keyword
MENU ▼
Read by QxMD icon Read
search

Bioorthogonal chemistry

keyword
https://www.readbyqxmd.com/read/29147682/synthesis-and-application-of-injectable-bioorthogonal-dendrimer-hydrogels-for-local-drug-delivery
#1
Leyuan Xu, Remy C Cooper, Juan Wang, W Andrew Yeudall, Hu Yang
We developed novel dendrimer hydrogels (DH)s on the basis of bioorthogonal chemistry, in which polyamidoamine (PAMAM) dendrimer generation 4.0 (G4) functionalized with strained alkyne dibenzocyclooctyne (DBCO) via PEG spacer (Mn = 2,000 g/mol) underwent strain-promoted azide-alkyne cycloaddition (SPAAC) with polyethylene glycol bisazide (PEG-BA) (Mn= 20,000 g/mol) to generate a dendrimer-PEG cross-linked network. This platform offers a high degree of functionality and modularity. A wide range of structural parameters including dendrimer generation, degree of PEGylation, loading density of clickable DBCO groups, PEG-BA chain length as well as the ratio of clickable dendrimer to PEG-BA and their concentrations can be readily manipulated to tune chemical and physical properties of DHs...
August 14, 2017: ACS Biomaterials Science & Engineering
https://www.readbyqxmd.com/read/29121649/spatiotemporal-dynamics-of-hsv-genome-nuclear-entry-and-compaction-state-transitions-using-bioorthogonal-chemistry-and-super-resolution-microscopy
#2
Eiki Sekine, Nora Schmidt, David Gaboriau, Peter O'Hare
We investigated the spatiotemporal dynamics of HSV genome transport during the initiation of infection using viruses containing bioorthogonal traceable precursors incorporated into their genomes (HSVEdC). In vitro assays revealed a structural alteration in the capsid induced upon HSVEdC binding to solid supports that allowed coupling to external capture agents and demonstrated that the vast majority of individual virions contained bioorthogonally-tagged genomes. Using HSVEdC in vivo we reveal novel aspects of the kinetics, localisation, mechanistic entry requirements and morphological transitions of infecting genomes...
November 9, 2017: PLoS Pathogens
https://www.readbyqxmd.com/read/29109777/improved-tumor-targeting-and-longer-retention-time-of-nir-fluorescent-probes-using-bioorthogonal-chemistry
#3
Xianghan Zhang, Bo Wang, Na Zhao, Zuhong Tian, Yunpeng Dai, Yongzhan Nie, Jie Tian, Zhongliang Wang, Xiaoyuan Chen
The traditional labeling method for targeted NIR fluorescence probes requires directly covalent-bonded conjugation of targeting domains and fluorophores in vitro. Although this strategy works well, it is not sufficient for detecting or treating cancers in vivo, due to steric hindrance effects that relatively large fluorophore molecules exert on the configurations and physiological functions of specific targeting domains. The copper-free, "click-chemistry"-assisted assembly of small molecules in living systems may enhance tumor accumulation of fluorescence probes by improving the binding affinities of the targeting factors...
2017: Theranostics
https://www.readbyqxmd.com/read/29097747/antibody-pegylation-in-bioorthogonal-pretargeting-with-trans-cyclooctene-tetrazine-cycloaddition-in-vitro-and-in-vivo-evaluation-in-colorectal-cancer-models
#4
Aurélie Rondon, Nancy Ty, Jean-Baptiste Bequignat, Mercedes Quintana, Arnaud Briat, Tiffany Witkowski, Bernadette Bouchon, Claude Boucheix, Elisabeth Miot-Noirault, Jean-Pierre Pouget, Jean-Michel Chezal, Isabelle Navarro-Teulon, Emmanuel Moreau, Françoise Degoul
Bioorthogonal chemistry represents a challenging approach in pretargeted radioimmunotherapy (PRIT). We focus here on mAb modifications by grafting an increase amount of trans-cyclooctene (TCO) derivatives (0 to 30 equivalents with respect to mAb) bearing different polyethylene glycol (PEG) linkers between mAb and TCO (i.e. PEG0 (1), PEG4 (2) and PEG12 (3)) and assessing their functionality. We used colorectal xenograft (HT29/Ts29.2) and peritoneal carcinomatosis (A431-CEA-Luc/35A7) as tumor cells/mAbs models and fluorescent tetrazines (TZ)...
November 2, 2017: Scientific Reports
https://www.readbyqxmd.com/read/29095606/ex-uno-plura-differential-labeling-of-phospholipid-biosynthetic-pathways-with-a-single-bioorthogonal-alcohol
#5
Timothy W Bumpus, Felice J Liang, Jeremy M Baskin
Imaging approaches that track biological molecules within cells are essential tools in modern biochemistry. Lipids are particularly challenging to visualize, as they are not directly genetically encoded. Phospholipids, the most abundant subgroup of lipids, are structurally diverse and accomplish many cellular functions, acting as major structural components of membranes and as signaling molecules that regulate cell growth, division, apoptosis, cytoskeletal dynamics, and numerous other physiological processes...
