EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS
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2017
·
IF 4.159
Jinyu Li,Guoxin Tan,Bingchao Cheng,Dandan Liu,Weisan Pan
To facilitate the hydrophobic drugs modeled by coumarin-6 (Cou-6) acrossing the cornea to the anterior chamber of the rabbit eye, chitosan (CS) derivatives including chitosan-N-acetyl- l -cysteine (CS-NAC), chitosan oligosaccharides (COS) and carboxymethyl chitosan (CMCS) modified nanostructured lipid carriers (NLCs) were designed and characterized. We found that, with similar size distribution and positive charges, different CS derivatives based on NLCs led to distinctive delivery performance. In vivo precorneal retention study on rabbits revealed that these CS derivatives coating exhibited a stronger resistant effect than Cou-6 eye drops and Cou-6-NLC (P < 0.05), moreover, the AUC (0−∞) , C max and MRT (0−∞) of them followed the sequence of CMCS-Cou-6-NLC < COS-Cou-6-NLC < CS-NAC-Cou-6-NLC. Confocal laser fluorescence microscopy (CLSM) for in vitro corneal penetration study showed that COS-, and CS-NAC-coated NLCs penetrated through the whole corneal epithelium barrier (about 40 μm), while CMCS failed to significantly enhance the intraocular drug penetration as expected, displayed a negligible fluorescence at 30 μm deep. In addition, penetration through the intact cornea was achieved and the penetration levels through the ocular tissues were increased thoroughly for the COS and CS-NAC coating ones compared with CMCS-NLC (P < 0.05), and successfully reduced the conjunctival-to-corneal permeability ratio (ratio (C - S/C) ) thus resulted in a higher bioavailability, which was confirmed by ex vivo fluorescence imaging on ocular tissues. In summary, CS-NAC-NLC and COS-NLC are promising ocular drug delivery systems to achieve prolonged precorneal retention, higher corneal permeability and enhanced ocular bioavailability. And comparatively speaking, CS-NAC-NLC possesses the highest potential for ocular drug delivery.
研究领域:
药剂学
·
眼科研究
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Acta Biomaterialia
·
2024
·
IF 9.4
Yueze Hong,Dong Liu,Haoyu Zou,Qingqing Jia,Sihan Tang,Quankui Lin
Intraocular lens (IOL) implantation is currently the most effective clinical treatment for cataracts. Nevertheless, due to the growth of the eye axis in patients with congenital cataracts during the process of growth and development, the progressive incapacity of an IOL with a fixed focus does not meet the demands of practical usage, leading to the occurrence of ametropia. This work describes an innovative class of an IOL bulk material that offers good biosafety and light-controlled refractive index adjustment. Acrylate materials were synthesized for the preparation of IOLs by free radical polymerization of ethylene glycol phenyl ether methacrylate (EGPEMA), hydrophilic monomer 2-(2-ethoxyethoxy) ethyl acrylate (EA), and functional monomer hydroxymethyl coumarin methacrylate (CMA). Under 365/254 nm ultraviolet (UV) irradiation, the coumarin group could adjust the polymer material's refractive index through reversible photoinduced dimerization/depolymerization. Meanwhile, the potential for the IOL use is enabled by its satisfactory biosafety. Such a light-induced diopter adjustable IOL will be more appropriate for implantation during cataract surgery since it will not require the correction needed for ametropia and will offer more accurate and humane treatment. Statement of significance • A coumarin group containing-copolymer was synthesized and fabricated into intraocular lenses (IOL). • A functional IOL is diopter adjustable by light irradiation through triggering the [2 + 2] cycloaddition of the coumarin groups. • Such light-triggered diopter-adjustable copolymer IOLs have a great potential in clinical application.
