JOURNAL OF MOLECULAR LIQUIDS
·
2019
·
IF 4.561
Shaolei Zhao,Yiming Ma,Junbo Gong,Baohong Hou,Weiwei Tang
The structure and properties of griseofulvin (GSF) were investigated in both solution and solid phases. The intermolecular interactions within griseofulvin crystal structure probed by Hirshfeld surface analysis reveal that the H⋯H and O⋯H contacts apparently dominate in the solid-state structure. The solution thermodynamic properties including solid-liquid phase equilibrium solubility and thermodynamic functions of mixing were determined in twelve solvents (methanol, ethanol, n-propanol, n-butanol, isobutanol , methyl acetate , ethyl acetate , n-propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate and acetonitrile). The equilibrium solubility data was measured by gravimetric method at temperature ranging from 283.15 to 323.15 K, and the measurement results show the solubility is monotonously rising with increasing temperature as expected in all solvents. Besides, the investigations over the effect of solvent properties in terms of solvent polarity, hydrogen bonding donor and acceptor propensity, as well as cohesive energy density on solid-liquid phase equilibrium behaviors reveal that the solvent polarity determines the solubility of griseofulvin in the studied solvent systems. Further, the statistical correlations were well performed by the modified Apelblat equation, λh equation, and NRTL model, in which the modified Apelblat equation receives the best fitting performance. Finally, thermodynamic functions of mixing (enthalpy, entropy, and Gibbs energy) were derived, and the results suggest a spontaneous, exothermic and entropy-driven mixing process. All the thermodynamic data and models presented here will certainly provide fundamental basis for separation and purification of griseofulvin in industrial production.
研究领域:
药学
·
物理化学
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产品关联
DOI
高影响因子
CRYSTAL GROWTH & DESIGN
·
2022
·
IF 4.01
Xiao Ou,Shuting Li,Yunyun Chen,Haowei Rong,Ao Li,Ming Lu
Griseofulvin (GSF) is a clinically used antifungal drug that was reported to have three true polymorphs (Forms I–III) over the past eight decades. Here, we present the discovery of two new polymorphs (denoted Forms IV and V) that are accessible only in the presence of polyethylene glycol (PEG). The crystal structures of Forms IV and V were determined by X-ray crystallography using single crystals cultivated by melt crystallization. The identification and crystallization behavior of Forms IV and V were fully investigated. A solid-form landscape of melt-crystallized GSF in the presence of PEG was established to describe the complicated phase conversions among six solid forms, including five true polymorphs and a previously known GSF-PEG inclusion complex. The influence of the molecular weight and content of PEG on the polymorphism of GSF was studied. This work suggests that PEG addition is an alternative strategy that cannot be neglected in polymorphism screening. The results also expand our understanding of the complicated crystallization behavior of GSF in dispersions with PEG and highlight the importance of polymorphism control during the manufacture and storage of PEG-based solid dispersions to achieve reproducible and consistent pharmaceutical performance.
研究领域:
药学
·
晶体化学
·
材料科学
✓ 已验证
DOI
高影响因子
Materials Science & Engineering C-Materials for Biological Applications
·
2018
·
IF 5.08
Yue-Hong Yang,Lan-Tao Liu,Mei-Jun Chen,Song Liu,Cheng-Bin Gong,Yu-Bo Wei,Cheuk-Fai Chow,Qian Tang
A new photoresponsive surface molecularly imprinted polymer shell (PMIPS) was developed for determination of trace griseofulvin from milk. The PMIPS was prepared by surface imprinting technique using poly(styrene- co -methacrylic acid) (PS- co -PMMA) microspheres as the sacrificial substrate, griseofulvin as the template, a photoresponsive azobenzene derivative 4-((4-(methacryloyloxy)phenyl)diazenyl)-3,5-dimethyl benzenesulfonic acid as the functional monomer, and triethanolamine trimethacrylate as the cross-linker. The PMIPS was obtained after the removal of the sacrificial PS- co -PMMA core from the surface imprinted core-shell microspheres, PS- co -PMAA@PMIP. Compared with PS- co -PMAA@PMIP, PMIPS displayed better properties such as higher surface area and pore volume, rapid photo-isomerization rate, and higher adsorption capacities, specific binding constant and binding density. The PMIPS could efficiently detect griseofulvin in complex samples such as milk.
