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Zhe Zhou, Feiyi Wang, Guichun Yang, CuiFen Lu, Junqi Nie, Zuxing Chen, Jun Ren, Qi Sun, Chunchang Zhao, Wei-Hong Zhu
Leucine aminopeptidase (LAP) is an important cancer-related biomarker, which shows significant overexpression in malignant tumor cells like liver cancer, Developing an effective method to monitor LAP in tumor cells holds great potential for cancer diagnosis, treatment and management. In this work, we report a novel BODIPY-based fluorescent probe (BODIPY-C-Leu) capable of monitoring LAP in vitro and in vivo in both ratiometric and turn-on model. BODIPY-C-Leu contains an asymmetrical BODIPY dye for fluorescent signaling, and a dipeptide (Cys-Leu) as the triggered moiety...
October 10, 2017: Analytical Chemistry
Sandeep Cherumukkil, Samrat Ghosh, Vakayil K Praveen, Ayyappanpillai Ajayaghosh
We report an unprecedented strategy to generate and amplify near-infrared (NIR) emission in an organic chromophore by mechanical stress or gelation pathways. A greenish-yellow emitting film of π-extended Bodipy-1, obtained from n-decane, became orange-red upon mechanical shearing, with a 15-fold enhancement in NIR emission at 738 nm. Alternatively, a DMSO gel of Bodipy-1 exhibited a 7-fold enhancement in NIR emission at 748 nm with a change in emission color from yellow to orange-red upon drying. The reason for the amplified NIR emission in both cases is established from the difference in chromophore packing, by single crystal analysis of a model compound (Bodipy-2), which also exhibited a near identical emission spectrum with red to NIR emission (742 nm)...
August 1, 2017: Chemical Science
Richard Lincoln, Lana E Greene, Wenzhou Zhang, Sheena Louisia, Gonzalo Cosa
Protein and DNA alkylation by endogenously produced electrophiles is associated with the pathogenesis of neurodegenerative diseases, to epigenetic alterations and to cell signaling and redox regulation. With the goal of visualizing, in real-time, the spatiotemporal response of the cell milieu to electrophiles, we have designed a fluorogenic BODIPY-acrolein probe, AcroB, that undergoes a >350-fold fluorescence intensity enhancement concomitant with protein adduct formation. AcroB enables a direct quantification of single post-translational modifications occurring on cellular proteins via recording fluorescence bursts in live-cell imaging studies...
October 13, 2017: Journal of the American Chemical Society
Utso Bhattacharyya, Brijesh Kumar, Aditya Garai, Arnab Bhattacharyya, Arun Kumar, Samya Banerjee, Paturu Kondaiah, Akhil R Chakravarty
Ternary oxidovanadium(IV) complexes of curcumin (Hcur), dipicolylamine (dpa) base, and its derivatives having pendant noniodinated and di-iodinated boron-dipyrromethene (BODIPY) moiety (L1 and L2, respectively), namely, [VO(dpa)(cur)]ClO4 (1), [VO(L1)(cur)]ClO4 (2), and [VO(L2)(cur)]ClO4 (3) and their chloride salts (1a-3a) were prepared, characterized, and studied for anticancer activity. The chloride salts were used for biological studies due to their aqueous solubility. Complex 1 was structurally characterized by single-crystal X-ray crystallography...
October 3, 2017: Inorganic Chemistry
Meijuan Jiang, Xinggui Gu, Jacky W Y Lam, Yilin Zhang, Ryan T K Kwok, Kam Sing Wong, Ben Zhong Tang
Lipid droplets are dynamic organelles involved in various physiological processes and their detection is thus of high importance to biomedical research. Recent reports show that AIE probes for lipid droplet imaging have the superior advantages of high brightness, large Stokes shift and excellent photostability compared to commercial dyes but suffer from the problem of having a short excitation wavelength. In this work, an AIE probe, namely TPA-BI, was rationally designed and easily prepared from triphenylamine and imidazolone building blocks for the two-photon imaging of lipid droplets...
August 1, 2017: Chemical Science
Gajendra Gupta, Abhishek Das, Sourav Panja, Ji Yeon Ryu, Junseong Lee, Nripendranath Mandal, Chang Yeon Lee
Novel Ru (2+2) rectangles were designed and synthesized by self-assembly of a new thiophene-functionalized dipyridyl BODIPY ligand, BDPS, and ruthenium (II) precursors. The complexes exhibited dose-dependent antiproliferative activities against cancer cells, where some compounds selectively kill cancer cells. The net fluorescence due to BODIPY allowed us to visualize their location inside cancer cells. Moreover, the metalla-rectangles displayed substantial propensity to bind with biomolecules.
