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Yiliu Liu, Silvia Pujals, Patrick J M Stals, Thomas Pauloehrl, Stanislav I Presolski, E W Meijer, Lorenzo Albertazzi, Anja R A Palmans
Dynamic single-chain polymeric nanoparticles (SCPNs) are intriguing, bioinspired architectures that result from the collapse or folding of an individual polymer chain into a nanometer-sized particle. Here we present a detailed biophysical study on the behavior of dynamic SCPNs in living cells and an evaluation of their catalytic functionality in such a complex medium. We first developed a number of delivery strategies that allowed the selective localization of SCPNs in different cellular compartments. Live/dead tests showed that the SCPNs were not toxic to cells while spectral imaging revealed that SCPNs provide a structural shielding and reduced the influence from the outer biological media...
February 19, 2018: Journal of the American Chemical Society
E R Reis, L P Ferreira, E M D Nicola, I Borissevitch
Protoporphyrin IX (PpIX) is a precursor of heme synthesis and is known to be an active photosensitizer and precursor of photosensitizers applied in photodynamic therapy (PDT) and photodynamic diagnostics (PDD). On irradiation with visible light, PpIX undergoes phototransformation, producing photoproducts which may also be phototoxic and increase its efficacy. The mechanism of PpIX phototransformation depends on environmental characteristics and can be different in vitro and in vivo. In this paper, we present a comparative study of the photoactivity of synthetic PpIX and PpIX extracted from the Harderian gland of ssp Rattus novergicus albinus rats, along with their photoproducts toward murine B16F-10 melanoma cells...
February 16, 2018: European Biophysics Journal: EBJ
Bartosz Szyszko, Monika Przewoznik, Michal J Bialek, Agata Bialonska, Piotr J Chmielewski, Jakub Cichos, Lechoslaw Latos-Grazynski
Incorporation of phenanthrene into a hexaphyrin( frame resulted in the intramolecular fusion giving rise to chiral helicenophyrins, i.e. molecules which convolute helicene and porphyrin features incorporating aza[5]helicene or heptacyclic S-shaped aza[5]helicene.
February 16, 2018: Angewandte Chemie
Weiyu Ning, Zhenghan Di, Yingjie Yu, Pingmei Zeng, Chunzhi Di, Daquan Chen, Xueqian Kong, Guangjun Nie, Yuliang Zhao, Lele Li
Surface functionality is an essential component for processing and application of metal-organic frameworks (MOFs). A simple and cost-effective strategy for DNA-mediated surface engineering of zirconium-based nanoscale MOFs (NMOFs) is presented, capable of endowing them with specific molecular recognition properties and thus expanding their potential for applications in nanotechnology and biotechnology. It is shown that efficient immobilization of functional DNA on NMOFs can be achieved via surface coordination chemistry...
February 16, 2018: Small
Aijian Wang, Jun Ye, Mark G Humphrey, Chi Zhang
In recent years, there has been a rapid growth in studies of the optoelectronic properties of graphene, carbon nanotubes (CNTs), and their derivatives. The chemical functionalization of graphene and CNTs is a key requirement for the development of this field, but it remains a significant challenge. The focus here is on recent advances in constructing nanohybrids of graphene or CNTs covalently linked to porphyrins or phthalocyanines, as well as their application in nonlinear optics. Following a summary of the syntheses of nanohybrids constructed from graphene or CNTs and porphyrins or phthalocyanines, explicit intraconjugate electronic interactions between photoexcited porphyrins/phthalocyanines and graphene/CNTs are introduced classified by energy transfer, electron transfer, and charge transfer, and their optoelectronic applications are also highlighted...
February 16, 2018: Advanced Materials
R R Valiev, V N Cherepanov, G V Baryshnikov, D Sundholm
A method for calculating the rate constants for internal-conversion (k IC ) and intersystem-crossing (k ISC ) processes within the adiabatic and Franck-Condon (FC) approximations is proposed. The applicability of the method is demonstrated by calculation of k IC and k ISC for a set of organic and organometallic compounds with experimentally known spectroscopic properties. The studied molecules were pyrromethene-567 dye, psoralene, hetero[8]circulenes, free-base porphyrin, naphthalene, and larger polyacenes...
February 16, 2018: Physical Chemistry Chemical Physics: PCCP
Xin Wang, Peisong Wang, Shuai Xue, Xiaohua Zheng, Zhigang Xie, Guang Chen, Tingting Sun
Self-assembled small molecules, as a novel form of drug presentation, have splendid capabilities for water stability and cell endocytosis. Photodynamic therapy (PDT) is regarded as a promising cancer treatment because it is less invasive and has fewer side effects. In this work, an amphiphilic glycyrrhetinic acid-porphyrin conjugate (TPP-GA) was designed and synthesized, and this could self-assemble into nanoparticles (TPP-GA NPs) in water. The morphology of the TPP-GA NPs was observed using transmission electron microscopy (TEM) and their stability in water was revealed by dynamic light scattering (DLS)...
