Article
Chemistry, Analytical
Mutsuo Nuriya, Yosuke Ashikari, Takanori Iino, Takuya Asai, Jingwen Shou, Keiko Karasawa, Kaho Nakamura, Yasuyuki Ozeki, Yukari Fujimoto, Masato Yasui
Summary: The development of alkyne-tagged dopamine compounds (ATDAs) provides a minimally invasive and uniquely identifiable tool to mimic dopamine in neurons and brain tissues, allowing for detailed characterization of dopamine dynamics. This approach can potentially be applied to other small-sized neurotransmitters as well, facilitating research on their dynamics in the brain.
ANALYTICAL CHEMISTRY
(2021)
Article
Engineering, Environmental
Guansong Hu, Junjian Chen, Yan Fan, Haiyan Zhou, Kunzhong Guo, Zhou Fang, Liangxu Xie, Lin Wang, Yingjun Wang
Summary: This study established a facile and efficient CuAAC-Bor system, finding that CuNCs showed stronger efficiency in immobilizing multiple peptides on titanium implants. Mechanistic insights into the significance of peptide size on CuAAC efficiency were revealed through all-atom molecular dynamics simulation and machine learning.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Physical
Guoneng Chen, Riyan Lin, Yanshi Lei, Peng Cai, Yifu Huang, Hefeng Zhang
Summary: In this study, a new spiropyran-containing polyurethane ionogel with photochromic, photomechanical, and photoconductive properties was successfully prepared through thiol-ene chemistry. It was found that the participation of the ring-opened spiropyran in the thiol-ene reaction affected its reverse photochromic behavior.
Article
Chemistry, Applied
Stefano Torresi, Tamara Calvo-Correas, Senda Basasoro, Olatz Guaresti, Ana Alonso-Varona, Nagore Gabilondo, Arantxa Eceiza
Summary: A new biobased polyurethane formulation containing furan was synthesized and functionalized via Diels-Alder and retro Diels-Alder reactions, showing potential for versatile applications. The polymer, with high renewable content and spinnability, exhibits good biocompatibility and can be used in biomedical tissue engineering.
REACTIVE & FUNCTIONAL POLYMERS
(2022)
Article
Chemistry, Applied
Stefano Torresi, Tamara Calvo-Correas, Senda Basasoro, Olatz Guaresti, Ana Alonso-Varona, Nagore Gabilondo, Arantxa Eceiza
Summary: A biobased polyurethane formulation containing furan was synthesized and functionalized via reaction. The formulation was processed into nanofiber membranes using electrospinning. The polymer has the advantages of being catalyst-free, having high renewable content, and being easily producible. The membranes are highly hydrophobic, allowing for functionalization reactions in water with minimal impact on membrane integrity. The material also exhibits good biocompatibility, making it suitable for biomedical tissue applications.
REACTIVE & FUNCTIONAL POLYMERS
(2022)
Article
Chemistry, Multidisciplinary
Biswa Ranjan Swain, Soumya Ranjan Jena, Swaraj Kumar Beriha, Chandra Sekhara Mahanta, Bibhuti Bhusan Jena, Thumpati Prasanth, Luna Samanta, Rashmirekha Satapathy, Barada P. Dash
Summary: Boron-rich glycodendrimers containing multiple glucose moieties and ortho-carborane clusters were synthesized and found to be completely water soluble due to increased hydrophilicity. In vitro evaluation showed that the glycodendrimer with nine glucose moieties exhibited the highest cytotoxicity against MCF-7 breast cancer cells, with a 600-fold higher potency than cisplatin. The study suggests that these glycodendrimers could serve as tumor-specific anticancer agents.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Biochemical Research Methods
Lisa Milchram, Regina Soldo, Valerie Regele, Silvia Schoenthaler, Markus Degeorgi, Sophie Baumgartner, Elena Kopp, Andreas Weinhaeusell
Summary: ELISA is the current standard for antibody diagnostics, but peptide-based protocols are rarely available. In this study, the authors investigated an indirect ELISA protocol using peptides conjugated onto a protein carrier based on click chemistry and immobilized in standard plastics, and compared it with the common biotin-avidin system. The results showed a slightly improved limit of detection with the peptide-based approach. This method offers a reliable alternative to standard plastics and plate readers.
