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In vitro 3D malignant melanoma model for the evaluation of hypericin-loaded oil-in-water microemulsion in photodynamic therapy

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Bio-Design and Manufacturing 2022年第4期5卷 660-673页

作者： Hui LMa Wanlu Li Mian Wang Laudemir C.Varanda Janice R.Perussi Y.Shrike Zhang Emanuel Carrilho Instituto de Química de São Carlos Universidade de São PauloUSPAv.Trabalhador São-carlenseSão CarlosSP 13566-590Brazil Instituto Nacional de Ciência e Tecnologia de Bioanalítica INCTBioCampinasSP 13083-970Brazil Division of Engineering in Medicine Department of MedicineBrigham and Women’s HospitalHarvard Medical SchoolCambridgeMA 02139USA

Advances in biomimetic three-dimensional(3D) melanoma models have brought new prospects of drug screening and disease modeling, since their physiological relevancy for recapitulating in vivo tumor architectures is more accurate than traditional two-dimensional(2D) cell culture. Gelatin methacryloyl(GelMA) is widely used as a tissue-engineered scaffold hydrogel for 3D cell culture. In the present study, an in vitro 3D malignant melanoma model based on Gel MA was fabricated to evaluate the efficiency of hypericin(Hy)-loaded microemulsion(ME) in photodynamic therapy against melanoma. The ME was produced by the spontaneous emulsification method to enhance the bioavailability of Hy at tumor sites. Hy-loaded MEs were applied to a 3D malignant melanoma model made using 6% Gel MA and the co-culture of B16F10 and Balb/c 3T3 cells,followed by crosslinking using violet light(403 nm). The observation revealed excellent cell viability and the presence of F-actin cytoskeleton network. Hy-loaded MEs exhibited higher phototoxicity and cell accumulation(about threefold) than free Hy, and the cells cultured in the 3D system displayed lower susceptibility(about 2.5-fold) than those in 2D *** findings indicate that the developed MEs are potential delivery carriers for Hy;furthermore, Gel MA hydrogel-based modeling in polydimethylsiloxane(PDMS) molds is a user-friendly and cost-effective in vitro platform to investigate drug penetration and provide a basis for evaluating nanocarrier efficiency for skin cancer and other skin-related diseases.

关键词： Malignant melanoma 3D cell culture hypericin Microemulsion Photodynamic therapy

Signal interaction between nitric oxide and hydrogen peroxide in heat shock-induced hypericin production of Hypericum perforatum suspension cells

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Science China(Life Sciences) 2008年第8期51卷 676-686页

作者： XU MaoJun, DONG JuFang & ZHANG XinBo Institute of Natural Resource and Environmental Sciences, Zhejiang Gongshang University, Hangzhou 310035, China Institute of Natural Resource and Environmental Sciences Zhejiang Gongshang University Hangzhou China

Heat shock(HS, 40℃, 10 min) induces hypericin production, nitric oxide(NO) generation, and hydrogen peroxide(H2O2) accumulation of Hypericum perforatum suspension ***(CAT) and NO spe-cific scavenger 2-4-carboxyphenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide(cPTIO) suppress not only the HS-induced H2O2 generation and NO burst, but also the HS-triggered hypericin *** contents of the cells treated with both NO and H2O2 are significantly higher than those of the cells treated with NO alone, although H2O2 per se has no effects on hypericin production of the cells, which suggests the synergistic action between H2O2 and NO on hypericin *** treatment enhances H2O2 levels of *** cells, while external application of H2O2 induces NO generation of ***, the results reveal a mutually amplifying action between H2O2 and NO in *** *** treatment inhibits both HS-induced H2O2 accumulation and NO generation, while cPTIO can also suppress H2O2 levels of the heat shocked *** results imply that H2O2 and NO may enhance each other's levels by their mutually amplifying action in the heat shocked *** NAD(P)H oxidase inhibitor diphenylene iodonium(DPI) and nitric oxide synthase(NOS) inhibitor S,S′-1,3-phenylene-bis(1,2-ethanediyl)-bis-isothiourea(PBITU) not only inhibit the mutually amplifying action between H2O2 and NO but also abolish the synergistic effects of H2O2 and NO on hypericin production, showing that the synergism of H2O2 and NO on secondary metabolite biosynthesis might be dependent on their mutual *** together, data of the present work demonstrate that both H2O2 and NO are essential for HS-induced hypericin production of *** suspension ***, the results reveal a special interaction between the two signal molecules in mediating HS-triggered secondary metabolite biosynthesis of the cells.

