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Green synthesis of chlorin e6 and tests of its photosensitive bactericidal activities

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Journal of Forestry Research 2019年第6期30卷 2349-2356页

作者： Guocai Zhang Jing Yang Chunping Hu Xiucheng Zhang Xiao Li Shan Gao Xiao Ouyang Ning Ma Hao Wei Northeast Forestry University 26 Hexing RoadHarbin 150040People’s Republic of China College of Material Science and Chemical Engineering Harbin Engineering UniversityHarbin 150001People’s Republic of China

Phototoxic treatments of pathogenic bacteria and fungi of trees induce oxidative damage that is preferable to toxic chemical ***,we used green methods to synthesize chlorin e6 from chlorophyll a,which was extracted from crude silkworm excrement using concentrated(strong)alkali hydrolysis and *** photosensitive bactericidal activities of the new chlorin were tested in vitro,and possible mechanisms of action are *** results showed that chlorin e6 can be lightactivated to have bactericidal activity against Escherichia coli,Bacillus subtilis and Fusarium oxysporum,but it had little bactericidal effect in the *** kind of chlorin compounds has great potential as a natural phototoxic antimicrobial compound to control harmful bacteria on the leaves in forestry systems.

关键词： chlorin e6 Photosensitive bactericidal activities

Anti-tumor activities of a novel chlorin derivative for photodynamic therapy in vitro and in vivo

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Journal of Innovative Optical Health Sciences 2015年第1期8卷 77-87页

作者： Li-Jun Zhang Lai-Xing Wang Wei-Li Zhang Yi-Jia Yan Zhi-Long Chen Department of Pharmaceutical Science&Technology College of Chemistry and Biology Donghua University Shanghai 201620P.R.China Changhai Hospital Second Military Medical University Shanghai 200433P.R.China

In this study,a novel photosensitizer mesc-tetra(3-prrolidinomethyl-4-methoxyphenyl)chlorin(TPMC)was *** displays a characteristic long wavelength absorption peak at 656 nm and it shows a singlet oxygen quantum yield of *** light iradiation with 650 nm laser,it can kill Eca-109 and SMMC-7721 cells in vitro(25 mW/cm^(2),1.2 to 3.6J/cm^(2))and destroy Eca-109 tumor in nude mice(50 mW/cm^(2),90J/cm^(2)).It has the perspective to be developed as a new anti-tumor drug in photodynamic therapy(PDT)photodiagnosis,and deserves further investigation.

关键词： TPMC chlorin tumor photosensitizer photodynamic therapy

Synthesis of Styryl-substituted Z/E-chlorin Derivatives with Chlorophyll-a Skeleton

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Chinese Journal of Chemistry 2006年第7期24卷 933-938页

作者：王进军李家柱邬旭然沈荣基 Department of Applied Chemistry Yantai University Yantai Shandong 264005 China School of Nano Engineering Inje University Pusan South Korea

The Wittig reaction of methyl pyropheophorbide-d 2, obtained from methyl pyropheophorbide-a 1, with benzyltriphenylphosphonium bromide was performed to yield isomers 3a and 3b. The Vilsmeier reaction of nickel complex 4 or 7 with 3-dimethylaminoacrolein in the presence of phosphoryl chloride was carried out to form 20-meso-2＇-formylvinylpyropheophorbide-a 5 or 8, which was reacted with Wittig reagent to afford nickel complex isomers 6a and 6b or 9a and 9b, 10a and 10b.

关键词： chlorophyll-a derivative chlorin Wittig reaction Vilsmeier reaction photodynamic therapy

Design and synthesis of novel water-soluble amino acid derivatives of chlorin p6 ethers as photosensitizer

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Chinese Chemical Letters 2019年第1期30卷 247-249页

作者： Xingjie Zhang Zhi Meng Zhiqiang Ma Junhong Liu Guiyan Han Fujia Ma Ningyang Jia Zhenyuan Miao Wannian Zhang Chunquan Sheng Jianzhong Yao Department of Medicinal Chemistry School of Pharmacy Second Military Medical University Department of Pharmacy 455th Hospital of Chinese People’s Liberation Army Department of Radiology Shanghai Eastern Hepatobiliary Surgery Hospital Second Military Medical University

