1606-67-3Relevant articles and documents
Highly selective turn-on probe for H2S with imaging applications in vitro and in vivo
Thirumalaivasan, Natesan,Venkatesan, Parthiban,Wu, Shu-Pao
, p. 13510 - 13515 (2017)
Hydrogen sulfide (H2S) is the third endogenous gaseous signaling molecule, and its distribution affects several biological processes. To clarify the roles of H2S in living systems, the exact determination of H2S in living cells in vivo has become an important issue. Herein, we report a novel pyrene-based fluorescent probe, PyN3, as a H2S turn-on sensor via reduction of azide to amine, which subsequently undergoes self-immolation through intramolecular 1,6-elimination of the p-aminobenzyl moiety, releasing 1-aminopyrene and leading to the recovery of fluorescence intensity. With its high sensitivity, good selectivity, and low cytotoxicity, PyN3 was able to recognize both exogenous and endogenously produced H2S in biological systems. In contrast to the traditional azide-based H2S probes, PyN3 shows efficient and effective selectivity to H2S at biological pH ranges. Because of these promising properties, PyN3 is an excellent probe for visualizing endogenous H2S in vitro and in vivo.
Quantification of DNA and Protein Adducts of 1-Nitropyrene: Significantly Higher Levels of Protein than DNA Adducts in the Internal Organs of 1-Nitropyrene Exposed Rats
Chan, Wan,Wong, Sum-Kok,Li, Weiwei
, p. 680 - 687 (2018)
1-Nitropyrene (1NP) level is closely associated with the mutagenicity of diesel exhaust and is being used as the marker molecule for diesel exhaust. Thus, quantitation of the exposure to 1NP may provide an efficient method for biomonitoring human exposure to diesel exhaust and risk assessment. Using ultra-performance liquid chromatography coupled with fluorescence or tandem mass spectrometric detection methods, we quantitated and compared in this study the DNA and protein adducts of 1NP in internal organs of 1NP-exposed rats. While previous studies using radioactivity-based detection methods were descriptive in nature and focused on the mutation-associated genetic materials, the results of our quantitative analysis showed, for the first time, a significantly higher concentration of the protein adduct than the DNA adduct in the tissue samples. The data also revealed higher in vivo stability of the protein adduct than that of the DNA adduct. Our results provide solid evidence that demonstrates that the protein adduct might be a more-sensitive dosimeter for 1-NP and, thus, diesel-exhaust exposure.
A new processable and fluorescent polydithienylpyrrole electrochrome with pyrene appendages
Tirke?, Seha,Mersini, Jetmire,?zta?, Zahide,Algi, Melek Pamuk,Algi, Fatih,Cihaner, Atilla
, p. 295 - 301 (2013)
A new hybrid compound, namely 1-(pyren-3-yl)-2,5-di(thiophen-2-yl)-1H- pyrrole (SNS-P), was polymerized via both chemical and electrochemical methods. Chemically obtained soluble polydithienylpyrrole (c-PSNS-P) bearing pyrene appendages is a homogeneous and uniform polymer with a number averaged molecular weight of 15,200 g/mol. The polymer exhibits both multi-electrochromic and fluorescent properties. Upon oxidation, the color of electrochemically obtained polymer (e-PSNS-P) changes from yellowish orange to greenish yellow and to green/blue and finally to blue. In addition, the polymer induces yellowish orange (564 nm) and bright orange emission (613 nm) in solution and solid states, respectively.
4-(Pyren-1-ylimino)methylphenol and its silylated derivative as chromogenic chemosensors highly selective for fluoride or cyanide
Buske, Jonatan L. O.,Nicoleti, Celso R.,Cavallaro, Aluisio A.,Machado, Vanderlei G.
, p. 2507 - 2519 (2015)
Two novel compounds, 4-(pyren-1-ylimino)methylphenol and 4-[(triisopropylsilyl)oxy] phenylmethylenepyren-1-amine) were synthesized. Solutions of 4-(pyren-1-ylimino)methylphenol in dimethyl sulfoxide (DMSO) are colorless, but on addition of cyanide and fluoride they become colored due to the deprotonation of the chemosensor. The system is highly selective toward cyanide with the addition of water. This compound can be solubilized in water with addition of cetyltrimethylammonium bromide above its critical micellar concentration. The pKa of the compound in water was determined as 10.49 ± 0.02 and this value is lowered in micellar medium to 7.49 ± 0.02, which means that only cyanide is sufficiently basic to achieve the deprotonation of the compound. Solutions of 4-[(triisopropylsilyl)oxy]phenylmethylenepyren-1-amine) in DMSO are colorless, but they are colored in the presence of cyanide and fluoride and only cyanide could be detected in DMSO-water mixture. The nucleophilic attack of the anions on the silicon center of the compound releases colored 4-(pyren-1-ylimino)methylphenolate, enabling the detection of nucleophilic analytes.