研究领域:
眼科
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生物材料学
·
高分子化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
LANGMUIR
·
2015
·
IF 4.457
Huihui Li,Houjuan Zhu,Mingtai Sun,Yehan Yan,Kui Zhang,Dejian Huang,Suhua Wang
Herein, we report a novel approach to the rapid visual detection of gaseous sulfur dioxide (SO2) by manipulating the surface chemistry of 3-aminopropyltriethoxysilane (APTS)-modified quantum dots (QDs) using fluorescent coumarin-3-carboxylic acid (CCA) for specific reaction with SO2. The CCA molecules are attached to the surface amino groups of the QDs through electrostatic attraction, thus the fluorescence of CCA is greatly suppressed because of the formation of an ion-pair complex between the ATPS-modified QDs and CCA. Such an interaction is vulnerable to SO2 because SO2 can readily react with surface amino groups to form strong charge-transfer complexes and subsequently release the strongly fluorescent CCA molecules. The mechanism has been carefully verified through a series of control experiments. Upon exposure to different amounts of SO2, the fluorescent color of the nanoparticle-based sensor displays continuously changes from red to blue. Most importantly, the approach owns high selectivity for SO2 and a tolerance of interference, which enables the sensor to detect SO2 in a practical application. Using this fluorescence-based sensing method, we have achieved a visual detection limit of 6 ppb for gaseous SO2.
研究领域:
分析化学
·
环境科学
✓ 已验证
DOI
PubMed
高影响因子
Journal of Chemical Information and Modeling
·
2025
·
IF 5.3
Sijie Liu,Jie Wu,Ya Chen,Clemens Alexander Wolf,Matthias Bureik,Johannes Kirchmair,Mario Andrea Marchisio,Gerhard Wolber
The human cytochrome P450 19A1 (CYP19A1, aromatase) is a heme-containing protein catalyzing the final steps of the biosynthesis of the steroid hormone 17β-estradiol. It is a key target for the treatment of sex-hormone-related disorders due to its role in mediating the conversion of androgens to estrogens. Here, we report the development of a virtual screening workflow incorporating machine learning and structure-based modeling that has led to the discovery of new CYP19A1 inhibitors. The machine learning models were built on comprehensive CYP19A1 data sets extracted from the ChEMBL and PubChem Bioassay databases and subjected to thorough validation routines. Ten promising hits that resulted from the virtual screening campaign were selected for experimental testing in an enzymatic assay based on heterologous expression of human CYP19A1 in yeast. Among the seven structurally diverse compounds identified as new CYP19A1 inhibitors, compound 9, a novel, noncovalent inhibitor based on coumarin and imidazole substructures, stood out by its high potency, with an IC50 value of 271 ± 51 nM.
研究领域:
药物化学
·
计算生物学
·
内分泌学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CARBOHYDRATE POLYMERS
·
2018
·
IF 5.158
Yuexin Sun,Chao Shi,Jiebing Yang,Shuangling Zhong,Zhanfeng Li,Lifeng Xu,Shengnan Zhao,Yan Gao,Xuejun Cui
In this present study, original, biodegradable, biocompatible, non-immunogenic and non-poisonous folic acid (FA) decorated reductive-responsive starch-based microcapsules (FA-RSMCs) were designed and fabricated via the sonochemical method for targeted delivery and controlled release of hydrophobic drugs. A green hydrophobic fluorescent dye, Coumarin 6 (C6), was encapsulated into the FA-RSMCs as a substitute of hydrophobic drugs. The as-synthesized C6-loaded FA-RSMCs were characterized by DLS, SEM and TEM. The results indicated that the obtained C6-loaded FA-RSMCs had an appropriate size range and could enter into the bloodstream with their splendid stability. Moreover, C6-loaded FA-RSMCs showed a high selectivity to Hela cells, and a brilliant targeted drugs delivery and reductive-responsive release ability for hydrophobic drugs, particularly for hydrophobic anti-cancer drugs.
