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Bioconjugate Chemistry

Chenguang Lou, Simone V Samuelsen, Niels Johan Christensen, Birte Vester, Jesper Wengel
Mono- and diaminated 2'-amino-LNA monomers were synthesized and introduced into oligonucleotides. Each modification imparts significant stabilization of nucleic acid duplexes and triplexes, excellent sequence selectivity and significant nuclease resistance. Molecular modelling suggested that structural stabilization occurs via intrastrand electrostatic attraction between the protonated amino groups of the aminated 2'-amino-LNA monomers and the host oligonucleotide backbone.
March 23, 2017: Bioconjugate Chemistry
Devora Cohen-Karni, Marina Kovaliov, Shaohua Li, Stephen Jaffee, Nestor D Tomycz, Saadyah Averick
The targeted delivery of polymers to neurons is a challenging yet important goal for polymer based drug delivery. We prepared a fentanyl based atom transfer radical polymerization (ATRP) initiator to target the Mu opioid receptor (MOR) for neuronal targeting. We incorporated our recently discovered rigid acrylate linking group into the initiator to retain a high degree of binding to the MOR and grafted random or block copolymers of poly(oligo(ethylene oxide) methacrylate)-block-(glycidyl methacrylate). Trifluoroethanol promoted amine ring opening of the glycidyl methacrylate was used for post-polymerization modification of the fentanyl initiated polymers to attach a near-infrared fluorescent dye (ADS790WS) or to build a targeted siRNA delivery system via modification with secondary amines...
March 22, 2017: Bioconjugate Chemistry
Francois Fay, Line Hansen, Stefanie J C G Hectors, Brenda L Sanchez-Gaytan, Yiming Zhao, Jun Tang, Jazz Munitz, Amr Alaarg, Mounia S Braza, Anita Gianella, Stuart A Aaronson, Thomas Reiner, Jørgen Kjems, Robert Langer, Freek J M Hoeben, Henk M Janssen, Claudia Calcagno, Gustav J Strijkers, Zahi A Fayad, Carlos Perez-Medina, Willem J M Mulder
Active targeting of nanoparticles through surface functionalization is a common strategy to enhance tumor delivery specificity. However, active targeting strategies tend to work against long polyethylene glycol's shielding effectiveness and associated favorable pharmacokinetics. To overcome these limitations, we developed a matrix metalloproteinase-2 sensitive surface-converting polyethylene glycol coating. This coating prevents nanoparticle-cell interaction in the bloodstream but once exposed to matrix metalloproteinase-2, i...
March 19, 2017: Bioconjugate Chemistry
Ludmila N Turino, Maria Ruggiero, Rachele Stefania, Juan Carlos Cutrin, Silvio Aime, Simonetta Geninatti Crich
PolyLactic and Glycolic Acid nanoparticles (PLGA-NPs), coated with L-Ferritin, are exploited for the simultaneous delivery of paclitaxel and an amphiphilic Gd based MRI contrast agent into breast cancer cells (MCF7). L-Ferritin has been covalently conjugated to the external surface of PLGA-NPs exploiting NHS activated carboxylic groups. The results confirmed that nanoparticles decorated with L-Ferritin have many advantages with respect both albumin-decorated and non-decorated particles. Ferritin moieties endow PLGA-NPs with targeting capability, exploiting SCARA5 receptors overexpressed by these tumour cells, that results in an increased paclitaxel cytotoxicity...
March 16, 2017: Bioconjugate Chemistry
Sascha Rode, Manuel Hayn, Annika Röcker, Stefanie Sieste, Marcus Lamla, Daniel Markx, Christoph Meier, Frank Kirchhoff, Paul Walther, Marcus Fändrich, Tanja Weil, Jan Muench
Retroviral gene transfer is the method of choice for the stable introduction of genetic material into the cellular genome. However, efficient gene transfer is often limited by low transduction rates of the viral vectors. We have recently described a 12-mer peptide, termed EF-C that forms amyloid-like peptide nanofibrils (PNF) strongly increasing viral transduction efficiencies. These nanofibrils are polycationic and bind negatively charged membranes of virions and cells, thereby overcoming charge repulsions and resulting in increased rates of virion attachment and gene transfer...
