Hypocrellins are novel photosensitizers from China, which are demonstrated to have significant anti-tumor and anti-virus activity and to be potential photo-dynamic therapy (PDT) agents. As compared with hemato-porphyr...Hypocrellins are novel photosensitizers from China, which are demonstrated to have significant anti-tumor and anti-virus activity and to be potential photo-dynamic therapy (PDT) agents. As compared with hemato-porphyrin, the only approved photosensitizer, hypocrellins have several advantages, such as easy preparation and easy purification, high triplet quantum yield, high singlet-oxygen quantum yield, high phototoxicity but low dark toxicity, and rapid clearance from normal issues. This article reviews briefly the photophysics, photochemistry and photobiology of hypocrellins on the basis of the domestic and international research results.展开更多
Hypocrellins are major bioactive perylenequinones from Shiraia fruiting bodies and have been developed as efficient photosensitizers for photodynamic therapy.Pseudomonas is the second dominant genus inside Shiraia fru...Hypocrellins are major bioactive perylenequinones from Shiraia fruiting bodies and have been developed as efficient photosensitizers for photodynamic therapy.Pseudomonas is the second dominant genus inside Shiraia fruiting bodies,but with less known actions on the host fungus.In this work,the effects of bacterial volatiles from the Shiraia-associated Pseudomonas on fungal hypocrellin production were investigated.Pseudomonas putida No.24 was the most active to promote significantly accumulation of Shiraia perylenequinones including hypocrellin A(HA),HC,elsinochrome A(EA)and EC.Headspace analysis of the emitted volatiles revealed dimethyl disulfide as one of active compounds to promote fungal hypocrellin production.The bacterial volatiles induced an apoptosis in Shiraia hyphal cell,which was associated with the generation of reactive oxygen species(ROS).ROS generation was proved to mediate the volatile-induced membrane permeability and up-regulation of gene expressions for hypocrellin biosynthesis.In the submerged volatile co-culture,the bacterial volatiles stimulated not only HA content in mycelia,but also HA secretion into the medium,leading to the enhanced HA production to 249.85 mg/L,about 2.07-fold over the control.This is the first report on the regulation of Pseudomonas volatiles on fungal perylenequinone production.These findings could be helpful to understand the roles of bacterial volatiles in fruiting bodies and also provide new elicitation method using bacterial volatiles to stimulate fungal secondary metabolite production.展开更多
1 Introduction Much research work has been done on the mechanism of photo-induced reduction of quinone dyes by electron donors with visible light. Two ways to obtain the net two-electron reduction product QH^- bave be...1 Introduction Much research work has been done on the mechanism of photo-induced reduction of quinone dyes by electron donors with visible light. Two ways to obtain the net two-electron reduction product QH^- bave been proposed. One is the direct two-electron transfer (electron-proton-electron transfer) within the complex and the other is the disproportionatioh of the semiquinone radical QH·formed by one-electron transfer.展开更多
Hypocrellins, as a kind of novel phototherapeu-tic agents, have several advantages over the clinically used hematoporphyrin derivatives, including high-excited triplet state yield, high phototoxicity, low dark toxicit...Hypocrellins, as a kind of novel phototherapeu-tic agents, have several advantages over the clinically used hematoporphyrin derivatives, including high-excited triplet state yield, high phototoxicity, low dark toxicity, and rapid metabolism. However, they exhibit little absorption in the photodynamic window (600—900 nm) and are not water soluble, which limits their application in photodynamic therapy. Sulfonated and metal-ioned hypocrellins have been designed and synthesized to improve their water solubility. Unfortunately, the water-soluble derivatives obtained exhibit lower photodynamic activity than the parent hypocrellins. Thiolated and aminated hypocrellins have also been designed and synthesized to enlarge their photoresponse. Among them, the aminated hypocrellins possess the highest photodynamic activity. We recently have further designed and synthesized some amphiphilic aminated hypocrellin derivatives. Thus, not only the photoresponse but also the water solubility is enhanced. The experiments in vitro and in vivo on the deriva-tives are under way at present.展开更多
A new aminated-perylenequinone derivative 2 was synthesized by the reaction of 1 (hypocrellin B) with 6-aminohexanoic-acid. The structure of 2 was identified by UV-Vis, MS, IR and H-1-NMR. Thc amphiphility spectrum an...A new aminated-perylenequinone derivative 2 was synthesized by the reaction of 1 (hypocrellin B) with 6-aminohexanoic-acid. The structure of 2 was identified by UV-Vis, MS, IR and H-1-NMR. Thc amphiphility spectrum and photochemical properties of 2 were reported.展开更多
Photodynamic therapy(PDT)has been a routine treatment of tumors and some microvascular diseases,but clinically available photosensitizers are still scarce.Among all kinds of photo-sensitizers,hypocellins possess the m...Photodynamic therapy(PDT)has been a routine treatment of tumors and some microvascular diseases,but clinically available photosensitizers are still scarce.Among all kinds of photo-sensitizers,hypocellins possess the most characteristics of ideal photosensitizers,such as,high photo-activity but low dark toxicity,fast clearance from tssues.This review is focused on two main topics,drug-delivery problem of hypocrellins and how the environment-sensitive fluorescence of bypecrellins was used for recognition of various biomolecules.Drug-delivery of hypocrellins was mainly achieved in two strategies一preparing the drugdelivery vehicles and finding quantitatively amphiphilic derivatives.Hypocrellin fAuorescence originated from the intramolecular proton transfer is very distinct from other kinds of photosensitizers.Recently,it was proved that quan-titative hypocrellin ftuorescence could not only reoognize various biomolecules,including proteins,polysaocharides and lipids,but also distinguish the specific binding from nonspedifie binding with some kind of biomolecules.Meantime,hypocrellin fluorescence was pH sensitive.It is known that tumor cells or tses have the features of a large amount of lipid,neonatal collagen,over expression of polysaccharides,and lower pH values compared to normal tissues.According to the relative but not absolute specifcity,further studies on quantitative recognition of various biomolecules at a cellular level,may find a new clue to treat tumors by joint usage of photodynamic diagnosis(PDD)and PDT.展开更多
文摘Hypocrellins are novel photosensitizers from China, which are demonstrated to have significant anti-tumor and anti-virus activity and to be potential photo-dynamic therapy (PDT) agents. As compared with hemato-porphyrin, the only approved photosensitizer, hypocrellins have several advantages, such as easy preparation and easy purification, high triplet quantum yield, high singlet-oxygen quantum yield, high phototoxicity but low dark toxicity, and rapid clearance from normal issues. This article reviews briefly the photophysics, photochemistry and photobiology of hypocrellins on the basis of the domestic and international research results.
