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Interaction of 4-aminosalicylic acid and Surfactants in Aqueous Solutions Using UV-Vis Spectra and Steady-state Fluorescence Spectroscopy

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Journal of Wuhan University of Technology(Materials Science) 2011年第5期26卷 879-882页

作者：许东颖廖正福 College of Light Industry and Food Sciences South China University of Technology Faculty of Materials and Energy Guangdong University of Technology Key Laboratory of Cellulose and Lignocellulosics Chemistry Guangzhou Institute of ChemistryChinese Academy of Sciences

The interactions of 4-aminosalicylic acid （4-ASA） and surfactants in aqueous solutions were investigated by using UV-Vis spectra and steady-state fluorescence *** results showed that the strongest peak at UV-vis spectra of 4-ASA aqueous solution in the presence of cationic surfactant and cetyltrimethyl ammonium bromide （CTAB） appeared at 206 nm and took a red shift from 206 nm to 221 nm with the increase of 4-ASA concentrations from 0.8×10-5 to 4.4×10-4 mol/***,the strongest peak at UV-vis spectra of 4-ASA aqueous solution in the presence of nonionic surfactant and polyvinylpyrrolidone （PVP） appeared at 206 nm and took a red shift from 206 nm to 219 nm with the increase of 4-ASA concentrations from 0.8×10-5 to 4.4×10-4 mol/***,the similar phenomena did not appeared in the presence of anion surfactant,sodium dodecyl sulfate （SDS）,the UV-vis spectra of 4-ASA aqueous solution remained the same peak position and the peak value increased with the 4-ASA concentration *** results could be attributed to the electrostatic attraction between 4-ASA and CTAB or PVP,as well as the electrostatic repulsion between 4-ASA and ***,the value of critical micelle concentration （CMC） of surfactants in the presence of 4-ASA was determined with Fluorescence *** first and second CMC of CTAB was 1.2×10-4 M and 2.4×10-4 M,*** first and second CMC of PVP was 1.2×10-4 M and 2.8×10-4 *** realized the multiple micellizations to form multiple CMC.

关键词： 4-aminosalicylic acid surfactant interaction UV-vis spectra steady-state fluorescence

Synthesis of phenol-class azo derivatives of 4-aminosalicylic acid

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Chinese Chemical Letters 2008年第4期19卷 419-422页

作者： Shi Fei Sheng Hui Xia Zheng Jiang Liu Zheng Bao Zhao School of Pharmaceutical Science Shanxi Medical UniversityTaiyuan 030001China First Clinical College Shanxi Medical UniversityTaiyuan 030001China

To explore the better prodrug of 4-aminosalicylic acid（4-ASA）with higher activity and less side effects against the inflammatory bowel disease.4-ASA,after a succession of synthesis process,was conjugated with various carder molecules to get seven azo derivatives of *** compounds were characterized by FT-IR,^1H NMR,^13C NMR spectras in *** derivatives of 4-ASA were definituded.

关键词： 4-aminosalicylic acid Azo derivatives of 4-aminosalicylic acid Inflammatory bowel disease

Colon-specific prodrugs of 4-aminosalicylic acid for inflammatory bowel disease

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World Journal of Gastroenterology 2014年第13期20卷 3564-3571页

作者： Suneela S Dhaneshwar Department of Pharmaceutical Chemistry Poona College of PharmacyBharati Vidyapeeth Deemed UniversityPune-411 038MaharashtraIndia

Despite the advent of biological products, such as anti-tumor necrosis factor-α monoclonal antibodies (infliximab and adalimumab), for treatment of moderate to severe cases of inflammatory bowel disease (IBD), most patients depend upon aminosalicylates as the conventional treatment option. In recent years, the increased knowledge of complex pathophysiological processes underlying IBD has resulted in development of a number of newer pharmaceutical agents like low-molecular-weight heparin, omega-3 fatty acids, probiotics and innovative formulations such as high-dose, once-daily multi-matrix mesalamine, which are designed to minimize the inflammatory process through inhibition of different targets. Optimization of delivery of existing drugs to the colon using the prodrug approach is another attractive alternative that has been utilized and commercialized for 5-aminosalicylic acid (ASA) in the form of sulfasalazine, balsalazide, olsalazine and ipsalazine, but rarely for its positional isomer 4-ASA - a well-established antitubercular drug that is twice as potent as 5-ASA against IBD, and more specifically, ulcerative colitis. The present review focuses on the complete profile of 4-ASA and its advantages over 5-ASA and colon-targeting prodrugs reported so far for the management of IBD. The review also emphasizes the need for reappraisal of this promising but unexplored entity as a potential treatment option for IBD.