March 16, 2017: Bioconjugate Chemistry
Jorick J Bruins, Adrie H Westphal, Bauke Albada, Koen Wagner, Lina Bartels, Hergen Spits, Willem J H van Berkel, Floris L van Delft
Genetically encoded tyrosine (Y-tag) can be utilized as a latent anchor for inducible and site-selective conjugation. Upon oxidation of tyrosine with mushroom tyrosinase, strain-promoted cycloaddition (SPOCQ) of the resulting 1,2-quinone with various bicyclo[6.1.0]nonyne (BCN) derivatives led to efficient conjugation. The method was applied for fluorophore labeling of laminarinase A and for the site-specific preparation of an antibody-drug conjugate.
March 16, 2017: Bioconjugate Chemistry
Aline Mongis, Friedrich Piller, Véronique Piller
The present study investigated the potential of metabolic glycoengineering followed by bioorthogonal click chemistry for introducing into cell surface glycans different immunomodulating molecules. Mouse tumor models EG7 and MC38-OVA were treated with Ac4GalNAz and Ac4ManNAz followed by ligation of immunostimulants to modified cell surface glycans of the living cells through bioorthogonal click chemistry. The presence of covalently bound oligosaccharide and oligonucleotide immunostimulants could be clearly established...
March 15, 2017: Bioconjugate Chemistry
Samata Chaudhuri, Till Korten, Stefan Diez
Engineering cargo-loading strategies is crucial to developing nanotechnological applications of microtubule-based biomolecular transport systems. Here, we report a highly efficient and robust bioconjugation scheme to load antibodies to microtubules. Our method takes advantage of the inverse-electron-demand Diels-Alder addition reaction between tetrazine and trans-cyclooctene: the fastest known bioorthogonal reaction, characterized by its excellent selectivity and biocompatibility. As proof of concept, we performed kinesin-1 gliding motility assays with antibody-conjugated microtubules and demonstrated the highly sensitive detection of fluorescent protein analyte down to 0...
March 14, 2017: Bioconjugate Chemistry
Stuart A Whitehead, Christopher D McNitt, Samuel I Mattern-Schain, Adam J Carr, Shahrina Alam, Vladimir V Popik, Michael D Best
Artificial systems for controlled membrane fusion applicable for drug delivery would ideally use triggers that are orthogonal to biology. To apply the strain-promoted alkyne-azide cycloaddition (SPAAC) to drive membrane fusion, oxo-dibenzocyclooctyne (ODIBO)-lipid 1 was designed, synthesized, and studied alongside azadibenzocyclooctyne (ADIBO)-lipids 2-4 to assess fusion with liposomes containing azido-lipid 5. Lipids 1-2 were first shown to be effective for liposome derivatization. Next, fusion was evaluated using liposomes containing 1 and varying ratios of PC and PE via a FRET dilution fusion assay, and a 1:1 PC-to-PE ratio yielded the greatest signal change attributed to fusion...
March 14, 2017: Bioconjugate Chemistry
Alexandre Lancelot, Rebeca González-Pastor, Alberto Concellón, Teresa Sierra, Pilar Martín-Duque, José L Serrano
In the search for effective vehicles to carry genetic material into cells, we present here new pseudodendrimers that consist of a hyperbranched polyester core surrounded by amino-terminated 2,2-bis(hydroxymethyl)propionic acid (bis-MPA) dendrons. The pseudodendrimers are readily synthesized from commercial hyperbranched bis-MPA polyesters of the second, third, and fourth generations and third-generation bis-MPA dendrons, bearing eight peripheral glycine moieties, coupled by the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC)...
