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https://www.readbyqxmd.com/read/28225218/synthesis-of-n-n-dialkylamino-nor-dihydroxanthene-hemicyanine-fused-near-infrared-fluorophores-and-their-first-water-soluble-and-or-bioconjugatable-analogues
#1
Jean-Alexandre Richard, Michelle Jui Hsien Ong, Sylvain Debieu, Mathieu Moreau, Anthony Romieu
The effective synthesis of extended conjugated N,N-dialkylamino-nor-dihydroxanthene-based fluorophores is described from diversely functionalized salicylic aldehydes. The access to these original fluorescent derivatives proceeded in two steps through a one-pot construction of the unusual nor-dihydroxanthene (nor-DHX) scaffold followed by a diversification step providing a wide variety of nor-DHX-hemicyanine fused dyes emitting in the range 730-790 nm. The versatility of our approach has enabled a further extension to the late-stage introduction of negatively/positively charged polar groups onto their terminal nitrogen heterocyclic subunit giving access to the first water-soluble and/or bioconjugatable members of this emerging class of NIR fluorophores...
February 22, 2017: Chemistry, An Asian Journal
https://www.readbyqxmd.com/read/28225196/effective-access-to-multivalent-inhibitors-of-carbonic-anhydrases-promoted-by-peptide-bioconjugation
#2
Nasreddine Kanfar, Muhammet Tanc, Pascal Dumy, Claudiu Supuran, Sébastien Ulrich, Jean-Yves Winum
Multivalency has impressive effects on (bio)molecular recognition, through the simultaneous presentation of multiple copies of a ligand, which can change a weak millimolar binder into a potent nanomolar one. The implementation of multivalency in enzyme inhibition is rather recent, being exemplified by few serendipitous discoveries, and hitherto relying on the random exploration of new multivalent structures as potential enzyme inhibitors. We report here a straightforward and versatile method that enables the construction of multivalent systems for the inhibition of carbonic anhydrases (CA), widespread enzymes that catalyse a fundamental biochemical reaction...
February 22, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28223423/modulating-therapeutic-activity-and-toxicity-of-pyrrolobenzodiazepine-antibody-drug-conjugates-with-self-immolative-disulfide-linkers
#3
Thomas H Pillow, Melissa Schutten, Shang-Fan Yu, Rachana Ohri, Jack Sadowsky, Kirsten Achilles Poon, Willy Solis, Fiona Zhong, Geoffrey Del Rosario, Mary Ann T Go, Jeffery Lau, Sharon Yee, Jintang He, Luna Liu, Carl Ng, Keyang Xu, Douglas D Leipold, Amrita V Kamath, Donglu Zhang, Luke Masterson, Stephen J Gregson, Philip W Howard, Fan Fang, Jinhua Chen, Janet Gunzner-Toste, Katherine K Kozak, Susan Spencer, Paul Polakis, Andrew G Polson, John A Flygare, Jagath R Junutula
A novel disulfide linker was designed to enable a direct connection between cytotoxic pyrrolobenzodiazepine (PBD) drugs and the cysteine on a targeting antibody for use in antibody-drug conjugates (ADCs). ADCs composed of a cysteine-engineered antibody were armed with a PBD using a self-immolative disulfide linker. Both the chemical linker and the antibody site were optimized for this new bioconjugation strategy to provide a highly stable and efficacious ADC. This novel disulfide ADC was compared to a conjugate containing the same PBD drug, but attached to the antibody via a peptide linker...
February 21, 2017: Molecular Cancer Therapeutics
https://www.readbyqxmd.com/read/28213214/bifunctional-polydopamine-thin-film-coated-zinc-oxide-nanorods-for-label-free-photoelectrochemical-immunoassay
#4
Yan Yang, Weihua Hu
Photoelectrochemical (PEC) detection is a promising method for label-free immunoassay by reporting the specific biological recognition events with electrical signals. However, it is challenging to rationally incorporate immunosensing components with a photocurrent conversion interface, which generally necessitates multistep fabrication and careful tailoring of various components such as photoactive material and biological probe. For high detection reliability and reproducibility, it is highly desirable to rationally construct an efficient PEC interface with architecture as simple as possible...
