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Bioconjugate Chemistry

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https://read.qxmd.com/read/31117345/hierarchical-self-assembly-of-cholesterol-dna-nanorods
#1
Yunlong Zhang, Ruizi Peng, Fengyuan Xu, Yonggang Ke
Amphiphilic DNA block copolymers have been utilized in preparing self-assembled amphiphilic structures in aqueous solution. These block copolymers usually contain specifically designed hydrophobic regions, and typically assemble under near-physiological conditions. Here, we report self-assembly of spherical micelles and one-dimensional nanorods under acidic conditions from cholesterol-conjugated DNA strands (Cholesterol-DNA). Further study also revealed that the nanorods were hierarchically assembled from the micelle nanostructures...
May 24, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31117351/%C3%AE-thialysine-versus-lysine-an-insight-into-the-epigenetic-methylation-of-histones
#2
Abbas H K Al Temimi, Renate van der Wekken-de Bruijne, Giordano Proietti, Hong Guo, Ping Qian, Jasmin Mecinovic
Biomedicinally important histone lysine methyltransferases (KMTs) transfer a methyl group from S-adenosylmethionine to lysine residues in histones and other proteins. Here, we report comparative studies on epigenetic methylation of lysine and γ-thialysine, the simplest cysteine-derived lysine analog, which can be introduced to histone peptides and histone proteins via site-specific bioconjugation-based cysteine alkylation. Enzyme assays and computational studies demonstrate that human KMTs catalyze an efficient methylation of histones that possess γ-thialysine...
May 22, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31117347/an-albumin-binding-t1-t2-dual-modal-mri-contrast-agents-for-improved-sensitivity-and-accuracy-in-tumor-imaging
#3
Zijian Zhou, Ruiliang Bai, Zhantong Wang, Henry Bryant, Lixin Lang, Hellmut Merkle, Jeeva Munasinghe, Longguang Tang, Wei Tang, Rui Tian, Guocan Yu, Ying Ma, Gang Niu, Jinhao Gao, Xiaoyuan Chen
Magnetic resonance imaging (MRI) diagnosis is better assisted by contrast agents that can augment the signal contrast in the imaging appearance. However, this technique is still limited by the inherently low sensitivity on the recorded signal changes in conventional T1 or T2 MRI in a qualitative manner. Here, we provide a new paradigm of MRI diagnosis using T1-T2 dual-modal MRI contrast agents for contrast-enhanced post-imaging computations on T1 and T2 relaxation changes. An albumin-binding molecule (i.e., truncated Evans blue) chelated with paramagnetic manganese ion was developed as a novel T1-T2 dual-modal MRI contrast agent at high magnetic field (7 T)...
May 22, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31117346/photoradiosynthesis-of-68ga-labelled-hbed-cc-azepin-metmab-for-immuno-pet-of-c-met-receptors
#4
Rachael Fay, Melanie Gut, Jason P Holland
In an alternative approach for radiotracer design, a photoactivatable HBED-CC-PEG3-ArN3 chelate was synthesised and photoconjugated to the anti-c-MET antibody MetMAb (onartuzumab). Photoconjugation gave the functionalised protein HBED-CC-azepin-MetMAb with a photochemical conversion of 18.5±0.5% (n = 2) which was then radiolabelled with 68Ga3+ ions. The purified and formulated [68Ga]GaHBED-CC-azepin-MetMAb radiotracer was evaluated in vitro and in vivo. Standard stability tests and cellular binding assays confirmed that the radiotracer remained radiochemically pure and immunoreactive after photochemical conjugation...
May 22, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31117344/triazine-modified-7-deaza-2-deoxyadenosines-are-better-suited-for-bioorthogonal-labelling-of-dna-by-pcr-than-2-deoxyuridines
#5
Ulrike Reisacher, Bastian Groitl, Ralf Strasser, Gergely B Cserép, Peter Kele, Hans-Achim Wagenknecht
6-Ethynyl-1,2,4-triazine is a small bioorthogonally reactive group we applied for fluorescent labelling of oligonucleotides by Diels-Alder reactions with inverse electron demand. We synthetically attached this functional group to the 7-position of 7-deaza-2'-deoxyadenosine triphosphate and to the 5-position of 2'-deoxyuridine triphosphate. Both modified nucleotide triphosphates were used in comparison for primer extension experiments (PEX) and PCR amplification to finally yield multilabelled oligonucleotides by the postsynthetic reaction with a highly reactive bicyclo[6...
