Article
Biochemistry & Molecular Biology
Zexiang Chen, Gitali Devi, Amena Arif, Phillip D. Zamore, Erik J. Sontheimer, Jonathan K. Watts
Summary: This study reports a tetrazine ligation method for the synthesis of sgRNA, which enables the formation of sgRNA under mild conditions by introducing corresponding moieties on the ends of crRNA and tracrRNA. This method allows efficient genome editing in human cells.
ACS CHEMICAL BIOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Kui Wu, Maksim Royzen
Summary: A chemiluminescent probe, consisting of phenoxy-dioxetane moiety covalently attached to trans-cyclooctene, has been developed to emit green light through a series of spontaneous rearrangements. This probe can be used to study bioconjugation chemistry with tetrazine-modified biomaterials, which have potential for anticancer drug delivery. In vitro studies, including NMR and spectroscopic investigation, pave the way for future in vivo bioconjugation experiments.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tatsiana Auchynnikava, Antti Aarela, Heidi Liljenback, Juulia Jarvinen, Putri Andriana, Luciana Kovacs, Jarkko Rautio, Johan Rajander, Pasi Virta, Anne Roivainen, Xiang-Guo Li, Anu J. Airaksinen
Summary: Pretargeted concept in positron emission tomography (PET) utilizing radiotracers labeled with short-lived radionuclides is an elegant solution to study processes with slow pharmacokinetics. Radiotracers based on tetrazine ligation with trans-cyclooctene (TCO) have become a state-of-the-art for pretargeted PET imaging. F-18-Fluoroglycosylation is an indirect radiofluorination method preferred for labeling tetrazine scaffolds. This study reports the biological evaluation of [F-18]FDG-Tz as a tracer for pretargeted PET imaging of TCO-functionalized molecular spherical nucleic acids (MSNA) against human epidermal growth factor receptor 2 (HER2) mRNA. Evaluation in healthy mice showed favorable pharmacokinetics, quick blood clearance, urinary excretion, and absence of GLUT1 transportation. Successful pretargeted experiments with TCO-functionalized MSNA demonstrated higher tumor uptake compared to preclicked MSNA.
Article
Medicine, Research & Experimental
Zhen Wang, Dingpeng Zhang, Xinya Hemu, Side Hu, Janet To, Xiaohong Zhang, Julien Lescar, James P. Tam, Chuan-Fa Liu
Summary: Bio-orthogonal tandem ligation using two asparaginyl peptide ligases with differential substrate specificities is a straightforward approach for the preparation of multifunctional protein biologics as potential theranostics.
Article
Chemistry, Multidisciplinary
Subhashis Jana, Eric G. B. Evans, Hyo Sang Jang, Shuyang Zhang, Hui Zhang, Andrzej Rajca, Sharona E. Gordon, William N. Zagotta, Stefan Stoll, Ryan A. Mehl
Summary: Site-directed spin labeling (SDSL) combined with double electron-electron resonance (DEER) spectroscopy has become a powerful technique for studying the structure and conformational dynamics of biomacromolecules. In this study, a novel family of tetrazine-bearing noncanonical amino acids (Tet-v4.0) was genetically encoded and used for specific and quantitative spin labeling of proteins in live cells. The fast reaction rate of Tet-v4.0 with strained trans-cyclooctene (sTCO)-functionalized nitroxides allowed efficient spin labeling of proteins within minutes, even at sub-micromolar concentrations. DEER measurements from intact cells showed distance distributions consistent with those obtained from proteins purified and labeled in vitro. This approach enables structural and functional studies of proteins directly in cells without the need for protein purification.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
Patrick Keppel, Barbara Sohr, Walter Kuba, Marion Goldeck, Philipp Skrinjar, Jonathan C. T. Carlson, Hannes Mikula
Summary: Bond-cleavage reactions triggered by bioorthogonal tetrazine ligation have been used to chemically control the function of (bio)molecules and activate prodrugs. However, current methods for releasing phenols are limited. To address this issue, we developed a self-immolative linker that connects cleavable amines and phenols, allowing for controlled release of prodrugs.
