{"title":"BODIPYS and aza-BODIPY derivatives as promising fluorophores for in vivo molecular imaging and theranostic applications","authors":"E. Bodio, F. Denat, C. Goze","doi":"10.1142/s1088424619501268","DOIUrl":"https://doi.org/10.1142/s1088424619501268","url":null,"abstract":"Since their discovery in 1968, the BODIPYs dyes (4,4-difluoro-4-bora-3a, 4a diaza-s-indacene) have found an exponentially increasing number of applications in a large variety of scientific fields. In particular, studies reporting bioapplications of BODIPYs have increased dramatically. However, most of the time, only in vitro investigations have been reported. The in vivo potential of BODIPYs and aza-BODIPYs is more recent, but considering the number of in vivo studies with BODIPY and aza-BODIPY which have been reported in the last five years, we can now affirm that this family of fluorophores can be considered important as cyanine dyes for future in vivo and even clinical applications. This review aims to present representative examples of recent in vivo applications of BODIPYs or aza-BODIPYs, and to highlight the potential of these dyes for optical molecular imaging.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"49 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77521415","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}
K. Abdullah, X. Kong, M. Imran, G. Mustafa, Yanli Chen
{"title":"Excellent ambipolar gas sensing response of Eu[Pc(OC4H9)8]2/acidified multiwalled carbon nanotubes hybrid at room temperature","authors":"K. Abdullah, X. Kong, M. Imran, G. Mustafa, Yanli Chen","doi":"10.1142/s1088424619501554","DOIUrl":"https://doi.org/10.1142/s1088424619501554","url":null,"abstract":"A new hybrid material has been developed by mixing a sandwich-type double-decker, Eu[Pc(OC4H9)8]2 = 2,3,9,10,16,17,23,24-octabutoxyphthalocyaninate] with acidified multiwalled carbon nanotubes (aMWCNTs) through non-covalent interactions. The UV-vis spectrum, X-ray diffraction and scanning electron microscope have been employed to reveal the [Formula: see text]-aggregate mode and optimized morphology of Eu[Pc(OC4H9)8]2 molecules in the Eu[Pc(OC4H9)8]2/aMWCNTs hybrid material. The gas-sensing devices based on this hybrid material are fabricated by a simple solvent-processing quasi-Langmuir–Shäfer (QLS) progress. The [Formula: see text]-type and [Formula: see text]-type response is shown by the Eu[Pc(OC4H9)8]2/aMWCNTs hybrid film at room temperature. The detection limit of the hybrid for ammonia and nitrogen dioxide gas is 0.5 ppm and 0.3 ppm, respectively.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"41 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89295251","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":"Synthesis of new water soluble silicon phthalocyanine substituted by linker sulfur atom and photophysicochemical studies for photodynamic therapy","authors":"Göknur Yaşa Atmaca, A. Erdoğmuş","doi":"10.1142/s1088424619501487","DOIUrl":"https://doi.org/10.1142/s1088424619501487","url":null,"abstract":"In this work, 5-(trifluoromethyl)-2-thiopyridine substituted SiPc (1) and its quaternized derivative (2) were synthesized, and the effect of the linker sulfur atom on silicon phthalocyanines has been investigated for the first time in the literature. Both of the complexes have been characterized by standard spectroscopy methods. The complexes have good solubility in organic solvents and showed monomeric tendencies in all studied solvents. Only complex 2 had some aggregation in water because of solvent effects, as expected. In order to determine the therapeutic effect for cancer treatment, photophysicochemical properties were investigated in DMSO, DMF, toluene and water (for complex 2). The synthesized complexes were found to have about 3.5 times higher singlet oxygen quantum yields than the yields of unsubstituted SiPcCl2 ([Formula: see text] = 0.15 (in DMSO), 0.12 (in DMF), 0.10 (in toluene)) because of the effects of bulky axial groups.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"14 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89641942","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}
Yumeela Ganga-Sah, E. Tajbakhsh, Rachel H. Platel, Wen Zhou, D. Leznoff
{"title":"Synthesis, structures and reduction chemistry of monophthalocyanine scandium hydroxides","authors":"Yumeela Ganga-Sah, E. Tajbakhsh, Rachel H. Platel, Wen Zhou, D. Leznoff","doi":"10.1142/s1088424619501992","DOIUrl":"https://doi.org/10.1142/s1088424619501992","url":null,"abstract":"The preparation and structural characterization of a pair of scandium(III) phthalocyanine hydroxide complexes were achieved by reaction of PcScCl with alkali metal alkoxides, likely via hydrolysis of soluble PcSc-alkoxide intermediates. A Sc[Formula: see text]Li[Formula: see text]-OH)[Formula: see text] cubane supported by two distorted Pc rings of the form (PcSc)[Formula: see text]-OH)[Formula: see text]Li[Formula: see text](THF)(DME) was isolated from the reaction of PcScCl with LiO[Formula: see text]Pr, while a simpler alkali-metal-free [Pc[Formula: see