Eight new water-soluble amino acid conjugates 6 a-h of chlorin p6 ethers(5 a-d) were synthesized and preliminarily investigated for their in vitro PDT antitumor activity and structure-activity relationship(SAR). The results showed that all compounds exhibited much higher phototoxicity against tumor cells than talaporfin. SAR analysis indicated that PDT antitumor effect enhanced with the increase of carbon chain length of alkoxyl ether bonds at 3~1-position, and L-aspartic acid was superior to L-glutamic acid. In particular, the IC_50 values of most phototoxic compound 6 d were 0.20 mmol/L against A549 cell and0.41υmmol/L against B16-F10 cell, which individually represented 31-and 24-fold increase of antitumor potency compared to talaporfin, suggesting that it was a promising candidate photosensitizer(PS) for PDT applications due to its strong absorption at long wavelength, high phototoxicity, low dark cytotoxicity and good water-solubility.

关键词： Photodynamic therapy (PDT) Photosensitizer Silkworm excrement chlorin P6 Antitumor

chlorin e6在S180肉瘤荷瘤小鼠体内的分布

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西部医学 2012年第7期24卷 1239-1242页

作者：刘端张为民王晓怀郝建冬南方医科大学研究生院广东广州510515 广州军区广州总医院肿瘤科广东广州510010 华南师范大学化学与环境学院

目的研究chlorin e6在肿瘤组织的富集情况,探索给药后最佳的超声辐射时间。方法 S180肉瘤荷瘤小鼠腹腔注射chlorin e6后,利用共聚焦显微镜观测其在肿瘤和周围肌肉组织的富集变化及代谢。结果腹腔给药18h后,chlorin e6在肿瘤和周围肌肉... 详细信息

目的研究chlorin e6在肿瘤组织的富集情况,探索给药后最佳的超声辐射时间。方法 S180肉瘤荷瘤小鼠腹腔注射chlorin e6后,利用共聚焦显微镜观测其在肿瘤和周围肌肉组织的富集变化及代谢。结果腹腔给药18h后,chlorin e6在肿瘤和周围肌肉组织含量均达最高峰,且差异最明显,此时为最佳的超声辐射时间。结论 chlorin e6具有肿瘤靶向性好、正常组织清除快的优点。chlorin e6声动力疗法的时间点应选择在18h左右。

关键词： chlorin e6 S180肉瘤共聚焦显微镜超声波声动力疗法

Studies on photodynamic mechanism of a novel chlorine derivative(TDPC)and its antitumor effect forphotodynamic therapy in vitro and in vivo

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Journal of Innovative Optical Health Sciences 2015年第1期8卷 60-67页

作者： Ying Ye Lai-Xing Wang Dan-Ping Zhang Yi-Jia Yan Zhi-Long Chen Department of Pharmaceutical Science&Technology College of Chemistry and Biology Donghua University Shanghai 201620P.R.China Changhai Hospital Second Military Medical University Shanghai 200433P.R.China

Photodynamic therapy(PDT)represents a promising method for treatment of cancerous *** chemical and physical properties of used photosensitizer(PS)play key roles in the treat ment *** this study,a novel PS,5,10,15,20-tetrais((5-dipropylamino)pentyl)-chlorin(TDPC)which displayed a characteristic long wavelength absorption peak at 650 nm were *** also shows a singlet oxygen generation rate of 4.257 min^(-1).Generally,TDPC is localized in mitochondria and nucleus of *** light irradiation with 650 nm laser,it can kill many types of cell,in addition,TDPC-PDT can destroy ECA-109 tunor in nude mice and a necrotic scab was formed *** expression levels of many genes which regulated cell growth and apoptosis were determined by RT-PCR following *** results showed that it either increased or decreased,among which,the expression level of TNFSF13,a member of tumor necrosis factor superfamily,increased *** general,TDPC is an elective antitumor PS in vitro and in vito and is worthy of further study as a new drug ***13 will be an important molecular target for the discovery of new PSs.