September 29, 2017: Chemistry: a European Journal
Guichao Kuang, Jiafu Yin, Yi Hu, Huan Wang, Zhong Jin, Yi Zhang
A novel near-infrared (NIR) emissive amphiphilic BODIPY derivative BBDP has been successfully prepared and thoroughly characterized. The photophysical properties in various organic solvents and THF/H2O mixtures with different fractions of water were both investigated. BBDP could self-assemble into nanofibers in the water environment due to the amphiphilic property. By utilizing the charge-transfer interaction, BBDP could co-assemble with perylene bisimide derivative (PBI) and viologen derivative (MV) respectively to generate two superamphiphiles...
September 27, 2017: Chemistry, An Asian Journal
Rajendra Prasad Paitandi, Sujay Mukhopadhyay, Roop Shikha Singh, Vinay Sharma, Shaikh M Mobin, Daya Shankar Pandey
A pyrazole-appended quinoline-based 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (L1, BODIPY) has been synthesized and used as a ligand for the preparation of iridium(III) complexes [Ir(phpy)2(L1)]PF6 (1; phpy = 2-phenylpyridine) and [(η(5)-C5Me5)Ir(L1)Cl]PF6 (2). The ligand L1 and complexes 1 and 2 have been meticulously characterized by elemental analyses and spectral studies (IR, electrospray ionization mass spectrometry, (1)H and (13)C NMR, UV/vis, fluorescence) and their structures explicitly authenticated by single-crystal X-ray analyses...
September 28, 2017: Inorganic Chemistry
Kondapa Naidu Bobba, Miae Won, Inseob Shim, Nithya Velusamy, Zhigang Yang, Junle Qu, Jong Seung Kim, Sankarprasad Bhuniya
Herein, we report rational design, synthesis, and application of a two-photon fluorescent probe (Tyro-1) for tracking intracellular tyrosinase activity. The chemoselective detection of tyrosinase is precluded from interference of other competitive omnipresent oxidizing entities in cellular milieu. The probe showed 12.5-fold fluorescence enhancement at λem = 450 nm in the presence of tyrosinase. The nontoxic probe Tyro-1 provides information about H2O2-mediated upregulation of tyrosinase through cellular imaging...
September 28, 2017: Chemical Communications: Chem Comm
Ben Shi, Xianfeng Gu, Zhijun Wang, Ge Xu, Qiang Fei, Jie Tang, Chunchang Zhao
Probes bearing good aqueous solubility and biocompatibility as well as fast response can serve as ideal tools for evaluating the underlying molecular mechanism of endogenous production H2S by drugs, which are still lacking but highly desirable. Here, we demonstrate a novel strategy for constructing highly efficient H2S nanoprobes through locking Förster resonance energy transfer borondipyrromethene (BODIPY) pairs in water-dispersible core-shell silica nanoparticles. Importantly, these nanocomposites can effectively confine complementary guests within the same cores due to the existence of a shield, thus guaranteeing efficient FRET...
September 28, 2017: ACS Applied Materials & Interfaces
Lukas J Patalag, Luong Phong Ho, Peter G Jones, Daniel B Werz
A versatile and rapid access to various chain-lengths of ethylene-bridged BODIPY motifs was discovered. Corresponding oligomers comprising up to eight monomeric units were studied with respect to their microstructures by photophysical, X-ray crystallographic and computational means. The investigation of three different dipyrrin cores revealed a crucial dependence on the substitution pattern of the core, whereas the nature of the meso-periphery is less critical. The impact of substituent effects on the conformational space was investigated by Monte Carlo simulations and a set of DFT methods (B3LYP, PBEh 3c, TPSS/PWPB95), including dispersion effects...
September 26, 2017: Journal of the American Chemical Society
Nawodi Abeyrathna, Kenyatta Washington, Christopher Bashur, Yi Liao
Carbon monoxide (CO) is a gasotransmitter that plays important roles in regulating cell functions and has shown therapeutic effects in clinic studies. CO releasing molecules (CORMs), which allow controlled release of CO in physiological conditions, have been intensively studied in the past decade. While most CORMs are metal complexes, several nonmetallic CORMs have also been developed and most of them were reported in recent years. The major advantages of nonmetallic CORMs are potentially low toxicity and easy modification for property tuning...
September 26, 2017: Organic & Biomolecular Chemistry
Yumin Lee, Saptaparna Das, Roy M Malamakal, Stephen Meloni, David M Chenoweth, Jessica M Anna
Boron-dipyrromethene (BODIPY) chromophores have a wide range of applications, spanning areas from biological imaging to solar energy conversion. Understanding the ultrafast dynamics of electronically excited BODIPY chromophores could lead to further advances in these areas. In this work, we characterize and compare the ultrafast dynamics of halogenated BODIPY chromophores through applying two-dimensional electronic spectroscopy (2DES). Through our studies, we demonstrate a new data analysis procedure for extracting the dynamic Stokes shift from 2DES spectra revealing an ultrafast solvent relaxation...