text]Sc[Formula: see text]-OH)[Formula: see text](THF)] was obtained from addition of NaO[Formula: see text]Bu; both structures are reminiscent of bent metallocenes, with dihedral angles between the two Pc rings of 50.8 and 37.7[Formula: see text]respectively. A soluble PcScOH material can also be obtained directly via hydrolysis of insoluble PcScCl in approximately 95:5 THF:water. Reduction of the Pc ring of PcScCl using KC[Formula: see text] is reversible and generates Pc[Formula: see text] and Pc[Formula: see text]-containing materials that were characterized via UV-vis spectroscopy and, where appropriate EPR and [Formula: see text]H NMR spectroscopy; analogous reductions of the PcScOH-based species were irreversible. Exposure of the air-sensitive, reduced PcScCl-based species to ambient atmosphere generated PcScOH materials analogous to the direct hydrolysis route.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"13 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-11-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85897218","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":"Properties and degradation of manganese(III) porphyrin thin films formed by high vacuum sublimation","authors":"H. Tseng, M. Serri, N. Harrison, S. Heutz","doi":"10.1142/s1088424619501700","DOIUrl":"https://doi.org/10.1142/s1088424619501700","url":null,"abstract":"Manganese porphyrins are of interest due to the optical, electronic and magnetic properties of the central metal ion, coupled to the low bandgap of the polyaromatic ring. These attractive characteristics are harnessed in solutions or in ultra-thin films, such as, for example, self-assembled monolayers. However, for devices, thicker films deposited using a controlled and reproducible method are required. Here we present the morphological, structural, chemical and optical properties of manganese(III) tetraphenylporphyrin chloride (MnTPPCl) thin films deposited using organic molecular beam deposition, typically employed to process analogue molecules for applications such as organic photovoltaics. We find, using a combination of UV-vis and X-ray photoelectron spectroscopies, that the sublimation process leads to the scission of the Mn–Cl bond. The resultant film is a Mn(II)TPP:Mn(III)TPPCl blend where approximately half the molecules have been reduced. Following growth, exposure to air oxidizes the Mn(II)TPP molecule. Through quantitative analysis of the time-dependent optical properties, the oxygen diffusion coefficient (D) [Formula: see text] is obtained, corresponding to a slow bulk oxidation following fast oxidation of a 8-nm-thick surface layer. The bulk diffusion D is lower than for analogous polycrystalline films, suggestion that grain boundaries, rather than molecular packing, are the rate-limiting steps in oxidation of molecular films. Our results highlight that the stability of the axial ligands should be considered when depositing metal porphyrins from the vapor phase, and offer a solvent-free route to obtain reproducible and smooth thin films of complex materials for engineering film functionalities.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"469 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83940093","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}
V. Bogoeva, Lidiya Petrova, J. Bouckaert, A. Yordanova, I. Ivanov, R. Vanderesse, C. Frochot
{"title":"Dual function of lectins — new perspectives in targeted photodynamic therapy","authors":"V. Bogoeva, Lidiya Petrova, J. Bouckaert, A. Yordanova, I. Ivanov, R. Vanderesse, C. Frochot","doi":"10.1142/s1088424619300209","DOIUrl":"https://doi.org/10.1142/s1088424619300209","url":null,"abstract":"Porphyrins and phthalocyanines are photosensitizers (PS) that are used in clinical imaging, detection of cancer cells and are particularly applied in photodynamic therapy (PDT). Many scientists have been focused on the design of different porphyrin compounds. However, similar to other anti-cancer agents, they cannot selectively recognize tumor tissues. Scientists are seeking new methods to overcome this problem and to find appropriate targeted delivery strategies. Plant lectins are especially suitable molecules for such targeting as they preferentially recognize specific antigens on the glycosylated cancer cells. This review will give more detailed information about the dual function of lectins and their interactions with PSs, which is a new perspective in targeted PDT. The implications and potential applications of such studies will also be discussed.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"71 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90380300","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}
Nthabeleng Molupe, B. Babu, E. Prinsloo, A. Kaassis, K. Edkins, J. Mack, T. Nyokong
