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Conjugate comprising pharmaceutical active compound covalently bound to mucoadhesive polymer and transmucosal delivery method of pharmaceutical active compound using the same

A mucoadhesive, covalently linked technology, applied in the field of conjugates comprising pharmacologically active compounds covalently linked to mucoadhesive polymers and transmucosal administration of pharmacologically active compounds using the conjugates, capable of solving drug Unsatisfactory treatment effect and other problems, to achieve the effect of high degradability in vivo

Inactive Publication Date: 2009-04-08
GWANGJU INST OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present inventors have developed a new type of compound that has good absorbance rates when given through mouth but also breaks down quickly inside the body for easy disposing without causing harmful side-effects on healthy tissues such as stomach walls during treatment. This makes it possible to administer this substances safely over large areas like the esophagus while still maintaining their effectiveness at treating diseases involving these organs.

Problems solved by technology

The technical problem addressed in this patents relates to finding ways to effectively transport highly hydrophobic small molecules like pacilcelet factor-2a(PTF2) across cellular barriers while maintaining good blood circulatory activity under physiological conditions. Existing transoral routes suffer drawbacks such as slow upright passage times and reduced retention rates. Additionally, existing techniques involving pH adjustments require complicated processes and often result in unsuccessful outcomes even if they were applied successfully overnight.

Method used

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  • Conjugate comprising pharmaceutical active compound covalently bound to mucoadhesive polymer and transmucosal delivery method of pharmaceutical active compound using the same
  • Conjugate comprising pharmaceutical active compound covalently bound to mucoadhesive polymer and transmucosal delivery method of pharmaceutical active compound using the same
  • Conjugate comprising pharmaceutical active compound covalently bound to mucoadhesive polymer and transmucosal delivery method of pharmaceutical active compound using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Example 1: Preparation of Insulin Intermediates with Insulin Linked to a Linker

[0084] 0.1g (17.22×10 -6 mol) insulin (Serologicals company) was dissolved in 10mL hydrochloric acid solution, and 0.008g (25.83×10 -6 mol) N-succinimidyl 3-(2-pyridyldithio)propionate (SPDP, Pierce) was dissolved in 0.2×10 -3 mL of DMF (Sigma), which was then added to the insulin solution. In order to obtain the regioselective combination of SPDP and the 29th amino acid lysine (B29) on the B chain of the insulin molecule, the above mixed solution was adjusted to a pH range of 9-10 with NaOH water and stirred at room temperature for 30 minutes . The resulting stirred solution was subjected to reverse-phase HPLC (Shimadzu) separation and freeze-dried (lyophilization) to prepare an insulin intermediate (see Equation 1).

Embodiment 2

[0085] Example 2: Chitosan intermediate with chitosan attached to linker product preparation

[0086] Each 0.1 g (16.67×10 -6 mol, monomer mole number = 0.67×10 -3 mol) was dissolved in 2mL phosphate buffered saline (PBS), and 0.016g (50.01×10 -6 mol) of SPDP dissolved in 0.2×10 -3 mL of DMF, which was then added to the above chitosan solution, followed by stirring at room temperature for 2 h. Acetone was added to the resulting stirred solution to precipitate particulate matter. The resulting granules were dissolved in distilled water and freeze-dried to prepare a chitosan intermediate (see Reaction Scheme 1).

[0087] [Reaction 1]

[0088]

Embodiment 3

[0089] Example 3: Construction of insulin-chitosan conjugates

[0090] In order to reduce the above-mentioned chitosan intermediate product, 0.008g (1.24×10 -6 mol) chitosan intermediate and 0.3mL of DTT (24.9×10 -6 mol) (Pierce) was dissolved in 0.3 mL of PBS and stirred at room temperature for 4 hours. 0.005g (0.83 × 10 -6 mol) insulin intermediate was dissolved in citrate buffer solution (500 μg), the reduced chitosan intermediate solution (100 μg) was added thereto, and the resulting mixture was stirred at room temperature for 12-24 hours. The stirred mixture was separated by reverse-phase HPLC and freeze-dried to prepare an insulin-chitosan conjugate (see Equation 2).

[0091] [Reaction 2]

[0092]

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Abstract

Provided is a conjugate comprising a pharmacologically active substance covalently bound to a mucoadhesive polymer and a method for transmucosal delivery of a pharmacologically active substance using the same. Specifically, the present invention is directed to a conjugate comprising a pharmacologically active substance covalently bound via a linker to a mucoadhesive polymer; a pharmaceutical composition for transmucosal administration of a drug, comprising the aforementioned conjugate and a pharmaceutically acceptable carrier; and a method for in vivo delivery of a pharmacologically active substance via a transmucosal route, by covalent binding of the active substance with a mucoadhesive polymer via a linker. The conjugate of the present invention exhibits excellent absorption rate and biocompatibility in biological mucous membranes, particularly mucous membranes of the alimentary canal (especially the gastrointestinal tract), in vivo degradability, and superior bioavailability even with oral administration, thus enabling treatment of diseases via oral administration of a drug.

Description

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Claims

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Application Information

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Owner GWANGJU INST OF SCI & TECH
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