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Bioconjugate Chemistry

Cagla Eren Cimenci, Gozde Uzunalli Kurtulus, Ozum S Caliskan, Mustafa O Guler, Ayse B Tekinay
Cadherins are vital for cell-to-cell interactions during tissue growth, migration and differentiation processes. Both biophysical and biochemical inputs are generated upon cell-to-cell adhesions, which determine the fate of the mesenchymal stem cells (MSCs). The effect of cadherin interactions on the MSC differentiation still remains elusive. Here we combined the N-Cadherin mimetic peptide (HAV-PA) with the self-assembling E-PA and the resultant N-cadherin mimetic peptide nanofibers promoted chondrogenic differentiation of MSCs in conjunction with chondrogenic factors as a synthetic extracellular matrix system...
August 15, 2019: Bioconjugate Chemistry
Joshua A Walker, John J Bohn, Francis Ledesma, Michelle R Sorkin, Sneha R Kabaria, Dana N Thornlow, Christopher A Alabi
Site-specific modification of native antibodies has proven advantageous, as it enhances the properties of antibody-based bioconjugates without the need to manipulate the genetic code. However, native antibody modification is typically limited to strategies that introduce a single functional handle. In this work, we addressed this limitation by designing heterobifunctional substrates for microbial transglutaminase (MTG) that contain both azide and methyltetrazine "click" handles. Structure-conjugation relationships for these substrates were evaluated using the Her2-targeted antibody trastuzumab...
August 13, 2019: Bioconjugate Chemistry
Yaping Ju, Hao Guo, Frances Yarber, Maria C Edman, Santosh Peddi, Srikanth R Janga, John Andrew MacKay, Sarah F Hamm-Alvarez
Elastin-Like Polypeptides (ELP) are environmentally-responsive protein polymers which are easy to engineer and biocompatible, making them ideal candidates as drug carriers. Our team has recently utilized ELPs fused to FKBP12 to carry Rapamycin (Rapa), a potent immunosuppressant. Through high affinity binding to Rapa, FKBP carriers can yield beneficial therapeutic effects and reduce the off-site toxicity of Rapa. Since ICAM-1 is significantly elevated at sites of inflammation in diverse diseases, we hypothesized that a molecularly-targeted ELP carrier capable of binding ICAM-1 might have advantageous properties...
August 13, 2019: Bioconjugate Chemistry
Yanyan Huai, Md Nazir Hossen, Stefan Wilhelm, Resham Bhattacharya, Priyabrata Mukherjee
Compared to normal tissues, the tumor microenvironment (TME) has a number of aberrant characteristics including hypoxia, acidosis, and vascular abnormalities. Many researchers have sought to exploit these anomalous features of the TME to develop anti-cancer therapies, and several nanoparticle-based cancer therapeutics have resulted. In this review, we discuss the composition and pathophysiology of the TME, introduce nanoparticles (NPs) used in cancer therapy, and address the interaction between the TME and NPs...
August 13, 2019: Bioconjugate Chemistry
Li Shen, Kaimin Cai, Jin Yu, Jianjun Cheng
Comparing with the popular Ac4ManNAz applied on cell labelling via Cu-free click chemistry, two novel azido mannosamine lipids with C6 and C12 ester on anomeric hydroxyl group were prepared and encapsulated in liposome delivery system, which enhanced chemical stabilities and showed good cell-metabolizable labelling efficiency on MDA-MB-231 cells with strong fluorescene after the treatment of DBCO-Cy5 by triazole formation via click chemistry.
August 12, 2019: Bioconjugate Chemistry
Arnaud Masselin, Antoine Petrelli, Maxime Donzel, Sylvie Armand, Sylvain Cottaz, Sebastien Fort
Carbohydrate-protein interactions trigger a wide range of biological signalling pathways, the mainstays of physiological and pathological processes. However, there are an incredible number of carbohydrate-binding proteins (CBPs) that remain to be identified and characterised. This study reports for the first time the covalent labelling of CBPs by triazinyl glycosides, a new and promising class of affinity-based glycoprobes. Mono- and bis-clickable triazinyl glycosides were efficiently synthesised from unprotected oligosaccharides (chitinpentaose and 2'-fucosyl-lactose) in a single step...
August 12, 2019: Bioconjugate Chemistry
Marc Heitz, Sacha Javor, Tamis Darbre, Jean-Louis Reymond
Transfecting nucleic acids into cells is an essential procedure in biological research usually performed using nonviral transfection reagents. Unfortunately, most transfection reagents have polymeric or undisclosed structures and require nonstandard synthetic procedures. Herein we report peptide dendrimers accessible as pure products from standard building blocks by solid-phase peptide synthesis and acting as nontoxic single component siRNA transfection reagents for a variety of cell lines with equal or better performance than the gold standard lipofectamine L2000...
