Z. Khaldi, Jean K. Nzambe Takeki, T. Ouk, R. Lucas, R. Zerrouki
{"title":"Synthesis and photo-bactericidal properties of a cationic porphyrin grafted onto kraft pulp fibers","authors":"Z. Khaldi, Jean K. Nzambe Takeki, T. Ouk, R. Lucas, R. Zerrouki","doi":"10.1142/S1088424619500330","DOIUrl":"https://doi.org/10.1142/S1088424619500330","url":null,"abstract":"With the increased risk of infectious disease transmissions, photodynamic inactivation of some microorganisms for antimicrobial applications has been extensively studied in recent years. In this article, we describe the synthesis of novel photo-bactericidal materials by grafting propargylated 5,10,15,20-tetra(4-pyridyl)porphyrin on kraft pulp fibers. The grafting was carried out by a Huisgen’s 1,3-dipolar azide-alkyne cycloaddition reaction. This material has been investigated for its antibacterial properties against Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus. An interesting photo-bactericidal activity was shown: this material can be used to limit the growth of bacteria on surfaces and the formation of biofilms.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"98 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80606459","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}
Lucie P. Cailler, A. Martynov, Yulia G. Gorbunova, A. Tsivadze, A. Sorokin
{"title":"Carbene insertion to N–H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine","authors":"Lucie P. Cailler, A. Martynov, Yulia G. Gorbunova, A. Tsivadze, A. Sorokin","doi":"10.1142/S1088424619500354","DOIUrl":"https://doi.org/10.1142/S1088424619500354","url":null,"abstract":"Iron(III) phthalocyaninate decorated with crown ether substituents, [(15C5)4PcFe]Cl, efficiently catalyzed the insertion of carbene derived from ethyl diazoacetate to six amines functionalized with thiazole, thiazoline and thiadiazole heterocycles. The reactions were carried out under practical conditions using EDA:amine stoechiometric ratio with 0.05 mol% catalyst loading. Turnover numbers up to 3360 have been achieved. The aminoacid derivatives bearing heterocyclic moieties were obtained under catalytic conditions for the first time with 36–69% yields in the case of single N–H insertion products and up to 77% in the case of double N–H insertion products.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"23 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82377461","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}
Cátia Vieira, Adriele Santos, Mariana Q. Mesquita, A. Gomes, M. Neves, M. Faustino, A. Almeida
{"title":"Advances in aPDT based on the combination of a porphyrinic formulation with potassium iodide: Effectiveness on bacteria and fungi planktonic/biofilm forms and viruses","authors":"Cátia Vieira, Adriele Santos, Mariana Q. Mesquita, A. Gomes, M. Neves, M. Faustino, A. Almeida","doi":"10.1142/S1088424619500408","DOIUrl":"https://doi.org/10.1142/S1088424619500408","url":null,"abstract":"The increasing world-wide rate of antibiotic resistance as well as the capacity of microorganisms to form biofilms, have led to a higher incidence of mortal infections that require alternative methods for their control. Antimicrobial photodynamic therapy (aPDT) emerged as an effective solution against resistant strains. The present work aims to evaluate the aPDT efficiency of a photosensitizer (PS) based on a low-cost formulation constituted by five cationic porphyrins (FORM) and its potentiation effect by KI on a broad spectrum of microorganisms under white light (380–700 nm, 25 W/m[Formula: see text]. The aPDT assays were performed with different concentrations of FORM (0.1 to 5.0 [Formula: see text]M) and 100 mM of KI on planktonic and biofilm forms of gram-positive (methicillin resistant Staphylococcus aureus–MRSA) and gram-negative (Escherichia coli resistant to chloramphenicol and ampicillin) bacteria, of the fungi Candida albicans and on a T4-like bacteriophage as a mammalian virus model. The results indicate that the FORM alone is an efficient PS to photoinactivate not only gram-negative and gram-positive bacteria, but also C. albicans, in planktonic and biofilm forms, and T4-like phage at low concentrations (<5.0 [Formula: see text]M). The presence of KI enhanced the photodynamic effect of this FORM for all microorganisms on the planktonic form, allowing the reduction of PS concentration and treatment time. The results also show that the combination FORM/KI is highly efficient in the elimination of already well-established biofilms of E. coli,S. aureus and C. albicans. This effect is probably associated with longer-lived iodine reactive species produced during the aPDT treatment.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"5 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82629788","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}
Desiré Molina, M. A. Ruiz‐Preciado, Faranak Sadegh, M. J. Álvaro‐Martins, M. Grätzel, A. Hagfeldt, Á. Sastre‐Santos
