{"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}
Iva Habenšus, Ameen Ghavam, C. J. Curtis, A. Astashkin, E. Tomat
{"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}
{"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}
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}
Alejandra Romero-Morán, S. Hernández‐Anzaldo, Hugo Vazquez-Lima, Y. Reyes-Ortega
{"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}
Rong Yuan, Le Liu, Bangshao Yin, Ling Xu, Mingbo Zhou, Yutao Rao, Jianxin Song
{"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}
{"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}
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}
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}
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}