May 22, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31095372/multimodal-positron-emission-tomography-imaging-to-quantify-uptake-of-89zr-labeled-liposomes-in-the-atherosclerotic-vessel-wall
#6
Mark E Lobatto, Tina Binderup, Philip M Robson, Luuk F P Giesen, Claudia Calcagno, Julia Witjes, Francois Fay, Samantha Baxter, Chang Ho Wessel, Mootaz Eldib, Jason Bini, Sean D Carlin, Erik S G Stroes, Gert Storm, Andreas Kjær, Jason S Lewis, Thomas Reiner, Zahi A Fayad, Willem J M Mulder, Carlos Perez-Medina
Nanotherapy has recently emerged as an experimental treatment option for atherosclerosis. To fulfill its promise, robust noninvasive imaging approaches for subject selection and treatment evaluation are warranted. To that end, we here present a positron emission tomography (PET)-based method for quantification of liposomal nanoparticle uptake in the atherosclerotic vessel wall. We evaluated a modular procedure to label liposomal nanoparticles with the radioisotope zirconium-89 (89Zr). Their biodistribution and vessel wall targeting in a rabbit atherosclerosis model was evaluated up to 15 days after intravenous injection by PET/computed tomography (CT) and PET/magnetic resonance imaging (PET/MRI)...
May 16, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31091078/self-associating-peptides-for-modular-bifunctional-conjugation-of-tetramer-macromolecules-in-living-cells
#7
Marc Vigneron, Frank Dietsch, Laurent Bianchetti, Annick Dejaegere, Yves Nominé, Agnes M Cordonnier, Guy Zuber, Bruno Chatton, Mariel Donzeau
Monitoring the assembly of macromolecules to design entities with novel properties can be achieved either chemically creating covalent bonds or by non-covalent connections using appropriate structural motifs. In this report, two self-associating peptides (named K3 and E3) that originate from p53 tetramerization domain were developed as tools for highly specific and non-covalent heterotetramerization of two bio-molecules. The pairing/coupling preferences of K3 and E3 were first evaluated by molecular modeling data and confirmed using circular dichroism spectroscopy, size-exclusion chromatography and biological assays...
May 15, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31090399/correction-to-beyond-unpredictability-the-importance-of-reproducibility-in-understanding-the-protein-corona-of-nanoparticles
#8
Sandra Galmarini, Usawadee Hanusch, Manon Giraud, Noelie Cayla, Diego Chiappe, Nadia von Moos, Heinrich Hofmann, Lionel Maurizi
No abstract text is available yet for this article.
May 15, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31083974/dual-site-specific-antibody-conjugates-for-sequential-and-orthogonal-cargo-release
#9
Dana N Thornlow, Emily C Cox, Joshua A Walker, Michelle R Sorkin, Jacqueline B Plesset, Matt Delisa, Christopher A Alabi
Antibody drug conjugates utilize the antigen specificity of antibodies and the potency of chemotherapeutic and antibiotic drugs for targeted therapy. However, as cancers and bacteria evolve to resist the action of drugs, innovative controlled release methods must be engineered to deliver multi-drug cocktails. In this work, we engineer lipoate-acid ligase A (LplA) acceptor peptide (LAP) tags into the constant heavy and light chain of a humanized Her2 targeted antibody, Trastuzumab. These engineered LAP-tags, along with the glutamine 295 (Q295) residue in the heavy chain, were used to generate orthogonally-cleavable site-specific antibody conjugates via a one-pot chemoenzymatic ligation with microbial transglutaminase (mTG) and LplA...
May 14, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31083930/a-covalently-attached-progesterone-molecule-outcompetes-the-binding-of-free-progesterone-at-an-allosteric-site-of-cytochrome-p450-3a4
#10
Julie Ducharme, Vanja Polic, Karine Auclair
Because of its exceptional substrate promiscuity, human P450 3A4 (CYP3A4) is arguably the most important drug-metabolizing enzyme. CYP3A4 also has the particularity of binding multiple ligands simultaneously, which is associated with heterotropic or homotropic, positive or negative, cooperativity or allostery. Solving the kinetics of such complex systems remains challenging, and so is identifying the binding pockets involved. Progesterone (PRG) is a known allosteric activator of CYP3A4-catalyzed 7-benzyloxy-4-trifluoromethylcoumarin (BFC) debenzylation...
