4.7 Article

Selective ratiometric detection of H2O2 in water and in living cells with boronobenzo[b]quinolizinium derivatives

期刊

CHEMICAL COMMUNICATIONS
卷 50, 期 60, 页码 8242-8245

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4cc02283a

关键词

-

资金

  1. Deutsche Forschungsgemeinschaft

向作者/读者索取更多资源

Boronobenzo[b]quinolizinium derivatives exhibit several favorable properties for the fluorimetric detection of hydrogen peroxide, namely quantitative transformation to a product whose emission maximum is well separated from the one of the substrate, water solubility, and the ability to operate in living cells.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Review Chemistry, Organic

Ligands for Abasic Site-containing DNA and their Use as Fluorescent Probes

Julika Schlosser, Heiko Ihmels

Summary: Apurinic and apyrimidinic sites are residues of duplex DNA with missing bases, which can be used for DNA repair and provide binding sites for guest molecules. Ligands that selectively bind to abasic sites can be used for analytical and therapeutic purposes. This review provides an overview of different classes of ligands for abasic site-containing DNA, including covalently and non-covalently binding substrates. It also summarizes reports on the fluorescent response of ligands upon binding to AP-DNA and presents a perspective for future development of fluorescent probes for AP-DNA.

CURRENT ORGANIC SYNTHESIS (2023)

Article Chemistry, Medicinal

Cinnamic acid derivatives linked to arylpiperazines as novel potent inhibitors of tyrosinase activity and melanin synthesis

Romeo Romagnoli, Paola Oliva, Filippo Prencipe, Stefano Manfredini, Federico Ricci, Diana Corallo, Sanja Aveic, Elena Mariotto, Giampietro Viola, Roberta Bortolozzi, Maria Paola Germano, Laura De Luca

Summary: A series of cinnamide compounds linked with 1-aryl piperazines, derived from cinnamic acid derivatives, were synthesized and evaluated for their inhibitory activity against mushroom tyrosinase. The presence of a 3-chloro-4-fluorophenyl moiety at the N-1 position of the piperazine ring was found to be essential for a potent inhibitory effect. Molecular docking studies were conducted to investigate the interactions between the compounds and the active site of the enzyme. Some of the highly active compounds also showed potential in inhibiting melanogenesis. However, certain compounds exhibited toxicity at high concentrations.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2022)

Article Chemistry, Medicinal

Design, Synthesis and Biological Investigation of 2-Anilino Triazolopyrimidines as Tubulin Polymerization Inhibitors with Anticancer Activities

Romeo Romagnoli, Paola Oliva, Filippo Prencipe, Stefano Manfredini, Federica Budassi, Andrea Brancale, Salvatore Ferla, Ernest Hamel, Diana Corallo, Sanja Aveic, Lorenzo Manfreda, Elena Mariotto, Roberta Bortolozzi, Giampietro Viola

Summary: A study was conducted to synthesize a series of new compounds with potential antitumor activity. Among these compounds, three showed significantly higher activity compared to others. These compounds demonstrated strong antiproliferative effects on different cancer cell lines and were able to induce apoptosis through various mechanisms. In vivo experiments using a zebrafish model also showed promising results in reducing tumor mass.

PHARMACEUTICALS (2022)

Article Chemistry, Medicinal

New bioisosteric sulphur-containing choline kinase inhibitors with a tracked mode of action

Pilar M. Luque-Navarro, M. Paz Carrasco-Jimenez, Laura Goracci, Jose M. Paredes, Laura Espinar-Barranco, Javier Valverde-Pozo, Archimede Torretta, Emilio Parisini, Elena Mariotto, Chiara Marchioro, Alejandro Laso, Carmen Marco, Giampietro Viola, Daniela Lanari, Luisa Carlota Lopez Cara

Summary: We propose a series of bioisosteric inhibitors based on the introduction of sulphur, which are effective in inhibiting human choline kinase and reducing phosphatidylcholine biosynthesis. PL 48, PL 55, and PL 69 are identified as the most active compounds in the series. These compounds induce apoptosis through the mitochondrial pathway and significantly reduce the expression of anti-apoptotic protein Mcl-1.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2023)

Article Chemistry, Organic

Monoaryl-Substituted Norbornadiene Photoswitches as Molecular Solar Thermal Energy Storage Compounds: Synthesis and Investigation

