamic frequency sweep of CD-PEG 3 oo polymer (100 mg/ml) with 36.5 mg/ml of di-Adamantane-PEG cross linker. Temperature was 37 °C and strain was 0.5%.
  • Such assays are well known in the art.
  • One example of such an assay may be performed with live carcinoma cells, such as GT3TKB tumor cells, in the following manner: the sample is degraded in 1 M NaOH at 37 °C until complete degradation is observed. The solution is then neutralized with 1 M HCI. About 200 ⁇ L of various concentrations of the degraded sample products are placed in 96-well tissue culture plates and seeded with human gastric carcinoma cells (GT3TKB) at 104/well density. The degraded sample products are incubated with the GT3TKB cells for 48 hours. The results of the assay may be plotted as % relative growth vs.
  • GT3TKB human gastric carcinoma cells
  • biodegradable is art-recognized, and includes polymers, compositions and formulations, such as those described herein, that are intended to degrade during use.
  • Biodegradable polymers typically differ from non-biodegradable polymers in that the former may be degraded during use.
  • such use involves in vivo use, such as in vivo therapy, and in other certain embodiments, such use involves in vitro use.
  • degradation attributable to biodegradability involves the degradation of a biodegradable polymer into its component subunits, or digestion, e.g., by a biochemical process, of the polymer into smaller, non-polymeric subunits.
  • two different types of biodegradation may generally be identified.
  • the biodegradation rate of such polymer may be characterized by a release rate of such materials.
  • the biodegradation rate may depend on not only the chemical identity and physical characteristics of the polymer, but also on the identity of material(s) incorporated therein.
  • Degradation of the subject compositions includes not only the cleavage of intramolecular bonds, e.g., by oxidation and/or hydrolysis, but also the disruption of intermolecular bonds, such as dissociation of host/guest complexes by competitive complex formation with foreign inclusion hosts.
  • a biohydrolyzable bond refers to a bond that is cleaved (e.g., an ester is cleaved to form a hydroxyl and a carboxylic acid) under physiological conditions.
  • Physiological conditions include the acidic and basic environments of the digestive tract (e.g., stomach, intestines, etc.), acidic environment of a tumor, enzymatic cleavage, metabolism, and other biological processes, and preferably refer to physiological conditions in a vertebrate, such as a mammal.
  • Kit as used herein means a collection of at least two components constituting the kit. Together, the components constitute a functional unit for a given purpose. Individual member components may be physically packaged together or separately. For example, a kit comprising an instruction for using the kit may or may not physically include the instruction with other individual member components. Instead, the instruction can be supplied as a separate member component, either in a paper form or an electronic form which may be supplied on computer readable memory device or downloaded from an internet website, or as recorded presentation.
  • Aromatic rings may be unsubstituted or substituted with from 1 to about 5 substituents on the ring.
  • Preferred aromatic ring substituents include: halo, cyano, lower alkyl, heteroalkyl, haloalkyl, phenyl, phenoxy, or any combination thereof. More preferred substituents include lower alkyl, cyano, halo, and haloalkyl.
  • Haloalkyl' refers to a straight, branched, or cyclic hydrocarbon substituted with one or more halo substituents.
  • Preferred haloalkyl are C1-C12; more preferred are C1-C6; more preferred still are C1-C3.
  • Preferred halo substituents are fluoro and chloro. The most preferred haloalkyl is trifluoromethyl.
  • the substituents may be located at the ortho, meta or para position on the phenyl ring, or any combination thereof.
  • Preferred phenyl substituents include: halo, cyano, lower alkyl, heteroalkyl, haloalkyl, phenyl, phenoxy or any combination thereof. More preferred substituents on the phenyl ring include halo and haloalkyl. The most preferred substituent is halo.
  • Contemplated equivalents of the compounds described above include compounds which otherwise correspond thereto, and which have the same useful properties thereof, wherein one or more simple variations of substituents are made which do not adversely affect the efficacy of the compound.
  • the compounds of the present invention may be prepared by the methods illustrated in the general reaction schemes as, for example, described below, or by modifications thereof, using readily available starting materials, reagents and conventional synthesis procedures. In these reactions, it is also possible to make use of variants that are in themselves known, but are not mentioned here.
  • a therapeutic composition of the invention may be used in a variety of therapeutic methods (e.g. DNA vaccines, antibiotics, antiviral agents) for the treatment of inherited or acquired disorders such as, for example, cystic fibrosis, Gaucher's disease, muscular dystrophy, AIDS, cancers (e.g., multiple myeloma, leukemia, melanoma, and ovarian carcinoma), cardiovascular conditions (e.g., progressive heart failure, restenosis, and hemophilia), and neurological conditions (e.g., brain trauma).
  • subject compositions can be used in the treatment of wounds, such as incisions, diabetic ulcers, bedsores, lacerations, burns, etc.
