ChemBioChem最新文献

Cucurbit[7]uril-Styryl dye complexes for Fluorescent Recognition of DNA and Cell Imaging.

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-07 DOI: 10.1002/cbic.202400892

Ekaterina Y Chernikova, Maria A Ustimova, Yuri V Fedorov, Polina A Chernikova, Ivan A Godovikov, Nelly S Chmelyuk, Maxim A Abakumov, Olga A Fedorova

{"title":"Cucurbit[7]uril-Styryl dye complexes for Fluorescent Recognition of DNA and Cell Imaging.","authors":"Ekaterina Y Chernikova, Maria A Ustimova, Yuri V Fedorov, Polina A Chernikova, Ivan A Godovikov, Nelly S Chmelyuk, Maxim A Abakumov, Olga A Fedorova","doi":"10.1002/cbic.202400892","DOIUrl":"https://doi.org/10.1002/cbic.202400892","url":null,"abstract":"This paper focused on the DNA-binding properties of novel dicationic cyanine dyes, in which pyridinium centers are linked by bridges of different functionalities. We found that dye 1, bearing a flexible butyl-4-methylpyridinium terminal fragment, has the ability to bind to the DNA groove. The attachment of a quite rigid para-xylylene-4-methylpyridinium unit as a terminal group in dye 2 contributed to dual DNA-binding modes: intercalation and groove binding. We tested the encapsulation ability and the effect on the dye-DNA binding mode by using a synthetic molecular container such as CB[7]. Unexpectedly, monitoring dye-DNA interaction in the presence of CB[7] revealed that dye molecules partially remain in DNA frameworks, even though they had a higher affinity towards CB[7]. In the case of dye 1, the transformation of dimeric forms to the left-handed aggregates to yield a ternary system CB[7]-dye-DNA occurred. For dye 2, reversibility of intercalation and a slight right-handed aggregation templated by DNA are observed. A cytotoxicity and ability of dyes to stain the living cells in their free and encapsulated forms have been investigated. These findings provide useful information about ligand-DNA interactions, which are valuable for the rational design of drug delivery systems and platforms for cellular imaging and therapy.","PeriodicalId":140,"journal":{"name":"ChemBioChem","volume":" ","pages":"e202400892"},"PeriodicalIF":2.6,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143571777","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Lienhwalides: Unique Tropolone-Maleidride Hybrids from Hypoxylon lienhwacheense.

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-07 DOI: 10.1002/cbic.202500037

Katharina Schmidt, Esteban Charria-Girón, Tatiana E Gorelik, Christian Kleeberg, Jackson M Muema, Simone Heitkämper, Bart Verwaaijen, Eric Kuhnert, Jennifer Gerke, Jörn Kalinowski, Kevin D Hyde, Marc Stadler, Russell Cox, Frank Surup

{"title":"Lienhwalides: Unique Tropolone-Maleidride Hybrids from Hypoxylon lienhwacheense.","authors":"Katharina Schmidt, Esteban Charria-Girón, Tatiana E Gorelik, Christian Kleeberg, Jackson M Muema, Simone Heitkämper, Bart Verwaaijen, Eric Kuhnert, Jennifer Gerke, Jörn Kalinowski, Kevin D Hyde, Marc Stadler, Russell Cox, Frank Surup","doi":"10.1002/cbic.202500037","DOIUrl":"https://doi.org/10.1002/cbic.202500037","url":null,"abstract":"Hypoxylon lienhwacheense, a fungal species with an unclear taxonomic placement within the Hypoxylaceae, presented a highly rare stromatal secondary metabolite profile. Isolation of its major stromatal constituents led to the discovery of a novel tropolone-maleidride hybrid molecule, lienhwalide A 5, in addition to the known cordyanhydride B 6, its new derivative 7, and binaphthalenetetraol 8. Unexpectedly, H. lienhwacheense produced in liquid cultures various lienhwalide A congeners 9-11. Their structures and relative configurations were elucidated using HRMS and NMR spectroscopy, with their absolute configurations determined using X-ray analysis of a semisynthetic brominated derivative of 9 and synthesising MTPA-esters of 11. Feeding experiments with 13C-labelled precursors (13C-methionine, 1-13C- and U-13C6-glucose) revealed insights into the biogenesis of tropolone and maleidride moieties, according to 13C couplings and INADEQUATE NMR data. Genome analysis identified two separate BGCs responsible for these moieties, and heterologous expression experiments provided further insights into the interplay of both clusters during the biosynthesis of these hybrid natural products. Remarkably, lienhwalides exhibited reduced toxicity and enhanced antibacterial selectivity compared to related fungal tropolones.","PeriodicalId":140,"journal":{"name":"ChemBioChem","volume":" ","pages":"e202500037"},"PeriodicalIF":2.6,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143571779","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Expanding the substrate scope of C-N lyases by homologue discovery.