November 8, 2017: Biochemistry
https://www.readbyqxmd.com/read/29048718/azido-functionalized-5-cap-analogs-for-preparation-of-translationally-active-mrnas-suitable-for-fluorescent-labeling-in-living-cells
#6
Adam Mamot, Pawel Sikorski, Marcin Warminski, Joanna Kowalska, Jacek Jemielity
The 7-methylguanosine (m7G) cap structure is a unique feature present at the 5' ends of messenger RNAs (mRNAs) that can be subjected to extensive modifications, resulting in alterations to mRNA properties (e.g. translability, susceptibility to degradation). It also can provide molecular tools to study mRNA metabolism. Here, we developed new mRNA 5' cap-based tools that enable the site-specific labeling of RNA at the 5' end using strain-promoted azide-alkyne cycloaddition (SPAAC), i.e. bioorthogonal, copper-free click chemistry, and support the mRNA's basic function in protein biosynthesis...
October 19, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/29044851/a-bifunctional-fluorogenic-rhodamine-probe-for-proximity-induced-bioorthogonal-chemistry
#7
Philipp Werther, Jasper S Möhler, Richard Wombacher
Bioorthogonal reactions have emerged as a versatile tool in life sciences. The inverse electron demand Diels-Alder reaction (DAinv) stands out due to the availability of reactants with very fast kinetics. However, highly reactive dienophiles suffer the disadvantage of being less stable and prone to side reactions. Here, we evaluate the extent of acceleration of rather unreactive but highly stable dienophiles by DNA-templated proximity. To this end, we developed a modular synthetic route for a novel bifunctional fluorogenic tetrazine rhodamine probe that we used to determine the reaction kinetics of various dienophiles in a fluorescence assay...
October 16, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/29040808/independently-tuning-the-biochemical-and-mechanical-properties-of-3d-hyaluronan-based-hydrogels-with-oxime-and-diels-alder-chemistry-to-culture-breast-cancer-spheroids
#8
Alexander E G Baker, Roger Y Tam, Molly S Shoichet
For native breast cancer cell growth to be mimicked in vitro as spheroids, a well-defined matrix that mimics the tumor microenvironment is required. Finding a biomimetic material for 3D cell culture other than Matrigel has challenged the field. Because hyaluronan is naturally abundant in the tumor microenvironment and can be chemically modified, we synthesized a hyaluronan (HA) hydrogel with independently tunable mechanical and chemical properties for 3D culture of breast cancer cells. By modifying HA with distinct bioorthogonal functional groups, its mechanical properties are controlled by chemical cross-linking via oxime ligation, and its biochemical properties are controlled by grafting bioactive peptides via Diels-Alder chemistry...
October 31, 2017: Biomacromolecules
https://www.readbyqxmd.com/read/29022697/improved-photoinduced-fluorogenic-alkene-tetrazole-reaction-for-protein-labeling
#9
Xin Shang, Rui Lai, Xi Song, Hui Li, Wei Niu, Jiantao Guo
The 1,3-dipolar cycloaddition reaction between an alkene and a tetrazole represents one elegant and rare example of fluorophore-forming bioorthogonal chemistry. This is an attractive reaction for imaging applications in live cells that requires less intensive washing steps and/or needs spatiotemporal resolutions. In the present work, as an effort to improve the fluorogenic property of the alkene-tetrazole reaction, an aromatic alkene (styrene) was investigated as the dipolarophile. Over 30-fold improvement in quantum yield of the reaction product was achieved in aqueous solution...
November 15, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28971673/integrating-two-efficient-and-specific-bioorthogonal-ligation-reactions-with-natural-metabolic-incorporation-in-one-cell-for-virus-dual-labeling
#10
Li-Li Huang, Kejiang Liu, Qianmei Zhang, Jin Xu, Dongxu Zhao, Houshun Zhu, Hai-Yan Xie
Though techniques in bioorthogonal chemistry and metabolic incorporation have been developed over the past decade, it remains difficult to integrate different bioorthogonal reactions or metabolic incorporations into one system. In this report, the protein and DNA metabolic incorporations were combined with two bioorthogonal reactions in one cell to develop a facile and universal method for virus dual labeling. Azide and vinyl groups were introduced into the proteins or genomes of viruses, respectively, through the intrinsic biosynthesis of biomolecules, which were subsequently fluorescently labeled via copper-free click chemistry or alkene-tetrazine ligation reactions during natural propagation process in host cells...