May 1, 2017: Talanta
https://www.readbyqxmd.com/read/28208296/ultrasensitive-self-powered-aptasensor-based-on-enzyme-biofuel-cell-and-dna-bioconjugate-a-facile-and-powerful-tool-for-antibiotic-residue-detection
#5
Panpan Gai, Chengcheng Gu, Ting Hou, Feng Li
Herein, we reported a novel ultrasensitive one-compartment enzyme biofuel cells (EBFCs)-based self-powered aptasensing platform for antibiotic residue detection. By taking full advantage of the unique features of both EBFCs-based self-powered sensors and aptamers, the as-proposed aptasensing platform has the merits of simple instrumentation, anti-interference ability, high selectivity, and low cost. In this study, DNA bioconjugate, i.e., SiO2@gold nanoparticles-complementary strand of aptamer (SiO2@AuNPs-csDNA), was elaborately designed and played a key role in blocking the mass transport of glucose to the bioanode...
February 7, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28208258/tuning-the-aggregation-disaggregation-behavior-of-graphene-quantum-dots-by-structure-switching-aptamer-for-high-sensitivity-fluorescent-ochratoxin-a-sensor
#6
Song Wang, Yajun Zhang, Guangsheng Pang, Yingwei Zhang, Shaojun Guo
The design of graphene quantum dots (GQDs)-aptamer bioconjugates as the new sensing platform is very important for developing high-sensitivity fluorescent biosensors; however, achieving new bioconjugates is still a great challenge. Herein, we report the development of a new high-sensitivity fluorescent aptasensor for the detection of ochratoxin A (OTA) based on tuning aggregation/disaggregation behavior of GQDs by structure-switching aptamers. The fluorescence sensing process for OTA detection involved two key steps: (1) cDNA-aptamer (cDNA, complementary to part of the OTA aptamer) hybridization induced the aggregation of GQD (fluorescence quenching) after cDNA was added into the GQDs-aptamer bioconjugate solution, and (2) the target of OTA triggered disaggregation of GQD aggregates (fluorescence recovery)...
February 7, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28207247/ortho-methoxyphenols-as-convenient-oxidative-bioconjugation-reagents-with-application-to-site-selective-heterobifunctional-crosslinkers
#7
Adel M ElSohly, James Irving MacDonald, Nina B Hentzen, Ioana Laura Aanei, Kareem M El Muslemany, Matthew B Francis
The synthesis of complex protein-based bioconjugates has been facilitated greatly by recent developments in chemoselective methods for biomolecular modification. The oxidative coupling of o-aminophenols or catechols with aniline functional groups is chemoselective, mild, and rapid; however, the oxidatively sensitive nature of the electron-rich aromatics and the paucity of commercial sources pose some obstacles to the general use of these reactive strategies. Herein, we identify o-methoxyphenols as air-stable, commercially available derivatives that undergo efficient oxidative couplings with anilines in the presence of periodate as oxidant...
February 16, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28202518/prolactin-receptor-mediated-internalization-of-imaging-agents-detects-epithelial-ovarian-cancer-with-enhanced-sensitivity-and-specificity
#8
Karthik M Sundaram, Yilin Zhang, Anirban K Mitra, Jean-Louis K Kouadio, Katja Gwin, Brian R Roman, Anthony A Kossiakoff, Ernst Lengyel, Joseph Piccirilli
Poor prognosis of ovarian cancer (OvCa), the deadliest of the gynecologic malignancies, reflects major limitations associated with detection and diagnosis. Current methods lack high sensitivity to detect small tumors and high specificity to distinguish malignant from benign tissue, both impeding diagnosis of early and metastatic cancer stages and leading to costly and invasive surgeries. Tissue microarray analysis revealed that >98% of OvCa express the prolactin receptor (PRLR), forming the basis of a new molecular imaging strategy...
February 15, 2017: Cancer Research
https://www.readbyqxmd.com/read/28198180/engineering-recombinant-virus-like-nanoparticles-from-plants-for-cellular-delivery
#9
Lou Brillault, Philippe V Jutras, Noor Dashti, Eva C Thuenemann, Garry Morgan, George P Lomonossoff, Michael J Landsberg, Frank Sainsbury
Understanding capsid assembly following recombinant expression of viral structural proteins is critical to the design and modification of virus-like nanoparticles for biomedical and nanotechnology applications. Here, we use plant-based transient expression of the Bluetongue virus (BTV) structural proteins, VP3 and VP7, to obtain high yields of empty and green fluorescent protein (GFP)-encapsidating core-like particles (CLPs) from leaves. Single-particle cryo-electron microscopy of both types of particles revealed considerable differences in CLP structure compared to the crystal structure of infection-derived CLPs; in contrast, the two recombinant CLPs have an identical external structure...