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-07 DOI: 10.1002/cbic.202500068

Laura Bothof, Riccardo Iacovelli, Pieter Tepper, Gerrit J Poelarends

{"title":"Expanding the substrate scope of C-N lyases by homologue discovery.","authors":"Laura Bothof, Riccardo Iacovelli, Pieter Tepper, Gerrit J Poelarends","doi":"10.1002/cbic.202500068","DOIUrl":"https://doi.org/10.1002/cbic.202500068","url":null,"abstract":"The aspartase/fumarase superfamily is a group of homologous enzymes that promote the reversible elimination of functional groups from succinyl-containing compounds, typically yielding fumarate as the common product. Over the past 50 years, members of this superfamily have continuously demonstrated their power and significance as biocatalysts. This is exemplified by ethylenediamine-N,N-disuccinic acid (EDDS) lyase, which was shown to have an extraordinary amine scope, enabling the production of a wide variety of N-substituted aspartic acids. In this work, we used this enzyme as a starting point for a homology-based strategy to expand the biocatalytic toolbox of C-N bond-forming enzymes. We selected 13 enzymes for biochemical characterization, and identified several EDDS-lyase homologues that can accept L-amino acids as substrates in the hydroamination of fumarate to produce the corresponding aminopolycarboxylic acids. Lastly, we carried out a sequence similarity network analysis of the aspartase/fumarase superfamily, which suggests that EDDS lyase and its homologues may represent a distinct isofunctional subfamily, laying the foundations for future enzyme discovery and engineering campaigns.","PeriodicalId":140,"journal":{"name":"ChemBioChem","volume":" ","pages":"e202500068"},"PeriodicalIF":2.6,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143571778","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Genetically Encoded Fluorescent and Bioluminescent Probes for HDAC8.

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-06 DOI: 10.1002/cbic.202500096

Ying Wang, Lin Sun, Weimin Xuan

引用次数: 0

Characterization of ActVI-ORF3 and ActVI-ORF4 as Lactonizing and Delactonizing Enzymes in Relation to Metabolic Flux in Actinorhodin Biosynthesis.

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-06 DOI: 10.1002/cbic.202500049

Makoto Hashimoto, Kazuki Ishikawa, Yuri Fukushima, Sarina Shimazu, Mizuha Yabuzaki, Yuka Kamezawa, Takaaki Taguchi, Koji Ichinose

{"title":"Characterization of ActVI-ORF3 and ActVI-ORF4 as Lactonizing and Delactonizing Enzymes in Relation to Metabolic Flux in Actinorhodin Biosynthesis.","authors":"Makoto Hashimoto, Kazuki Ishikawa, Yuri Fukushima, Sarina Shimazu, Mizuha Yabuzaki, Yuka Kamezawa, Takaaki Taguchi, Koji Ichinose","doi":"10.1002/cbic.202500049","DOIUrl":"https://doi.org/10.1002/cbic.202500049","url":null,"abstract":"Actinorhodin (ACT) from Streptomyces coelicolor A3(2) is an aromatic polyketide antibiotic with a benzoisochromanequinone (BIQ) skeleton. Although actVI-ORF3 and actVI-ORF4 are not essential for ACT biosynthesis, homologous genes to these are present in the biosynthetic gene clusters of BIQ lactones. In this study, ActVI-ORF3 was identified as a cofactor-independent enzyme with lactonization activity, using ACT as a substrate. ActVI-ORF3 recognized dihydrokalafungin and 8-hydroxykalafafungin, which share the same pyran-ring configuration as ACT, but not nanaomycin A, which has an opposite configuration. In contrast, ActVI-ORF4 functioned as an NAD(P)-dependent oxidoreductase, catalyzing the delactonization of BIQ lactones. Conversion experiments using isotopically labeled compounds revealed that both lactonization and delactonization reactions of these enzymes yielded products in which the carboxyl oxygen at the C1 position was retained. Subsequently, we reexamined the accumulation of ACT-related compounds in the actVI-ORF3 and actVI-ORF-4 disruptants. The results suggested that ACT intermediates are predominantly pooled in the bacteria as (S)-DNPA rather than in lactone-form. The contribution of ActVI-ORF4 to metabolic flux is not significant, and endogenous reductases can convert these intermediates to the dihydro form, which subsequently re-enters the ACT biosynthetic pathway.","PeriodicalId":140,"journal":{"name":"ChemBioChem","volume":" ","pages":"e202500049"},"PeriodicalIF":2.6,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143571776","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Donor-acceptor (perylenethienyl)ethylenes as singlet oxygen-photogenerating viral inhibitors.

