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J Han, A Schmidt, T Zhang, H Permentier, G M M Groothuis, R Bischoff, F E Kühn, P Horvatovich, A Casini
Supramolecular Pd2L4 cages (L = ligand) hold promise as drug delivery systems. With the idea of achieving targeted delivery of the metallacages to tumor cells, the bioconjugation of exo-functionalized self-assembled Pd2L4 cages to peptides following two different approaches is reported for the first time. The obtained bioconjugates were analyzed and identified by high-resolution mass spectrometry.
January 12, 2017: Chemical Communications: Chem Comm
Dimpy Kalia, Sharad P Pawar, Jyoti S Thopate
Maleimide-mediated thiol-specific derivatization of biomolecules is one of the most efficacious bioconjugation approaches currently available. Alarmingly, however, recent work demonstrates that the resulting thiomaleimide conjugates are susceptible to breakdown via thiol exchange reactions. Herein, we report a new class of maleimides, namely o-CH2 NH(i) Pr phenyl maleimides, that undergo unprecedentedly rapid ring hydrolysis after thiol conjugation to form stable thiol exchange-resistant conjugates. Furthermore, we overcome the problem of low shelf lives of maleimide reagents owing to their propensity to undergo ring hydrolysis prior to bioconjugation by developing a photocaged version of this scaffold that resists ring hydrolysis...
January 12, 2017: Angewandte Chemie
Ruslan Cusnir, Cinzia Imberti, Robert C Hider, Philip J Blower, Michelle T Ma
Derivatives of 3,4-hydroxypyridinones have been extensively studied for in vivo Fe(3+) sequestration. Deferiprone, a 1,2-dimethyl-3,4-hydroxypyridinone, is now routinely used for clinical treatment of iron overload disease. Hexadentate tris(3,4-hydroxypyridinone) ligands (THP) complex Fe(3+) at very low iron concentrations, and their high affinities for oxophilic trivalent metal ions have led to their development for new applications as bifunctional chelators for the positron emitting radiometal, (68)Ga(3+), which is clinically used for molecular imaging in positron emission tomography (PET)...
January 8, 2017: International Journal of Molecular Sciences
Yiping Chen, Yunlei Xianyu, Xingyu Jiang
As one of the major tools for and by chemical science, biochemical analysis is becoming increasingly important in fields like clinical diagnosis, food safety, environmental monitoring, and the development of chemistry and biochemistry. The advancement of nanotechnology boosts the development of analytical chemistry, particularly the nanoparticle (NP)-based approaches for biochemical assays. Functional NPs can greatly improve the performance of biochemical analysis because they can accelerate signal transduction, enhance the signal intensity, and enable convenient signal readout due to their unique physical and chemical properties...
January 9, 2017: Accounts of Chemical Research
Alexandra A P Mansur, Fernanda G de Carvalho, Rafael L Mansur, Sandhra M Carvalho, Luiz Carlos de Oliveira, Herman S Mansur
In this study, it is reported the use of sodium carboxymethyl cellulose (CMCel) as a multifunctional biocompatible polysaccharide for the direct synthesis of fluorescent alloyed-ZnCdS quantum dot (QD) nanoconjugates via aqueous "green" process at room temperature. The nanoconjugates were extensively characterized by spectroscopical (NMR, FTIR, UV-vis, PL) and morphological techniques (DLS, TEM) for accessing their structural and physicochemical properties associated with X-ray photoelectron spectroscopy (XPS) for surface and interface analysis...
December 31, 2016: International Journal of Biological Macromolecules
Sanne Anna Maria van Lith, Sander M J van Duijnhoven, Anna C Navis, Edward Dolk, Jos W H Wennink, Cornelus F van Nostrum, Jan C M van Hest, William P J Leenders
Conjugation of llama single domain antibody fragments (Variable Heavy chain domains of Heavy chain antibodies, VHHs) to diagnostic or therapeutic nanoparticles, peptides, proteins or drugs offers many opportunities for optimized targeted cancer treatment. Currently, mostly nonspecific conjugation strategies or genetic fusions are used that may compromise VHH functionality. In this paper we present a versatile modular approach for bioorthogonal VHH modification and conjugation. First, sortase A mediated transPEGylation is used for introduction of a chemical click moiety...
January 3, 2017: Bioconjugate Chemistry
Stefano Parisotto, Beatrice Lace, Emma Artuso, Chiara Lombardi, Annamaria Deagostino, Roberto Scudu, Claudio Garino, Claudio Medana, Cristina Prandi
As part of our ongoing work on the synthesis of a new class of plant hormones named Strigolactones (SLs) and their analogues, we became interested in tracing bioactive molecules with red emitting BODIPY fluorophores in order to unravel signaling and distribution of SLs in plants. In this paper we report on an unprecedented Heck functionalization of azadipyrromethenes (aza-DIPY) which allows for the introduction of suitable functional groups to convert aza-BODIPY in bioconjugate complexes useful for untangling biological processes...
