111790-37-5Relevant articles and documents
Two-Photon-Induced CO-Releasing Molecules as Molecular Logic Systems in Solution, Polymers, and Cells
Ramu, Vadde,Upendar Reddy, Gandra,Liu, Jingjing,Hoffmann, Patrick,Sollapur, Rudrakant,Wyrwa, Ralf,Kupfer, Stephan,Spielmann, Christian,Bonnet, Sylvestre,Neugebauer, Ute,Schiller, Alexander
, p. 8453 - 8458 (2019)
Phototherapeutic applications of carbon monoxide (CO)-releasing molecules are limited because they require harmful UV and blue light for activation. We describe two-photon excitation with NIR light (800 nm)-induced CO-release from two MnI tricarbonyl complexes bearing 1,8-naphthalimide units (1, 2). Complex 2 behaves as a logic OR gate in solution, nonwovens, and in HeLa cells. CO release, indicated by fluorescence enhancement, was detected in solution, nonwoven, and HeLa cells by single- (405 nm) and two-photon (800 nm) excitation. The photophysical properties of 1 and 2 have been measured and supported by DFT and TDDFT quantum chemical calculations. Both photoCORMs are stable in the dark in solution and noncytotoxic, leading to promising applications as phototherapeutics with NIR light.
A rationally designed peptidomimetic biosensor for sialic acid on cell surfaces
Chaudhary, Preeti Madhukar,Murthy, Raghavendra Vasudeva,Yadav, Rohan,Kikkeri, Raghavendra
, p. 8112 - 8115 (2015)
We have developed peptidomimetic sialic acid (Sia) biosensors using boronic acid and arginine groups on the peptide backbone. The designed peptides were conjugated to fluorescent streptavidin via biotin enabling the optical labeling of cells. This approach provides unique opportunities to detect Sia composition on the cell surfaces and filopodia. This journal is
Synthesis, Characterization, and Evaluation of Near-IR Boron Dipyrromethene Bioconjugates for Labeling of Adenocarcinomas by Selectively Targeting the Epidermal Growth Factor Receptor
Kaufman, Nichole E. M.,Meng, Qianli,Griffin, Kaitlin E.,Singh, Sitanshu S.,Dahal, Achyut,Zhou, Zehua,Fronczek, Frank R.,Mathis, J. Michael,Jois, Seetharama D.,Vicente, M. Gra?a H.
, p. 3323 - 3335 (2019)
A series of five boron dipyrromethene (BODIPY) bioconjugates containing an epidermal growth factor receptor (EGFR)-targeted pegylated LARLLT peptide and/or a glucose or biotin ethylene diamine group were synthesized, and the binding capability of the new conjugates to the extracellular domain of EGFR was investigated using molecular modeling, surface plasmon resonance, fluorescence microscopy, competitive binding assays, and animal studies. The BODIPY conjugates with a LARLLT peptide were found to bind specifically to EGFR, whereas those lacking the peptide bound weakly and nonspecifically. All BODIPY conjugates showed low cytotoxicity (IC50 > 94 μM) in HT-29 cells, both in the dark and upon light activation (1.5 J/cm2). Studies of nude mice bearing subcutaneous human HT-29 xenografts revealed that only BODIPY conjugates bearing the LARLLT peptide showed tumor localization 24 h after intravenous administration. The results of our studies demonstrate that BODIPY bioconjugates bearing the EGFR-targeting peptide 3PEG-LARLLT show promise as near-IR fluorescent imaging agents for colon cancers overexpressing EGFR.
Design and Construction of a Smart Targeting Drug Delivery System Based on Phototriggered Competition of Host–Guest Interaction
Zhao, Dan,Yi, Xiaoqing,Yuan, Gongdao,Zhuo, Renxi,Li, Feng
, (2017)
A smart targeting drug delivery nanocarrier is successfully constructed based on phototriggered competition of host–guest interaction. The targeting motif, i.e., biotin is first concealed by β-cyclodextrin (β-CD) via host–guest interaction. When the nanoparticles are exposed to UV light, the cleavage of photosensitive groups results in the exposure of adamantane (Ad) groups initially located in the interior of nanoassemblies, and β-CDs capped on biotin ligands can be replaced by Ad because of the higher binding constant between Ad and β-CD than that between biotin and β-CD. The competition of host–guest interaction leads to the recovery of targeting capacity of biotin ligands on the nanocarriers. By virtue of photoregulation, the nanocarriers exhibit controllable ligand-receptor recognition, which is proved by flow cytometry, laser confocal microscopy, and cytotoxicity assay. This strategy has a potential to improve the selectivity and safety of targeting drug delivery systems.
An optimized immunoaffinity fluorescent method for natural product target elucidation
Yu, Wei-Luen,Guizzunti, Gianni,Foley, Timothy L.,Burkart, Michael D.,La Clair, James J.
, p. 1659 - 1666 (2010)
Understanding the mode of action of small molecules is an integral facet of drug discovery. We report an optimized immunoaffinity fluorescent method that allows one to conduct parallel studies at both the cellular and molecular level using a single probe construct. Viability of the method has been evaluated analytically and applied using glycyrrhetic acid as a model.
PHOTOPROXIMITY PROFILING OF PROTEIN-PROTEIN INTERACTIONS IN CELLS
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Page/Page column 73; 81-82, (2021/04/01)
Photoactive probes and probe systems for detecting biological interactions are described. The photoactive probes include probes that combine both photocleavable and photoreactive moieties. The photoactive probe systems can include a first probe comprising a photocatalytic group and a second probe comprising a group that can act as a substrate for the reaction catalyzed by the photocatalytic group. The probes and probe systems can also include groups that can specifically bind to a binding partner on a biological entity of interest and a detectable group or a precursor thereof. The probes and probe systems can detect spatiotemporal interactions of proteins or cells. In some embodiments, the interactions can be detected in live cells. Also described are methods of detecting the biological interactions.
Condensation of 2-((Alkylthio)(aryl)methylene)malononitrile with 1,2-Aminothiol as a Novel Bioorthogonal Reaction for Site-Specific Protein Modification and Peptide Cyclization
Gao, Wei,Li, Xuefei,Li, Zhuoru,Luk, Louis Y. P.,Meng, Xiaoting,Tsai, Yu-Hsuan,Wu, Chuanliu,Zhao, Yibing,Zheng, Xiaoli
, (2020/03/16)
Site-specific modification of peptides and proteins has wide applications in probing and perturbing biological systems. Herein we report that 1,2-aminothiol can react rapidly, specifically and efficiently with 2-((alkylthio)(aryl)methylene)malononitrile (TAMM) under biocompatible conditions. This reaction undergoes a unique mechanism involving thiol-vinyl sulfide exchange, cyclization, and elimination of dicyanomethanide to form 2-aryl-4,5-dihydrothiazole (ADT) as a stable product. An 1,2-aminothiol functionality can be introduced into a peptide or a protein as an N-terminal cysteine or an unnatural amino acid. The bioorthogonality of this reaction was demonstrated by site-specific labeling of not only synthetic peptides and a purified recombinant protein but also proteins on mammalian cells and phages. Unlike other reagents in bioorthogonal reactions, the chemical and physical properties of TAMM can be easily tuned. TAMM can also be applied to generate phage-based ADT-cyclic peptide libraries without reducing phage infectivity. Using this approach, we identified ADT-cyclic peptides with high affinity to different protein targets, providing valuable tools for biological studies and potential therapeutics. Furthermore, the mild reaction conditions of TAMM condensation warrant its use with other bioorthogonal reactions to simultaneously achieve multiple site-specific modifications.