Robin Schulte, Sandra Afflerbach, Heiko Ihmels

Summary: In this study, eight monoaryl-substituted norbornadienes with naphthyl, anthracenyl, or donor-acceptor-phenyl substituents were presented as improved photochromic systems for efficient reversible conversion of light into chemical energy. These compounds were synthesized by Suzuki-Miyaura coupling reactions and their absorption properties, key parameters of photochromic equilibrium, and energy storage density were examined. The results showed that these compounds had favorable properties for chemical energy storage, especially 2-(1-naphthyl)norbornadiene, which exhibited a pronounced red shift of absorption, long half-life (35 d), and relatively high energy storage density (361 KJ/Kg) of the respective quadricyclane. Therefore, monoaryl-norbornadienes should be considered as a useful and complementary class of compounds in the development of efficient molecular solar thermal energy storage (MOST) compounds.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Organic

Switching between DNA binding modes with a photo- and redox-active DNA-targeting ligand

Christoph Dohmen, Heiko Ihmels

Summary: A disulfide-functionalized bis-benzo[b]quinolizinium undergoes a quantitative intramolecular [4 + 4] photocycloaddition reaction to form cyclomers. Both the bis-quinolizinium and the photocyclomers react with glutathione (GSH) or dithiothreitol (DTT) to yield 9-(sulfanylmethyl)benzo[b]quinolizinium as the sole product. The different DNA-binding properties of the components in this reaction sequence allow for external control and switching of DNA association.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Article Plant Sciences

Iboga-type alkaloids from the leaves of Tabernaemontana penduliflora (Apocynaceae)

Alexis Bienvenue Nama, Thomas Paululat, Guy Roland Ebede, Patrick Herve Diboue Betote, Dieudonne Emmanuel Pegnyemb, Joseph Thierry Ndongo, Heiko Ihmels, Hartmut Laatsch

Summary: Isolation studies on Tabernaemontana penduliflora leaves led to the discovery of two previously undescribed indole alkaloids, 7,10-dihydroxyindolenine (1a) and pendulifloramine (2), along with four known compounds. The structures of 1a and 2 were determined using NMR, mass spectra, and computer-assisted structure elucidation. Both compounds exhibited moderate radical-trapping activity and anti-inflammatory properties.

PHYTOCHEMISTRY LETTERS (2023)

Article Chemistry, Multidisciplinary

Selective Fluorimetric Detection of Pyrimidine Nucleotides in Neutral Aqueous Solution with a Styrylpyridine-Based Cyclophane

Julika Schlosser, Julian F. M. Hebborn, Daria V. Berdnikova, Heiko Ihmels

Summary: A cyclophane containing styrylpyridine and diethylenetriamine linkers was used as a host system to study the association with nucleotides through photometric and fluorimetric titrations. 1:1 complexes were formed with log K-b values ranging from 2.3 to 3.2 for pyrimidine nucleotides and 3.8 to 5.0 for purine nucleotides. The fluorimetric response to complex formation differed depending on the type of nucleotide, with quenching observed for purine bases and significant fluorescence enhancement for pyrimidine bases.

CHEMISTRY-SWITZERLAND (2023)

Article Chemistry, Multidisciplinary

Bis- and Tris-norbornadienes with High Energy Densities for Efficient Molecular Solar Thermal Energy Storage

Robin Schulte, Sandra Afflerbach, Thomas Paululat, Heiko Ihmels

Summary: Molecular solar thermal energy storage (MOST) systems using phenyl- and naphthyl-linked bis- and tris-norbornadienes show high energy densities and have potential for efficient solar energy conversion and storage. These substrates were synthesized using Suzuki-Miyaura coupling reactions and their absorption properties and characteristics for MOST applications were investigated. The norbornadiene derivatives showed absorption onsets at 386 nm and photoisomerization quantum yields of 56% per photoisomerization event. The resulting quadricyclane products have half-lifes up to 14 days and very high energy densities of up to 734 kJ/kg.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Chemistry, Physical

Photoinduced Reactions of Styrylpyridine Derivatives for the In Situ Formation of Selective Ligands for Apyrimidinic DNA

Julika Schlosser, Nils Stotzel, Yuri Fedorov, Heiko Ihmels

Summary: The photocyclization reaction of sterically demanding styrylpyridine derivatives was investigated, and the interaction with DNA was found to depend on the DNA type. Specifically, this ligand preferentially binds to DNA containing abasic sites, and the complex formation can be achieved by irradiation of the styrylpyridine substrate.