关键词： Photosensitizer photodynamic therapy tumor chlorin TDPC

Potential Adverse Outcome Pathways of chlorinated Organophosphate Flame Retardants

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China CDC weekly 2024年第23期6卷 542-546,I0008-I0011页

作者： Meiyu Zhou Huilin Zhang Qi Xiao Kexin Li Xiaoting Li Haiyan Chu Department of Environmental Genomics Jiangsu Key Laboratory of Cancer BiomarkersPrevention and TreatmentCollaborative Innovation Center for Cancer Personalized MedicineSchool of Public HealthNanjing Medical UniversityNanjing CityJiangsu ProvinceChina Department of Genetic Toxicology The Key Laboratory of Modern Toxicology of Ministry of EducationCenter of Global HealthSchool of Public HealthNanjing Medical UniversityNanjing CityJiangsu ProvinceChina Department of Nutrition and Food Safety School of Public HealthNanjing Medical UniversityNanjing CityJiangsu ProvinceChina

What is already known about this topic?chlorinated organophosphate flame retardants(Cl-OPFRs)are frequently detected chemicals in the environment and biological samples,yet there is a lack of systematic evaluation regarding the adverse effects and toxicological mechanisms of *** is added by this report?This study utilizes the adverse outcome pathway(AOP)framework to assess the health implications and mechanisms of Cl-OPFRs,identifying multi-system toxicity,with a particular emphasis on reproductive issues and the possible toxic *** are the implications for public health practice?These results enhance knowledge of the health hazards linked to Cl-OPFRs,supporting the creation of focused risk evaluations and suitable regulatory actions.

关键词： utilize supporting chlorin

Synthesis of δ-meso-formylvinylchlorin and Benzoisobacterichlorin by Vilsmeier Reaction with Methyl Pyropheophorbide-a

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Chinese Journal of Chemistry 2005年第1期23卷 76-80页

作者：王进军邬旭然沈荣基 DepartmentofAppliedChemistry YantaiUniversityYantaiShandong264005China SchoolofNanoEngineering InjiUniversityGyongnam621-749Korea

From methyl pyropheophorbide-a (MPPa, 1), the vinyl group of methylpyropheophorbide-a was converted into alkylcarbonyl group by Grignard reaction and oxidization togive chlorins 2, 3 and 5. The Vilsmeier reaction of nickel 3-substituent-3-devinylpyropheophorbide-a(6), which was prepared by the metallation with nickel acetate, with3-dimethylamino-acrolein/phosphoryl chloride (3-DMA/POCl_3) was carried out to giveδ-meso-formylvinyl-pyropheophorbide-a (7) in good yield. The benzoisobacterichlorin (8) wasobtained by the treatment of 7b with concentrated sulfuric acid.

关键词： chlorin benzoisobacterichlorin vilsmeier reaction photodynamic therapy

Variations in paleoproductivity and the environmental implications over the past six decades in the Changjiang Estuary

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Acta Oceanologica Sinica 2010年第3期29卷 38-45页

作者： JIN Haiyan CHEN Jianfang WENG Huanxin LI Hongliang ZHANG Weiyan XU Jie BAI Youcheng WANG Kui Institute of Environment ＆ Biogeochemistry Zhejiang University Hangzhou 310027 China Laboratory of Marine Ecosystem and Biogeochemistry of State Ocean Administration Second Institute of Oceanography State Ocean Administration. Hangzhou 310012 China Laboratory of Submarine Geosciences of State Ocean Administration Second Institute of Oceanography State Ocean Administration Hangzhou 310012 China

Total organic carbon and organic carbon stable isotope, biogenic silica, chlorin were measured from a high resolution sediment core to indicate the variation in paleoproductivity and the environmental implications over the past decades （1942 to 1997） in the Changjiang Estuary. Based on these biomarkers, the shift in the phytoplankton community structure in the past decades was discussed in response to the long-term variations in nutrient concentrations and nutrient ratios. The results showed that the δ 13 C values varied from –26.15‰ to –19.5‰, suggesting the combined organic carbon sources of riverine and marine organisms. Based on the biogenic proxies, paleoproductivity changes were categorized into three stages： low production before 1950; an increase in production with the dominance of diatoms during 1950 to 1980, consistent with increasing of nutrient concentrations; a decrease in production after 1980 when the diatom production decreased while the production of non-silicious phytoplankton increased due to high nutrient inputs, and high N/P and P/Si ratios in the Changjiang Estuary. The sedimentation records also indicated that the riverine organic carbon increased since 1980.

关键词： paleoproductivity organic carbon stable isotope biogenic silica chlorin the Changjiang Estuary