August 9, 2019: Bioconjugate Chemistry
Anne-Sophie Navarro, Thomas LE Bihan, Patricia Le Saec, Nathalie Le Bris, Clément Bailly, Catherine Sai-Morel, Mickaël Bourgeois, Michel Cherel, Raphael Tripier, Alain Faivre-Chauvet
Following the successful synthesis of a C-functionalized version of the TE1PA ligand, a monopicolinate cyclam, we looked to demonstrate its in vivo properties versus DOTA and NOTA, after conjugation on the 9E7.4 rat antibody, an IgG2a against CD138 murine, which has relevant properties for multiple myeloma targeting. For each ligand, different conjugation approaches had been considered to select the most appropriate for the comparative study. The p-SCN-Bn-TE1PA, NHS-DOTA and p-SCN-Bn-NOTA were finally chosen for conjugation and radiolabeling tests...
August 6, 2019: Bioconjugate Chemistry
Eveline Tan, Banglin Li, Katsuhiko Ariga, Chwee Teck Lim, Slaven Garaj, David Tai Leong
2D layered materials (2D LMs) are taking over the scientific world by storm. Graphene epitomizes 2D LMs with many interesting properties and corresponding applications. Following the footsteps of graphene, many other types of 2D LMs like transition metal dichalcogenides, black phosphorus, graphitic-phase C3N4 nanosheets are emerging to be equally interesting as graphene and its derivatives. Some of these applications like nanomedicine do have a high probability of human exposure. This review focusses on the biological and toxicity effects of 2D LMs; their associated mechanisms linking their chemistries to their biological endpoints...
August 5, 2019: Bioconjugate Chemistry
Andre H St Amant, Fengying Huang, Jia Lin, Daniel Lemen, Chacko Chakiath, Shenlan Mao, Christine Fazenbaker, Haihong Zhong, Jay Harper, Wenshu Xu, Neki V Patel, Lauren R Adams, Balakumar Vijayakrishnan, Philip W Howard, Marcello Marelli, Herren Wu, Changshou Gao, Javier Read de Alaniz, Ronald James Christie
The normal electron-demand Diels-Alder (DA) cycloaddition is a classic transformation routinely used in synthesis, however applications in biological systems are limited. Here, we report a spiro[2.4]hepta-4,6-diene-containing non-canonical amino acid (SCpHK) capable of efficient incorporation into antibodies and subsequent coupling with maleimide via a DA reaction. SCpHK was stable throughout protein expression in mammalian cells and enabled covalent attachment of maleimide drug-linkers yielding DA antibody-drug conjugates (DA-ADCs) with nearly quantitative conversion in a one-step process...
August 5, 2019: Bioconjugate Chemistry
Ozioma Udochukwu Akakuru, M Zubair Iqbal, Saeed Madiha, Chuang Liu, Tatjana Paunesku, Gayle E Woloschak, Narayan S Hosmane, Aiguo Wu
Magnetic resonance imaging (MRI) has received a significant attention as the non-invasive diagnostic technique for complex diseases. Image-guided therapeutic strategy for diseases such as cancer has also been at the frontline of biomedical research; thanks to the innovative MRI, enhanced by the prior delivery of contrast agents (CAs) into patients' body through injection. These CAs have contributed a great deal to the clinical utility of MRI but have been based on metal-containing compounds such as gadolinium, manganese, and iron oxide...
August 5, 2019: Bioconjugate Chemistry
Tatyana I Rokitskaya, Natalia V Terekhova, Lyudmila S Khailova, Elena A Kotova, Egor Y Plotnikov, Dmitry B Zorov, Dmitry A Tatarinov, Yuri Antonenko
2-(2-hydroxyaryl)alkenylphosphonium salts (here coined as PPR) representing derivatives of quaternary phosphonium with two phenyl (P) and one alkyl (R) substituents linked through alkenyl bridge to substituted phenol were applied here to planar bilayer lipid membranes (BLM), isolated mitochondria and cell culture. PPR with 6 carbon atoms in R (PP6) induced proton-selective currents across BLM and caused mitochondrial uncoupling. In particular, such derivatives at submicromolar concentrations accelerated respiration, decreased membrane potential and reduced ATP synthesis in isolated rat liver mitochondria (RLM)...
August 2, 2019: Bioconjugate Chemistry
Kristina Ilina, William MacCuaig, Matthew Laramie, Jannatun Noor Jeouty, Lacey R McNally, Maged Henary
Squaraine dyes are a class of organic dyes with strong and narrow absorption bands in the near infrared. Despite high molar absorptivities and fluorescence quantum yields, these dyes have been less explored than other dye scaffolds due to their susceptibility to nucleophilic attack. Recent strategies in probe design including encapsulation, conjugation to biomolecules, and new synthetic modifications have seen squaraine dyes emerging into the forefront of biomedical imaging and other applications. Herein, we provide a concise overview of 1) the synthesis of symmetrical and unsymmetrical squaraine dyes; 2) the relationship between structure and photophysical properties of squarine dyes; 3) current applications of squaraine dyes in the literature...