1,3-Bis(pyren-1-yliminomethyl)calix[4]arene as a selective fluorescent turn-on sensor for mercury(II) ion
Tanaka, Shinya,Hirasawa, Kengo,Watanabe, Kyohei,Hattori, Tetsutaro
, p. 179 - 183 (2018)
A novel calixarene-based diimine, 1,3-bis(pyren-1-yliminomethyl)calix[4]arene (5), serves as a turn-on-type fluorescent sensor, which selectively detects Hg2+ in THF/H2O (99:1, v/v) in the presence of various other metal ions. Such selectivity is not seen with half salen 1 derived from salicylaldehyde and 1-aminopyrene. 1H NMR analysis reveals that it is a chemodosimetric sensor based on its hydrolysis mediated by Hg2+ to release 1-aminopyrene molecules as fluorescent chromophores.
Reduction of nitroaromatics by non-metal hydrazinolysis
Abdel-Baky,Zhuang,Giese
, p. 161 - 165 (1991)
High temperature (160°C) can substitute for a metal catalyst in achieving the complete reduction of nitroaromatic compounds to corresponding amines by hydrazine.
A new pyrene-based Schiff-base: A selective colorimetric and fluorescent chemosensor for detection of Cu(II) and Fe(III)
Bhorge, Yeshwant Ramchandra,Tsai, Haw-Tyng,Huang, Keh-Feng,Pape, Albert J.,Janaki, Sudhakar Narasimha,Yen, Yao-Pin
, p. 7 - 12 (2014)
A new receptor 1 was prepared, for the detection of Cu2+ and Fe3+ in solutions as a colorimetric and fluorescent sensor, respectively. Receptor 1 shows highly selective and sensitive recognition toward Cu2+ and Fe3+ by naked eye UV-Vis and fluorescent color changes in aqueous solution (DMSO/H2O = 8/2, v/v), respectively. The sensitivity toward Cu2+ or Fe3+ was not interfered with by the presence of other metal ions such as Mg2+, Cd2+, Ag+, Zn2+, Ni2+, Co2+, Mn 2+, Cr3+, Ca2+, Na+, Pb 2+, K+, Fe2+, Li+ and Hg 2+ ions. Receptor 1 can be used for semi-quantitative recognition of Cu2+ ions at ppm level. The fluorescence microscopy experiments showed that the receptor is efficient for detection of Fe3+ in vitro, developing a good image of the biological organelles.
Preparation and characterization of pyrene modified uridine derivatives as potential electron donors in RNA
Frommer, Jennifer,Karg, Beatrice,Weisz, Klaus,Müller, Sabine
, p. 7663 - 7673 (2018)
Charge transfer across double stranded DNA was observed for the first time about 20 years ago, and ever since it has been the subject of a large number of studies. RNA has been hardly investigated in this regard, which not least is due to the lack of suitably functionalized ribonucleotide building blocks to serve as electron sources upon incorporation into oligoribonucleotides. We have synthesized two uridine derivatives carrying pyrene or dimethylaminopyrene linked to C5 of the nucleobase. The key to successful synthesis was the adaptation of Suzuki-Miyaura conditions to the coupling of the pyrene moiety with the ribonucleoside. Final decoration of the pyrenylated nucleosides with standard 5′-O- and 2′-O-protecting groups and subsequent 3′-O-phosphitylation delivered the building blocks for incorporation into RNA. Spectroscopic analysis of the two pyrenylated uridines and of the accordingly modified oligonucleotides showed that in particular the dimethyaminopyrene functionalized nucleoside is a promising candidate as an electron source for RNA charge transport studies.
Uncovering the true mechanism of optical detection of HSO4 - in water by Schiff-base receptors - Hydrolysis vs. hydrogen bonding
Kumar, Virendra,Kumar, Ajit,Diwan, Uzra,Upadhyay
, p. 9540 - 9542 (2012)
The mechanism of optical detection of HSO4- in aqueous medium by Schiff-base receptors has previously been proposed to depend on selective hydrogen-bond interactions. Here, we clearly demonstrate for the first time that the acidic na
Assembly of plasmid DNA with pyrene-amines cationic amphiphiles into nanoparticles and their visible lysosome localization
Sheng, Ruilong,An, Feifei,Wang, Zhao,Li, Mingrui,Cao, Amin
, p. 12338 - 12345 (2015)
In this study, we constructed a visible model for drug/gene dual delivery. Firstly, we prepared a series of pyrene fluorophore bearing cationic amphiphiles (Py-amines), which could be further employed as amphiphilic gene carriers and antitumor polyamine drug models. Then, the Py-amines fluorescent amphiphiles were utilized to bind/load plasmid DNA via electrostatic interactions to form nano-sized particles in aqueous solution. The average size, zeta potential and morphology of the self-assembled Py-amines/pDNA complexes were found to be largely dependent on the molecular structures of Py-amines amphiphiles. Moreover, the Py-amines and their pDNA complexes showed an evident cell proliferation inhibition capability in H1299 (human lung cancer) cells. Notably, the lysosomal localization of the Py-amines/pDNA complexes could be directly visualized using fluorescence microscopy in vitro. In summary, this current study could provide new and visible approach to design polyamine-based anti-tumor drug/plasmid DNA dual delivery systems, which could facilitate a greater understanding of the intracellular trafficking/localization of polyamine-based cationic gene/drug payloads.