February 15, 2017: ACS Nano
https://www.readbyqxmd.com/read/28196420/editorial-for-virtual-issue-on-polymer-bioconjugates-in-biology-and-medicine
#10
Jan van Hest, Brent Sumerlin, Kristi S Anseth, Molly Shoichet, Sharon Hammes-Schiffer
No abstract text is available yet for this article.
February 15, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28195736/oxidative-fragmentations-and-skeletal-rearrangements-of-oxindole-derivatives
#11
Hendrik F T Klare, Alexander F G Goldberg, Douglas C Duquette, Brian M Stoltz
An oxidative sequence for the conversion of oxindoles to structurally distinct heterocyclic scaffolds and aniline derivatives is disclosed by the combination of a copper-catalyzed C-H peroxidation and subsequent base-mediated fragmentation reaction. In contrast to classic enzymatic (i.e., kynurenine pathway) and biomimetic methods (i.e., Witkop-Winterfeldt oxidation) for oxidative indole cleavage, this protocol allows for the incorporation of external nucleophiles. The new transformation displays broad functional group tolerance and is applicable to tryptophan derivatives, opening potential new avenues for postsynthetic modification of polypeptides, bioconjugation, and unnatural amino acid synthesis...
February 14, 2017: Organic Letters
https://www.readbyqxmd.com/read/28195376/irreversible-cysteine-selective-protein-labeling-employing-modular-electrophilic-tetrafluoroethylation-reagents
#12
Jiří Václavík, Reinhard Zschoche, Iveta Klimánková, Václav Matoušek, Petr Beier, Donald Hilvert, Antonio Togni
Fluoroalkylation reagents based on hypervalent iodine are widely used to transfer fluoroalkyl moieties to various nucleophiles. However, the transferred groups have so far been limited to simple structural motifs. We herein report a reagent featuring a secondary amine that can be converted to amide, sulfonamide, and tertiary amine derivatives in the last step. The resulting reagents bear manifold functional groups, many of which would not be compatible with the original synthetic pathway. Exploiting this structural versatility and the known high reactivity toward thiols, the new-generation reagents were used in bioconjugation with an artificial retro-aldolase, containing an exposed cysteine and a reactive catalytic lysine...
February 13, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28192167/re-programming-pullulan-for-targeting-and-controlled-release-of-doxorubicin-to-the-hepatocellular-carcinoma-cells
#13
Anna Balasso, Stefano Salmaso, Patrizia Pontisso, Antonio Rosato, Santina Quarta, Alessio Malfanti, Francesca Mastrotto, Paolo Caliceti
A novel bioconjugate for hepatocellular carcinoma (HCC) targeting was obtained by pullulan re-programming, which involves the backbone oxidation and conjugation of targeting peptide and doxorubicin (Doxo) through a releasable linker. Preliminary in vivo studies showed that the oxidation of 40 glucopyranose units (GPU) out of 100 remarkably reduced the pullulan unspecific liver tropism. This oxidized polymer was functionalized with PreS1 to selectively target the HCC and with rhodamine (Rhod) as label to perform in vitro cell up-take investigations...
February 10, 2017: European Journal of Pharmaceutical Sciences
https://www.readbyqxmd.com/read/28191931/laser-synthesis-and-processing-of-colloids-fundamentals-and-applications
#14
Dongshi Zhang, Bilal Gökce, Stephan Barcikowski
Driven by functionality and purity demand for applications of inorganic nanoparticle colloids in optics, biology, and energy, their surface chemistry has become a topic of intensive research interest. Consequently, ligand-free colloids are ideal reference materials for evaluating the effects of surface adsorbates from the initial state for application-oriented nanointegration purposes. After two decades of development, laser synthesis and processing of colloids (LSPC) has emerged as a convenient and scalable technique for the synthesis of ligand-free nanomaterials in sealed environments...
