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Cyclodextrin grafted biocompatible amphiphilic polymer and methods of preparation and use thereof

A technology of biocompatible and hydrophilic polymers, applied in the direction of non-active ingredients of polymer compounds, medical preparations of non-active ingredients, medical preparations containing active ingredients, etc.

Inactive Publication Date: 2007-06-20
GENTA SALUS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, cyclodextrins can cause secondary systemic effects by increasing gastrointestinal elimination of certain nutrients and bile acids

Method used

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  • Cyclodextrin grafted biocompatible amphiphilic polymer and methods of preparation and use thereof
  • Cyclodextrin grafted biocompatible amphiphilic polymer and methods of preparation and use thereof
  • Cyclodextrin grafted biocompatible amphiphilic polymer and methods of preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0069] Materials and methods : PEG with propionic acid pendant groups (PEG-10PA and PEG-8PA Mw=~20KD, SunBio Company, Anyang City, South Korea) was dried overnight at room temperature under vacuum. β-Cyclodextrin (TCI (USA), Portland, OR) was dried overnight at 130° C. under vacuum before use. Other chemicals were from Aldrich Chemical Company (Milwaukee, WI) and used as supplied without further purification. HPLC (High Pressure Liquid Chromatography) analysis was performed on a Waters system equipped with RI detector and Ultrahydrogel 120 and Ultrahygel 500SEC columns. 1 H-NMR was recorded on a Varian 400 MHz machine.

[0070] PEG-SS-CD Synthesis of (Compound 2)

[0071] Mono-6-(6-amino-3,4-dithio-hexylamino)-6-deoxy-β-cyclodextrin (Compound 1):

[0072] 2,2'-Dithiodiethylamine dihydrochloride (10 g, 4.44 mol, Fw=225.2) was dissolved in 30 mL of distilled water, followed by the addition of 1.0 M KOH (8.88 mol) and mono-6-toluenesulfonyl-β- Cyclodextrin (0.5 g, Fw=128...

example 2

[0077] PEG-SS-AcCD Synthesis of (Compound 3)

[0078] PEG-SS-CD (compound 2, 1.0g, about 5CD / 20 KD-PEG) in P 2 o 5 Dry in a desiccator, then co-evaporate with 50 mL of anhydrous pyridine. The residue was dissolved in 30 mL of pyridine under the protection of argon, and then added to 2.0 mL of acetic anhydride (Fw=102.1, d=1.08). The mixture was stirred at room temperature for 2 days and dried on a rotary evaporator. The crude product was purified by repeated ether precipitation from methanol. HPLC (GPC) analysis showed that the product was longer than the base polymer by 0.46 min compared to the base polymer (Rt = 19.70 min for the product vs. Rt = 19.24 min for the reactant polymer). 1 H-NMR analysis indicated about 5 CD moieties per 20KD PEG and all hydroxyl groups were acetylated.

[0079] 1 H-NMR (400MHz, D 2 O): δ, 4.7-5.5(s, 14H, H1', ​​H3'), 3.4-5.5(m, 382H, 35H-CD, 347H-PEG), 2.05(m, 20H, H-Ac).

example 3

[0081] PEG-SS-DECD Synthesis of (compound 7)

[0082] PEG-SS-NH2 (Compound 4):

[0083] PEG grafted with carboxyl groups (PEG-8PA, 2.6 g, about 2.0 mmol COOH groups) was dissolved in 30 mL of anhydrous DMF and cooled on ice to 0 °C. Tributylamine (0.35 mL, 1.5 mmol, Fw=185.36, d=0.778) was added thereto, followed by isobutyl chloroformate (0.20 mL, 1.5 mmol, Fw=136.6, d=1.053). The mixture was stirred at 0°C for 80 min, then carefully added to a solution of 2,2'-dithiodiethylamine (3.5 g, Fw = 152.2, 23 mmol) in 50 mL of anhydrous DMF. The mixture was stirred at room temperature for 20 h, concentrated to about 20 mL at 40 °C on a rotary evaporator, then dialyzed against distilled water after dilution with 50 mL of water (4 x 5 L, 26 h, Sigma D-0655, MWCO=12,000). The dialysis solution was concentrated by rotary evaporation at 40°C, resulting in 4.1 g of slurry. The slurry was dissolved in 10 mL of methanol and subsequently precipitated by adding 80 mL of ethyl ether. T...

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Abstract

Amphiphilic biocompatible cyclodextrin grafted polymers comprising a hydrophobically modified cyclodextrin moiety, a linear linker and a biocompatible hydrophilic polymer backbone, wherein said cyclodextrin moiety is grafted to said biocompatible hydrophilic polymer backbone by said linker are disclosed. The cyclodextrin-grafted biocompatible polymers of this invention may be used as bioactive agent carriers. Methods of making and using such cyclodextrin-grafted biocompatible polymers are disclosed.

Description

Background technique [0001] The present invention relates to novel polymeric bioactive agent carriers. More specifically, the present invention relates to cyclodextrin-grafted biocompatible polymers useful as carriers for bioactive agents and methods for their preparation. [0002] Many biologically active molecules, such as antiviral agents, anticancer agents, peptides / proteins, and DNA, have been commercially available through advances in recombinant DNA and other technologies, with various therapeutic utility. However, there is always a need for an ideal carrier for certain drugs and active agents to enhance their solubility, release and efficacy. [0003] Cyclodextrins (CDs) are cyclic oligosaccharides, usually composed of 6 to 8 glucose units, which have a truncated cone shape, including a wide opening composed of secondary hydroxyl groups (2-OH and 3-OH). The narrower side formed by the side and the primary hydroxyl group (6-OH). Cyclodextrins provide a unique micro-h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16A61K47/40A61K31/337A61K31/7088A61K38/00A61K47/48A61K48/00C08G65/333C08G85/00
CPCC08B37/0012A61K47/48969B82Y5/00A61K47/6951
Inventor L·王D·E·鲁夫纳
Owner GENTA SALUS
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