Pub Date : 2023-07-24DOI: 10.1142/s1088424623300124
David Sánchez-García
The aim of this review is to offer a brief account of the functionalization of porphycenes for the preparation of conjugates useful as photosensitizers for biomedical applications.
本文的目的是简要介绍卟啉的功能化，以制备可作为生物医学应用的光敏剂的偶联物。
{"title":"Porphycene conjugates for biomedical applications","authors":"David Sánchez-García","doi":"10.1142/s1088424623300124","DOIUrl":"https://doi.org/10.1142/s1088424623300124","url":null,"abstract":"The aim of this review is to offer a brief account of the functionalization of porphycenes for the preparation of conjugates useful as photosensitizers for biomedical applications.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42569970","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-19DOI: 10.1142/s1088424623501109
Iva Habenšus, Ameen Ghavam, C. J. Curtis, A. Astashkin, E. Tomat
Biopyrrin pigments, which result from the degradation of heme in biological settings, feature three or two pyrrole rings and characteristic pyrrolin-2-one termini. These scaffolds serve as redox-active ligands and electron reservoirs in coordination compounds. Tripyrrin-1,14-dione coordinates divalent transition metals as a dianionic ligand hosting a delocalized radical. Herein, we report the synthesis and characterization of palladium(II) and platinum(II) tripyrrindione complexes featuring a primary amine (i.e., aniline, tert-butylamine, 1,2-ethylenediamine) at the fourth coordination site within square planar geometries. Interligand hydrogen-bonding interactions are observed between the coordinated amine and the carbonyl groups on the tripyrrindione scaffold. Notably, 1,2-ethylenediamine is employed to link two Pt(II) tripyrrindione complexes. As revealed by optical absorption and electron paramagnetic resonance (EPR) spectroscopy, all resulting complexes present ligand-based radicals that are stable at room temperature and when exposed to air. Spin pairing through multicenter interactions leads to [Formula: see text]-dimerization of the tripyrrindione radicals and a decrease in the EPR signal at low temperatures. Electrochemical measurements indicate that the ligand system undergoes quasi-reversible one-electron oxidation and reduction, thus confirming the ability of tripyrrindione to form square planar complexes in three different redox states.
{"title":"Primary amines as ligands and linkers in complexes of tripyrrindione radicals","authors":"Iva Habenšus, Ameen Ghavam, C. J. Curtis, A. Astashkin, E. Tomat","doi":"10.1142/s1088424623501109","DOIUrl":"https://doi.org/10.1142/s1088424623501109","url":null,"abstract":"Biopyrrin pigments, which result from the degradation of heme in biological settings, feature three or two pyrrole rings and characteristic pyrrolin-2-one termini. These scaffolds serve as redox-active ligands and electron reservoirs in coordination compounds. Tripyrrin-1,14-dione coordinates divalent transition metals as a dianionic ligand hosting a delocalized radical. Herein, we report the synthesis and characterization of palladium(II) and platinum(II) tripyrrindione complexes featuring a primary amine (i.e., aniline, tert-butylamine, 1,2-ethylenediamine) at the fourth coordination site within square planar geometries. Interligand hydrogen-bonding interactions are observed between the coordinated amine and the carbonyl groups on the tripyrrindione scaffold. Notably, 1,2-ethylenediamine is employed to link two Pt(II) tripyrrindione complexes. As revealed by optical absorption and electron paramagnetic resonance (EPR) spectroscopy, all resulting complexes present ligand-based radicals that are stable at room temperature and when exposed to air. Spin pairing through multicenter interactions leads to [Formula: see text]-dimerization of the tripyrrindione radicals and a decrease in the EPR signal at low temperatures. Electrochemical measurements indicate that the ligand system undergoes quasi-reversible one-electron oxidation and reduction, thus confirming the ability of tripyrrindione to form square planar complexes in three different redox states.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42742947","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-19DOI: 10.1142/s108842462350116x
H. Konno, Yoichi Nonomura, Yasushi Kishimoto
{"title":"Distortion effect on the ligation of imidazoles to water-insoluble iron(III) porphyrin","authors":"H. Konno, Yoichi Nonomura, Yasushi Kishimoto","doi":"10.1142/s108842462350116x","DOIUrl":"https://doi.org/10.1142/s108842462350116x","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45904999","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-18DOI: 10.1142/s1088424623501171
Vythao Tran, Pengzhi Wang, Nobuyuki Matsumoto, Sijia Liu, Haoyu Jing, Phattananawee Nalaoh, K. Nguyen, M. Taniguchi, J. Lindsey
{"title":"Bacteriochlorin syntheses - Status, problems, and exploration","authors":"Vythao Tran, Pengzhi Wang, Nobuyuki Matsumoto, Sijia Liu, Haoyu Jing, Phattananawee Nalaoh, K. Nguyen, M. Taniguchi, J. Lindsey","doi":"10.1142/s1088424623501171","DOIUrl":"https://doi.org/10.1142/s1088424623501171","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41775904","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-10DOI: 10.1142/s1088424623501055
