{"title":"Propentdyopents: Brief history of a family of dipyrrolic pigments","authors":"E. Tomat","doi":"10.1142/s1088424619300210","DOIUrl":"https://doi.org/10.1142/s1088424619300210","url":null,"abstract":"Propentdyopents are naturally occurring dipyrroles deriving from the metabolism of heme and characterized by a dipyrrin-1,9-dione motif. The unusual name propentdyopent is due to the first colorimetric method (the Stokvis reaction) for the detection of these compounds, which were initially isolated from urine samples. Upon reduction in alkaline solutions, they produced red species that were termed pentdyopents to describe with Greek numerals their absorption maximum (525 nm) in the visible range. The precursors to the red pentdyopents were thus indicated as propentdyopents.Over the course of several decades, these dipyrrolic compounds have appeared in several studies of human physiology, typically associated to conditions of abnormal heme metabolism and/or oxidative stress. Concurrently, synthetic investigations have confirmed their chemical structure, reactivity, and ability to coordinate metals as bidentate monoanionic ligands. Notably, the planar dipyrrindione platform can undergo reversible one-electron redox processes and thereby act as an electron reservoir in metal complexes. In combination with the documented ability of the carbonyl groups to act as hydrogen-bonding acceptors, the coordination chemistry of propentdyopents could lead to new applications for this old class of pigments. Furthermore, the observation of these pigments in several clinical contexts could potentially delineate a role of propentdyopents as diagnostic biomarkers. This mini-review summarizes both the chemistry and biology of propentdyopents while highlighting the ample space for new discoveries.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"18 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78394010","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
N. Taşaltın, Cihat Tasaltin, H. Aydın, U. Şahintürk, A. Gürek
{"title":"Hexylsulfanyl-substituted CoPc and GO-CoPc on Ni foam as electroactive material for supercapacitors","authors":"N. Taşaltın, Cihat Tasaltin, H. Aydın, U. Şahintürk, A. Gürek","doi":"10.1142/s1088424619501955","DOIUrl":"https://doi.org/10.1142/s1088424619501955","url":null,"abstract":"For energy storage applications, hexylsulfanyl-substituted CoPc and GO-CoPc electrodes were prepared on Ni foam, and then electrochemical properties of the materials were investigated. The GO-CoPc nanocomposite electrode exhibits 56 mFcm[Formula: see text] at 1.4 mAcm[Formula: see text] current density. The results show that the GO-CoPc nanocomposite electrode is a promising electroactive material for supercapacitors.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"53 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77277556","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Mitochondria-targeted porphyrin-based photosensitizers containing triphenylphosphonium cations showing efficient in vitro photodynamic therapy effects","authors":"Xing Guo, Hao Wu, W. Miao, Yangchun Wu, Erhong Hao, Lijuan Jiao","doi":"10.1142/s1088424619501682","DOIUrl":"https://doi.org/10.1142/s1088424619501682","url":null,"abstract":"Subcellular organelle-targeted photosensitizers have recently reported to be effective photodynamic therapy (PDT) agents. In this work, three porphyrin-derived photosensitizers, containing one, two or four triphenylphosphonium targeting groups, were synthesized and characterized by NMR, HRMS, UV-vis and fluorescence spectroscopy. These photosensitizers showed similar photophysical properties to classical porphyrins and exhibited excellent [Formula: see text]O[Formula: see text] quantum yields in acetonitrile. Subcellular colocalization indicated that all three photosensitizers specifically stain the mitochondria of HeLa cells. Photosensitizer mito-dp, containing two triphenylphosphonium cations was found to be the most uptaken by cells and exhibited the best PDT effect with an effective phototoxicity (IC[Formula: see text] (light) [Formula: see text] 12.4 nM), suggestive of a higher practicable potential of mitochondria-targeted PDT agents in cancer therapy.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"12 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75096795","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
S. Dubey, Sai K. Pradyuth, R. Saha, Gautam Singhvi, A. Alexander, Mukta Agrawal, B. Shapiro, A. Puri