{"title":"p-Phenylene-bridged zinc phthalocyanine-dimer as hole-transporting material in perovskite solar cells","authors":"Desiré Molina, M. A. Ruiz‐Preciado, Faranak Sadegh, M. J. Álvaro‐Martins, M. Grätzel, A. Hagfeldt, Á. Sastre‐Santos","doi":"10.1142/S1088424619500457","DOIUrl":"https://doi.org/10.1142/S1088424619500457","url":null,"abstract":"The synthesis and characterization of a [Formula: see text]-phenylene-bridged ZnPc dimer along with a preliminary study of this material as hole transporting material (HTM) in perovskite solar cells is described. The maximum efficiencies that obtained are 15.2% for ZnPc-[Formula: see text]-ZnPc 1, thus demonstrating the potential of the Pc dimers that could pave the path to achieve highly efficient PSCs (PCE >20%).","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"19 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76706740","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}
F. Kus, Cihat Tasaltin, Mohamad Albakour, A. Gürek, İ. GÜrol
{"title":"Macromolecular hexa-asymmetric zinc(II) phthalocyanines bearing triazole-modified triphenylene core: Synthesis, spectroscopy and analysis towards volatile organic compounds on Surface Acoustic Wave devices","authors":"F. Kus, Cihat Tasaltin, Mohamad Albakour, A. Gürek, İ. GÜrol","doi":"10.1142/S1088424619500342","DOIUrl":"https://doi.org/10.1142/S1088424619500342","url":null,"abstract":"The synthesis and characterization of novel asymmetric zinc(II) phthalocyanines (4–9) and their linking through peripheral and nonperipheral positions on the phthalocyanine ring via click coupling to alkyne-functionalized 2,3,6,7,10,11-hexakis(prop-2-ynyloxy)triphenylene core are described for the first time. These phthalocyanines (Pcs) (4–12) were characterized by elemental analysis and different spectroscopic techniques such as UV-vis, 1H-NMR, FT-IR and mass spectroscopy. Furthermore, the utilization of thin films of novel Pcs as a sensitive layer for detection of lung cancer from exhaled human breath at room temperature under exposure to marker volatile organic compounds (VOCs) are presented. The developed sensors were tested for acetone, ethanol, [Formula: see text]-hexane, toluene, chloroform and isoprene in a range of 300–14560 ppm. The obtained results have confirmed the possibility of utilization of Pc-based Surface Acoustic Wave (SAW) sensors for medical diagnosis based on exhaled breath analysis.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"14 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90908205","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}
Veronica Ambrosini, Mohammad Issawi, Stéphanie Leroy-Lhez, C. Riou
{"title":"How protoporphyrinogen IX oxidase inhibitors and transgenesis contribute to elucidate plant tetrapyrrole pathway","authors":"Veronica Ambrosini, Mohammad Issawi, Stéphanie Leroy-Lhez, C. Riou","doi":"10.1142/S1088424619300076","DOIUrl":"https://doi.org/10.1142/S1088424619300076","url":null,"abstract":"Several families of herbicides, especially diphenyl ether (DPE) and pyrimidinedione, target the plant tetrapyrrole biosynthesis pathways and in particular one key enzyme, protoporphyrinogen IX oxidase (PPO). When plants are treated with DPE or pyrimidinedione, an accumulation of protoporphyrin IX, the first photosensitizer of this pathway, is observed in cytosol where it becomes very deleterious under light. Indeed these herbicides trigger plant death in two distinct ways: (i) inhibition of chlorophylls and heme syntheses and (ii) a huge accumulation of protoporphyrin IX in cytosol. Recently, a strategy based on plant transgenesis that induces deregulation of the tetrapyrrole pathway by up- or down-regulation of genes encoding enzymes, such as glutamyl-[Formula: see text]RNA reductase, porphobilinogen deaminase and PPO, has been developed. Against all expectations, only transgenic crops overexpressing PPO showed resistance to DPE and pyrimidinedione. This herbicide resistance of transgenic crops leads to the hypothesis that the overall consumption of herbicides will be reduced as previously reported for glyphosate-resistant transgenic crops. In this review, after a rapid presentation of plant tetrapyrrole biosynthesis, we show how only PPO enzyme can be the target of DPE and how transgenic crops can be further resistant not only to herbicide but also to abiotic stress such as drought or chilling. Keeping in mind that this approach is mostly prohibited in Europe, we attempt to discuss it to interest the scientific community, from plant physiologists to chemists, who work on the interface of photosensitizer optimization and agriculture.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"33 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88637896","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":"Truncated vitamin B12 derivative with the phosphate group retained","authors":"Sidra Hassan, Agnieszka Jackowska, D. Gryko","doi":"10.1142/S1088424619500421","DOIUrl":"https://doi.org/10.1142/S1088424619500421","url":null,"abstract":"Cobyric acid and cobinamide are valuable building blocks for the synthesis of artificial cobalamins modified at the nucleotide loop. However, truncated vitamin B[Formula: see text] derivatives are devoid of the phosphate group. We have found that 2-iodoxy benzoic acid-mediated phosphorolysis leads to the cleavage of only one of the phosphodiester bond giving a vitamin B[Formula: see text] analogue with the phosphate moiety preserved. Subsequent alkylation with an organic halide establishes its role as a precursor for the synthesis of vitamin B[Formula: see text] mimics modified at the nucleotide loop.