May 14, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31082220/peptide-oligonucleotide-hybrid-molecules-for-bioactive-nanomaterials
#11
Nicholas Stephanopoulos
Peptides and oligonucleotides are two of the most interest molecular platforms for making bioactive materials. Peptides provide bioactivity that can mimic those of proteins, whereas oligonucleotides like DNA can be used as scaffolds to immobilize other materials with nanoscale precision. In this Topical Review, we discuss covalent conjugates of peptides and DNA for creating bioactive materials that can interface with cells. In particular, we focus on two areas. The first is multivalent presentation of peptides on a DNA scaffold, both linear assemblies and more complex nanostructures...
May 13, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31082216/affibody-indocyanine-green-based-contrast-agent-for-photoacoustic-and-fluorescence-molecular-imaging-of-b7-h3-expression-in-breast-cancer
#12
Rakesh Bam, Makenna Laffey, Katharine Nottberg, Patrick S Lown, Benjamin J Hackel, Katheryne Wilson
Spectroscopic photoacoustic (sPA) molecular imaging has high potential for identification of exogenous contrast agents targeted to specific markers. Antibody-dye conjugates have recently been used extensively for preclinical sPA and other optical imaging modalities for highly specific molecular imaging of breast cancer. However, antibody-based agents suffer from long circulation times that limit image specificity. Here, the efficacy of a small protein scaffold, the affibody (ABY), conjugated to indocyanine green (ICG), a near-infrared fluorescence dye, as a targeted molecular imaging probe is demonstrated...
May 13, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31082207/an-albumin-sandwich-enhances-in-vivo-circulation-and-stability-of-metabolically-labile-peptides
#13
Rui Tian, Shoujun Zhu, Qiao Zeng, Lixin Lang, Ying Ma, Dale Kiesewetter, Yi Liu, Xiao Fu, Joseph Lau, Guizhi Zhu, Orit Jacobson, Zhantong Wang, Yunlu Dai, Guocan Yu, Bernard Brooks, Gang Liu, Gang Niu, Xiaoyuan Chen
The effectiveness of numerous molecular drugs is hampered by their poor pharmacokinetics. Different from previous approaches with limited effectiveness, most recently, emerging high-affinity albumin binding moieties (ABMs) for in vivo hitchhiking endogenous albumin opens up an avenue to chaperon small molecules for long-acting therapeutics. Although several FDA approved fatty acids have showed prolonged residence and therapeutic effect, an easy-synthesized, water-soluble and high-efficiency ABM with versatile drug loading ability is extremely needed to improve therapeutic efficacy of short-lived constructs...
May 13, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31075200/psma-specific-antitumor-activity-of-a-self-immolative-tubulysin-conjugate
#14
Christopher P Leamon, Joseph Reddy, Alicia Bloomfield, Ryan Dorton, Melissa Nelson, Marilynn Vetzel, Paul Kleindl, Spencer Hahn, Kevin Wang, Iontcho R Vlahov
Prostate-specific membrane antigen (PSMA) is a biomarker that is overexpressed on prostate cancer, and it's also present on the neovasculature within many non-prostate solid tumors. Herein, we report on the construction and biological testing of novel tubulysin B-containing therapeutic agents for the treatment of PSMA-expressing cancer. One of these compounds, EC1169, emerged as a lead candidate for preclinical development and phase 1 clinical testing. This water-soluble conjugate was shown to have high affinity for PSMA-positive cells...
May 10, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31074621/correction-to-unprecedented-thiacalixarene-fucoclusters-as-strong-inhibitors-of-ebola-cis-cell-infection-and-hcmv-gb-glycoprotein-dc-sign-c-type-lectin-interaction
#15
Marwa Taouai, Vanessa Porkolab, Khouloud Chakroun, Coraline Cheneau, Joanna Luczkowiak, Rym Abidi, David Lesur, Peter J Cragg, Franck Halary, Rafael Delgado, Franck Fieschi, Mohammed Benazza
No abstract text is available yet for this article.
May 10, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31070357/surface-coordination-of-black-phosphorus-with-modified-cisplatin
#16
Jianing Zhang, Yue Ma, Kuan Hu, Yuan Feng, Si Chen, Xiaoyang Yang, Jacky Fong-Chuen Loo, Han Zhang, Feng Yin, Zigang Li
Black phosphorus (BP) is a two-dimensional (2D) nanomaterial with high charge-carrier mobility, tunable direct-bandgap and unique in-plane anisotropic structure, however, the easiness of BP oxidation into Px Oy species in the ambient conditions largely limits its applications. In this study, modified cisplatin-Pt-NO3 [Pt (NH3 )2 (NO3 )2 ] is used for surface coordination with BP nanosheets to generate Pt@BP, which maintains the surface morphology and properties of BP nanosheets for more than 24h in the ambient conditions...