Article
Electrochemistry
Clinton Adu, Mairead Boucher, Patrick C. Hillesheim, Arsalan Mirjafari
Summary: The continuous achievements of ionic liquids in various fields necessitate the development of new functional ionic liquids and practical synthetic methodologies. A recent study reported the compatibility of a full fluorosulfonyl electrolyte with a Li metal anode and metal-oxide cathode, crucial for high-voltage rechargeable lithium-metal batteries. Inspired by this, a series of sulfonyl fluoride-based ionic liquids were synthesized for the first time using an effective fluorosulfonylethylation procedure. Through computational modeling and X-ray crystallography, a detailed analysis of their structure-property correlations was presented.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
Mattias Berglin, Jorunn Pauline Cavanagh, Josefin Seth Caous, Balmukund Sureshkumar Thakkar, Jeddah Marie Vasquez, Wenche Stensen, Benny Lyven, John-Sigurd Svendsen, Johan Svenson
Summary: This paper describes the development of polyurethane materials with the capability to attach antibacterial compounds. The materials exhibit robustness and flexibility, and the attached antimicrobial peptides effectively reduce bacterial colonization and growth. The findings indicate the potential for medical applications in reducing the impact of bacterial biofilms.
MACROMOLECULAR BIOSCIENCE
(2023)
Article
Biochemistry & Molecular Biology
K. M. Tewari, R. Dondi, E. Yaghini, C. Pourzand, A. J. MacRobert, I. M. Eggleston
Summary: A novel peptide-targeted dendrimeric prodrug of 5-aminolevulinic acid (ALA) was successfully synthesized, which can effectively deliver ALA to specific cancer cell types. The prodrug system showed sustained and enhanced production of protoporphyrin IX (PpIX) in cancer cell lines over-expressing the epidermal growth factor receptor (EGFR+). This study provides proof of concept for the development of new generation prodrugs for ALA-based photodynamic therapy with enhanced ALA payload delivery to specific tissue types.
BIOORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Hong Xue, De-Shan Li, Hua-Wen Cai, Xiao-Li Sun, Wen-Ming Wan
Summary: Nontraditional intrinsic luminescent (NTIL) polymers are a new class of luminescent polymer materials. In this study, a series of aggregation-induced emission (AIE) type NTIL polymers were successfully synthesized through reversible addition-fragmentation chain transfer (RAFT) polymerization-induced emission (PIE). The triphenylmethyl azide moiety was found to be a novel PIE luminogen for the molecular design of NTIL polymers. These NTIL polymers showed potential applications in explosive detection and luminescence energy transfer.
Article
Nanoscience & Nanotechnology
Qin Yao, Jinyi Zhang, Guoqing Pan, Binghai Chen
Summary: Long-term indwelling catheters or stents often cause complications such as infection and encrustation. This study developed an antibacterial coating on urinary stents/catheters using a clickable mussel-inspired peptide and antimicrobial peptide. The coating exhibited excellent stability, bactericidal properties, and improved biological compatibility.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Medicinal
Md Toufiqur Rahman, Ann M. Decker, Lucas Laudermilk, Rangan Maitra, Weiya Ma, Sami Ben Hamida, Emmanuel Darcq, Brigitte L. Kieffer, Chunyang Jin
Summary: This study identified a series of novel GPR88 agonists, with one showing high potency and suitability for studying the function of GPR88 in the brain.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zunwei Ma, Huaiming Wang, Zhifeng Shi, Fengying Yan, Qingtao Li, Junjian Chen, Zhong-Kai Cui, Yunjiao Zhang, Xin Jin, Yong-Guang Jia, Lin Wang
Summary: We demonstrated that mesoporous silica nanoparticles loaded with DOX and AMP can effectively kill bacteria and tumor cells, modulate the tumor microenvironment, treat bacterial infections, and eliminate lung tumors. The MSN@DOX-AMP system can be inhaled and accumulate in the lung, leading to better therapeutic outcomes. This platform holds promise for treating bacterial infections in tumors and advancing the clinical treatment of lung cancer.