November 7, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28957709/nano-sized-metabolic-precursors-for-heterogeneous-tumor-targeting-strategy-using-bioorthogonal-click-chemistry-in%C3%A2-vivo
#11
Sangmin Lee, Seulhee Jung, Heebeom Koo, Jin Hee Na, Hong Yeol Yoon, Man Kyu Shim, Jooho Park, Jong-Ho Kim, Seulki Lee, Martin G Pomper, Ick Chan Kwon, Cheol-Hee Ahn, Kwangmeyung Kim
Herein, we developed nano-sized metabolic precursors (Nano-MPs) for new tumor-targeting strategy to overcome the intrinsic limitations of biological ligands such as the limited number of biological receptors and the heterogeneity in tumor tissues. We conjugated the azide group-containing metabolic precursors, triacetylated N-azidoacetyl-d-mannosamine to generation 4 poly(amidoamine) dendrimer backbone. The nano-sized dendrimer of Nano-MPs could generate azide groups on the surface of tumor cells homogeneously regardless of cell types via metabolic glycoengineering...
December 2017: Biomaterials
https://www.readbyqxmd.com/read/28926550/bioorthogonal-chemistry-click-on-click-off
#12
Caitlin Deane
No abstract text is available yet for this article.
September 19, 2017: Nature Chemical Biology
https://www.readbyqxmd.com/read/28915034/affinity-guided-oxime-chemistry-for-selective-protein-acylation-in-live-tissue-systems
#13
Tomonori Tamura, Zhining Song, Kazuma Amaike, Shin Lee, Sifei Yin, Shigeki Kiyonaka, Itaru Hamachi
Catalyst-mediated protein modification is a powerful approach for the imaging and engineering of natural proteins. We have previously developed affinity-guided 4-dimethylaminopyridine (AGD) chemistry as an efficient protein modification method using a catalytic acyl transfer reaction. However, because of the high electrophilicity of the thioester acyl donor molecule, AGD chemistry suffers from nonspecific reactions to proteins other than the target protein in crude biological environments, such as cell lysates, live cells, and tissue samples...
October 11, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28898061/postsynthetic-modification-of-bacterial-peptidoglycan-using-bioorthogonal-n-acetylcysteamine-analogs-and-peptidoglycan-o-acetyltransferase-b
#14
Yiben Wang, Klare M Lazor, Kristen E DeMeester, Hai Liang, Tyler K Heiss, Catherine L Grimes
Bacteria have the natural ability to install protective postsynthetic modifications onto its bacterial peptidoglycan (PG), the coat woven into bacterial cell wall. Peptidoglycan O-acetyltransferase B (PatB) catalyzes the O-acetylation of PG in Gram (-) bacteria, which aids in bacterial survival, as it prevents autolysins such as lysozyme from cleaving the PG. We explored the mechanistic details of PatB's acetylation function and determined that PatB has substrate specificity for bioorthgonal short N-acetyl cysteamine (SNAc) donors...
September 26, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28898047/transglutaminase-catalyzed-bioconjugation-using-one-pot-metal-free-bioorthogonal-chemistry
#15
Natalie M Rachel, Jacynthe L Toulouse, Joelle N Pelletier
General approaches for controlled protein modification are increasingly sought-after in the arena of chemical biology. Here, using bioorthogonal reactions, we present combinatorial chemoenzymatic strategies to effectuate protein labeling. A total of three metal-free conjugations were simultaneously or sequentially incorporated in a one-pot format with microbial transglutaminase (MTG) to effectuate protein labeling. MTG offers the particularity of conjugating residues within a protein sequence rather than at its extremities, providing a route to labeling the native protein...
October 18, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28892360/in-vivo-imaging-guided-photothermal-photoacoustic-synergistic-therapy-with-bioorthogonal-metabolic-glycoengineering-activated-tumor-targeting-nanoparticles
#16
Lihua Du, Huan Qin, Teng Ma, Tao Zhang, Da Xing