研究领域:
分析化学
·
食品科学
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产品关联
DOI
PubMed
高影响因子
Small
·
2025
·
IF 12.1
Yujie Guo,Lingfei Li,Maofeng Zhang,Shihao Xu,Changlong Jiang
Polymetallic MOFs heterostructural composites enhance their usage in a range of sensing domains by combining two or more different MOFs to produce a new MOF-on-MOF integrated module. As its widespread utilization of flavomycin (Fla), there are currently complications with agricultural residue and the environment, consequently, a highly sensitive, portable technology for identification will be required to handle environmental monitoring in real-time. In this work, the structural characterization and characteristics of the two-layer MOF-on-MOF heterostructure are investigated using the epitaxial growth method. Electrons migrate from the Fe metal center to the organic ligand primarily as a result of hydrogen bonding between Fla and the surface of Fe-MOF and energy transfer amongst the Fe atoms and NH 2 -MIL-101 (Eu). The synergistic impact of NH 2 -MIL-101(Eu) and Fe-MOF improves the sensitivity and accuracy of detection, which has a 4.8 n m detection limit, enabling the high sensitivity detection of Fla. Likewise, we put together a handheld sensing platform incorporating aerogel and sensing materials that can meet the expectations of real-time monitoring and multiple actual sample detection, and fluorescent MOFs materials offer an innovative viewpoint on the application of creating flexible sensors, enabling a new method of visualization for food safety and environmental early alerting.
研究领域:
材料科学
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环境科学
·
食品安全
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2023
·
IF 6.1
Yu-Bin Bai,Meng Zhang,Ding Li,Yu Zhao,Liang-Zhu Huang,Jin-Ming Gao
Natural products are important sources for the discovery of new pesticides. Chemical synthesis and structural modification can lead to pesticides. Despite abundant research in fungicide discovery for crop protection, there is an emerging need for the development of novel antifungal agrochemicals. Herein, 39 diversified griseofulvin derivatives were effectively synthesized from the natural product griseofulvin by diversity-oriented synthesis through the reactions of demethylation, ammonolysis, methylation, nitration, acylation, reduction, and chlorination. Among them, 31 derivatives were novel. All structures were characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometry (HR-MS), and the antifungal activity was investigated against five phytopathogenic fungi. Compounds 5h and 5l had excellent activity against Botrytis cinerea (5h, IC50 = 17.29 ± 0.64 μg/mL) and Alternaria solani (5l, IC50 = 22.52 ± 0.79 μg/mL), respectively. Compound 9 exhibited the more promising activities against three target fungi, especially against Colletotrichum gloeosporioides (IC50 = 7.24 ± 0.66 μg/mL), which is obviously better than positive control hymexazol, thifluzamide, and parent compound griseofulvin. In addition, compound 10 showed significant and extensive activities against four target fungi Cytospora sp. (IC50 = 18.72 ± 0.35 μg/mL), C. gloeosporioides (IC50 = 31.39 ± 1.48 μg/mL), A. solani (IC50 = 40.82 ± 1.04 μg/mL), and Fusarium solani (IC50 = 36.81 ± 0.82 μg/mL). Unexpectedly, 11 and 12, the chlorinated products of compound 9, exhibited the most promising activity against C. gloeosporioides (IC50 = 4.48 ± 0.54 μg/mL for 11, 2.24 ± 0.76 μg/mL for 12). Furthermore, 12 showed remarkable activity against Cytospora sp. (IC50 = 5.85 ± 0.72 μg/mL). Additionally, in vivo antifungal activity against C. gloeosporioides, homology modeling, and docking analysis of 11, 12, and griseofulvin were conducted. All results indicated that 11 and 12 had potency as antifungal agents against C. gloeosporioides, and the modifications of the 2′ and 4′ positions of griseofulvin should be further explored for higher-activity lead compounds or potential agricultural fungicides.