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-05 DOI: 10.1002/cbic.202401019

Vladimir A Korshun, Maxim S Krasilnikov, Roman V Mazur, Stepan P Chumakov, Vladislav S Denisov, Efim A Goldenderg, Yan I Nikolaenko, Evgeny A Bersenev, Timofei D Nikitin, Polina S Orinicheva, Vladimir A Brylev, Evgeny L Gulyak, Vera A Alferova, Daniil A Gvozdev, Alexey V Ustinov

{"title":"Donor-acceptor (perylenethienyl)ethylenes as singlet oxygen-photogenerating viral inhibitors.","authors":"Vladimir A Korshun, Maxim S Krasilnikov, Roman V Mazur, Stepan P Chumakov, Vladislav S Denisov, Efim A Goldenderg, Yan I Nikolaenko, Evgeny A Bersenev, Timofei D Nikitin, Polina S Orinicheva, Vladimir A Brylev, Evgeny L Gulyak, Vera A Alferova, Daniil A Gvozdev, Alexey V Ustinov","doi":"10.1002/cbic.202401019","DOIUrl":"https://doi.org/10.1002/cbic.202401019","url":null,"abstract":"The development of broad-spectrum antiviral drugs effective against a wide variety of viruses is of significant practical importance. Derivatives of perylene, a pentacyclic aromatic hydrocarbon, demonstrate pronounced antiviral activity. These compounds primarily act as membrane-active singlet oxygen photogenerators, disrupting virions and inhibiting their fusion with a host cell membrane. Modifying the perylene core allows for chemical diversification of antiviral photosensitizers. Additionally, achieving a bathochromic shift in absorbance is crucial for effective treatment of superficial lesions, as it facilitates deeper tissue penetration of therapeutic light. In this work, donor-acceptor perylenylethylenes and (perylenethienyl)ethylenes were synthesized and evaluated for their spectral properties, singlet oxygen photogeneration and inhibition activity against vesicular stomatitis virus (VSV), a representative enveloped virus. The incorporation of a thiophene unit into the molecule significantly enhanced both the singlet oxygen generation ability and the antiviral activity. These findings provide useful insights into the relationship between the structure, spectral/photochemical properties and biological activity of perylene-based photosensitizers.","PeriodicalId":140,"journal":{"name":"ChemBioChem","volume":" ","pages":"e202401019"},"PeriodicalIF":2.6,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143555404","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Concept and Development of Metal-Framework Nucleic Acids.

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-05 DOI: 10.1002/cbic.202401067