February 15, 2018: Organic & Biomolecular Chemistry
N Kaerkitcha, T Sagawa
Nanofibers with the cationic fluorescent molecules, 1-pyrenemethylamine hydrochloride (PyrMA) and α,β,γ,δ-tetrakis(1-methylpyridinium-4-yl)porphyrin p-toluenesulfonate (TMPyP), in the presence of complementary anionic chiral polysaccharide, hyaluronic acid (HA) and transparent polymer, polyethylene oxide (PEO) were successfully prepared using an electrospinning technique. The results showed that the fluorescence spectra of electrospun nanofibers (ENFs) of PEO-HA-PyrMA exhibit a higher amount of pyrene excimer emission when the [PyrMA]/[HA] ratio was increased from 0...
February 15, 2018: Photochemical & Photobiological Sciences
S M Kuzmin, S A Chulovskaya, V I Parfenyuk
This review is devoted to porphyrin-based film materials. Various technological and scientific applications of ones are close to surface and interface related phenomena. In the part I of review the following topics are discussed the recent progress in field of submonolayers, monolayers and multilayers films on the vapor-solid interfaces, including results on (i) conformational behavior of adsorbed molecules, (ii) aggregation and surface phases formation, (iii) on-surface coordination networks, and (iv) on-surface chemical reactions...
February 6, 2018: Advances in Colloid and Interface Science
Sen Li, Xin Geng, Wen-Quan Sun, Guo-Zhi Han
A kind of gold nanoparticles modified with metal crown ether porphyrin (GNPs-CP) was synthesized and characterized. The surface of the resulting gold particles was partially covered by metal crown ether porphyrin molecules through strong covalent Au-S bond. Based on the coupling effect of metal porphyrin and crown ether, the resulting composite gold nanoparticles can serve as a kind of ion probe. Raman and UV-Vis spectra were utilized to evaluate the ion recognition of the system, both of which changed dramatically when meeting metal ion corresponding to ligand of crown ether...
April 1, 2018: Journal of Nanoscience and Nanotechnology
Atsuhiro Osuka, Daiki Shimizu
A benzene-1,3,5-triaminyl radical fused with three Zn(II)-porphyrins was synthesized via a three-fold oxidative fusion reaction of 1,3,5-tris(Zn(II)-porphyrinylamino)benzene followed by oxidation with PbO2 as key steps. This triaminyl radical has been proved to possess a quartet ground state with a doublet-quartet energy gap of 3.1 kJ/mol by SQUID studies. Despite the high-spin nature, this triradical is remarkably stable, allowing for its separation and recrystallization under ambient conditions. Moreover, this triradical can be stored as solids more than one year without serious deterioration...
February 14, 2018: Angewandte Chemie
Sang Hyun Ryu, Chang Wan Kang, Jaewon Choi, Yoon Myung, Yoon-Joo Ko, Sang Moon Lee, Hae Jin Kim, Seung Uk Son
This work shows that the functions of microporous organic network materials can be enhanced through engineering of ma-terial structure. Velvet worms have an intriguing surface with many villi, which provides a very efficient sensing system for any sign of natural enemies. Mimicking the surface structure, we prepared the aligned 1D structure (rod) of microporous porphyrin networks by the Sonogashira coupling of tetra(4-ethynylphenyl)porphyrin with 1,4-diiodobenzene in an anodic aluminum oxide plate and by successive etching of the template...
February 14, 2018: ACS Applied Materials & Interfaces
Ismael Galván, María Del Mar Delgado, Pablo R Camarero, Rafael Mateo, Rui Lourenço, Vincenzo Penteriani
Porphyrins are pigments produced in most animal cells during the synthesis of heme, but their importance for external coloration is unclear. Owls (Order Strigiformes) are among the few animals that accumulate porphyrins in the integument, where it could serve as a means of signaling. Here we hypothesized that the porphyrin content of feathers may depend on body condition and breeding site quality in Eurasian eagle owl (Bubo bubo) fledglings and thus constitute amplifiers of the quality of the area where they are born...
February 13, 2018: Integrative Zoology
Jing Yu, Shukui Zhu, Liling Pang, Pin Chen, Gang-Tian Zhu
Stable and reusable porphyrin-based magnetic nanocomposites were successfully synthesized for efficient extraction of polycyclic aromatic hydrocarbons (PAHs) from environmental water samples. Meso-Tetra (4-carboxyphenyl) porphyrin (TCPP), a kind of porphyrin, can connect the copolymer after amidation and was linked to Fe3O4@SiO2 magnetic nanospheres via cross-coupling. Several characteristic techniques such as field emission scanning electron microscopy, transmission electron microscopy, X-ray diffraction, Fourier transform infrared spectrometry, vibrating sample magnetometry and a tensiometer were used to characterize the as-synthesized materials...
