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Bis-[6-oxa-(2-carboxylbenzenesulfonyl-butanedioic acid 1,4 monoester-4)-beta-cyclodextrin, preparation method and application thereof

A technology of carboxybenzenesulfonyl chloride and benzenesulfonyl, applied in bis-[6-oxo-(2-m-carboxybenzenesulfonyl-succinic acid 1,4 monoester-4)]-β-cyclodextrin and In the field of preparation and application, it can solve the problems of low production cost, insufficient separation, low solubility of β-CD and application range

Active Publication Date: 2010-12-29
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0006] (1) There are three types of natural cyclodextrins: α-CD, β-CD and γ-CD: α-CD has a small molecular cavity, and usually can only contain small guest substances with a narrow range of applications; γ-CD The molecular hole is large and can include larger molecular objects, but the production cost of γ-CD is high, and it cannot be mass-produced industrially; the molecular hole size of β-CD is moderate to make it include a wide range of inclusions, and the production cost is low. It is currently the only cyclodextrin product produced on an industrial scale, but the low solubility of β-CD in water limits its application range
(2) The chiral recognition effect caused by β-CD itself is limited due to the geometric symmetry inside the cavity of β-CD
(3) β-CD itself is not charged, so as a chiral additive of HPCE, neutral substances cannot be separated
(4) Binary CD system, some people use binary CD system, including a highly sulfonated (α-, β-, γ-HSCD) and a neutral CD, any seven (2,3,6 -3-O-methyl)-β-CD (TMCD), seven (2,6-bis-O-methyl)-β-CD (DMCD) or hydroxypropyl-β-CD (HPCD), can be separated The results of 25 drugs with different acid-base properties (16 kinds of basic drugs, 8 kinds of acidic drugs, and 1 kind of neutral drugs) show that the binary CD system is very effective in separating chiral substances, but HP-CD alone cannot fully separate them ,
In addition, the toxicity of drugs is a combination of many factors, such as the selectivity of receptors, the in vivo process of drugs and their metabolites, and the selectivity of metabolites to side effects. Therefore, racemates and enantiomers, enantiomers and Enantiomers can vary widely in toxicity

Method used

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  • Bis-[6-oxa-(2-carboxylbenzenesulfonyl-butanedioic acid 1,4 monoester-4)-beta-cyclodextrin, preparation method and application thereof
  • Bis-[6-oxa-(2-carboxylbenzenesulfonyl-butanedioic acid 1,4 monoester-4)-beta-cyclodextrin, preparation method and application thereof
  • Bis-[6-oxa-(2-carboxylbenzenesulfonyl-butanedioic acid 1,4 monoester-4)-beta-cyclodextrin, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Embodiment one β-CD-B 2 Preparation and application effect of chiral HPCE column

[0140] Using a new chiral separation material synthesized by ourselves - β-CD-B 2 Prepare high-efficiency capillary electrophoresis HPCE column, optimize the preparation conditions, and use scanning electron microscopy to confirm that the inner surface of the capillary column has been bonded to β-CD-B 2 . Specific method: A 75 μm chiral capillary electrophoresis column was prepared by combining physical coating, chemical bonding and monolithic column preparation. Use a static coating device to pretreat the capillary electrophoresis column by chemical bonding to expose more silicon hydroxyl groups on the inner wall of the tube. According to the principle of sol-gel, choose a suitable "arm" - coupling agent, Connect the inner wall of the column with the chiral selector——β-CD derivative, use β-CD-B 2 Bonded capillary electrophoresis columns. The method for preparing the chiral capillary...

Embodiment 2

[0159] Embodiment two uses chiral β-CD-B 2＝ Column Separation of Caine-like Chiral Drugs

[0160] The chiral drugs procaine hydrochloride and bupivacaine hydrochloride are common local anesthetics and antiarrhythmic drugs. Samir Cherkaoui et al. used different β-CD derivatives to coat HPCE columns and separated bupivacaine hydrochloride by HPCE-mass spectrometry (MS). Caine, lidocaine, mebivacaine, ketamine, the chiral separation of the four drugs can be achieved within 12 minutes. Ivanildo Joséda Silva et al. used HPLC to separate bupivacaine with self-made compound as stationary phase and n-hexane / 2-propanol / acetonitrile / triethylamine as mobile phase. The separation of the two enantiomers was achieved within 15 minutes. The degree is 3.50.