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"21 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75342186","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":"Update of the situation of clinical photodynamic therapy in Europe in the 2003–2018 period","authors":"C. Frochot, S. Mordon","doi":"10.1142/S1088424619300027","DOIUrl":"https://doi.org/10.1142/S1088424619300027","url":null,"abstract":"Photodynamic therapy has become of interest in many European countries. Since, most of national authorities and all medical journals require the registration of the clinical study on the database ClinicalTrials. gov in order to be published, information regarding clinical studies are now available. This article aims to synthetize data gathered thanks to this database. The keywords used for this analysis was: (i) status: “All studies “(recruiting, completed, terminated, we did not take into account unknown status), (ii) condition or disease: “Photodynamic Therapy”, (iii) country: name of each European country. Since 2003, 76 clinical trials were registered in Europe. Most clinical studies are performed in Germany (22), France (20) and UK (19). These 3 countries represent 80% of all studies performed in Europe. However 21 European countries have one or more studies on PDT. Clinical studies were mainly performed on skin. Actinic Keratosis treatment (20 studies) represents more than 45% of all studies. 21% were focused on eye, mainly on Age Macular Degeneration (AMD) (8 studies). In 2018, ten (10) clinical trials are in the recruitment phase. On November, 10, 2017, Padeliporfin (STEBA Biotech S.A, Luxembourg) obtained the marketing authorization throughout the European Union. Despite the critical importance of trial registration, compliance with requirements from governmental regulators which mandate the prospective registration of clinical trials has been imperfect. Besides, a large proportion of registry entries are never updated to reflect study completion. However, this review clearly demonstrated that PDT is progressively used in most European countries.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"85 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83491067","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":"Synthetic aspects of carbazole containing porphyrins and porphyrinoids","authors":"Sudipta Das, Iti Gupta","doi":"10.1142/S1088424619300052","DOIUrl":"https://doi.org/10.1142/S1088424619300052","url":null,"abstract":"Porphyrins are tetrapyrrolic aromatic macrocycles and ubiquitous in nature. They are excellent dyes with strong absorption in the visible region (400–700 nm) and they exhibit decent fluorescence in the red region (620–900 nm). Carbazole is a nitrogen-containing electron rich aromatic heterocycle which can be linked to porphyrins and other chromophores. This review provides an overview of the different synthetic strategies that have been employed to prepare carbazole-substituted porphyrins and carbazole-fused porphyrinoids and similar systems. It also shows that how the substitution of carbazole occurs on the porphyrin core can alter its optical and electronic features. Introduction of carbazole moieties in the porphyrin ring resulted in fused porphyrinoids with changed aromaticity and significantly altered electronic features of the molecules.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"71 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90892173","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}
Hiroaki Kitagishi, K. Ohara, Daiki Shimoji, Maxime Vonesch, J. Weiss, J. Wytko
{"title":"Hydrogen bond directed molecular recognition in water in a strapped-porphyrin-cyclodextrin assembly","authors":"Hiroaki Kitagishi, K. Ohara, Daiki Shimoji, Maxime Vonesch, J. Weiss, J. Wytko","doi":"10.1142/S1088424619500494","DOIUrl":"https://doi.org/10.1142/S1088424619500494","url":null,"abstract":"A water soluble, phenanthroline-strapped zinc porphyrin bearing four arylsulfonate groups formed a stable host–guest complex with two per-[Formula: see text]-methylated [Formula: see text]-cyclodextrin cavities. In the host–guest assembly, the zinc porphyrin was capable of binding imidazole within the cavity between the zinc(II) ion and the phenanthroline strap in an aqueous medium. The formation of a hydrogen bond between the imidazole NH and the nitrogen atoms of the phenanthroline was an essential element of the binding event, as shown by comparative binding studies with a non-strapped tetrasulfonated zinc porphyrin and with [Formula: see text]-methylimidazole. This hydrogen bonding in an aqueous medium was possible due to the protected hydrophobic environment created by the cyclodextrins around the phenanthroline strap. This type of binding event may provide a biomimetic approach to study water soluble heme protein models.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"28 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79546741","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}