Article
Chemistry, Multidisciplinary
Vladimir Kardelis, Maria M. Denk, Alex Adronov
Summary: A soluble poly(tetrazine) polymer was prepared through Suzuki polycondensation, which can efficiently react with TCO derivatives via Diels-Alder click reactions. After oxidation, the resulting polymers showed enhanced fluorescence intensity and longer retention times, while maintaining relatively constant degrees of polymerization. Graft copolymers and cross-linked foam were easily prepared by reacting with TCO-functionalized poly(ethylene glycol) chains and a bis-TCO crosslinker, respectively.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Philipp Geng, Eileen List, Franziska Ronicke, Hans-Achim Wagenknecht
Summary: Two green fluorescent tetrazine-modified cyanine-styryl dyes were synthesized for bioorthogonal labelling of DNA. The fluorescence of these dyes can be released by their interaction with DNA and through the conjugated tetrazine as quencher moiety. The dyes can penetrate cells at low concentrations and undergo fluorogenic reactions with BCN-modified DNA in living cells. The two-factor fluorescence release significantly improves the signal-to-noise ratio, eliminating the need for washing procedures prior to cell imaging.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Virology
Jennifer S. H. Im, Laura R. Newburn, Gregory Kent, K. Andrew White
Summary: This study investigated the impact of the structural context of the TABS in RNA1 on the TA-TABS interaction and sg mRNA transcription, revealing that the TABS is partially base paired with proximal upstream sequences, limiting TA access and modulating the TA-TABS interaction.
Article
Chemistry, Multidisciplinary
Lukas V. Hoff, Simon D. Schnell, Elie Benchimol, Fabio Pereira Foutinho, Andrea Tomio, Michel Rickhaus, Karl Gademann
Summary: This study presents a seven-step protocol for the preparation of monosubstituted 3-bromo-1,2,4,5tetrazine. The procedure starts from commercially readily available starting materials and employs efficient transformations and purification methods. The title compound is obtained on a gram scale with 13% overall yield in reliable purity (>97%), allowing its application in various fields such as bioconjugation, protein labeling, bio-orthogonal chemistry, heterocycle syntheses, high energy materials, and drug release.
HELVETICA CHIMICA ACTA
(2023)
Review
Chemistry, Analytical
Aihua Liao, Wei Du, Huanghao Yang
Summary: Pretargeted bioimaging has played a significant role in disease diagnosis and real-time visualization of biological processes. The Tz-TCO click reaction, based on the inverse electron demand Diels-Alder reaction between tetrazine (Tz) and trans-cyclooctene (TCO), has shown great potential in pretargeted bioimaging applications due to its rapid kinetics, specific reactivity, biorthogonality, and biocompatibility. This review focuses on the Tz-TCO click reaction and summarizes its applications in pretargeted bioimaging, discussing the design principles and recent advances in imaging probes. The challenges and future perspectives of the Tz-TCO click reaction in pretargeted bioimaging are also presented.
ANALYSIS & SENSING
(2023)
Article
Engineering, Biomedical
Jie Sun, Yingkang Huang, Huan Zhao, Junjie Niu, Xuwei Ling, Can Zhu, Lin Wang, Huilin Yang, Zhilu Yang, Guoqing Pan, Qin Shi
Summary: This study successfully resolved the difficulty of osseointegration between bioinert titanium implants and bone tissues through a biomimetic surface modification strategy using bio-orthogonal reaction. The method is convenient and feasible, and can improve the success rate of implants, especially in osteoporotic or inflammatory conditions.
BIOACTIVE MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Shizhen He, Shanshan Yu, Ruomeng Li, Yingying Chen, Qing Wang, Yuqiu He, Xiaoqing Liu, Fuan Wang
Summary: This study develops an efficient non-enzymatic circuitry activation strategy to achieve high-fidelity microRNA imaging inside live cells. The catalytic DNA circuit can detect targets sensitively through multiply guaranteed molecular recognition and progressively accelerated signal amplification.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Xuling Xue, Chenggen Qian, Qin Tao, Yuanxin Dai, Mengdi Lv, Jingwen Dong, Zhi Su, Yong Qian, Jing Zhao, Hong-Ke Liu, Zijian Guo
Summary: Through a bio-orthogonally catalyzed lethality (BCL) strategy, a targeting anti-tumor metallodrug Ru-rhein was successfully generated and demonstrated significant anti-tumor efficacy in vitro and in vivo. This strategy could also be extended to other metal complexes for potential cancer treatment applications.