研究领域:
农药化学
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植物保护
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药物化学
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产品关联
DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF PHARMACEUTICS
·
2024
·
IF 5.3
Ariana Sheng-Chu Leon,Kenneth C. Waterman,Guanhua Wang,Likun Wang,Ting Cai,Xiaohua Zhang
Amorphous solid dispersions (ASDs) represent an important approach for enhancing oral bioavailability for poorly water soluble compounds; however, assuring that these ASDs do not recrystallize to a significant extent during storage can be time-consuming. Therefore, various efforts have been undertaken to predict ASD crystallization levels with kinetic models. However, only limited success has been achieved due to limits on crystal content quantification methods and the complexity of crystallization kinetics . To increase the prediction accuracy, the accelerated stability assessment program (ASAP), employing isoconversion (time to hit a specification limit) and a modified Arrhenius approach, are employed here for predictive shelf-life modeling. In the current study, a model ASD was prepared by spray drying griseofulvin and HPMC-AS-LF. This ASD was stressed under a designed combinations of temperature, relative humidity and time with the conditions set to ensure stressing was carried out below the glass transition temperature (T g ) of the ASD. Crystal content quantification method by X-ray powder diffraction (XRPD) with sufficient sensitivity was developed and employed for stressed ASD. Crystallization modeling of the griseofulvin ASD using ASAP prime ® demonstrated good agreement with long-term (40 °C/75 %RH) crystallinity levels and support the use of this type of accelerated stability studies for further improving ASD shelf-life prediction accuracy.
研究领域:
药剂学
·
药物化学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Yu-Bin Bai,Kai-Ming Yang,Meng Zhang,Yi-Xiang Li,Yu Zhao,Liang-Zhu Huang,Hua Yang,Xiao-Jun Yang,Ding Li,Jin-Ming Gao
The extensive and repeated application of chemical fungicides results in the rapid development of fungicide resistance. Novel antifungal pesticides are urgently required. Natural products have been considered precious sources of pesticides. It is necessary to discover antifungal pesticides by using natural products. Herein, 42 various griseofulvin derivatives were synthesized. Their antifungal activities were evaluated in vitro. Most of them showed good antifungal activity, especially 3d exhibited a very broad antifungal spectrum and the most significant activities against 7 phytopathogenic fungi. In vivo activity results suggested that 3d protected apples and tomatoes from serious infection by phytopathogenic fungi. These proved that 3d had the potential to be a natural product-derived antiphytopathogenic fungi agent. Furthermore, docking analysis suggested that tubulin might be one of the action sites of 3d. It is reasonable to believe that griseofulvin derivatives are worth further development for the discovery of new pesticides.
研究领域:
农药学
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植物病理学
·
药物化学
✓ 已验证
DOI
PubMed
高影响因子
Arabian Journal of Chemistry
·
2019
·
IF 3.298
Kamran Bashir,Pengqi Guo,Guoning Chen,Yunzhe Li,Yanhui Ge,Hua Shu,Qiang Fu
In present study, an investigation was carried out to develop and validate an analytical method for the selective extraction and determination of griseofulvin (GSF) from plasma samples. For this purpose, a rational approach was made to synthesize and characterize the surface molecularly imprinted polymers (SMIPs). The SMIPs were utilized as solid phase extraction (SPE) sorbents. The SMIPs were prepared by using GSF as template molecule on the surface of modified silica particles through a non-covalent technique. The particles demonstrated high adsorption capacity (119.1 µg/mL), fast adsorption equilibrium time (30 min) and good recognition selectivity for the template drug. The scanning electron microscopy and infrared spectroscopy were used to explain the structural and morphological characteristics of the SMIPs and surface non-imprinted polymers. The SPE method was combined with HPLC for plasma analysis. The method validation results demonstrated that the established method possessed good linearity for GSF ranging from 0.1 to 50 µg/mL (R 2 = 0.997). The limit of detection for this method was 0.02 µg/mL for rat plasma samples. The recoveries of GSF from spiked plasma samples were (90.7–97.7%) and relative standard deviations were (0.9–4.5%). Moreover, the SMIPs as selective SPE sorbent can be reused more than 8 times which is a clear advantage over commercial SPE sorbents. Finally, the usefulness of the proposed strategy was assessed by extraction and detection of GSF in real rat plasma samples.