March 13, 2017: Bioconjugate Chemistry
Xiaochao Huang, Rizhen Huang, Shaohua Gou, Zhimei Wang, Heng-Shan Wang
A novel class of platinum(IV) complexes comprising a mono-aminophosphonate ester moiety, which can not only act as a bone-targeting group but also inhibit matrix metalloproteinases (MMPs), were designed and synthesized. Biological assay of these compounds showed that they had potent antitumor activities against the tested cancer cell lines compared with cisplatin and oxaliplatin and indicated low cytotoxicity to human normal liver cells. Particularly, the platinum(IV) complexes were much sensitive to cisplatin resistant cancer cell lines...
March 9, 2017: Bioconjugate Chemistry
Zheng Han, Yajuan Li, Sarah Roelle, Zhuxian Zhou, Yuchi Liu, Rob Sabatelle, Aidan DeSanto, Xin Yu, Hui Zhu, Cristina Magi-Galluzzi, Zheng-Rong Lu
Accurate detection and risk stratification are paramount to the clinical management of prostate cancer. Current diagnostic methods, including prostate specific antigen (PSA) screening, are unable to differentiate high-risk tumors from low-risk tumors, resulting in overdiagnosis and overtreatment. A peptide targeted contrast agent, ZD2-Gd(HP-DO3A), specific to an oncoprotein in tumor microenvironment, EDB-FN, was synthesized for noninvasive detection and characterization of aggressive prostate cancer. EDB-FN, one of the subtypes of oncofetal fibronectin, is involved in tumor epithelial-to-mesenchymal transition (EMT), which is implicated in drug resistance and metastasis...
March 9, 2017: Bioconjugate Chemistry
Rubul Mout, Moumita Ray, Yi-Wei Lee, Federica Scaletti, Vincent M Rotello
The successful use of CRISPR/Cas9 based gene editing for therapeutics requires efficient in vivo delivery of the CRISPR components. There are, however, major challenges on the delivery front. In this Topical Review, we will highlight recent developments in CRISPR delivery, and we will present hurdles that still need to be overcome to achieve effective in vivo editing.
March 6, 2017: Bioconjugate Chemistry
Yanyan Jiang, Sandy Wong, Fan Chen, Teddy Chang, Hongxu Lu, Martina Heide Stenzel
Albumin based nanoparticles are widely used to delivery anti-cancer drug as they promote the accumulation of drugs in tumors. Nanoparticles with surface immobilized albumin are widely described in literature, though mixed nanoparticles with systematically modified ratios between albumin and PEG-based material are less common. In this work, mixed hybrid nanoparticles were prepared by self-assembly of a PEG-based amphiphilic block copolymer together with a polymer-protein conjugate. Poly(oligo(ethylene glycol) methyl ether acrylate)-poly(ε-caprolactone) (POEGMEA-PCL) was prepared by a combination of ring-opening polymerization and reversible addition fragmentation chain transfer (RAFT) polymerization while the polymer-protein conjugate was obtained by reacting poly(ε-caprolactone) with bovine serum albumin (BSA-PCL)...
March 6, 2017: Bioconjugate Chemistry
Katharina Schmid, Maria Adobes-Vidal, Mark Helm
Bioconjugation of RNA is a dynamic field recently reinvigorated by a surge in research on posttranscriptional modification. This work focusses on the bioconjugation of 4-thiouridine, a nucleoside that occurs as a post-transcriptional modification in bacterial RNA, and is used as a metabolic label and for crosslinking purposes in eukaryotic RNA. A newly designed coumarin compound, named 7-propargyloxy-4-bromomethylcoumarin (PBC) is introduced, which exhibits remarkable selectivity for 4-thiouridine. Bearing a terminal alkyne group, it is conductive to secondary bioconjugation via "click chemistry", thereby offering a wide range of preparative and analytical options...