February 13, 2017: Chemical Reviews
https://www.readbyqxmd.com/read/28191563/dendritic-poly-chelator-frameworks-for-multimeric-bioconjugation
#15
Dominik Reich, Alexander Wurzer, Martina Wirtz, Veronika Stiegler, Philipp Spatz, Julia Pollmann, Hans-Jürgen Wester, Johannes Notni
Starting from multifunctional triazacyclononane-triphosphinate chelator cores, dendritic molecules with the ability to bind metal ions within their framework were synthesized. A cooperative interaction of the chelator cages resulted in a markedly increased affinity towards (67/68)Ga(III). A hexameric PSMA inhibitor conjugate with high affinity (IC50 = 1.2 nM) and favorable in vivo PET imaging properties demonstrated practical applicability. The novel scaffolds are useful for synthesis of structurally well-defined multimodal imaging probes or theranostics...
February 13, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28190348/editorial-for-virtual-issue-on-polymer-bioconjugates-in-biology-and-medicine
#16
Jan van Hest, Brent Sumerlin, Kristi S Anseth, Molly Shoichet, Sharon Hammes-Schiffer
No abstract text is available yet for this article.
February 13, 2017: Biomacromolecules
https://www.readbyqxmd.com/read/28186733/utilizing-selenocysteine-for-expressed-protein-ligation-and-bioconjugations
#17
Jun Liu, Qingqing Chen, Sharon Rozovsky
Employing selenocysteine-containing protein fragments to form the amide bond between respective protein fragments significantly extends current capabilities of the widely used protein engineering method, expressed protein ligation. Selenocysteine-mediated ligation is noteworthy for its high yield and efficiency. However, it has so far been restricted to solid-phase synthesized seleno-peptides and thus constrained by where the selenocysteine can be positioned. Here we employ heterologously expressed seleno-fragments to overcome the placement and size restrictions in selenocysteine-mediated chemical ligation...
February 10, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28186176/dual-immunomagnetic-nanobeads-based-lateral-flow-test-strip-for-simultaneous-quantitative-detection-of-carcinoembryonic-antigen-and-neuron-specific-enolase
#18
Wenting Lu, Kan Wang, Kun Xiao, Weijian Qin, Yafei Hou, Hao Xu, Xinyu Yan, Yanrong Chen, Daxiang Cui, Jinghua He
A novel immunomagnetic nanobeads -based lateral flow test strip was developed for the simultaneous quantitative detection of neuron specific enolase (NSE) and carcinoembryonic antigen (CEA), which are sensitive and specific in the clinical diagnosis of small cell lung cancer. Using this nanoscale method, high saturation magnetization, carboxyl-modified magnetic nanobeads were successfully synthesized. To obtain the immunomagnetic probes, a covalent bioconjugation of the magnetic nanobeads with the antibody of NSE and CEA was carried out...
February 10, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28183972/redox-based-reagents-for-chemoselective-methionine-bioconjugation
#19
Shixian Lin, Xiaoyu Yang, Shang Jia, Amy M Weeks, Michael Hornsby, Peter S Lee, Rita V Nichiporuk, Anthony T Iavarone, James A Wells, F Dean Toste, Christopher J Chang
Cysteine can be specifically functionalized by a myriad of acid-base conjugation strategies for applications ranging from probing protein function to antibody-drug conjugates and proteomics. In contrast, selective ligation to the other sulfur-containing amino acid, methionine, has been precluded by its intrinsically weaker nucleophilicity. Here, we report a strategy for chemoselective methionine bioconjugation through redox reactivity, using oxaziridine-based reagents to achieve highly selective, rapid, and robust methionine labeling under a range of biocompatible reaction conditions...
February 10, 2017: Science
https://www.readbyqxmd.com/read/28181831/basic-concepts-and-recent-advances-in-nanogels-as-carriers-for-medical-applications
#20
Iordana Neamtu, Alina Gabriela Rusu, Alina Diaconu, Loredana Elena Nita, Aurica P Chiriac
Nanogels in biomedical field are promising and innovative materials as dispersions of hydrogel nanoparticles based on crosslinked polymeric networks that have been called as next generation drug delivery systems due to their relatively high drug encapsulation capacity, uniformity, tunable size, ease of preparation, minimal toxicity, stability in the presence of serum, and stimuli responsiveness. Nanogels show a great potential in chemotherapy, diagnosis, organ targeting and delivery of bioactive substances...
November 2017: Drug Delivery
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