October 10, 2017: Journal of the American Chemical Society
Feihong Deng, Yuan Fang, Zhiyong Shen, Wei Gong, Tao Liu, Jing Wen, Wanling Zhang, Xianjun Zhu, Hui Zhong, Tong Wang, Fachao Zhi, Biao Nie
Endoscopic treatment for early colorectal cancer closely correlates with patient prognosis. However, endoscopic differentiation between carcinomas and non-neoplastic lesions remains difficult. Here, we topically stained colorectal neoplasms with a fatty acid analogue (BODIPY-FA) and quantified the fluorescent signals using confocal laser endomicroscopy (CLE) and fluorescence microscopy. We also analyzed protein expression in colorectal cancer tissues. We found that expression of fatty acid synthase was elevated, while the expression of fatty acid transporters was reduced in colorectal cancer...
August 29, 2017: Oncotarget
Igor K Petrushenko, Konstantin B Petrushenko
The S0→Si, i=1-5 electronic transitions of four 8-(4-aniline)-BODIPY and four 8-(N,N-dimethyl)-BODIPY dyes, differ by number and position of methyl substituents in the BODIPY frame, were investigated theoretically using ab initio the coupled cluster doubles (CC2) and TD-CAM-B3LYP methods. Methyl substituents in the BODIPY frame and the aniline fragment at the meso position disturb energy of local excitations S0→S1, S0→S3, and S0→S4 weakly in comparison with the fully unsubstituted BODIPY molecule. These transitions in experimental spectra form the most long-wave absorption bands at ca...
September 13, 2017: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
T Papalia, A Barattucci, S Campagna, F Puntoriero, T Salerno, P Bonaccorsi
The synthesis of an efficient energy donor-acceptor system is reported, together with its photophysical properties. The bichromophoric species has been conceived to show potentialities for biological applications since a biocompatible disaccharide spacer, constituted of d-galactose and d-glucose derivatives, was used in compound 12 to connect two BODIPY units with different absorption/emission properties. The luminescence spectrum in acetonitrile of 12 shows an intense fluorescence band with a maximum at about 770 nm that is almost identical to that of the lowest-energy BODIPY, regardless of the excitation wavelength used...
October 4, 2017: Organic & Biomolecular Chemistry
Vijayakumar Rajendran, Anilkumar Krishnegowda, Vasanthi Nachiappan
The Cassia auriculata herb has been traditionally used in India for medicinal purposes to treat hyperglycemia, diabetes, rheumatism, asthma, and skin diseases. In the present study, ethanolic extract of Cassia auriculata flower (Et-CAF) depicted anti-hyperlipidemic effect in the budding yeast cells. The hyperlipidemic conditions were induced in the yeast cells with oleic acid which showed an increase in triacylglycerol (TAG) and sterol esters (SE), and was supported by the mRNA expression of LRO1 and DGA1 (involved in TAG formation); as well as ARE1 and ARE2 (involved in SE formation)...
August 2017: Journal of Food Science and Technology
Mohamed Jemaà, Myriam Fezai, Rosi Bissinger, Florian Lang
Suicidal erythrocyte death or eryptosis contributes to or even accounts for anemia in a wide variety of clinical conditions, such as iron deficiency, dehydration, hyperphosphatemia, vitamin D excess, chronic kidney disease (CKD), hemolytic-uremic syndrome, diabetes, hepatic failure, malignancy, arteriitis, sepsis, fever, malaria, sickle-cell disease, beta-thalassemia, Hb-C and G6PD-deficiency, Wilsons disease, as well as advanced age. Moreover, eryptosis is triggered by a myriad of xenobiotics and endogenous substances including cytotoxic drugs and uremic toxins...
September 1, 2017: Cellular Physiology and Biochemistry
Chang Gao, Lan Lin, Wan Sun, Zheng-Li Tan, Jun-Ru Huang, Lan He, Zhong-Lin Lu
A mitochondria-targetable probe Mito-DHP for nitric oxide (NO) was designed and synthesized by introducing dihydropyridine and triphenylphosphonium (TPP) moieties into boron dipyrromethene (BODIPY) dye. Mito-DHP was able to effectively detect nitric oxide through the aromatization of dihydropyridine to fluorescent pyridine product under oxygen-free conditions. The probe Mito-DHP showed high selectivity to NO over a number of reactive oxygen/nitrogen species (ROS/RNS) as well as high sensitivity (detection limit at 25nM), pH stability and bio-compatibility...
January 1, 2018: Talanta
Rongguang Shi, Lu Huang, Xiaoxue Duan, Guohao Sun, Gui Yin, Ruiyong Wang, Jun-Jie Zhu
Fluorescence imaging with tumor-specific fluorescent probe has emerged as a tool to aid surgeons in the identification and removal of tumor tissue. We report here a new lysosome-targeting fluorescent probe (NBOH) with BODIPY fluorephore to distinguish tumor tissue out of normal tissue based on different pH environment. The probe exhibited remarkable pH-dependent fluorescence behavior in a wide pH range from 3.0 to 11.0, especially a sensitive pH-dependent fluorescence change at pH range between 3.5 and 5.5, corresponding well to the acidic microenvironment of tumor cells, in aqueous solution...
October 2, 2017: Analytica Chimica Acta
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