February 7, 2018: Journal of Chromatography. A
Aaron Chin Yit Tay, Benjamin J Frogley, David C Ware, Penelope J Brothers
Boron complexes of calix[4]phyrins ( were prepared by reacting the free-base ligands with BF3·Et2O. The reaction conditions can be efficiently tailored to produce mono- or di-boron calixphyrins. Mono-BF2 calixphyrins with boron coordinating to either the dipyrrin, BF2[H(Calix)], or dipyrromethane, BF2[H(Calix)] and BF2[H2(Calix)]+, bonding sites were isolated. The dipyrromethane isomer, BF2[H(Calix)], isomerises into BF2[H(Calix)] which kinetic studies and DFT calculations indicate is an intramolecular process...
February 12, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Jun Liang, Ya-Qiang Xie, Qiao Wu, Xiu-Yun Wang, Tao-Tao Liu, Hong-Fang Li, Yuan-Biao Huang, Rong Cao
The design and synthesis of metal-organic frameworks (MOFs) enclosed with multiple catalytic active sites is favorable for cooperative catalysis, but is is still challenging. Herein, we developed a sequential postsynthetic ionization and metalation strategy to prepare bifunctional multivariate Zr-MOFs incorporating zinc porphyrin and imidazolium functionalities. Using this facile strategy, tetratopic [5,10,15,20-tetrakis(4-carboxyphenyl)porphyrinato]zinc(II) (ZnTCPP) ligands were successfully installed into the cationic Zr-MOF to obtain ZnTCPP⊂(Br-)Etim-UiO-66...
February 12, 2018: Inorganic Chemistry
Bo Yu, Shreya Goel, Dalong Ni, Paul A Ellison, Cerise M Siamof, Dawei Jiang, Liang Cheng, Lei Kang, Faquan Yu, Zhuang Liu, Todd E Barnhart, Qianjun He, Han Zhang, Weibo Cai
Nanoengineering of cell membranes holds great potential to revolutionize tumor-targeted theranostics, owing to their innate biocompatibility and ability to escape from the immune and reticuloendothelial systems. However, tailoring and integrating cell membranes with drug and imaging agents into one versatile nanoparticle are still challenging. Here, multicompartment membrane-derived liposomes (MCLs) are developed by reassembling cancer cell membranes with Tween-80, and are used to conjugate 89 Zr via deferoxamine chelator and load tetrakis(4-carboxyphenyl) porphyrin for in vivo noninvasive quantitative tracing by positron emission tomography imaging and photodynamic therapy (PDT), respectively...
February 12, 2018: Advanced Materials
Jiazhi Shen, Zhongwei Zou, Xuzhou Zhang, Lin Zhou, Yuhua Wang, Wanping Fang, Xujun Zhu
Purple-leaf tea plants, as anthocyanin-rich cultivars, are valuable materials for manufacturing teas with unique colors or flavors. In this study, a new purple-leaf cultivar "Zixin" ("ZX") was examined, and its biochemical variation and mechanism of leaf color change were elucidated. The metabolomes of leaves of "ZX" at completely purple, intermediately purple, and completely green stages were analyzed using ultra-performance liquid chromatography quadrupole time of flight mass spectrometry (UPLC-QTOF-MS). Metabolites in the flavonoid biosynthetic pathway remained at high levels in purple leaves, whereas intermediates of porphyrin and chlorophyll metabolism and carotenoid biosynthesis exhibited high levels in green leaves...
2018: Horticulture Research
Hiroaki Ozawa, Shunsuke Kusaba, Mariko Matsunaga, Masa-Aki Haga
We found the utilization of porphyrin-based metal-organic network composed of tetra(catechol-substituted) porphyrin (cPor) and Fe ions for robust wrapping materials of graphene oxide (GO), which can keep the dispersion state under the chemical reduction of GO to reduced graphene oxide (rGO) in water. The tetra(catechol-substituted)porphyrin (cPor) was designed for soft-wrapping methods since the aromatic porphyrin moieties can be strongly adsorbed onto the surface of GO or reduced graphene oxide (rGO) via both π-π interactions and the catechol-Fe coordination network formation...
February 8, 2018: Langmuir: the ACS Journal of Surfaces and Colloids
Miki Nishi, Ryuta Ishii, Mitsuo Ikeda, Noriaki Hanasaki, Norihisa Hoshino, Tomoyuki Akutagawa, Michinori Sumimoto, Masaki Matsuda
A porphyrin-based octahedrally ligated complex with high-spin iron(iii) was designed, and the resulting electrically conducting crystal TPP[FeIII(tbp)Br2]2 (TPP = tetraphenylphosphonium and tbp = tetrabenzoporphyrin) was synthesised. Although TPP[Fe(tbp)Br2]2 was isostructural to the reported TPP[Fe(Mc)L2]2 systems (Mc = macrocyclic ligands such as phthalocyanine (Pc) or tbp; and L = CN, Cl, or Br), the bond lengths between Fe and ligands in the [Fe(tbp)Br2] unit were evidently longer than those in the other units, because of the different spin states of Fe: high-spin in TPP[Fe(tbp)Br2]2 and low-spin in others...
February 8, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
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