January 3, 2017: Organic & Biomolecular Chemistry
Brad A Kairdolf, Ximei Qian, Shuming Nie
Bioconjugated nanoparticles are of considerable current interest because materials on the nanometer scale have unique optical, electronic, and magnetic properties with broad applications in biosensing, molecular imaging, and medical diagnostics. In particular, recent advances have led to the development of nanomaterials for a variety of applications, including iron oxide nanocrystals for magnetic resonance imaging (MRI), fluorescent quantum dots (QDs) for multiplexed molecular diagnosis and in vivo imaging, and gold nanoparticles for surface-enhanced Raman scattering...
December 19, 2016: Analytical Chemistry
Agata Piotrowska, Sylwia Męczyńska-Wielgosz, Agnieszka Majkowska-Pilip, Przemysław Koźmiński, Grzegorz Wójciuk, Edyta Cędrowska, Frank Bruchertseifer, Alfred Morgenstern, Marcin Kruszewski, Aleksander Bilewicz
INTRODUCTION: Alpha particle emitting isotopes are of considerable interest for radionuclide therapy because of their high cytotoxicity and short path length. Among the many α emitters, (223)Ra exhibits very attractive nuclear properties for application in radionuclide therapy. The decay of this radioisotope and its daughters is accompanied by the emission of four α-particles, releasing 27.9MeV of cumulative energy. Unfortunately the lack of an appropriate bifunctional ligand for radium has so far been a main obstacle for the application of (223)Ra in receptor targeted therapy...
November 17, 2016: Nuclear Medicine and Biology
Guangda Han, Jin-Tao Wang, Xiaotian Ji, Li Liu, Hanying Zhao
Proteinosomes are a type of protein-based spherical capsules, which have potential applications in drug delivery, cell imaging, gene expression and biocatalysis. In this research, a novel approach to the fabrication of proteinosomes entirely composed of protein molecules based on self-assembly of a supramolecular protein-polymer conjugate, is proposed. A supramolecular protein-polymer conjugate was prepared by mixing βCD-modified bovine serum albumin (BSA) and adamantane-terminated poly(N-isopropylamide) (Ad-PNIPAM) in aqueous solution...
December 30, 2016: Bioconjugate Chemistry
Jirina Zackova Suchanova, Jitka Neburkova, Hana Spanielova, Jitka Forstova, Petr Cigler
Virus-like particles based on polyomaviruses (PVLPs) are promising delivery devices for various cargoes, including nucleic acids, imaging probes, and therapeutic agents. In biological environments, the major coat protein VP1 interacts with ubiquitously distributed sialic acid residues, and therefore PVLPs show a broad tropism. For selective targeting, appropriate engineering of the PVLP surface is needed. Here, we describe a chemical approach to retarget PVLPs to cancer cells displaying abnormally high levels of transferrin receptor...
January 10, 2017: Bioconjugate Chemistry
Xiaobao Bi, Kalyan Kumar Pasunooti, Julien Lescar, Chuan-Fa Liu
α-Oxo aldehyde-based bioconjugation chemistry has been widely explored in peptide and protein modifications for various applications in biomedical research during the past decades. The generation of α-oxo aldehyde via sodium periodate oxidation is usually limited to the N-terminus of a target protein. Internal-site functionalization of proteins with the α-oxo aldehyde handle has not been achieved yet. Herein we report a novel method for site-specific peptide and protein modification using synthetically or genetically incorporated thiazolidine-protected α-oxo aldehyde...
December 27, 2016: Bioconjugate Chemistry
Ayşe Göksu Kaya-Özsan, Ayşe Filiz Öner
Protein bioconjugates can be synthesized by using chemical reactions, enzymatic reactions or genetic engineering technologies. Naturally occurred protein fusion event is used on purpose in the development of better biopharmaceuticals by applying genetic engineering methodologies. This review will mainly focus on the types of fusion proteins produced with the use of recombinant DNA technology, by combining genes or parts of genes from the same or different organisms, in order to be used in pharmaceutical applications for several purposes...
December 22, 2016: Current Topics in Medicinal Chemistry
Suhair Sunoqrot, Rania Hamed, Heba Abdel-Halim, Ola Tarawneh
Over the last few decades, nanotechnology has given rise to promising new therapies and diagnostic tools for a wide range of diseases, especially cancer. The unique properties of nanocarriers such as liposomes, polymeric nanoparticles, micelles, and bioconjugates have mainly been exploited to enhance drug solubility, dissolution, and bioavailability. The most important advantage offered by nanotechnology is the ability to specifically target organs, tissues, and individual cells, which ultimately reduces the systemic side effects and improves the therapeutic index of drug molecules...