May 9, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31067032/gold-nanoparticles-disrupt-tumor-microenvironment-endothelial-cell-crosstalk-to-inhibit-angiogenic-phenotypes-in-vitro
#17
Yushan Zhang, Xunhao Xiong, Yanyan Huai, Anindya Dey, Md Nazir Hossen, Ram Vinod Roy, Chandra Kumar Elechalawar, Geeta Rao, Resham Bhattacharya, Priyabrata Mukherjee
It is currently recognized that perpetual crosstalk among key players in tumor microenvironment such as cancer associated fibroblasts (CAFs), cancer cells (CCs) and endothelial cells (ECs) play a critical role in tumor progression, metastasis and therapy resistance. Disruption of the crosstalk may be useful to improve the outcome of therapeutics for which limited options are available. In the current study we investigate a use of gold nanoparticles (AuNPs) as a therapeutic tool to disrupt the multicellular crosstalk within the TME cells with an emphasis on inhibiting angiogenesis...
May 8, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31067031/efficient-conjugation-to-phosphorothioate-oligonucleotides-by-cu-catalyzed-huisgen-1-3-dipolar-cycloaddition
#18
Malgorzata Honcharenko, Dmytro Honcharenko, Roger Stromberg
Improving oligonucleotide delivery is critical for the further development of oligonucleotide-based therapeutics. Covalent attachment of reporter molecules is one of the most promising approaches towards efficient oligonucleotide-based therapies. An efficient methods for the attachment of a variety of reporter groups is Cu(I)-catalyzed Huisgen azide‒alkyne 1,3-dipolar cycloaddition. However, the majority of potential oligonucleotide (ON) therapeutics in clinical trials are carrying phosphorothioate (PS) linkages, and this robust conjugation method is not yet established for these ONs due to a general concern of Cu-S interaction...
May 8, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31063685/improved-in-vivo-targeting-capability-and-pharmacokinetics-of-99mtc-labeled-isodgr-by-dimerization-and-albumin-binding-for-glioma-imaging
#19
Hannan Gao, Chuangwei Luo, Guangjie Yang, Shuaifan Du, Xiaoda Li, Huiyun Zhao, Jiyun Shi, Fan Wang
Previously, we have successfully developed the c(phg-isoDGRk) peptide as a novel integrin α5β1-targeted SPECT imaging probe 99mTc-HisoDGR for Glioma imaging. However, the fast clearance of 99mTc-HisoDGR in blood reduced its tumor accumulation and retention, which would be the obstacles for further application in clinical. Dimerization and albumin-binding strategies have been proved as effective approaches to improve tumor targeting capability and blood circulation time of radiotracers. In this study, the novel PEGylated dimeric isoDGR peptides (termed 3PisoDGR2) with an albumin binder (termed AB-3PisoDGR2) were designed, and the corresponding radiotracers 99mTc-3PisoDGR2 and 99mTc-AB-3PisoDGR2 were fabricated and assessed for tumor-targeting and in vivo pharmacokinetics properties in subcutaneous and orthotopic tumor models...
May 7, 2019: Bioconjugate Chemistry
https://read.qxmd.com/read/31050882/clickable-methyltetrazine-indocarbocyanine-lipids-a-multicolor-tool-kit-for-efficient-modifications-of-cell-membranes
#20
Hanmant Gaikwad, Guankui Wang, Weston J Smith, Keisha L Alexander, Angelo D'Alessandro, Wei Zhang, Enkhtsetseg Purev, Dmitri Simberg
Cell-based therapeutics are one of the most promising and exciting breakthroughs in modern medicine. Modification of the cell surface with ligands, biologics, drugs, and nanoparticles can further enhance the functionality. Previously, we described the synthesis of a dioctadecyl indocarbocyanine Cy3 analog (aminomethyl-DiI) for efficient and stable modification (painting) of mouse erythrocytes with small molecules, enzymes, and biologics. Here, we synthesized a near-infrared aminomethyl dioctadecyl derivative of Cy7 (aminomethyl-DOCy7) and systematically compared it to aminomethyl-DiI as an anchor for the modification of human erythrocytes, Jurkat cells, and primary T cells with immunoglobulin G...
May 3, 2019: Bioconjugate Chemistry
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