研究领域:
药学
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生物材料科学
·
纳米医学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL DE MYCOLOGIE MEDICALE
·
2018
·
IF 1.606
K. Xu,J.L. Wang,M.P. Chu,C. Jia
Objective The aim of this study was to investigate the antibiofilm activity of coumarin against Candida albicans . Methods The efficacy of coumarin against biofilm formation and the mature biofilm of C. albicans was quantified by crystal violet (CV) staining and the 2,3-bis (2-methoxy-4-nitro-5-sulfophenyl)-5-[(phenylamino)carbonyl]-2H-tetrazolium hydroxide (XTT) reduction assay. The effect of coumarin on C. albicans adhesion was assessed on polystyrene plates and by using the cell surface hydrophobicity (CSH) assay. The morphological transition of C. albicans was conducted in two types of hyphae-inducing media at 37 °C. The expression of hypha/biofilm-related genes was evaluated using qRT-PCR analysis. A rescue experiment involving addition of exogenous cyclic adenosine monophosphate (cAMP) was performed to investigate the involvement of cAMP in the yeast-to-hyphae transition. A C. albicans -infected Caenorhabditis elegans model was used to test the anti-virulence efficacy of coumarin. Results Treatment with coumarin strongly affected the capacity of C. albicans to form biofilm and significantly impaired the preformed mature biofilm. The addition of coumarin notably inhibited C. albicans adhesion, CSH, and filamentation . The expression of some adhesion- and hypha-related genes, including HWP1 , HYR1 , ECE1 , and ALS3 , was remarkably down-regulated upon exposure to coumarin. Supplementation with cAMP partly rescued the coumarin-induced defects in hyphal development. Finally, coumarin prolonged survival in C. albicans -infected nematodes. Conclusion Coumarin inhibited C. albicans biofilm, which was associated with attenuated adhesion and hyphal growth.
研究领域:
微生物学
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药理学
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分子生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Journal of Physical Chemistry C
·
2018
·
IF 4.484
Feng Wang,Hui Liu
Dual-functional emulsifying/antifogging polymeric micelles have been prepared by the self-assembly of poly(2-(dimethylamino)ethyl methacrylate-co-methyl methacrylate-co-7-acryloxy-4-methylcoumarin) P(DMAEMA-co-MMA-co-AOM). On one hand, the polymeric micelles have spherical morphology and exhibit triple responsive behaviors. The sample with the DMAEMA/MMA/AOM molar ratio of 5/3/3 (T2) is chosen to investigate the influence of pH on the emulsifying performance, and the configuration of polymeric micelles on the oil/water interface is investigated. The amount of micelles arranged on the surface of solidified polymerized beads gradually decreases as the pH changes from 12 to 5, and then total phase separation and demulsification occur at pH 3. On the other hand, we prepare an effective antifogging coating by forming an interchain network (ICN) resulting from self-assembled micelles and photo-cross-linked coumarin units. The ICN-T2 coating can not only absorb water vapor rapidly but also avoid excessive swelling of the amphiphilic terpolymer, thus leading to excellent antifogging performance. To the best of our knowledge, the photo-cross-linkable coumarin derivative is first introduced into an antifogging polymer coating at the molecular level, successfully avoiding the use of chemical cross-linking agents. The coumarin-containing polymeric micelle may be applied in many industrial processes and will provide new insight into the interface or surface property of macromolecular materials.
研究领域:
高分子科学
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材料化学
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表面工程
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胶体与界面科学
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纳米技术
✓ 已验证
DOI
高影响因子
MACROMOLECULAR CHEMISTRY AND PHYSICS
·
2017
·Vol. 219
·期 2
·1700398
·
IF 2.5
Wei Ji,Minggao Qin,Chuanliang Feng
Recently, photoresponsive hydrogels have attracted increasing interest due to their ability to provide precise spatial and temporal control of drug release. Herein, a new kind of coumarin-based photoresponsive supramolecular hydrogelator without conventional gelation motif is designed and synthesized through a facile one-pot method. The gelation process, photoresponsiveness, self-assembly morphology, self-assembly mechanism, and release kinetics are fully investigated by various characterization methods (e.g., scanning electron microscopy, single crystal X-ray diffraction, high pressure liquid chromatography, UV–vis spectroscopy). Furthermore, encapsulated methyl violet dye molecules can be precisely released from the hydrogel by manipulating photoirradiation time. The study reveals that the coumarin-based photoresponsive hydrogel holds great potential as soft materials for controllable drug release.