关键词： Hypericum perforatum cells hypericin heat shock nitric oxide hydrogen peroxide signal interaction

Effects of Different Geographical Aspects and Ontogenetic Variability on Total hypericin Content of Hypericum triquetrifolium Turra. and Hypericum scabrum L.

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Phyton-International Journal of Experimental Botany 2020年第4期89卷 1091-1099页

作者： Emine Aslan Dogan Arslan Field Crops Department Faculty of AgricultureSiirt UniversitySiirt56000Turkey

The present study was conducted to determine the total hypericin contents of Hypericum triquetrifolium *** Hypericum scabrum *** which are naturally distributed in the flora of Siirt province,*** contents of Hypericum species grown in different geographical aspects(North,South,East,and West),and it was measured at different harvest times(full bloom-ing and post blooming period).In the current study,it has been determined that total hypericin content varies considerably according to aspects,plant developmental stages(ontogenetic variance),and *** to species x aspect interaction,the highest total hypericin content was recorded from the west aspect(3.13 mg/g)in Hypericum triquetrifolium,while,the lowest hypericin content was also obtained from the west aspect(1.22 mg/g)in Hypericum *** the highest total hypericin content was analyzed according to aspect x species x harvest time interaction,the highest total hypericin content was produced from Hypericum triquetrifolium at the harvest of west aspect with 5.28 mg/g,while the minimum amount of hypericin was obtained from the same aspect in Hypericum scabrum with 0.50 mg/*** species x harvest time interaction,the highest total hypericin content was obtained from the full bloom(3.10 mg/g)harvest in Hypericum triquetrifolium,while the lowest hypericin was obtained from the full bloom(1.26 mg/g)harvest in Hypericum *** data suggest that the aver-age total hypericin content was 2.26 mg/g in Hypericum triquetrifolium and 1.28 mg/g in Hypericum scabrum.

关键词： Hypericum triquetrifolium Hypericum scabrum aspect hypericin

The Patterns of Secretory Structure and Their Relation to hypericin Content in Hypericum

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Acta Botanica Sinica 2001年第10期43卷 1085-1088页

作者：吕洪飞沈宗根李景原胡正海西北大学植物研究所

利用整体透明、石蜡制片和半薄切片法 ,对金丝桃属 (HypericumL .) 8组 2 0种 1变种植物的分泌结构进行了比较解剖研究 ,结果表明 :该属植物的分泌结构可分为分泌细胞团和分泌囊两种类型。但在不同植物种和不同器官内 ,分泌结构的类型... 详细信息

利用整体透明、石蜡制片和半薄切片法 ,对金丝桃属 (HypericumL .) 8组 2 0种 1变种植物的分泌结构进行了比较解剖研究 ,结果表明 :该属植物的分泌结构可分为分泌细胞团和分泌囊两种类型。但在不同植物种和不同器官内 ,分泌结构的类型和分布密度存在差异。对上述植物的提取物进行薄层层析和高效液相层析检测 ,结果表明 :具有分泌细胞团的植物器官含有金丝桃素 ;而无分泌细胞团的植物器官 ,则不含金丝桃素 ,从而证明金丝桃素由分泌细胞团合成和贮藏。在前者中 ,其金丝桃素的含量与其分泌细胞团密度成正相关。

关键词： Hypericum nodule cavity hypericin high-performance liquid chromatography thin layer chromatography

Effect of Photoactivated hypericin on Growth and Antibiotic Susceptibility of Hospital-Related Staphylococcus aureus and Enterococcus sp. Clinical Strains

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Advances in Biological Chemistry 2022年第4期12卷 116-129页

作者： Maria Nagyova Leonard Siegfried Daniel Jancura Daniel Jancura Zuzana Nadova Department of Medical and Clinical Microbiology Faculty of Medicine Pavol Jozef Safarik University Kosice Slovakia Department of Biophysics Institute of Physics Faculty of Science Pavol Jozef Safarik University in Kosice Kosice Slovakia