Alejandra Romero-Morán, S. Hernández‐Anzaldo, Hugo Vazquez-Lima, Y. Reyes-Ortega
The synthesis and characterization of a novel hexacoordinated compound as a product of the reaction between chlorodimethylesterprotoprphyrin–Fe(III) 1 and 2–methylpiridine (2–CH3Py) was performed. The [bis(o–methylpyridino)(dimethylesterprotoporphyrinato)Fe(III)] chloride 2 is a compound of the family of the pinch–porphyrins, a model of peroxidase enzymes. We analyzed 2 using UV-Vis, 1H NMR, and EPR spectroscopies, as well as kinetic quantifications of its peroxidase activity and computational analysis, to evaluate the presence of the pinch-ligand coordinated to 1 in a series of pinch-ironprotoporphyrin complexes, as previously reported. Our investigation revealed that the oxidant activity of Compound I derived from peroxidase activity determination of 1 and 2, respectively, is better controlled when a heterohydrocarbonated chain is attached to the pyridyl groups that coordinate axially to 1; an effect evidenced by a decrease of the activation energy value associated with Compound 0 formation during the reaction performed by pinch–porphyrin, with the picdien axial ligand and hydrogen peroxide. When correlating the contribution of [Formula: see text]3/2 in the quantum mixed-spin state (qms), [Formula: see text]3/2, [Formula: see text]5/2, of iron(III)-based complexes with their peroxidase activity, we found that when the qms [Formula: see text]3/2, [Formula: see text]5/2, of iron(III) had 80% character [Formula: see text]3/2, the peroxide activity increased significantly. This could be a fundamental trait that could affect the peroxidase activity owing to the distortion of the iron geometry associated with its coordination number when [Formula: see text]methylpyridine is used as an axial ligand.
{"title":"Investigating axial ligand impact on pinch-porphyrin peroxidase activity with [bis(o-methylpyridino) (dimethylesterprotoporphyrinato)Fe(III)] chloride","authors":"Alejandra Romero-Morán, S. Hernández‐Anzaldo, Hugo Vazquez-Lima, Y. Reyes-Ortega","doi":"10.1142/s1088424623501055","DOIUrl":"https://doi.org/10.1142/s1088424623501055","url":null,"abstract":"The synthesis and characterization of a novel hexacoordinated compound as a product of the reaction between chlorodimethylesterprotoprphyrin–Fe(III) 1 and 2–methylpiridine (2–CH3Py) was performed. The [bis(o–methylpyridino)(dimethylesterprotoporphyrinato)Fe(III)] chloride 2 is a compound of the family of the pinch–porphyrins, a model of peroxidase enzymes. We analyzed 2 using UV-Vis, 1H NMR, and EPR spectroscopies, as well as kinetic quantifications of its peroxidase activity and computational analysis, to evaluate the presence of the pinch-ligand coordinated to 1 in a series of pinch-ironprotoporphyrin complexes, as previously reported. Our investigation revealed that the oxidant activity of Compound I derived from peroxidase activity determination of 1 and 2, respectively, is better controlled when a heterohydrocarbonated chain is attached to the pyridyl groups that coordinate axially to 1; an effect evidenced by a decrease of the activation energy value associated with Compound 0 formation during the reaction performed by pinch–porphyrin, with the picdien axial ligand and hydrogen peroxide. When correlating the contribution of [Formula: see text]3/2 in the quantum mixed-spin state (qms), [Formula: see text]3/2, [Formula: see text]5/2, of iron(III)-based complexes with their peroxidase activity, we found that when the qms [Formula: see text]3/2, [Formula: see text]5/2, of iron(III) had 80% character [Formula: see text]3/2, the peroxide activity increased significantly. This could be a fundamental trait that could affect the peroxidase activity owing to the distortion of the iron geometry associated with its coordination number when [Formula: see text]methylpyridine is used as an axial ligand.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49659315","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-06DOI: 10.1142/s1088424623501079
Rong Yuan, Le Liu, Bangshao Yin, Ling Xu, Mingbo Zhou, Yutao Rao, Jianxin Song
[Formula: see text]-Unsubstituted 5-monoazaporphyrin (MAP) copper complex 10,15,20-tritolyl-5-monoazaporphyrinato copper(II) (Cu-MAP) 3 was synthesized by reaction of 1,19-dibromotetrapyrrane with NaN3-CuI in good yield. Following successive reactions of demetallation, metallation and bromination, the important precursor 3,7-dibromo-10,15,20-tritolyl-5-monoazaporphyrinato nickel(II) ([Formula: see text],[Formula: see text]′-dibromo Ni-MAP) 6was prepared smoothly. Suzuki-Miyaura coupling reactions of 6 with three organic borides resulted in the “earring” Ni-MAP 7, pyrrole bridged Ni-MAP oligomers 8 and 9, and benzene bridged Ni-MAP oligomers 10 and 11, respectively. The structures of MAPs 3, 6, 7, 8, 10 and 11 were confirmed by X-ray diffraction analysis. Optical and electrochemical studies were performed to understand their electronic properties.