[0161] This embodiment uses the prepared β-CD-B 2 Bonded HPCE chiral column to separate procaine hydrochloride and bupivacaine hydrochloride two chiral drugs of caine. At 8%, 12% and 20% β-CD-B 2 The baseline separation of bupivacai...

Embodiment 3

[0190] Example 3 β-CD-B 2 Separation of chiral drugs in HPCE as a chiral stationary phase

[0191] 1 Main instruments and reagents

[0192] 1.1 The instrument is the same as before. 1.2 Reagents

[0193] Chlorpheniramine injection Chlorpheniramine (drugs, Hubei Huazhong Pharmaceutical Co., Ltd., chlorpheniramine maleate, reference substance, 100mg, China Institute for the Control of Pharmaceutical and Biological Products), anisodamine (drugs, Hangzhou Minsheng Pharmaceutical Group Co., Ltd. company); propafenone (drug, Jiangsu Yunyang Group Pharmaceutical Co., Ltd.); DL-phenylglycine (purity: 99%) (Shanghai Qiude Biochemical Co., Ltd.); D.L-phenylglycine (purity: 98.5%); Tris (Tris) AR, Amreso packing; H 3 PO 4 AR (Tianjin Jinnan Chemical Reagent Factory); Citric Acid AR (Shanghai Chemical Reagent Company, Sinopharm Group); Boric Acid AR (China Yunling Chemical Factory); NaOHAR (Tianjin Kemiou Chemical Reagent Co., Ltd.) Chiral Drug Structural Formula as follows:

[01...

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Abstract

The invention relates to bis-[6-oxa-(2-carboxylbenzenesulfonyl-butanedioic acid 1,4 monoester-4)-beta-cyclodextrin, a preparation method and application thereof as chiral selective agent in high performance capillary electrophoresis (HPCE), namely being prepared into a chiral electrophoresis column and a mobile phase chiral additive for detachment of chiral substances. The molecular formula of the bis-[6-oxa-(2-carboxylbenzenesulfonyl-butanedioic acid 1,4 monoester-4)-beta-cyclodextrin is determined to be C64H84O49S2; beta-CD-B2 is used as the HPCE mobile phase chiral additive to separate chiral substances of phenylglycinol, anisodamine, isoprenaline and propafenone to realize baseline separation; beta-CD-B2 is used for preparing a chiral HPCE column to separate chlortrimeton, bupivacaine, procaine, atenolol, anisodamine, propafenone, lobeline and other chiral substances to realize the baseline separation. Therefore, a novel HPCE quantitative measurement method for a single enantiomerof various chiral substances can be established.

Description

technical field [0001] The present invention relates to bis-[6-oxo-(2-m-carboxybenzenesulfonyl-succinic acid 1,4 monoester-4)]-β-cyclodextrin and its preparation method and as a chiral selective agent in high-efficiency capillary electrophoresis (HPCE) applications, that is, the preparation of chiral HPCE electrophoresis columns and mobile phase chiral additives for the resolution of chiral substances. Background technique [0002] In the biological chiral environment, living substance molecules, drug molecules, and pesticide molecules with different chirality will show completely different physiological, pharmacological, and toxicological effects. In the pharmaceutical industry, about 30%-40% of the known drugs are photoactive chiral drugs. In the pesticide industry, all agricultural natural pesticides are optically active; 17% of synthetic pesticides are chiral pesticides. With the development of biochemistry and medicinal chemistry, there is an increasing demand for opt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16C25B7/00G01N27/447
CPCG01N27/447B01J20/29C08L5/16G01N2030/8877C08B37/0012G01N27/44747C25B7/00
Inventor 沈静茹
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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