Resistance against commonly used antibiotics is a serious clinical problem in recent medical practice. There exist several bacterial strains in which the possibilities of their inhibition are very limited due to multidrug resistance. Antimicrobial photodynamic therapy (aPDT) represents an option how to effectively suppress the growth of resistant pathogens. In this work we have studied interactions of potent photosensitizer hypericin (Hyp) with hospital-related gram positive (Gram+) and gram negative (Gram-) bacterial strains and the effects of photodynamic activated Hyp on bacterial susceptibility and/or resistance of these strains to antibiotics. We demonstrated a significant influence of photoactivated Hyp on growth of Staphylococcus aureus and Enterococcus sp. We have also shown that it is extremely important to use the effective concentrations of Hyp for aPDT, which completely inhibit the growth of microorganisms. Otherwise, there appears an increase in resistance, probably due to the activation of efflux mechanisms, which are involved in the efflux of Hyp and antibiotics as well.

关键词： Antimicrobial Photodynamic Therapy hypericin Antibiotic Resistance Methicillin-Resistant Staphylococcus aureus Vancomycin-Resistant Enterococcus sp.

Differential diagnosis of gallstones by using hypericin as a fluorescent optical imaging agent

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World Journal of Gastroenterology 2016年第29期22卷 6690-6705页

作者： Marlein Miranda Cona Ye-Wei Liu Antoine Hubert Ting Yin Yuan-Bo Feng Peter de Witte Etienne Waelkens Yan-Sheng Jiang Jian Zhang Stefaan Mulier Qian Xia Gang Huang Raymond Oyen Yi-Cheng Ni Department of Imaging and Pathology Faculty of Medicine Biomedical Sciences Group University HospitalsKU Leuven Department of Cellular and Molecular Medicine Biomedical Sciences GroupKU Leuven Molecular Biodiscovery Laboratory Faculty of Pharmaceutical Sciences Biomedical Sciences GroupKU Leuven Laboratory of Translational Medicine Jiangsu Province Academy of Traditional Chinese Medicine Department of Nuclear Medicine Ren Ji Hospital School of Medicine Shanghai Jiao Tong University

AIM: To explore the feasibility of using hypericin as an optical imaging probe with affinity for cholesterol for differential fluorescent detection of human ***: Cholesterol, mixed and pigment stones from cholecystectomy patients were incubated with hypericin or solvent. After 72 h, the stones were analysed for fluorescence(365 nm) and treated with 2-propanol/dimethyl sulfoxide for high performance liquid chromatography(HPLC) analysis. Rats with virtual gallbladder containing human cholesterol, mixed or pigment gallstones(VGHG) received 5 mg/kg hypericin or solvent and VGHG rats with cholesterol stones were given different hypericin doses(5-15 mg/kg). Twelve hours later, the stones were analysed at 365 nm. Biliary excretion and metabolites of hypericin were assessed in common bile duct(CBD) cannulated rats for 9 h using fluorospectrometry, HPLC and matrixassisted laser desorption/ionization-time-of-flight mass spectrometry(MALDI-TOF MS).RESULTS: Homogeneous high fluorescence was seen on cholesterol stones either pre-incubated with hypericin or extracted from VGHG rats receiving hypericin. Mixed stones showed a dotted fluorescent pattern, whereas pigment and solvent-treated ones lacked fluorescence. HPLC showed 7.68, 6.65 and 0.08 × 10^(-3) M of cholesterol in extracts from cholesterol, mixed, and pigment gallstones, respectively. hypericin accounted for 2.0, 0.5 and 0.2 × 10-6 M in that order. On cholesterol stones from VGHG rats receiving different hypericin doses, a positive correlation was observed between dose and fluorescence. In the bile from CBD-cannulated rats, fluorescence represented 20% of the injected dose with two peaks in 9 h. HPLC analysis revealed that hypericin conjugates reached 60% of the peak area. By MALDI-TOF MS, hypericinglucuronide was detected. CONCLUSION: This study proves the potential use of hypericin for differential fluorescent detection of human gallstones regarding their chemical composition.