{"title":"β-Unsubstituted 5-monoazaporphyrin and its derivatives","authors":"Rong Yuan, Le Liu, Bangshao Yin, Ling Xu, Mingbo Zhou, Yutao Rao, Jianxin Song","doi":"10.1142/s1088424623501079","DOIUrl":"https://doi.org/10.1142/s1088424623501079","url":null,"abstract":"[Formula: see text]-Unsubstituted 5-monoazaporphyrin (MAP) copper complex 10,15,20-tritolyl-5-monoazaporphyrinato copper(II) (Cu-MAP) 3 was synthesized by reaction of 1,19-dibromotetrapyrrane with NaN3-CuI in good yield. Following successive reactions of demetallation, metallation and bromination, the important precursor 3,7-dibromo-10,15,20-tritolyl-5-monoazaporphyrinato nickel(II) ([Formula: see text],[Formula: see text]′-dibromo Ni-MAP) 6was prepared smoothly. Suzuki-Miyaura coupling reactions of 6 with three organic borides resulted in the “earring” Ni-MAP 7, pyrrole bridged Ni-MAP oligomers 8 and 9, and benzene bridged Ni-MAP oligomers 10 and 11, respectively. The structures of MAPs 3, 6, 7, 8, 10 and 11 were confirmed by X-ray diffraction analysis. Optical and electrochemical studies were performed to understand their electronic properties.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47956160","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-07-01DOI: 10.1142/s1088424623501092
Zhouxia Lu, Yan Guo, Conghui Wang, Song Xiao
Porphyrin PSs, possessing high photosensitivity and stability, have widespread use in phototherapy. Furthermore, the use of Q[n]s as a carrier for PSs has contributed to enhancing the efficacy of photodynamic therapy. In the present study, we synthesized 2TMeQ[6]-TPPPA self-assembled compounds, comprising TMeQ[6] and 5, 10, 15, 20-tetra (4-pyridyl, N-propyl ammonia) porphyrin derivatives (TPPPA) (in a 2:1 ratio), to investigate their capacity to generate reactive oxygen species (ROS) and their effect of self-assembly with TMeQ[6] on the efficacy of human neuroblastoma cell line (SH-SY5Y). Our results demonstrate that both TPPPA and 2TMeQ[6]-TPPPA generate substantial amounts of ROS under laser irradiation, which is directly proportional to the duration of illumination. Furthermore, both compounds exhibited significant cytotoxic effects on SH-SY5Y cells, as demonstrated by the MTT assay. Western blotting revealed a marked increase in the expression of Cleaved caspase-3, Cleaved caspase-9, and Bax, and a decrease in the expression of Bcl-2, confirming that caspase-dependent apoptosis is involved in SH-SY5Y cell death induced by TPPPA photodynamic therapy. ROS overproduction plays a crucial role in this process, and NAC preconditioning was shown to reduce cytotoxicity and inhibit pro-apoptotic protein molecules. However, 2TMeQ[6]-TPPPA was less effective than TPPPA in terms of ROS production capacity and toxicity to SH-SY5Y cells after self-assembling with TMeQ[6]. In conclusion, our study explored that TPPPA can induce ROS overproduction leading to apoptosis, and its mediated photodynamic therapy is a highly effective treatment option for SH-SY5Y cells. After self-assembling with TMeQ[6], TPPPA retains its apoptotic pathway-inducing characteristics and acts as a carrier, but this is not conducive to the photodynamic enhancement of TPPPA.