Article
Biochemistry & Molecular Biology
Lucie Dardevet, Feten Najlaoui, Sonia Aroui, Mayeul Collot, Celine Tisseyre, Michael W. Pennington, Jean-Maurice Mallet, Michel De Waard
Summary: Natural peptide analogs of chlorotoxin, including Lqh-8/6, were synthesized and evaluated for their ability to label, detect, and inhibit glioma growth. It was found that a biotinylated version of Lqh-8/6 could label glioma cell lines and detect glioma in brain sections. Lqh-8/6 exhibited anti-invasive properties and was non-toxic to glioma cells. Moreover, the conjugation of doxorubicin to Lqh-8/6 efficiently induced apoptosis in glioma cells.
Article
Chemistry, Organic
Andrew D. W. Earl, Freda F. F. Li, Chao Ma, Daniel P. P. Furkert, Margaret A. A. Brimble
Summary: This research describes a facile and efficient synthesis of the [7,6]-spirocyclic core of 13-desmethyl spirolide C, a marine natural product with remarkable bioactivity against biomarkers of Alzheimer's Disease. The synthesis involves an aza-Claisen rearrangement and a highly exo-selective Diels-Alder cycloaddition. This strategy not only provides a more efficient access to the spirocyclic core for the total synthesis of 13-desmethyl spirolide C, but also allows for convenient preparations of analogues for biological evaluation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Johanes K. Kasim, Jiwon Hong, Anthony J. R. Hickey, Anthony R. J. Phillips, John A. Windsor, Paul W. R. Harris, Margaret A. Brimble, Iman Kavianinia
Summary: Pancreatic ductal adenocarcinoma is a debilitating disease with no effective treatments. Trichoderin A, a natural product, shows promise as an anticancer agent. It selectively kills pancreatic cancer cells under glucose deprivation, which is significant given the nutrient-deprived nature of the disease.
Article
Chemistry, Medicinal
Tyla I. Alexander, Zoe Tasma, Andrew Siow, Tayla A. Rees, Margaret A. Brimble, Paul W. R. Harris, Debbie L. Hay, Christopher S. Walker
Summary: The peptides PACAP and VIP, along with their corresponding receptors, have potential as drug targets for neurological and pain-related disorders. This study developed fluorescently labeled analogues of these peptides to study receptor regulation through processes such as internalization. The labeled peptides were found to be functional at their receptors and underwent time-dependent internalization.
ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE
(2023)
Article
Biochemistry & Molecular Biology
Shama Dissanayake, Junming He, Sung H. Yang, Margaret A. Brimble, Paul W. R. Harris, Alan J. Cameron
Summary: A novel antimicrobial peptide called cathelicidin-PY was successfully synthesized, which exhibited broad-spectrum antibacterial and antifungal activity with low toxicity to human cells. Derivatives of this peptide were also synthesized and showed selective inhibition against Gram-negative bacteria E.coli.
Article
Chemistry, Organic
Eilidh G. Young, Phillip S. Grant, Daniel P. Furkert, Margaret A. Brimble
Summary: Lycibarbarines A-C are spirocyclic alkaloids with a unique tetracyclic framework. The first total syntheses of lycibarbarines A-C were achieved over 10 steps. The spiroketal unit of lycibarbarines A-C exhibits unusually high resistance to acid-mediated isomerization and epimerization.
Article
Chemistry, Medicinal
Alexander J. Craig, Yuri Ermolovich, Alan Cameron, Agnes Rodler, Helen Wang, Jeffrey A. Hawkes, Madlen Hubert, Fredrik Bjoerkling, Natalia Molchanova, Margaret A. Brimble, Lindon W. K. Moodie, Johan Svenson
Summary: Small synthetic mimics of cationic antimicrobial peptides are promising compounds for treating persistent microbial infections. In this study, we investigated the activity of 19 linear cationic tripeptides against pathogenic bacteria and fungi, including clinical isolates. Modified hydrophobic amino acids inspired by bioactive marine secondary metabolites were used to create compounds with improved safety profiles. Several compounds showed high activity, particularly against fungal strains, with low off-target toxicity to erythrocytes and HeLa cells, indicating effective ways to tune the activity and selectivity of short antimicrobial peptides.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Saawan Kumar, Mie Riisom, Stephen M. F. Jamieson, Iman Kavianinia, Paul W. R. Harris, Nils Metzler-Nolte, Margaret A. Brimble, Christian G. Hartinger
Summary: Researchers conjugated a derivative of plecstatin-1 with peptides to enhance their targeting ability towards cancer cells. Metal-peptide conjugates were successfully synthesized and tested for their anticancer activity. Although the activity was relatively low, this study provides a potential strategy to design other metal complexes utilizing the targeting properties of peptides.
