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Conjugate of polymer and biological stain and preparation method and application thereof

A technology of biological dyes and polymers, applied in the medical field, can solve problems such as no reports, achieve long developing time, sufficient clinical operation and observation time, and good water solubility

Inactive Publication Date: 2014-01-29
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, macromolecular contrast agents such as dextran-DTPA-Gd have been developed [Desser et al: J Magn Reson Imaging 1994; 4: 467], but only a few reports have been used for the detection of lymphatic vessels [Yan et al: Pharm Res 2010; 27 : 1884], dye reagents used for auxiliary lymphatic detection in surgery have not been reported

Method used

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  • Conjugate of polymer and biological stain and preparation method and application thereof
  • Conjugate of polymer and biological stain and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1, the preparation of toluidine blue acylate

[0027] Take toluidine blue (2.00g, 6.54mmol), succinic anhydride (0.65g, 6.54mmol), 4-dimethylaminopyridine (DMAP) (0.80g, 6.54mmol) in a 100ml two-necked bottle, and dry under reduced pressure for 1 hour. Under the protection of nitrogen, 50 ml of dry dimethylformamide (DMF) was added, stirred at room temperature for 10 hours, and TLC detected that the reaction was complete. 500ml of ethyl acetate was added to the reaction solution, stirred thoroughly, filtered, and vacuum-dried to obtain 2.02g of toluidine blue acylate as a blue solid, with a yield of 83.5%.

Embodiment 2

[0028] Embodiment 2, the preparation of Evans blue acylate

[0029] Take Evans blue (2.00g, 2.08mmol), succinic anhydride (0.42g, 4.19mmol), 4-dimethylaminopyridine (0.52g, 4.19mmol) in a 100ml two-necked bottle, and dry under reduced pressure for 1 hour. Under the protection of nitrogen, 50 ml of dry DMF was added, stirred at room temperature for 10 hours, and TLC detected that the reaction was complete. 500ml of ethyl acetate was added to the reaction solution, stirred thoroughly, filtered, and vacuum-dried to obtain 1.8g of Evans blue acylate as a blue solid, with a yield of 80.1%.

[0030] In addition to toluidine blue and Evans blue, the biological staining agent can also be other dyes used for cell or tissue staining such as methylene blue, neutral red, Kenna green or bright tar violet.

Embodiment 3

[0031] Embodiment 3, the preparation of dextran and toluidine blue coupling compound

[0032] Take the prepared toluidine blue acylate (2.00g, 4.92mmol), dextran 40 (2.40g, 14.81mmol in terms of glucose units), EDC·HCl (1.42g, 7.39mmol), HOBt (1.00g , 7.39mmol), 4-dimethylaminopyridine (1.20g, 9.86mmol) in a 100ml three-necked flask, vacuum-dried for 0.5 hours. Add 50ml of dimethyl sulfoxide (DMSO) under ice bath, ultrasonically dissolve, stir at room temperature for 12 hours, TLC detection shows that the reaction is complete. Add 500ml of ethyl acetate to the reaction solution, stir for 0.5 hours, filter, and vacuum dry to obtain 3.32g of dextran-toluidine blue conjugate with a yield of 75%.

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Abstract

The invention provides a conjugate of a polymer and a biological stain and a preparation method and application of the conjugate. The conjugate has the formula G-X-B, wherein the polymer G is selected from the group consisting of glucans, fructosans, polymannuronic acid, polyguluronic acid, heteropolysaccharides, mono- or hetero-polysaccharides, mono- or hetero-polyuronic acid polysaccharides, mono- or hetero-polyuronic acid sulfate esters, hydrophilic alcohol high polymers, polylysine, polyglutamic acid and polyaspartic acid; the linking group X is a C1-C10 organic group; and the biological stain or a derivative B thereof may be toluidine blue, methylene blue, Evans blue, neutral red, Janus green or bright cresol purple. The conjugate can stain bilateral neck and submaxillary or submental lymphatic vessels and lymph nodes in New Zealand white rabbits by indirect lymph staining method, without diffusion in tongue body. No obvious toxic and adverse effects appear in all experimental animals in each group, and no obvious pathological changes appear in histological examination of internal organs.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a conjugate of a polymer and a biological dye, a preparation method and application thereof. Background technique [0002] Tumor treatment methods are mainly radiotherapy, chemotherapy, targeted therapy and surgery. The main purpose of tumor treatment is to obtain a higher survival rate. To achieve this result, not only the primary tumor must be completely removed during surgery, but more importantly, tumor metastasis must be prevented. Among them, the ability of tumor cells to transfer through the lymphatic system has been proved by many experiments [Steven et al: Carcinogenesis 2006; 27(9): 1729]. If there is no metastasis in the sentinel lymph node, the possibility of metastasis in other lymph nodes is very small, even if there is skip metastasis, the probability is less than 1% [Shoaib et al: Cancer 2001; 91(10): 2077]. In order to prevent tumor metastasis, sentinel lymph nodes are ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B69/10A61K49/00
Inventor 万升标尚伟江涛李学敏刘凤桐张晓瑜
Owner OCEAN UNIV OF CHINA
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