{"title":"Application of photodynamic therapy drugs for management of glioma","authors":"S. Dubey, Sai K. Pradyuth, R. Saha, Gautam Singhvi, A. Alexander, Mukta Agrawal, B. Shapiro, A. Puri","doi":"10.1142/s1088424619300192","DOIUrl":"https://doi.org/10.1142/s1088424619300192","url":null,"abstract":"Human gliomas are one of the most prevalent and challenging-to-treat adult brain tumors, and thus result in high morbidity and mortality rates worldwide. Current research and treatments of gliomas include surgery associated with conventional chemotherapy, use of biologicals, radiotherapy, and medical device applications. The selected treatment options are often guided by the category and aggressiveness of this deadly disease and the patient’s conditions. However, the effectiveness of these approaches is still limited due to poor drug efficacy (including delivery to desired sites), undesirable side effects, and high costs associated with therapies. In addition, the degree of leakiness of the blood–brain barrier (BBB) that regulates trafficking of molecules in and out of the brain also modulates accumulation of adequate drug levels to tumor sites. Active research is being pursued to overcome these limitations to obtain a superior therapeutic index and enhanced patient survival. One area of development in this direction focuses on the localized application of photodynamic therapy (PDT) drugs to cure brain cancers. PDT molecules potentially utilize multiple pathways based on their ability to generate reactive oxygen species (ROS) upon photoactivation by a suitable light source. In this communication, we have attempted to provide a brief overview of PDT and cancer, photoactivation pathways, mechanism of tumor destruction, effect of PDT on tumor cell viability, immune activation, various research attempted by applying PDT in combination with novel strategies to treat glioma, role of BBB and clinical status of PDT therapy for glioma treatment.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"6 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84921129","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
E. Fazio, M. J. Vicente-Arana, M. Alonso, T. Torres, G. Torre
{"title":"Selective guest recognition by a metallo-organic phthalocyanine-based host","authors":"E. Fazio, M. J. Vicente-Arana, M. Alonso, T. Torres, G. Torre","doi":"10.1142/s1088424619501712","DOIUrl":"https://doi.org/10.1142/s1088424619501712","url":null,"abstract":"In this manuscript, we have studied the selectivity in the complexation of fullerene species by a Fe[Formula: see text]Pc[Formula: see text] metallo-organic helicate (1) assembled using a bidentate phthalocyanine (Pc) as ligand. The large aromatic internal surface of this helicate shows a strong selectivity towards the encapsulation of C[Formula: see text] from a mixture of C[Formula: see text] and C[Formula: see text]. On the other hand, a bisimidazole-containing naphthalenediimide was used to perform guest exchange experiments over [fullerene [Formula: see text] 1] complexes, taking advantage of the strong coordination bond of the imidazole ring to the Zn centers in the Pc cavity.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"104 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80860465","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. Terasaki, Hiromi Kurokawa, H. Indo, H. Bando, H. Hara, H. Majima, H. Matsui, H. Ito
{"title":"Enhancement of PDT-cytotoxicity via ROS induced by indomethacin in metastatic breast cancer","authors":"A. Terasaki, Hiromi Kurokawa, H. Indo, H. Bando, H. Hara, H. Majima, H. Matsui, H. Ito","doi":"10.1142/s1088424619501542","DOIUrl":"https://doi.org/10.1142/s1088424619501542","url":null,"abstract":"Breast cancer is one of the most common types of cancers prevalent in women. Several types of breast cancers can easily metastasize to bone and cause disease complications such as hypercalcemia and pathologic fracture, thus compromising the quality of life of people affected by it. Bisphosphonate drugs are often used for the treatment of bone metastasis to suppress osteoclastic bone resorption. However, bisphosphonate has adverse effects on the gastrointestinal tract and kidneys and also induces osteonecrosis of the jaw. Photodynamic therapy (PDT) is an alternative cancer treatment approach with minimal invasiveness. It is a combination treatment that uses photosensitizers, which accumulate in tumor cells, followed by laser irradiation. We previously reported that the cellular incorporation of 5-aminolevulinic acid (5-ALA), which was a precursor of protoporphyrin IX (PpIX), was regulated by reactive oxygen species derived from mitochondria (mitROS). In this study, we investigated the incorporation of 5-ALA, accumulation of PpIX, and subsequent effects on cell viability after laser irradiation of two different breast cancer cell lines with different metastaticites. The highly metastatic breast cancer cell line 4T1E/M3 showed a significant increase in ROS production after treatment with indomethacin (IND). In addition, IND treatment enhanced the cellular uptake of 5-ALA via PEPT1 upregulation in 4T1E/M3, but not in the non-metastatic cell line. Overall, metastatic breast cancer is likely to be sensitive to ROS and activate signaling pathways associated with 5-ALA transportation, suggesting that ALA-PDT could be an effective treatment with low invasiveness for metastatic breast cancer.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"16 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83538711","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
D. Laurencin, P. Yot, C. Gervais, Y. Guari, S. Clément, E. Elkaim, M. Paillet, D. Cot, Sébastien Richeter