Developing multifunctional phototheranostics with nanoplatforms offers promising potential for effective eradication of malignant solid tumors. In this study, we develop a multifunctional phototheranostic by combining photothermal therapy (PTT) and photoacoustic therapy (PAT) based on a tumor-targeting nanoagent (DBCO-ZnPc-LP). The nanoagent DBCO-ZnPc-LP was facilely prepared by self-assembling of a single lipophilic near-infrared (NIR) dye zinc(II)-phthalocyanine (ZnPc) with a lipid-poly(ethylene glycol) (LP) and following modified further with dibenzyl cyclootyne (DBCO) for introducing the two-step chemical tumor-targeting strategy based on metabolic glycoengineering and click chemistry...
September 26, 2017: ACS Nano
https://www.readbyqxmd.com/read/28884571/clickable-multifunctional-dumbbell-particles-for-in-situ-multiplex-single-cell-cytokine-detection
#17
Peng Zhao, Justin George, Bin Li, Nooshin Amini, Janet Paluh, Jun Wang
We report a novel strategy for fabrication of multifunctional dumbbell particles (DPs) through click chemistry for monitoring single-cell cytokine releasing. Two different types of DPs were prepared on a large scale through covalent bioorthogonal reaction between methyltetrazine and trans-cyclooctene on a microchip under a magnetic field. After collection of the DPs, the two sides of each particle were further functionalized with different antibodies for cell capturing and cytokine detection, respectively. These DPs labeled with different fluorescent dyes have been used for multiplex detection and analysis of cytokines secreted by single live cells...
September 27, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28876890/bioorthogonal-cycloadditions-computational-analysis-with-the-distortion-interaction-model-and-predictions-of-reactivities
#18
Fang Liu, Yong Liang, K N Houk
Bioorthogonal chemistry has had a major impact on the study of biological processes in vivo. Biomolecules of interest can be tracked by using probes and reporters that do not react with cellular components and do not interfere with metabolic processes in living cells. Much time and effort has been devoted to the screening of potential bioorthogonal reagents experimentally. This Account describes how our groups have performed computational screening of reactivity and mutual orthogonality. Our collaborations with experimentalists have led to the development of new and useful reactions...
September 19, 2017: Accounts of Chemical Research
https://www.readbyqxmd.com/read/28825822/copper-catalyzed-alkene-aminoazidation-as-a-rapid-entry-to-1-2-diamines-and-installation-of-an-azide-reporter-onto-azahetereocycles
#19
Kun Shen, Qiu Wang
A copper-catalyzed aminoazidation of unactivated alkenes is achieved for the synthesis of versatile unsymmetrical 1,2-diamine derivatives. This transformation offers an effective approach to installing an amide and an azide from two diffenent amino precursors onto both terminal and internal alkenes, with remarkable regio- and stereoselectivity. Mechanistic studies show that this diamination reaction proceeds via a nucleophilic amino cyclization followed by an intermolecular C-N bond formation using electrophilic azidoiodinane...
September 20, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28752889/computationally-guided-discovery-of-a-reactive-hydrophilic-trans-5-oxocene-dienophile-for-bioorthogonal-labeling
#20
William D Lambert, Samuel L Scinto, Olga Dmitrenko, Samantha J Boyd, Ronald Magboo, Ryan A Mehl, Jason W Chin, Joseph M Fox, Stephen Wallace
The use of organic chemistry principles and prediction techniques has enabled the development of new bioorthogonal reactions. As this "toolbox" expands to include new reaction manifolds and orthogonal reaction pairings, the continued development of existing reactions remains an important objective. This is particularly important in cellular imaging, where non-specific background fluorescence has been linked to the hydrophobicity of the bioorthogonal moiety. Here we report that trans-5-oxocene (oxoTCO) displays enhanced reactivity and hydrophilicity compared to trans-cyclooctene (TCO) in the tetrazine ligation reaction...
August 9, 2017: Organic & Biomolecular Chemistry
keyword
keyword
39357
1
2
Fetch more papers »
Fetching more papers... Fetching...
Read by QxMD. Sign in or create an account to discover new knowledge that matter to you.
Remove bar
Read by QxMD icon Read
×

Search Tips

Use Boolean operators: AND/OR

diabetic AND foot
diabetes OR diabetic

Exclude a word using the 'minus' sign

Virchow -triad

Use Parentheses

water AND (cup OR glass)

Add an asterisk (*) at end of a word to include word stems

Neuro* will search for Neurology, Neuroscientist, Neurological, and so on

Use quotes to search for an exact phrase

"primary prevention of cancer"
(heart or cardiac or cardio*) AND arrest -"American Heart Association"