Li Sun, Xiangyuan Ouyang

{"title":"Concept and Development of Metal-Framework Nucleic Acids.","authors":"Li Sun, Xiangyuan Ouyang","doi":"10.1002/cbic.202401067","DOIUrl":"https://doi.org/10.1002/cbic.202401067","url":null,"abstract":"Based on the Watson-Crick base pairing principle, precisely programmable metal framework nucleic acids (mFNA) have evolved from one-dimensional to three-dimensional nanoscale structures, a technological advancement attributed to progress in DNA nanotechnology. mFNA are a new type of nanomaterial formed by using FNAs as precise templates to guide the ordered assembly and self-assembly of metal ions, metal salts (such as calcium phosphate, calcium carbonate, etc.), metal nanoclusters, metal nanoparticles, or metal oxide nanoparticles. Compared to traditional FNAs, mFNA not only inherits the powerful programmed self-assembly capabilities of nucleic acids but also incorporates the unique physicochemical properties of inorganic metal nanomaterials. This intersection of organic and inorganic chemistry presents broad application prospects in fields such as biology, chemistry, materials science, and energy science. This review, based on the principles related to FNAs, introduces the concept of mFNA for the first time, aiming to explore the fundamental connections between nanoscale FNAs and metal materials. Additionally, the article focuses on the construction methods and functional characteristics of mFNA. Finally, the current challenges faced by mFNA are reviewed, and their future development is anticipated, providing detailed information for a comprehensive understanding of the research progress in mFNA.","PeriodicalId":140,"journal":{"name":"ChemBioChem","volume":" ","pages":"e202401067"},"PeriodicalIF":2.6,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143555382","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Front Cover: Discovery of 18F Labeled AZD5213 Derivatives as Novel Positron Emission Tomography (PET) Radioligands Targeting Histamine Subtype-3 Receptor (ChemBioChem 5/2025)

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-03 DOI: 10.1002/cbic.202580501

Zhendong Song, Yinlong Li, Kenneth Dahl, Ahmad Chaudhary, Zhenkun Sun, Xin Zhou, Jiahui Chen, Yabiao Gao, Jian Rong, Chunyu Zhao, Jimmy S. Patel, Lee Collier, Chongzhao Ran, Chuangyan Zhai, Linqi Zhang, Achi Haider, Kim S. Mühlfenzl, Hongjie Yuan, Charles S. Elmore, Magnus Schou, Steven H Liang

{"title":"Front Cover: Discovery of 18F Labeled AZD5213 Derivatives as Novel Positron Emission Tomography (PET) Radioligands Targeting Histamine Subtype-3 Receptor (ChemBioChem 5/2025)","authors":"Zhendong Song, Yinlong Li, Kenneth Dahl, Ahmad Chaudhary, Zhenkun Sun, Xin Zhou, Jiahui Chen, Yabiao Gao, Jian Rong, Chunyu Zhao, Jimmy S. Patel, Lee Collier, Chongzhao Ran, Chuangyan Zhai, Linqi Zhang, Achi Haider, Kim S. Mühlfenzl, Hongjie Yuan, Charles S. Elmore, Magnus Schou, Steven H Liang","doi":"10.1002/cbic.202580501","DOIUrl":"https://doi.org/10.1002/cbic.202580501","url":null,"abstract":"The histamine subtype 3 receptor (H3R) is mainly expressed in the brain, where it plays a key role in various neurological functions. This brain imaging, featuring glowing neural connections, highlights the high expression of H3R. The molecular structure approaching the brain represents new Positron Emission Tomography (PET) probes for precise brain imaging. The light trail indicates the potential of this PET probe to visualize H3R, providing insights into brain function and pathology. More details can be found in Research Article 10.1002/cbic.202400655 by Magnus Schou, Steven H Liang, and co-workers.<figure>\u0000 <div><picture>\u0000 <source></source></picture>\u0000 </div>\u0000 </figure>\u0000 ","PeriodicalId":140,"journal":{"name":"ChemBioChem","volume":"26 5","pages":""},"PeriodicalIF":2.6,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cbic.202580501","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143535945","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Cover Feature: Compartmentalized Sesquiterpenoid Biosynthesis and Functionalization in the Chlamydomonas reinhardtii Plastid (ChemBioChem 5/2025)

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-03 DOI: 10.1002/cbic.202580504

Sergio Gutiérrez, Sebastian Overmans, Gordon B. Wellman, Kyle J. Lauersen

引用次数: 0

Cover Feature: Dinuclear Ru(II) Complexes Containing Tetrapyrido[3,2-a : 2,3-c : 3,2-h : 2′′′,3′′′-j]Phenazine Ligand for Biomedical Applications (ChemBioChem 5/2025)

IF 2.6 4区生物学

ChemBioChem Pub Date : 2025-03-03 DOI: 10.1002/cbic.202580502

Rajesh Kushwaha, Dr. Samya Banerjee

引用次数: 0