  • a method of treatment administers a therapeutically effective amount of a therapeutic composition of the invention.
  • a therapeutically effective amount as recognized by those of skill in the art, will be determined on a case by case basis. Factors to be considered include, but are not limited to, the disorder to be treated and the physical characteristics of the one suffering from the disorder.
  • the linker groups can be biologically inactive, such as a PEG, polyglycolic acid, or polylactic acid chain, or can be biologically active, such as an oligo- or polypeptide that, when cleaved from the moieties, binds a receptor, deactivates an enzyme, etc.
  • oligomeric linker groups that are biologically compatible and/or bioerodible are known in the art, and the selection of the linkage may influence the ultimate properties of the material, such as whether it is durable when implanted, whether it gradually deforms or shrinks after implantation, or whether it gradually degrades and is absorbed by the body.
  • the linker group may be attached to the moieties by any suitable bond or functional group, including carbon- carbon bonds, esters, ethers, amides, amines, carbonates, carbamates, sulfonamides, etc.
  • Copolymers of poly(ethylenimine) that bear nucleophilic amino substituents susceptible to derivatization with cyclodextrin moieties can also be used to prepare cyclodextrin-modified polymers within the scope of the present invention.
  • the RNAi construct is in the form of a hairpin structure (named as hairpin RNA).
  • hairpin RNAs can be synthesized exogenously or can be formed by transcribing from RNA polymerase III promoters in vivo. Examples of making and using such hairpin RNAs for gene silencing in mammalian cells are described in, for example, Paddison et al., Genes Dev, 2002, 16:948-58; McCaffrey et al., Nature, 2002, 418:38-9; McManus et al., RNA, 2002, 8:842-50; Yu et al., Proc Natl Acad Sci U S A, 2002, 99:6047-52).
  • hairpin RNAs are engineered in cells or in an animal to ensure continuous and stable suppression of a desired gene. It is known in the art that siRNAs can be produced by processing a hairpin RNA in the cell.
  • CD-PEG polymers were prepared by the polymerization of a difunctionalized ⁇ -cyclodextrin monomer (A) with a difunctionalized polyethylene glycol comonomer (B) to give an ABAB product.
  • the synthesis procedure involves first the preparation of the difunctionalized ⁇ -cyclodextrin (6A,6D-dideoxy-6A,6D-di(2- aminoethanethio)- ⁇ -cyclodextrin (denoted dicysteamine- ⁇ -cyclodextrin) according to literature procedures (Gonzalez et al. 1999 Bioconiugate Chem. 10:1068-1074; and Hwang et al. 2001 Bioconiugate Chem. 12(2):280-290). The polymerization step was carried using commercially available difunctionalized polyethylene glycol. Three methods were investigated.
  • the polymer Mw increased to around 80 kDa over a 5 h time course.
  • the polymer Mw can be controlled between 50 to 80 kDa.
  • Polyethylene glycol (Mw 1000) (1 mmol, Aldrich, Milwaukee, WI) is dried by heating under vacuum at 70 °C overnight.
  • 1-Adamantaneacetic acid 2.2 mmol, Aldrich, Milwaukee, WI
  • /?-Toluenesulfonic acid (Aldrich, Milwaukee, WI) is then added in a catalytic amount.
  • the resulting mixture is azeotropically refluxed for 16 h using Dean-Stark apparatus. After completion of the reaction, the solvent is removed under vacuum and the resulting polymer is precipitated with ether.
  • CD-BisCys (2 g, 1.49 mmol) and SPA-PEG3400-SPA (5.07 g, 1.49 mmol, Shearwater Inc.) were dissolved in dry DMSO (40 mL). After 10 minutes diisopropylethylamine (DIEA, 0.571 mL, 2.2 eq, Aldrich) was added under argon. The reaction mixture was stirred under argon for 2-6 days. An increase of viscosity was observed as a function of polymerization time. Water (200 mL) was added to the polymerization solution with vigorous stirring. The solution was then dialyzed in 25,000 MWCO Spectra/Por 7 membrane for 2.5 days at a concentration of ca. 10 mg polymer/mL water. After lyophilization, a white fluffy powder (6.2 g, 92% yield) was obtained.
  • DIEA diisopropylethylamine
  • Matrix 1 60 kD polymer prepared according to Example 3, method II and crosslinking agent prepared according to Example 9, method ⁇
  • Matrix 2 80 kD polymer prepared according to Example 3, method II and crosslinking agent prepared according to Example 9, method II
  • Cyclodextrin/PEI ratio was calculated based on the proton integration of ⁇ NMR (Varian 300 MHz, D 2 O) ⁇ 5.08 ppm (s br., H of CD), 3.3-4.1 ppm (m br. C 2 H- C 6 H of CD), 2.5-3.2 ppm (m br. CH 2 of PEI).

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US20130315980A1 (en) 2013-11-28
US8357377B2 (en) 2013-01-22
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