{"title":"Synthesis, characterization and modeling of self-assembled porphyrin nanorods","authors":"D. Laurencin, P. Yot, C. Gervais, Y. Guari, S. Clément, E. Elkaim, M. Paillet, D. Cot, Sébastien Richeter","doi":"10.1142/s1088424619501451","DOIUrl":"https://doi.org/10.1142/s1088424619501451","url":null,"abstract":"Porphyrin nanorods were prepared by ion-association between free-base meso 5,10,15,20-tetrakis-(4-[Formula: see text]-methylpyridinium)porphyrin cations and tetraphenylborate anions. The nanorods have variable lengths (up to a few micrometers long) and diameters ([Formula: see text]50–500 nm). Their structure at the molecular level was elucidated by combining multinuclear solid state NMR spectroscopy, synchrotron X-ray powder diffraction and DFT calculations.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"29 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76637763","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Elena Prigorchenko, Lukas Ustrnul, V. Borovkov, R. Aav
{"title":"Heterocomponent ternary supramolecular complexes of porphyrins: A review","authors":"Elena Prigorchenko, Lukas Ustrnul, V. Borovkov, R. Aav","doi":"10.1142/s108842461930026x","DOIUrl":"https://doi.org/10.1142/s108842461930026x","url":null,"abstract":"Porphyrins are prominent host molecules which are widely used due to their structural characteristics and directional interaction sites. This review summarizes non-covalently bound ternary complexes of porphyrins, constructed from at least three non-identical species. Progress in supramolecular chemistry allows the creation of complex molecular machinery tools, such as rotors, motors and switches from relatively simple structures in a single self-assembly step. In the current review, we highlight the collection of sophisticated molecular ensembles including sandwich-type complexes, cages, capsules, tweezers, rotaxanes, and supramolecular architectures mediating oxygen-binding and oxidation reactions. These diverse structures have high potential to be applied in sensing, production of new smart materials as well as in medical science.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"13 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82311888","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Peripherally substituted soluble nickel phthalocyanines: Synthesis, characterization, aggregation behavior and antioxidant properties","authors":"S. Yazici, S. Kahraman, S. Yıldız, M. D. Yilmaz","doi":"10.1142/s1088424619501645","DOIUrl":"https://doi.org/10.1142/s1088424619501645","url":null,"abstract":"Tetra-zwitterionic-substituted nickel(II) phthalocyanine derivatives were newly synthesized starting from nonionic 2(3),9(10),16(17),23(24)-tetrakis-[2-([Formula: see text]-((3-dimethylamino)propyl)carbamate)oxyethyl)phthalocyaninato nickel (II). The novel compounds have been characterized by a combination of UV-vis, FT-IR and mass spectroscopies and elemental analysis. The critical micelle concentrations of the prepared compounds were measured, and the antioxidant activities were analyzed with radical scavenging ability of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and with 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS). The zwitterionic molecules showed aggregated spectra in the UV-vis region, and they might be good surfactant candidates for the detergent industry with their appropriate critical micelle concentration (CMC) properties in water. The compounds exhibited ABTS radical scavenging activity and thus they have antioxidant activity.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"52 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89925747","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M. Chahal, N. Velychkivska, Whitney A Webre, J. Labuta, Shinsuke Ishihara, K. Ariga, F. D’Souza, Jonathan P. Hill
{"title":"Increasing the complexity of oxoporphyrinogen colorimetric sensing chromophores: N-alkylation and β-substitution","authors":"M. Chahal, N. Velychkivska, Whitney A Webre, J. Labuta, Shinsuke Ishihara, K. Ariga, F. D’Souza, Jonathan P. Hill","doi":"10.1142/s1088424619501463","DOIUrl":"https://doi.org/10.1142/s1088424619501463","url":null,"abstract":"Meso-5,10,15,20-tetrakis-3,5-di-tert-butyl-4-oxocyclohexadienylideneporphyrinogen, OxP, is a versatile, highly colored chromophore derived from meso-5,10,15,20-tetrakis(3,5-di-tert-butyl-4-hydroxyphenyl)porphyrin. It exhibits a wide range of chromogenic responses to solvents (solvatochromism), anions and acidic media (halochromism) making it potentially useful as an analytical reagent. The chromogenic responses of OxP can be modulated by varying its chemical structure, and this is reviewed here based on the introduction of substituents at central nitrogen atoms or pyrrolic [Formula: see text]-positions. OxP and its N-alkylated derivates Bn2OxP and Bn4OxP have been used to estimate acidity in non-polar solvents. Bn2OxP can also be used to determine enantiomeric excesses of chiral substances. N-alkylation has also been used to introduce higher functional groups such as porphyrins to prepare self-assembling systems. [Formula: see text]-Substitution has been used to introduce selectivity of anion interactions including towards basic anions (fluoride, cyanide) and polyoxoanions (nitrate, perchlorate, etc.). These aspects make OxP a highly adaptable tetrapyrrole molecule for sensing and other applications.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"26 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77360221","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}