研究领域:
药物分析
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材料科学
·
生物医学工程
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DOI
高影响因子
INTERNATIONAL JOURNAL OF PHARMACEUTICS
·
2024
·
IF 5.3
Yue Cai,Xinrui Zhang,Wentao Hu,Fuhang Song,Hong Wang,Huawei Zhang,Xuanrong Sun
Transdermal drug delivery represents a promising avenue for the treatment of dermatologic diseases, such as cutaneous melanoma and skin infections. This study involves the development of a novel therapeutic strategy that employs a skin-penetrating peptide SPACE-modified flexible liposomal chrysomycin A (CA@SPACE-LP) with a particle size of 111.5 nm. In vitro transdermal experiments demonstrated that CA@SPACE-LP was effective in enhancing the ability of the drug to penetrate the stratum corneum and enter deep into the skin tissue, increasing the intradermal drug concentration up to threefold compared to free CA. Furthermore, CA@SPACE-LP was observed to maintain the biological activity of CA against planktonic Methicillin-resistant Staphylococcus aureus (MRSA) and melanoma cells. In vivo studies demonstrated that the topical administration of CA@SPACE-LP was efficacious in controlling the progression of cutaneous melanoma, with a tumor suppression rate of approximately 60 %, which was more pronounced than that observed with intravenous Taxol. Furthermore, CA@SPACE-LP demonstrated efficacy in the management of intradermal MRSA infections, with a significantly reduced area of ulceration in the treated mice (0.25 cm 2 ) compared to the positive control drug (Mupirocin Ointment). These results suggest that the topical delivery system developed in this study has the potential to be used for the simultaneous treatment of skin cancer and invasive MRSA infection.
研究领域:
药剂学
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皮肤病学
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肿瘤学
·
微生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
International Journal of Environmental Research and Public Health
·
2019
·Vol. 17
·期 1
·134
·
IF 2.468
Kamran Bashir,Zhimin Luo,Guoning Chen,Hua Shu,Xia Cui,Wen Li,Wang Lu,Qiang Fu
Griseofulvin (GSF) is clinically employed to treat fungal infections in humans and animals. GSF was detected in surface waters as a pharmaceutical pollutant. GSF detection as an anthropogenic pollutant is considered as a possible source of drug resistance and risk factor in ecosystem. To address this concern, a new extraction and enrichment method was developed. GSF-surface molecularly imprinted polymers (GSF-SMIPs) were prepared and applied as solid phase extraction (SPE) sorbent. A dispersive solid phase extraction (DSPE) method was designed and combined with HPLC for the analysis of GSF in surface water samples. The performance of GSF-SMIPs was assessed for its potential to remove GSF from water samples. The factors affecting the removal efficiency such as sample pH and ionic strength were investigated and optimized. The DSPE conditions such as the amount of GSF-SMIPs, the extraction time, the type and volume of desorption solvents were also optimized. The established method is linear over the range of 0.1–100 µg/mL. The limits of detection and quantification were 0.01 and 0.03 µg/mL respectively. Good recoveries (91.6–98.8%) were achieved after DSPE. The intra-day and inter-day relative standard deviations were 0.8 and 4.3% respectively. The SMIPs demonstrated good removal efficiency (91.6%) as compared to powder activated carbon (67.7%). Moreover, the SMIPs can be reused 10 times for water samples. This is an additional advantage over single-use activated carbon and other commercial sorbents. This study provides a specific and sensitive method for the selective extraction and detection of GSF in surface water samples.Keywords:dispersive solid phase extraction;griseofulvin;HPLC;removal and analysis;pharmaceutical pollutants;surface water