NATIONAL SCIENCE REVIEW
(2021)
Article
Chemistry, Multidisciplinary
Niall M. McLoughlin, Arne Kuepper, Saskia Neubacher, Tom N. Grossmann
Summary: Peptide-DNA conjugates designed for binding with RNA through Watson-Crick base pairing combined with peptide-mediated major groove recognition represent a structure-based approach to novel biomolecular assemblies. By designing two distinct conjugate families with tunable binding characteristics for adjacent binding to a specific RNA sequence, a ternary complex is formed. The proximity of peptide elements in the complex enables an RNA-templated click reaction, introducing a new approach for functional biomolecular assemblies.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Irfan Khan, Paul F. Agris, Mehmet V. Yigit, Maksim Royzen
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Inorganic & Nuclear
Leah M. Seebald, Christopher M. DeMott, Srivathsan Ranganathan, Papa Nii Asare Okai, Anastasia Glazunova, Alan Chen, Alexander Shekhtman, Maksim Royzen
INORGANIC CHEMISTRY
(2017)
Article
Biochemistry & Molecular Biology
Leah M. Seebald, Christopher M. DeMott, Srivathsan Ranganathan, Papa Nii Asare-Okai, Anastasia Glazunova, Alan Chen, Alexander Shekhtman, Maksim Royzen
JOURNAL OF INORGANIC BIOCHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Neil M. Robertson, Yang Yang, Irfan Khan, Vincent E. LaMantia, Maksim Royzen, Mehmet V. Yigit
Article
Chemistry, Multidisciplinary
Irfan Khan, Leah M. Seebald, Neil M. Robertson, Mehmet V. Yigit, Maksim Royzen
Article
Chemistry, Multidisciplinary
Magdalena Czuban, Sangeetha Srinivasan, Nathan A. Yee, Edgar Agustin, Anna Koliszak, Ethan Miller, Irfan Khan, Ilenis Quinones, Hasina Noory, Christopher Motola, Rudolf Volkmer, Mariagrazia Di Luca, Andrej Trampuz, Maksim Royzen, Jose M. Mejia Oneto
ACS CENTRAL SCIENCE
(2018)
Article
Chemistry, Organic
Yuanwei Dai, Jiaping Weng, Justin George, Huan Chen, Qishan Ling, Jun Wang, Maksim Royzen, Qiang Zhang
Article
Biochemical Research Methods
Thomas Kenderdine, Reza Nemati, Andrew Baker, Martin Palmer, Jakub Ujma, Molly FitzGibbon, Limin Deng, Maksim Royzen, James Langridge, Daniele Fabris
JOURNAL OF MASS SPECTROMETRY
(2020)
Article
Biochemical Research Methods
Miguel Macias-Contreras, Huan He, Kevin N. Little, Justin P. Lee, Ryan P. Campbell, Maksim Royzen, Lei Zhu
BIOCONJUGATE CHEMISTRY
(2020)
Article
Chemistry, Medicinal
Taha Bilal Uyar, Kui Wu, Muhan He, Irfan Khan, Maksim Royzen, Mehmet V. Yigit
Article
Materials Science, Biomaterials
Magdalena Czuban, Michael W. Kulka, Lei Wang, Anna Koliszak, Katharina Achazi, Christoph Schlaich, Ievgen S. Donskyi, Mariagrazia Di Luca, Jose M. Mejia Oneto, Maksim Royzen, Rainer Haag, Andrej Trampuz
MATERIALS SCIENCE AND ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS
(2020)
Article
Chemistry, Organic
Xunshen Wu, Kui Wu, Fatima Gaye, Maksim Royzen
Article
Chemistry, Multidisciplinary
Muhan He, Nidhi Nandu, Taha Bilal Uyar, Maksim Royzen, Mehmet Yigit
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
K. Wu, M. He, I. Khan, P. N. Asare Okai, Q. Lin, G. Fuchs, M. Royzen
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Andrea K. Steiger, Yang Yang, Maksim Royzen, Michael D. Pluth
CHEMICAL COMMUNICATIONS
(2017)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