July 31, 2019: Bioconjugate Chemistry
Xiaofeng Zhang, Bin Lan, Sicheng Wang, Peng Gao, Tianshuai Liu, Junyan Rong, Feng Xiao, Lichun Wei, Huanyu Lu, Cui Pang, Li Fan, Wenli Zhang, Hongbing Lu
X-ray excited photodynamic therapy (X-PDT), which uti-lizes X-rays as the energy source and X-ray luminescent na-noparticles (XLNPs) as the transducer to excite photosensi-tizers (PS), resolves the penetration problem of light in tradi-tional PDT to enable the treatment of deep-seated tumors. Nevertheless, the high X-ray dosage used in X-PDT ham-pers its potential applications in clinics. In this study, to alle-viate the dose problem, β-NaLuF4: Tb3+ spherical nanopar-ticles (NPs) with ultra-strong green X-ray excited optical luminescence (XEOL) due to the less non-radiative relaxa-tion probability and high X-ray absorption mass coefficient, which perfectly matches the absorption spectrum of a pho-tosensitizer named rose bengal (RB), were synthesized and employed as the energy transducer for X-PDT...
July 25, 2019: Bioconjugate Chemistry
Liat Katrivas, Benjamin Kempinski, Kfir Kuchuk, Uri Sivan, Alexander B Kotlyar
Here we report synthesis of long (thousands of base pairs) uniform double-stranded (ds) DNA comprising short (6-15 base pairs) tandem repeats. The synthesis method is based on self-assembly of short (6-15 bases) half-complementary 5'-end phosphorylated single-stranded oligonucleotides into long ds polymer molecules and covalent association of the oligonucleotide fragments in the polymer by DNA Ligase to yield complete non-nicked ds DNA. The method is very flexible in regard to the sequence of the oligonucleotides and their length...
July 25, 2019: Bioconjugate Chemistry
Hanfei Wu, Qi Zhuang, Jun Xu, Ligeng Xu, Yuhuan Zhao, Chenya Wang, Zongjin Yang, Fengyun Shen, Zhuang Liu, Rui Peng
The development of effective cancer vaccines is an important direction in the area of cancer immunotherapy. Although certain types of preventive cancer vaccines have already been used in clinic, therapeutic cancer vaccines for treatment of already-established tumors are still highly demanded. In this study, we develop a new type of cancer vaccines by mixing cell-penetrating peptide (CPP) conjugated antigen as the enhanced antigen, together with CpG as the immune adjuvant. A special CPP, cytosol-localizing internalization peptide 6 (CLIP6), which has the ability to enter cells exclusively via a non-endosomal mechanism, i...
July 24, 2019: Bioconjugate Chemistry
Igor Dovgan, Oleksandr Koniev, Sergii Kolodych, Alain Wagner
Antibody-oligonucleotide conjugates (AOCs) are a novel class of synthetic chimeric biomolecules that has been continually gaining traction in different fields of modern biotechnology. This is mainly due to the unique combination of the properties of their two constituents, exceptional targeting abilities and antibody biodistribution profiles, in addition to an extensive scope of oligonucleotide functional and structural roles. Combining these two classes of biomolecules in one chimeric construct has therefore become an important milestone in the development of numerous biotechnological applications, including imaging (DNA-PAINT), detection (PLA, PEA), and therapeutics (targeted siRNA/antisense delivery)...
July 24, 2019: Bioconjugate Chemistry
Jian-Yuan Li, Gabriella Miklossy, Ram K Modukuri, Kurt Bohren, Zhifeng Yu, Murugesan Palaniappan, John C Faver, Kevin Riehle, Martin M Matzuk, Nicholas Simmons
A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chemical con-jugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chemical library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets...
July 22, 2019: Bioconjugate Chemistry
Nicolai Stuhr-Hansen, Charikleia Despoina Vagianou, Ola Blixt
Access to clusters of cell-sized globular objects such as giant unilamellar vesicles (GUVs) is of increasing interest due to their potential applications in prototissue and cell-cell adhesion studies. Aggregations of GUVs by four different approaches were observed via covalent as well as non-covalent bond participa-tions of functional groups at membrane embedded cholesterylpeptides using optical microscopy. Passive air oxidation of GUV-surface thiols into trans-GUV disulfide bonds promoted multi-vesicle aggregation...
July 19, 2019: Bioconjugate Chemistry
Ryosuke Mizuta, Yoshihiro Sasaki, Riku Kawasaki, Kiyofumi Katagiri, Shin-Ichi Sawada, Sada-Atsu Mukai, Kazunari Akiyoshi
All cells in vivo secrete exosomes consisting of lipid bilayers. Exosomes are involved in intercellular information and material transmission over relatively long distances. Furthermore, nucleic acids and proteins encapsulated in exosomes are involved in the control of cellular functions, such as proliferation and differentiation of cells, and application to advanced medicine including regenerative medicine is expected. To apply exosomes to regenerative medicine, methods have been developed, which confer various functions such as improvement of targeting properties by modifying exosomes...
July 19, 2019: Bioconjugate Chemistry
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