{"title":"Photodynamic activity of Sn(IV) meso-tetraacenaphthylporphyrin and its methyl-β-cyclodextrin inclusion complexes on MCF-7 breast cancer cells","authors":"Nthabeleng Molupe, B. Babu, E. Prinsloo, A. Kaassis, K. Edkins, J. Mack, T. Nyokong","doi":"10.1142/s1088424619501633","DOIUrl":"https://doi.org/10.1142/s1088424619501633","url":null,"abstract":"A novel Sn(IV) meso-tetraacenaphthylporphyrin (SnTAcP) has been synthesized and characterized. SnTAcP was complexed with methyl-[Formula: see text]-cyclodextrin (m[Formula: see text]-CD), a nanocarrier that enhances water solubility, and the complexes were evaluated as PDT agents using MCF-7 breast cancer cells. A relatively low singlet oxygen quantum yield value of 0.36 was obtained in DMF, and the lowest energy Q band lies at 608 nm on the edge of the therapeutic window. SnTAcP was found to be non-toxic in the dark and phototoxic towards MCF-7 breast cancer cells with a half-maximal inhibitory concentration (IC[Formula: see text] value of 11 ± 1.1 [Formula: see text]g · mL[Formula: see text] after 30 min of irradiation with a 625 nm Thorlabs LED that provides a dose of 432 J · cm[Formula: see text]. A higher IC[Formula: see text] value of 21 ± 1.1 [Formula: see text]g · mL-1 was obtained for the m[Formula: see text]-CD inclusion complex of SnTAcP.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"25 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83839073","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}
Sandra Hojniak-Thyssen, Michał Szczepaniak, Lechosław Latos-Grażyński, Ewa Pacholska-Dudziak
{"title":"A flexible expanded heterocorrole: Tellura[22]porphyrin(6.1.1.0)","authors":"Sandra Hojniak-Thyssen, Michał Szczepaniak, Lechosław Latos-Grażyński, Ewa Pacholska-Dudziak","doi":"10.1142/s1088424619501621","DOIUrl":"https://doi.org/10.1142/s1088424619501621","url":null,"abstract":"An expanded heterocorrole, meso-tetraaryl-tellura[22]porphyrin(6.1.1.0), containing a bipyrrole moiety and a six-carbon long link, has been synthesized. The reaction path proceeds through a controlled acid-promoted extrusion of one tellurium atom from meso-aryl-26,28-ditellurasapphyrin, leading to a structure where one tellurophene ring of the substrate is replaced by a bridging acyclic four-carbon unit. This aromatic porphyrin-annulene hybrid is conformationally flexible in solution, on account of the C4 unit adopting two different configurations: trans–cis–trans or all-trans. Studies of the dynamic behavior of tellura[22]porphyrin(6.1.1.0) in solution were performed by means of 1H and 125Te NMR spectroscopy. The X-ray structure of the all-trans form with trapezoid macrocyclic skeleton is also presented.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"418 3 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77840632","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":"Glycosylated porphyrin-cucurbituril conjugate for photodynamic inactivation of bacteria and doxorubicin carriage for anticancer drug delivery","authors":"Melis Özkan, Yağmur Keser, A. Koc, D. Tuncel","doi":"10.1142/s1088424619501578","DOIUrl":"https://doi.org/10.1142/s1088424619501578","url":null,"abstract":"Porphyrin derivatives are highly attractive in the construction of multifunctional molecular platforms with interesting properties and applications. In this regard, we report here the use of a multifunctional porphyrin-based molecular platform as a photosensitizer for photodynamic therapy and as a drug carrier. This molecular platform was constructed by conjugating a host molecule, cucurbit[7]uril to a triglycosylated tetraphenyl porphyrin and serves very efficiently as a photosensitizer in the inactivation of both gram-negative (Escherichia coli, E. coli) and gram-positive bacteria (Bacillus subtilis, B. subtilis) and growth inhibition of cancer cells as well as a doxorubicin (DOX) carrier for chemo-photodynamic dual cancer therapy. Another remarkable feature of this photosensitizer is that it shows negligible cytotoxicity in the dark.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"37 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90241435","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":"Tailored porphyrin–gold nanoparticles for biomedical applications","authors":"M. Grigore, R. Ion, L. Iancu, R. Grigorescu","doi":"10.1142/S108842461930012X","DOIUrl":"https://doi.org/10.1142/S108842461930012X","url":null,"abstract":"In this review we present an updated survey of the main synthesis methods of gold nanoparticles (AuNPs) in order to obtain various tailored nanosystems for biomedical imaging. The synthesis approach significantly impacts on the AuNPs properties such as surface chemistry, biocompatibility and cytotoxicity. In recent years, nanomedicine emphasized the development of functionalized AuNPs for biomedical imaging. AuNPs are a good option for used as delivery photosensitizer agents for PDT of cancer. For example, the complex formed from AuNPs functionalized with PEGylate porphyrins presents several advantages in the medical field such as a better use in photodynamic therapy because of high triplet states and singlet oxygen quantum yield efficiency of porphyrin molecules.","PeriodicalId":20283,"journal":{"name":"Porphyrin Science by Women","volume":"51 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78258996","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}