基金the National Natural Science Foundation of China(No.82073955 and 81773696)the Priority Academic Program Development of the Jiangsu Higher Education Institutes(PAPD).
文摘Hypocrellins are major bioactive perylenequinones from Shiraia fruiting bodies and have been developed as efficient photosensitizers for photodynamic therapy.Pseudomonas is the second dominant genus inside Shiraia fruiting bodies,but with less known actions on the host fungus.In this work,the effects of bacterial volatiles from the Shiraia-associated Pseudomonas on fungal hypocrellin production were investigated.Pseudomonas putida No.24 was the most active to promote significantly accumulation of Shiraia perylenequinones including hypocrellin A(HA),HC,elsinochrome A(EA)and EC.Headspace analysis of the emitted volatiles revealed dimethyl disulfide as one of active compounds to promote fungal hypocrellin production.The bacterial volatiles induced an apoptosis in Shiraia hyphal cell,which was associated with the generation of reactive oxygen species(ROS).ROS generation was proved to mediate the volatile-induced membrane permeability and up-regulation of gene expressions for hypocrellin biosynthesis.In the submerged volatile co-culture,the bacterial volatiles stimulated not only HA content in mycelia,but also HA secretion into the medium,leading to the enhanced HA production to 249.85 mg/L,about 2.07-fold over the control.This is the first report on the regulation of Pseudomonas volatiles on fungal perylenequinone production.These findings could be helpful to understand the roles of bacterial volatiles in fruiting bodies and also provide new elicitation method using bacterial volatiles to stimulate fungal secondary metabolite production.
基金Project supported by the National Natural Science Foundation of China
文摘1 Introduction Much research work has been done on the mechanism of photo-induced reduction of quinone dyes by electron donors with visible light. Two ways to obtain the net two-electron reduction product QH^- bave been proposed. One is the direct two-electron transfer (electron-proton-electron transfer) within the complex and the other is the disproportionatioh of the semiquinone radical QH·formed by one-electron transfer.
基金supported by the National Natural Science Foundation of China(Grant No.20172058).
文摘Hypocrellins, as a kind of novel phototherapeu-tic agents, have several advantages over the clinically used hematoporphyrin derivatives, including high-excited triplet state yield, high phototoxicity, low dark toxicity, and rapid metabolism. However, they exhibit little absorption in the photodynamic window (600—900 nm) and are not water soluble, which limits their application in photodynamic therapy. Sulfonated and metal-ioned hypocrellins have been designed and synthesized to improve their water solubility. Unfortunately, the water-soluble derivatives obtained exhibit lower photodynamic activity than the parent hypocrellins. Thiolated and aminated hypocrellins have also been designed and synthesized to enlarge their photoresponse. Among them, the aminated hypocrellins possess the highest photodynamic activity. We recently have further designed and synthesized some amphiphilic aminated hypocrellin derivatives. Thus, not only the photoresponse but also the water solubility is enhanced. The experiments in vitro and in vivo on the deriva-tives are under way at present.
基金the National Natural Science Foundation of China (Project No.39830090 and No.39970871) for their financial support to this resea
文摘A new aminated-perylenequinone derivative 2 was synthesized by the reaction of 1 (hypocrellin B) with 6-aminohexanoic-acid. The structure of 2 was identified by UV-Vis, MS, IR and H-1-NMR. Thc amphiphility spectrum and photochemical properties of 2 were reported.
基金supported by the National Natural Science Foundation of China (Nos.21303223 and 311706144).
文摘Photodynamic therapy(PDT)has been a routine treatment of tumors and some microvascular diseases,but clinically available photosensitizers are still scarce.Among all kinds of photo-sensitizers,hypocellins possess the most characteristics of ideal photosensitizers,such as,high photo-activity but low dark toxicity,fast clearance from tssues.This review is focused on two main topics,drug-delivery problem of hypocrellins and how the environment-sensitive fluorescence of bypecrellins was used for recognition of various biomolecules.Drug-delivery of hypocrellins was mainly achieved in two strategies一preparing the drugdelivery vehicles and finding quantitatively amphiphilic derivatives.Hypocrellin fAuorescence originated from the intramolecular proton transfer is very distinct from other kinds of photosensitizers.Recently,it was proved that quan-titative hypocrellin ftuorescence could not only reoognize various biomolecules,including proteins,polysaocharides and lipids,but also distinguish the specific binding from nonspedifie binding with some kind of biomolecules.Meantime,hypocrellin fluorescence was pH sensitive.It is known that tumor cells or tses have the features of a large amount of lipid,neonatal collagen,over expression of polysaccharides,and lower pH values compared to normal tissues.According to the relative but not absolute specifcity,further studies on quantitative recognition of various biomolecules at a cellular level,may find a new clue to treat tumors by joint usage of photodynamic diagnosis(PDD)and PDT.