关键词： 4-aminosalicylic acid 5-aminosalicylic acid Sulfasalazine Colon-specific prodrug Inflammatory bowel disease Ulcerative colitis 2,4,6-trinitrobenzene sulphonic acid Experimental colitis

Synthesis of 4-Aminosalicylglycine

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Chinese Chemical Letters 2005年第7期16卷 889-892页

作者： ZhengBaoZHAO JingGUO YuanGuiWEI TongDaLIANG CollegeofPharmacy ShanxiMedicalUniversityTaiyuan030001

To search for a better prodrug of 4-aminosalicylic acid that is expected to deliver stably parent drug to colon against the inflammatory bowel disease, a novel 4-aminosalicylic acid derivative was designed and synthesized from 4-aminosalicylic acid. 4-Aminosalicylglycine was prepared from 4-aminosalicylic acid by protecting amino and hydroxyl groups with benzyloxy- carbonyl and acetyl, respectively, then the carboxylic acid was converted to acyl chloride which was treated with glycine. After removing the protection groups, 4-aminosalicylglycine was obtained. All the compounds were characterized by FT-IR, 1H-NMR, 13C-NMR spectra. In vivo experiment on rats suggested that the curative effect of 4-aminosalicylglycine was more effective than that of 4-aminosalicylic acid.

关键词： 4-aminosalicylic acid 4-aminosalicylglycine inflammatory bowel disease.

Synthesis and Structure of a Titanocene-ferrocenyl Complex

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Chinese Journal of Structural Chemistry 2009年第3期28卷 271-278页

作者：王高峰高子伟孙述文高玲香董顺福刘昭铁毋登辉 Key Laboratory of Macromolecular Science of Shaanxi Province Shaanxi Normal University College of Pharmacy Jilin Medical College College of Materials Science and Engineering North University of China

A titanocene-ferrocenyl complex, （5-ferrocenyl-2-hydroxybenzenecarboxylato- O,O′）-bis（methylcyclopentadienyl）titanium（IV） 4, and an unexpected ionic complex, [C7H8NO3]- [（C5H5）Fe（C5H4）SO3]·H2O3 were synthesized and characterized by IR, ^1H NMR and elemental analysis. Compound 3 is of triclinic, space group P1 with a = 5.954（2）, b = 13.208（5）, c = 13.252（5） A, α = 60.993（7）,β = 84.342（8）,γ = 86.933（8）°, Z = 2, V = 906.8（6）A^3, Dc = 1.601 g/cm^3, μ（MoKα） = 0.987 mm^-1, F（000） = 452, the final R = 0.0647 and wR = 0.1333 for 2311 observed reflections （I 〉 2σ（I））. Compound 4 belongs to the monoclinic system, space group P2 1/c with α = 14.3310（9）, b = 12.5065（8）, c = 12.9406（10） A, β = 95.101（4）°, Z = 4, V = 2310.2（3） A^3, Dc = 1.513 g/cm^3, μ（MoKα） = 1.004 mm^-1, F（000） = 1088, the final R = 0.0461 and wR = 0.1048 for 2112 observed reflections （1 〉 2σ（I））.

关键词： fitanocene ferrocene heteronuclear ferrocenesulfonate 4-aminosalicylic acid

Synthesis and Kinetic Study on the Chromium（Ⅲ） Complex [Cr（ASA）（en）2]Cl·2H2O

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Chinese Journal of Chemistry 2007年第12期25卷 1802-1808页

作者：刘斌杨斌盛 Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education Institute of Molecular Science Shanxi University Taiyuan Shanxi 030006 China

In order to explore the transfer mechanism of chromium（Ⅲ） in mammals, a novel complex [Cr（ASA）（en）2]Cl·2H2O, bis（ethylenediamine-κ2 N,N′）（4-aminosalicylic acid-κ^2 O,O′） chromium（Ⅲ） monochloride dihydrate was synthesized （4-aminosalicylic acid=H2ASA, ethylenediamine=en）. The crystal structure belongs to orthorhombic system with the space group P212121 by means of X-ray diffraction. The characteristic for transfer of Cr^3＋ from the compound to the low-molecular-mass chelator EDTA and the iron-binding protein apoovotransferrin （apoOTf） was followed by UV-visible （UV-Vis） and fluorescence spectra in 0.01 mol·L^-1 Hepes at pH 7.4. The second order rate constants were calculated. Those spectra in conjunction were used to obtain more accurate information about the interaction of chromium complex with apoOTf. The experimental results indicate that Cr^3＋ can be transferred from the complex to apoOTf with the retention of the 4-aminosalicylic acid acting as a synergistic anion.

关键词： Chromium(Ⅲ) 4-aminosalicylic acid apoovotransferrin kinetics