研究领域:
环境科学
·
分析化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2019
·
IF 3.571
Yu-Bin Bai,Yu-Qi Gao,Xiao-Di Nie,Thi-Mai-Luong Tuong,Ding Li,Jin-Ming Gao
With environmental pollution, residual hazards accumulate and severe drug resistance and many other problems appear; some highly toxic drugs have been banned, and antifungal agents are far from satisfactory. Natural products play an important role in the discovery and development of new pesticides. The natural product griseofulvin (1) has been known as an antifungal agent in the treatment of dermatomycoses for decades. In this study, a series of new griseofulvin derivatives were synthesized with good yields. Their structures were characterized by 1H and 13C nuclear magnetic resonance and high-resolution mass spectrometry (electrospray ionization). The antifungal activities of griseofulvin analogues were first evaluated against five phytopathogenic fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani) in vitro. Of significance is that most of them showed excellent antifungal activities against C. gloeosporioides. The antifungal activities of the four best compounds (6a, 6c, 6e, and 6f) against C. gloeosporioides were further investigated in vivo using infected apples. The results suggested that compounds 6c, 6e, and 6f [half-maximal inhibitory concentration (IC50) = 47.25 ± 1.46, 49.44 ± 1.50, and 53.63 ± 1.74 μg/mL, respectively] were better than thiophanate-methyl (IC50 = 69.66 ± 6.07 μg/mL). Furthermore, comparative molecular field analysis was performed on the basis of the antifungal activity results of all 22 of the compounds against C. gloeosporioidesin vitro. The three-dimensional coefficient contour plots revealed that the suitable bulky and electronegative acyl-substituted groups seem to be more favorable for increasing activity at the 4′ position of griseofulvin. The structure–activity relationships were also discussed. Griseofulvin derivatives can be used for the development of highly effective and safe agricultural fungicides.
研究领域:
植物保护学
·
药物化学
·
分子生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
AAPS PHARMSCITECH
·
2022
·Vol. 23
·期 6
·1-16
·
IF 4.026
Ma Lin,Guo Song,Piao Jingshu,Piao Mingguan
Griseofulvin (GF) is used as an antifungal to treat superficial skin fungal infections such as tinea capitis and tinea pedis. Currently, GF is only available in traditional oral dosage forms and suffers from poor and highly variable bioavailability, hepatotoxicity, and long duration of treatment. Therefore, the main objective of this study was to reduce the side effects of the drug and to increase the concentration of the drug retained in the cutaneous stratum corneum (SC) and improve its efficacy through the preparation of drug-laden GF microsponge (GFMS). The emulsification-solvent-diffusion method was used to prepare GFMS, and the prescriptions were screened by a single-factor approach. The optimized formulation (GFF8) had a microsponge particle size (μm) of 28.36 ± 0.26, an encapsulation efficiency (%) of 87.53 ± 1.07, a yield (%) of 86.58 ± 0.42, and drug release (%) from 77.57 ± 3.88. The optimized microsponge formulation was then loaded into a Carbopol 934 gel matrix and skin retention differences between the microsponge gel formulation and normal gels were examined by performing skin retention and fluorescence microscopy tests. Finally, the hepatoprotective and cutaneous stratum corneum retention abilities of microsponge gel formulations compared to oral GF formulations were assessed by hepatotoxicity, pharmacokinetics, and tissue distribution studies. This provides a new perspective on GF dermal stratum corneum retention administration. Graphical abstract
研究领域:
药剂学
·
药学
·
皮肤病学
·
毒理学
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）