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Biodegradable proline-based polymers

A technology of polymers and compositions, applied in the field of biodegradable proline-based polymers, can solve problems such as reduced reactivity of secondary amines

Inactive Publication Date: 2011-09-14
MEDIVAS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the incorporation of proline as an amino acid into the backbone of PEA polymers synthesized using the above method has proven difficult because the secondary amines in proline are decreased responsiveness

Method used

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  • Biodegradable proline-based polymers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Product characterization

[0056] The chemical structures of monomers and polymers were characterized by standard chemical methods; Brucker AMX-500 spectrometer (Numega R.Labs Inc. San Diego, CA) was operated at 500MHz 1 H NMR spectrum experiment to record the NMR spectrum. Solvent CDCl 3 Or DMSO-d6 (Cambridge Isotope Laboratories, Inc., Andover, MA) together with tetramethylsilane (TMS) used as an internal standard.

[0057] A Mettler-Toledo FP62 automatic melting point meter (Columbus, OH) was used to determine the melting point of the synthesized monomer. The thermal properties of the synthesized monomers and polymers are characterized by a Mettler-Toledo DSC822e differential scanning calorimeter. Place the sample on the aluminum pan. The test is performed in a nitrogen stream at a scanning speed of 10°C / min.

[0058] A Model 515 gel permeation chromatograph (Waters Associates Inc. Milford, MA) equipped with a high pressure liquid chromatography pump and a Waters 2414 r...

Embodiment 2

[0093] Synthesis of PEA 8-Pro(6) polymer with metal chelating agent end groups

[0094] The covalent attachment of the metal chelating molecule to the hydroxyl end group of the polymer of the present invention changes the relationship between the PEA polymer of the present invention and various other cations (such as Zn 2+ , Ni 2+ , Ca 2+ )'S combined ability. These preparations with metal chelating end groups will bind to various biologics containing metal-bound amino acids (such as His-tagged proteins). Metal chelating molecules that can be used to cap the polymers of the present invention include, for example, iminodiacetic acids such as ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTPA) and ethylene glycol-bis(2 -Aminoethyl ether)-N,N,N',N'-tetraacetic acid (EGTA).

[0095] The combination of EDTA and PEA 8-Pro(6) polymer is completed according to the process described in Figure 3 below:

[0096]

[0097] PEA 8-Pro(6)-EDTA (5g scale): In a 40mL v...

Embodiment 3

[0103] Preparation of docetaxel nanoparticles

[0104] In 1.00mL ethanol, 4.29mg docetaxel and 10.0mg PEA-8-Pro(6) (formula I, where (R 1 =(CH 2 ) 8 , R 2 =(CH 2 ) 6 , N=110-160)). The docetaxel / polymer solution was slowly added to 9.00 mL of a stirred aqueous buffer solution (in this case citrate, pH=7) containing 0.1% Bovine Serum Albumin (BSA), and passed The precipitation leads to the formation of nanoparticles. The translucent dispersion of nanoparticles was transferred to a regenerated cellulose dialysis tube (MWCO 3500 Da), and dialyzed against an aqueous buffer solution (100xv / v) at room temperature for 16 hours to remove residual ethanol. The typical diameter of docetaxel / polymer particles is 200-240nm (PDI<0.15), and the zeta potential is -17 to -21mV (tested in Malvern Zetasizer). The comparative formulation omitting the PEA polymer of the present invention in the particle preparation produced only micron-sized crystals.

[0105] After the treatment, 77% of docetaxe...

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Abstract

The invention provides sequential poly(ester amide)s derived from Proline and that are synthesized by a two-step method, involving a final thermal polyesterification reaction. Molecular weights of polymers prepared by this method are from 14,000 Da to about 77,000Da.l When invention proline-based PEAs were thermally characterized,, their glass transition temperatures were lower than other alpha-amino acid based poly(ester amides) due to lack of internal hydrogen bonding. These Proline-based PEAs assemble as nano-particles in aqueous solutions and form complexes with various cations and biologies, including hydrophobic small molecule drugs and biologies. Therefore the invention Proline- based PEAs are useful for drug delivery applications requiring a polymer with a molecular weight in the range from 14,000 Da to about 77,000Da and for fabrication of nanoparticles for delivery of hydrophobic drugs.

Description

Technical field [0001] When implanting or injecting biological materials, there are major challenges in inflammation and immunology, so in the past, people have focused on identifying permanently biologically inert polymers. However, in many applications, such as the delivery of therapeutic drugs and biologics, fully resorbable polymers are desired. In the past 30 years, clearly characterized polyesters (such as poly(lactic-glycolic acid) copolymers) have become the highest standards for degradable polymers. However, in recent years, the use of enzymes to catalyze degradable, protein-like polymers New methods of design and development are promising. Background technique [0002] Polyesteramides (PEAs) are synthetic, amino acid-based copolymers in which the amino acid residues are separated by difunctional hydrocarbon spacers from diacids and diols. These amino acid-rich polymers have natural protein-like properties, resulting in high hydrogen bonding capabilities between polyme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61L15/16
CPCA61K9/5153A61K31/00C08L77/12C08G69/44
Inventor 威廉·G·图勒尔扎扎·D·高姆拉什维利杰弗里·尼尔·安德鲁
Owner MEDIVAS LLC
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