关键词： Differential detection Fluorescence Human gallstones hypericin Rat model of cholelithiasis

Topically applied hypericin exhibits skin penetrability on nude mice

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中国药理学与毒理学杂志 2017年第10期31卷 1020-1020页

作者： Zhuo-heng LI Yuan-yuan LI Lai-chun LU Xiao-yu XU College of Pharmaceutical Sciences & Chinese Medicine Southwest University Chongqing Key Laboratory of New Drug Screening from Traditional Chinese Medicine Pharmacology of Chinese Materia Medica-The Key Discipline Constructed by the State Administration of Traditional Chinese MedicineChongqing 400042 China Department of Pharmacy Institute of Surgery ResearchDaping Hospital Third Military Medical University Chongqing 400042 China

OBJECTIVE hypericin,a powerful naturally photosensitizer in photodynamic therapy(PDT),is suitable for treating skin diseases involving excess capillary *** the present study,we aimed to evaluate the skin penetrability of a topically applied hypericin,expecting reducing the risk of prolonged skin photosensitivity,which often occurs after systemic *** The Franz diffusion cell assay was performed to evaluate different penetration *** vivo studies,fluorescence microscopy was performed to examine the distribution of hypericin in the skin,macroscopic and microscopic analyses were also carried out to detect pathological changes in the skin after topical hypericin-PDT *** was used to determine the expression of PECAM-1 in the treated *** 5% menthol facilitated hypericin penetrate the skin of nude mice *** results of in vivo assays revealed that hypericin penetrated nude mice skin,spread to the dermis,and resulted in obvious photosensitivity reaction on the dermal ***,skin injured by the photosensitive reaction induced by hypericin was replaced by normal skin 7 d after hypericin-PDT *** Topical hypericin could penetrate nude mouse skin well and be great potential in PDT treatment of skin diseases.

关键词： hypericin photosensitizer skin penetrability photodynamic therapy

hypericin—有抗HIV活性的植物提取物

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现代药物与临床 1990年第1期 42-42页

纽约大学医疗中心的研究人员正在研究一种开花植物的提取物,它可能成为艾滋病治疗药。在体外,提取物hypericin抑制病毒的晚期成熟分裂;不久将向FDA申

关键词： HIV hypericin 植物提取物

Variation of Bioactive Compounds in Hypericum perforatum Growing in Turkey During Its Phenological Cycle

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Journal of Integrative Plant Biology 2007年第5期49卷 615-620页

作者： Cüneyt Cirak Jolita Radusiěne Birsen (Saglam) Karabük Valdimaras Janulis Liudas Ivanauskas Faculty of Agriculture Department of Agronomy University of Ondokuz Mayis Samsun 55139 Turkey Institute of Botany Zaliuju ezeru Vilnius LT-08406 Lithuania Kaunas University of Medicine Kaunas LT-44307 Lithuania

The present study was conducted to determine phenologic and morphogeneUc variation of hyperlcln, chlorogenlc acid and flavonoids, as rutin, hyperoside, apigenin-7-O-glucoside, quercitrin, quercetin content of Hypericum perforatum L. growing in Turkey. Wild growing plants were harvested at vegetative, floral budding, full flowering, fresh frulUng and mature fruiting stages and dissected into stem, leaf and reproductive tissues and assayed for bioacUve compounds by the High performance liquid chromatography （HPLC） method. hypericin concentration ranged between 0 and 2.73 mg/g DW, chlorogenic acid 0.00-3.64 mg/g DW, rutin 0.00-3.36 mg/g DW, hyperoside 0.04- 22.42 mg/g DW, quercitrin 0.03-3.46 mg/g DW and quercetin 0.04-1.02 mg/g DW depending on ontogenetic and morphogenetic sampling. Leaves were found to be superior to stems and reproductive parts with regard to phenolic accumulation for all compounds tested while flowers accumulated the highest levels of hypericln. Quercltrln, quercetln and hypericin content in all tissues increased with advancing of developmental stages and reached their highest level during flower ontogenesis. Similarly, chlorogenic acid, hyperoside and apigenin-7-O-glucoside content in different plant parts increased during plant development, however, the highest level was observed at different stages of plant phenology for each tissue. Chlorogenic acid was not detected in stems, leaves and reproductive parts in several stages of plant phenology and its variation during plant growth showed inconsistent manner. In contrast to the other compounds examined, rutin content of stems and leaves decreased with advanc- ing of plant development and the highest level for both tissues was observed at the vegetative stage. However, content of the same compound in reproductive parts was the highest at mature fruiting. The present findings might be useful to obtain increased concentration of these natural compounds.

关键词： chiorogenic acid flavonoids hypericin Hypericum perforatum morphogenetic variation phenologic variation.