December 22, 2016: Current Topics in Medicinal Chemistry
W Russ Algar, Ani Khachatrian, Joseph S Melinger, Alan L Huston, Michael H Stewart, Kimihiro Susumu, Juan B Blanco-Canosa, Eunkeu Oh, Philip E Dawson, Igor L Medintz
An emerging trend with semiconductor quantum dots (QDs) is their use as scaffolds to assemble multiple energy transfer pathways. Examples to date have combined various competitive and sequential Förster resonance energy transfer (FRET) pathways between QDs and fluorescent dyes, luminescent lanthanide complexes, and bioluminescent proteins. Here, we show that the photoluminescence (PL) of QD bioconjugates can also be modulated by a combination of FRET and charge transfer (CT), and characterize the concurrent effects of these mechanistically different pathways using PL measurements at both the ensemble and the single particle level...
December 23, 2016: Journal of the American Chemical Society
Yuan-Ye Jiang, Chen Wang, Yujie Liang, Xiaoping Man, Siwei Bi, Yao Fu
Acylborons, as a growing class of boron reagents, were successfully applied to amide ligation and showed potential in chemoselective bioconjugation reactions in recent years. In this manuscript, a density functional theory (DFT) study was performed to investigate the mechanism of the amide formation between monofluoroacylboronates and hydroxylamines. An updated pathway was clarified herein, including water-assisted hemiaminal formation, pyridine ligand dissociation, elimination via a six-membered-ring transition state, and water-assisted tautomerization...
January 5, 2017: Journal of Organic Chemistry
Imran Ozer, Ashutosh Chilkoti
As potent and selective therapeutic agents, peptides and proteins are an important class of drugs, but they typically have suboptimal pharmacokinetic profiles. One approach to solve this problem is their conjugation with "stealth" polymers. Conventional methods for conjugation of this class of polymers to peptides and proteins are typically carried out by reactions that have poor yield and provide limited control over the site of conjugation and the stoichiometry of the conjugate. To address these limitations, new chemical and biological approaches have been developed that provide new molecular tools in the bioconjugation toolbox to create stealth polymer conjugates of peptides and proteins with exquisite control over their properties...
January 6, 2017: Bioconjugate Chemistry
Lucian Mocan, Cristian Matea, Flaviu A Tabaran, Ofelia Mosteanu, Teodora Pop, Cosmin Puia, Lucia Agoston-Coldea, Gabriela Zaharie, Teodora Mocan, Anca Dana Buzoianu, Cornel Iancu
We have used albumin (BSA) bound to gold nanoparticles (GNPs) as active vectors to target liver cells. Our incentive to develop an original model of living liver cancer sprang from the ethical drawbacks that hindered the assessment of the selective character and the therapeutic capacity of these nano-biosystems in cancer patients. Ex vivo-perfused liver specimens were obtained from hepatocellular carcinoma patients similarly to the surgical technique of transplantation. Albumin bound to GNPs was inoculated intra-arterially onto the resulting specimen and determined the specific delivery of the nano-bioconjugate into the malignant tissue by means of the capillary bed...
March 2017: Biomaterials
Marta Janczuk, Łukasz Richter, Grażyna Hoser, Jerzy Kawiak, Marcin Łoś, Joanna Niedziółka-Jönsson, Jan Paczesny, Robert Hołyst
Robust detection of bacteria can significantly reduce risks of nosocomial infections, which are a serious problem even in developed countries (4.1 million cases each year in Europe). Here we demonstrate utilization of novel multifunctional bioconjugates as specific probes for bacteria detection. Bifunctional magnetic-fluorescent microparticles are coupled with bacteriophages. The T4 bacteriophage, due to its natural affinity to bacterial receptors, namely, OmpC and LPS, enables specific and efficient detection of Escherichia coli bacteria...
December 19, 2016: Bioconjugate Chemistry
Qi Liu, Pingchuan Ma, Lanxia Liu, Guilei Ma, Jingjing Ma, Xiaoxuan Liu, Yijin Liu, Wanjun Lin, Yingjun Zhu
Our study investigated poly(lactic-co-glycolic acid) (PLGA) as protein delivery vehicles encapsulate CTLA-4-antibody(anti-CTLA-4) which is essential for CD4+CD25+Treg cells suppressive function exposing superior potential for inhibiting endometriosis progress in mouse model than single anti-CTLA-4. Anti-CTLA-4 loaded PLGA combined to ligands CTLA-4 in surface of CD4+CD25+Treg cells which distributed in peritoneal fluid of mouse endometriosis model. The particle size,zeta potential of the anti-CTLA-4 loaded nanoparticles was detected by dynamic light scattering...
October 29, 2016: European Journal of Pharmaceutical Sciences
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