March 6, 2017: Bioconjugate Chemistry
Matthias Hartlieb, Tanja Bus, Joachim Kübel, David Pretzel, Stephanie Hoeppener, Meike N Leiske, Kristian Kempe, Benjamin Dietzek, Ulrich S Schubert
Controlling the size and charge of nanometer-sized objects is of upmost importance for their interactions with cells. We herein present the synthesis of poly(2-oxazoline) based nanogels comprising a hydrophilic shell and an amine containing core compartment. Amine groups were cross-linked using glutaraldehyde resulting in imine based nanogels. As a drug model, amino fluorescein was covalently immobilized within the core, quenching excessive aldehyde functions. By varying the amount of cross-linker, the zeta potential and, hence, the cellular uptake could be adjusted...
March 3, 2017: Bioconjugate Chemistry
Tõnis Lehto, Luis Vasconcelos, Helerin Margus, Ricardo Figueroa, Margus Pooga, Mattias Hällbrink, Ülo Langel
Modifying cell-penetrating peptides (CPPs) with fatty acids has long been used to improve peptide-mediated nucleic acid delivery. In this study we have revisited this phenomenon with a systematic approach where we developed a structure-activity relationship to describe the role of the acyl chain length in the transfection process. For that we took a well-studied CPP, PepFect14, as the basis and varied its N-terminal acyl chain length from 2 to 22 carbons. To evaluate the delivery efficiency, the peptides were noncovalently complexed with a splice-correcting oligonucleotide (SCO) and tested in HeLa pLuc705 reporter cell line...
March 2, 2017: Bioconjugate Chemistry
Stephanie Deshayes, Wujing Xian, Nathan W Schmidt, Shadi Kordbacheh, Juelline Lieng, Jennifer Wang, Sandra Zarmer, Samantha St Germain, Laura Voyen, Julia Thulin, Gerard C L Wong, Andrea M Kasko
We design hybrid antibiotic peptide conjugates that can permeate membranes. Integration of multiple components with different functions into a single molecule is often problematic, due to competing chemical requirements for different functions and to mutual interference. By examining the structure of antimicrobial peptides (AMPs), we show that it is possible to design and synthesize membrane active antibiotic peptide conjugates (MAAPCs) that synergistically combine multiple forms of antimicrobial activity, resulting in unusually strong activity against persistent bacterial strains...
March 1, 2017: Bioconjugate Chemistry
Reshma Lali Raveendran, Nishanth Kumar Sasidharan, Sudha J Devaki
The design of liquid crystalline hydrogels knitted with silver nanoparticles in macroscopic ordering is becoming a subject of research interest due to their promising multifunctional applications in biomedical and optoelectronic applications. The present work describes the development of liquid crystalline Schiff-based hydrogel decorated with silver nanoparticles and the demonstration of its antifungal applications. Schiff base was prepared from polyglucanaldehyde and chitosan, and the former was prepared by the oxidation of amylose (polyglucopyranose) isolated from abundantly available unutilized jackfruit seed starch...
March 1, 2017: Bioconjugate Chemistry
Chethana Kulkarni, James E Finley, Andrew J Bessire, Xiaotian Zhong, Sylvia Musto, Edmund I Graziani
As the antibody-drug conjugate (ADC) field grows increasingly important for cancer treatment, it is vital for researchers to establish a firm understanding of how ADCs function at the molecular level. To gain insight into ADC uptake, trafficking, and catabolism-processes that are critical to ADC efficacy and toxicity-imaging studies have been performed with fluorophore-labeled conjugates. However, such labels may alter the properties and behavior of the ADC under investigation. As an alternative approach, we present here the development of a "clickable" ADC bearing an azide-functionalized linker-payload (LP) poised for "click" reaction with alkyne fluorophores; the azide group represents a significantly smaller structural perturbation to the LP than most fluorophores...
March 1, 2017: Bioconjugate Chemistry
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