{"title":"The mechanism of novel potential porphyrin photosensitizer mediated phototherapy in SH-SY5Y cell lines and the effect of TMeQ[6] self-assembly in therapy","authors":"Zhouxia Lu, Yan Guo, Conghui Wang, Song Xiao","doi":"10.1142/s1088424623501092","DOIUrl":"https://doi.org/10.1142/s1088424623501092","url":null,"abstract":"Porphyrin PSs, possessing high photosensitivity and stability, have widespread use in phototherapy. Furthermore, the use of Q[n]s as a carrier for PSs has contributed to enhancing the efficacy of photodynamic therapy. In the present study, we synthesized 2TMeQ[6]-TPPPA self-assembled compounds, comprising TMeQ[6] and 5, 10, 15, 20-tetra (4-pyridyl, N-propyl ammonia) porphyrin derivatives (TPPPA) (in a 2:1 ratio), to investigate their capacity to generate reactive oxygen species (ROS) and their effect of self-assembly with TMeQ[6] on the efficacy of human neuroblastoma cell line (SH-SY5Y). Our results demonstrate that both TPPPA and 2TMeQ[6]-TPPPA generate substantial amounts of ROS under laser irradiation, which is directly proportional to the duration of illumination. Furthermore, both compounds exhibited significant cytotoxic effects on SH-SY5Y cells, as demonstrated by the MTT assay. Western blotting revealed a marked increase in the expression of Cleaved caspase-3, Cleaved caspase-9, and Bax, and a decrease in the expression of Bcl-2, confirming that caspase-dependent apoptosis is involved in SH-SY5Y cell death induced by TPPPA photodynamic therapy. ROS overproduction plays a crucial role in this process, and NAC preconditioning was shown to reduce cytotoxicity and inhibit pro-apoptotic protein molecules. However, 2TMeQ[6]-TPPPA was less effective than TPPPA in terms of ROS production capacity and toxicity to SH-SY5Y cells after self-assembling with TMeQ[6]. In conclusion, our study explored that TPPPA can induce ROS overproduction leading to apoptosis, and its mediated photodynamic therapy is a highly effective treatment option for SH-SY5Y cells. After self-assembling with TMeQ[6], TPPPA retains its apoptotic pathway-inducing characteristics and acts as a carrier, but this is not conducive to the photodynamic enhancement of TPPPA.","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45140088","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-06-28DOI: 10.1142/s1088424623501122
I. Mbakara, A. Gajewska, Krzysztof Nawara, J. Waluk
{"title":"Instability of 9-aminoporphycenes","authors":"I. Mbakara, A. Gajewska, Krzysztof Nawara, J. Waluk","doi":"10.1142/s1088424623501122","DOIUrl":"https://doi.org/10.1142/s1088424623501122","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42219607","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-06-28DOI: 10.1142/s1088424623501134
Daniil N Finogenov, Dmitriy A. Lazovskiy, Alina S. Kopylova, Yuriy A. Zhabanov, P. Stuzhin
{"title":"Spectral-luminescence, redox and photochemical properties of AlIII, GaIII and InIII complexes formed by peripherally chlorinated phthalocyanines and tetrapyrazinoporphyrazines","authors":"Daniil N Finogenov, Dmitriy A. Lazovskiy, Alina S. Kopylova, Yuriy A. Zhabanov, P. Stuzhin","doi":"10.1142/s1088424623501134","DOIUrl":"https://doi.org/10.1142/s1088424623501134","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":"1 1","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41458886","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-06-28DOI: 10.1142/s1088424623501146
Shagor Chowdhury, P. Hennequin, O. Cala, Sandrine Denis‐Quanquin, E. saint-Aman, Denis Frath, F. Chevallier, C. Bucher
{"title":"Redox-responsive 1D-assembly built from cucurbit[8]uril and a water-soluble metalloporphyrin-based tecton","authors":"Shagor Chowdhury, P. Hennequin, O. Cala, Sandrine Denis‐Quanquin, E. saint-Aman, Denis Frath, F. Chevallier, C. Bucher","doi":"10.1142/s1088424623501146","DOIUrl":"https://doi.org/10.1142/s1088424623501146","url":null,"abstract":"","PeriodicalId":16876,"journal":{"name":"Journal of Porphyrins and Phthalocyanines","volume":" ","pages":""},"PeriodicalIF":1.5,"publicationDate":"2023-06-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43518643","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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