INORGANIC CHEMISTRY
(2023)
Editorial Material
Chemistry, Organic
Margaret A. Brimble, Lutz Ackermann, Yan-Mei Li, Monika Raj
Article
Virology
Alice-Roza Eruera, Alice M. McSweeney, Geena M. McKenzie-Goldsmith, Helen K. Opel-Reading, Simone X. Thomas, Ashley C. Campbell, Louise Stubbing, Andrew Siow, Jonathan G. Hubert, Margaret A. Brimble, Vernon K. Ward, Kurt L. Krause
Summary: Norovirus is a major cause of viral gastroenteritis worldwide. This study provides new insights for drug design against GII.4 genogroup of noroviruses.
Article
Chemistry, Organic
C. H. Andy Wong, Jonathan G. Hubert, Kevin J. Sparrow, Lawrence D. Harris, Peter C. Tyler, Margaret A. Brimble
Summary: This study presents a one-pot method for synthesizing similar fleximers using a bifunctional copper catalyst, which can generate aryl azides in situ and react with terminal alkynes to form triazoles.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiao-Bo Ding, Alexander Wung, Daniel P. Furkert, Margaret A. Brimble
Summary: We report a facile synthesis of the spirocyclic core of portimines A and B, two natural products with remarkable anticancer, anti-HIV, and antifouling activities. Our strategy involves a scalable Diels-Alder addition and a diastereoselective lactonization, enabling differentiation of the carbonyl groups. This approach overcame issues encountered in previous studies and provided a useful intermediate for the synthesis of portimines.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Shengping Zhang, Luis De Leon M. Rodriguez, Freda F. F. Li, Margaret A. Brimble
Summary: Selective modification of peptides and proteins at tyrosine residues has gained significant attention in recent years. This review provides a comprehensive summary of the latest advancements in tyrosine-selective cleavage, functionalization, and conjugation, complementing the existing body of work on site-specific modification of peptides and proteins. This research holds great relevance across various disciplines, including chemical, biological, medical, and material sciences.
Review
Biochemistry & Molecular Biology
Louise A. A. Stubbing, Jonathan G. G. Hubert, Joseph Bell-Tyrer, Yann O. O. Hermant, Sung Hyun Yang, Alice M. M. McSweeney, Geena M. M. McKenzie-Goldsmith, Vernon K. K. Ward, Daniel P. P. Furkert, Margaret A. A. Brimble
Summary: Viral infections are a major cause of acute morbidity in humans, and efforts have been made to develop drugs to treat associated diseases. Peptide-based enzyme inhibitors, short sequences of three or four residues, are being developed to enhance their activity and pharmaceutical properties. This review focuses on the design of inhibitors targeting highly conserved viral proteases 3C/3CL(pro), which play a key role in viral replication and have minimal similarity with mammalian proteases. The development of P-1 glutamine isosteres to generate potent inhibitors mimicking the natural substrate sequence is highlighted.
RSC CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Organic
Dennise Palpal-latoc, Margaret A. Brimble, Paul W. R. Harris, Aimee J. Horsfall
Summary: Macrocyclic depsipeptides, a class of bioactive natural products, have gained increasing attention due to their antimicrobial activity. However, the low yields in peptide ester (depsipeptide) bond formation have hindered the access to these structures for further studies. In this study, we systematically investigated the factors influencing on-resin depsipeptide bond formation using simplified sequences derived from antibiotic peptides. Our findings highlight the importance of reaction solvent and the number of amino acids in improving the acylation efficiency. The impact of protecting groups and stereochemistry was also evaluated, while the addition of surfactants and 6-ClHOBt showed little effect, and no significant difference was observed between different resins.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Organic
Marzieh Ahangarpour, Iman Kavianinia, Margaret A. Brimble
Summary: Over the last few decades, synthetic organic chemists have been focusing on the design and discovery of chemical reactions that enable the modification of proteins at specific sites. The selective functionalization of peptides and proteins offers an exciting opportunity for creating valuable multicomponent conjugates with diverse applications. Various strategies, including the thia-Michael click addition reaction, have been developed for the selective modification of cysteine-containing proteins. This review summarizes the different reactions for cysteine-selective peptide and protein modification, with a specific focus on the thia-Michael click addition reaction and its applications.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