CHEMPHOTOCHEM (2023)

Article Chemistry, Organic

Switching between DNA binding modes with a photo- and redox-active DNA-targeting ligand, part II: the influence of the substitution pattern

Christoph Dohmen, Heiko Ihmels

Summary: We present a disulfide-functionalized photoactive DNA ligand that can control its DNA-binding properties by a photocycloaddition reaction and the redox reactivity of the sulfide/disulfide functionalities. The ligand initially binds to DNA through intercalation and groove-binding, but the binding is interrupted by an intramolecular [4 + 4] photocycloaddition. Cleavage of these cycloadducts with dithiothreitol (DTT) temporarily regains DNA-intercalating ligand and eventually converts it into a non-binding benzothiophene.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Article Biochemistry & Molecular Biology

Fluorimetric Cell Analysis with 9-Aryl-Substituted Berberine Derivatives as DNA-Targeting Fluorescent Probes

Philipp Gross, Renee S. Hoffmann, Mareike Mueller, Holger Schoenherr, Heiko Ihmels

Summary: DNA-sensitive fluorescent light-up probes based on berberine were developed, which exhibit predictable fluorescence quenching in aqueous solution and a fluorescence light-up effect upon DNA binding. These probes have high affinity for DNA and can generate distinct staining patterns in eukaryotic cells.

CHEMBIOCHEM (2023)

Article Chemistry, Medicinal

Design, synthesis and biological evaluation of novel 2,4-thiazolidinedione derivatives able to target the human BAG3 protein

Federica Budassi, Chiara Marchioro, Martina Canton, Annagiulia Favaro, Mattia Sturlese, Chiara Urbinati, Marco Rusnati, Romeo Romagnoli, Giampietro Viola, Elena Mariotto

Summary: A new compound FB49 with high affinity to BAG3 protein has been discovered, which exhibits antiproliferative activity in various human tumor cell lines without toxicity to healthy cells. Moreover, FB49 can block cell cycle and induce apoptosis and autophagy.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2023)

Meeting Abstract Oncology

METABOLIC REWIRING SUPPORT THE ONSET OF CHEMOTHERAPY RESISTANCE IN MEDULLOBLASTOMA

Roberta Bortolozzi, Elena Mariotto, Elena Rampazzo, Lorenzo Manfreda, Chiara Marchioro, Fatlum Rruga, Luca Persano, Giampietro Viola

NEURO-ONCOLOGY (2022)

Meeting Abstract Oncology

MULTI-OMICS INVESTIGATION OF MEDULLOBLASTOMA RESISTANT MODELS REVEALS FUNCTIONAL ASSOCIATION BETWEEN INTRACELLULAR REGULATORY NETWORKS AND DRUG SUSCEPTIBILITY

Elena Mariotto, Elena Rampazzo, Roberta Bortolozzi, Fatlum Rruga, Lorenzo Manfreda, Chiara Marchioro, Silvia Bresolin, Giampietro Viola, Luca Persano

NEURO-ONCOLOGY (2022)

Review Chemistry, Multidisciplinary

Trap suppression in ordered organic photovoltaic heterojunctions

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

Controversial mechanism of simultaneous photocatalysis and Fenton-based processes: additional effect or synergy?

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

Polymerization of monomer aggregates for tailoring and patterning water wettability

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

Pd/Brønsted acid catalysed intramolecular N-allylation of indoles and pyrroles with alkynes for the synthesis of N-fused heterocycles

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

Rh(III)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides

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

Modified minimal-size fragments of heparan sulfate as inhibitors of endosulfatase-2 (Sulf-2)

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

Reductive cyclodimerization of chalcones: exploring the self-adaptability of galvanostatic electrosynthesis

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

Rh(III)-catalyzed oxidative [4+2] annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols

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

PbTeB4O9: a lead tellurium borate with unprecedented fundamental building block [B4O10] and large birefringence

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

Wafer-scale synthesis of two-dimensional ultrathin films

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

Precise design of copolymer-conjugated nanocatalysts for active electron transfer

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)