A class of drug derivatives of moxifloxacin and their preparation method and application

A technology of moxifloxacin and derivatives, which is applied in the field of biomedical materials, can solve the problems that the fluorescence properties of drugs are rarely studied, and the application of fluorescence properties and drug activity is few, achieving excellent inhibitory effect, good selectivity, and reaction site point clear effect

Active Publication Date: 2022-05-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As a kind of broad-spectrum antibacterial drugs, quinolone antibiotics have been widely used in clinic due to their high antibacterial properties; however, the fluorescent properties of these drugs are rarely studied, and the application of fluorescent properties and drug activity is more important. less reported

Method used

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  • A class of drug derivatives of moxifloxacin and their preparation method and application
  • A class of drug derivatives of moxifloxacin and their preparation method and application
  • A class of drug derivatives of moxifloxacin and their preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] A kind of preparation of moxifloxacin drug derivative (MXF-P)

[0061] The synthetic route is as follows:

[0062]

[0063] MXF-P: Compound 1 (304 mg, 0.6 mmol) and MXF-HCl (219 mg, 0.5 mmol) were dissolved in a mixed solution of MeCN:DMF=9mL:1mL, and KHCO was added 3 (84 mg, 1.0 mmol); the reaction mixture was heated to 90° C. and reacted for 12 hours. After the solvent was removed by rotary evaporation under reduced pressure, water was added to the mixture. It was then extracted with DCM (3 x 30ml); the organic layers were combined and washed with anhydrous Na 2 SO 4 Drying, concentration, and silica gel column purification (eluent DCM:MeOH=20:1) gave MXF-P as a yellow solid in 58% yield. 1 H NMR (500MHz, CDCl 3 )δ15.16(brs,1H),8.37(s,1H),7.84–7.75(m,9H),7.71–7.65(m,7H),4.02–3.99(m,1H),3.80–3.71(m, 3H), 3.65–3.55 (m, 5H), 3.17 (brs, 1H), 2.76 (brs, 1H), 2.53 (brs, 1H), 2.39–2.23 (m, 3H), 1.82–1.41 (m, 10H) ,1.37–1.17(m,5H),0.99–0.92(m,2H). 13 C NMR (125MHz, ...

Embodiment 2

[0065] Preparation of Anions in the Structure of Moxifloxacin Derivatives

[0066] will get Br - The compound MXF-P (0.2 mmol, 166 mg) was dissolved in acetone, and an aqueous solution of potassium hexafluorophosphate (0.3 mmol, 55 mg) was added and stirred for 2 h. Water was added to the mixture and filtered. The filtered solid is washed with water to remove inorganic salts, and dried to obtain a product containing hexafluorophosphate anion.

Embodiment 3

[0068] Absorption and Fluorescence Characterization of Moxifloxacin Derivatives

[0069] Figure 1A Based on the absorption spectrum of the material MXF-P obtained in Example 1 in DMSO, it can be seen that the main absorption peak of the molecule is around 365 nm; Figure 1B is the fluorescence emission spectrum of MXF-P in DMSO solvent and solid state, it can be seen that the emission peak of this molecule is mainly around 475nm; Figure 1C for with H 2 O content increased in MXF-P (10 μM) in DMSO / H 2 Fluorescence emission spectrum in O(v / v) mixed solvent; when the molecule is in DMSO solution, the luminescence is weak, with the addition of water, it can be found that the fluorescence intensity is continuously enhanced, when the water content reaches 90%, The fluorescence intensity reaches a maximum value. This phenomenon is due to the continuous enhancement of fluorescence due to the aggregation of MXF-P molecules as the proportion of poor solvent water increases. These ...

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Abstract

The invention belongs to the field of biomedical materials, and discloses a moxifloxacin drug derivative, a preparation method and an application thereof. The structure of the moxifloxacin drug derivative is formula I, wherein: R is independently an organic cation of triphenylphosphine salt, pyridinium salt, or quaternary ammonium salt; X is a monovalent anion; n is any one of 1 to 17 integer. The invention also discloses the preparation method of the moxifloxacin derivatives. The moxifloxacin derivatives of the present invention have aggregation-induced luminescent properties, can realize rapid staining and identification of microorganisms, and exhibit specific, efficient and sensitive characteristics. The moxifloxacin derivatives of the invention have excellent antibacterial effects. The moxifloxacin drug derivatives of the present invention are used for preparing reagents for specifically staining mitochondria and negatively charged microorganisms on the surface, and simultaneously for preparing reagents and antibacterial agents for distinguishing the dead and alive states of microorganisms.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and in particular relates to a class of moxifloxacin drug derivatives and a preparation method and application thereof. Background technique [0002] In clinical practice, bacterial infections lead to a variety of diseases, which seriously threaten human health. In the process of antibacterial, rapid diagnosis and precise treatment of bacterial species are very important. At present, the main method for distinguishing bacterial species is Gram staining, which is complicated, time-consuming and labor-intensive, and cannot achieve real-time in-situ monitoring of live bacteria. Therefore, it is very important to develop accurate and rapid bacterial identification diagnostic reagents. [0003] Organic small molecule fluorescent probes have been widely used in rapid biological detection, biological imaging and treatment. They have the characteristics of low cost, simple operation and high sensiti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06G01N21/64C12Q1/00A61P31/04
CPCC07D471/04C09K11/06G01N21/6428C12Q1/00A61P31/04G01N2021/6432
Inventor 唐本忠秦安军王柄楠胡蓉蓉赵祖金王志明
Owner SOUTH CHINA UNIV OF TECH
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