研究领域:
材料科学
·
药物递送
·
化学
✓ 已验证
DOI
高影响因子
Chemistry of Heterocyclic Compounds
·
2020
·Vol. 56
·期 2
·219-225
·
IF 1.519
Li Shengling,Cao Duanlin,Hu Zhiyong,Li Zhichun,Meng Xianjiao,Han Xinghua,Ma Wenbing
In this study, three carbazole-coumarin hybrid dyes were successfully synthesized, and their UV-vis absorption spectra, fluorescence spectra, and structural properties were investigated. The results indicated that diethyl 12-hexyl-2,9-dioxo-9,12-dihydro-2 H -dipyrano[2,3- b :3',2'- h ]-carbazole-3,8-dicarboxylate showed a slight red shift of the maximum absorption wavelength, and its fluorescence intensity was above 4000 arb units, about 22 times higher than that of ethyl 10-hexyl-8-hydroxy-2-oxo-2,10-dihydropyrano[2,3- b ]carbazole-3-carboxylate and ethyl 10-hexyl-8-(hexyloxy)-2-oxo-2,10-dihydropyrano[2,3- b ]carbazole-3-carboxylate in CHCl 3 . The fluorescence intensity of the three compounds first increases and then decreases with the rise of concentration, and the maximum emission wavelength shows a slight red shift. The stability pH range of diethyl 12-hexyl-2,9-dioxo-9,12-dihydro-2 H -dipyrano[2,3- b :3',2'- h ]carbazole-3,8-dicarboxylate in THF was 2–10.
研究领域:
有机化学
·
光化学
·
材料科学
✓ 已验证
DOI
高影响因子
JOURNAL OF CHEMICAL RESEARCH
·
2021
·
IF 0.782
Tian Chai,Wen-Han Zhang,Hui Jiao,Yin Qiang
A new coumarin, 7-oxo-7H-furo-[3,2-g]chromen-9-yl dimethylcarbamate, is isolated from a methanol extract of Zanthoxylum bungeanum pericarps. The structure of this compound 1 is elucidated based on extensive spectroscopic analysis, including infrared, nuclear magnetic resonance, and mass spectrometry. This new compound is also synthesized by a simple acylation reaction with dimethylcarbamoyl chloride. The inhibitory activity of the isolated compound against HeLa and HepG2 cell lines is described. The protein tyrosine phosphatase 1B inhibitory activity against HeLa and HepG2 cancer cells and the sirtuin 1 inhibitory activity against HepG2 cancer cells are also evaluated.
研究领域:
药理学
·
化学
·
癌症研究
·
植物科学
✓ 已验证
DOI
高影响因子
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2017
·
IF 2.536
Zian Wang,Qianqian Wu,Jiale Li,Shuang Qiu,Duxia Cao,Yongxiao Xu,Zhiqiang Liu,Xueying Yu,Yatong Sun
Two new benzoyl coumarin amide derivatives with ortho hydroxyl benzoyl as terminal group have been synthesized. Their photophysical properties and recognition properties for cyanide anions in acetonitrile have also been examined. The influence of electron donating diethylamino group in coumarin ring and hydroxyl in benzoyl group on recognition properties was explored. The results indicate that the compounds can recognize cyanide anions with obvious absorption and fluorescence spectral change and high sensitivity. The import of diethylamine group increases smartly the absorption ability and fluorescence intensity of the compound, which allows the recognition for cyanide anions can be observed by naked eyes. The in situ hydrogen nuclear magnetic resonance spectra combining photophysical properties change and job's plot data confirm that Michael addition between the chemosensors and cyanide anions occurs. Molecular conjugation is interrupted, which leads to fluorescence quenching. At the same time, there is a certain extent hydrogen bond reaction between cyanide and hydroxyl group in the compounds, which is beneficial to the recognition.
研究领域:
分析化学
·
超分子化学
·
荧光传感
·
有机化学
✓ 已验证
DOI
高影响因子
MATERIALS CHEMISTRY AND PHYSICS
·
2015
·
IF 2.259
Qianqian Wu,Zhiqiang Liu,Duxia Cao,Ruifang Guan,Kangnan Wang,Yanyan Shan,Yongxiao Xu,Lin Ma
Four coumarin amide derivatives with 4-methyl coumarin or pyrene as terminal group have been synthesized. Their photophysical properties and recognition properties for cyanide anions have been examined. The results indicate that the compounds can recognize cyanide anions with obvious absorption and fluorescence spectra change, at the same time, obvious color and fluorescence change can be observed by naked eye. The in situ hydrogen nuclear magnetic resonance spectra and photophysical properties change confirm that Michael additions between the chemosensors and cyanide anions take place at the 4-position of coumarin.
研究领域:
分析化学
·
光物理化学
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）