Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

• Long K. San,
• Sebastian Balser,
• Brian J. Reeves,
• Tyler T. Clikeman,
• Yu-Sheng Chen,
• Steven H. Strauss and
• Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

• have promising applications in optoelectronics. For example, investigation of the photophysical and electronic properties of ANTH began in the 1960s [1][2][3], and since then many new ANTH derivatives have been synthesized and explored for their use as fluorescent probes, organic semiconductors, and

• [20][21] and are not suitable as emitters for OLEDs or fluorescent probes. A family of perfluorobenzylated derivatives of another PAH, viz. perylene (PERY), was recently reported by our group [22]. We showed that the acceptor strength of PERY(BnF)n derivatives (n = 1–5) significantly increased with

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA

• Laurin Flemmich and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

• reasonably fast labeling kinetics and up to quantitative conversion under quasi-physiological conditions [4]. Obviously, the rapid dissemination and widespread acceptance of such labeling methods depend on fast and simple access to the small molecule probes. Here, we report efficient synthetic routes to

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

• Asahi Kanno,
• Ryo Tanifuji,
• Satoshi Yoshida,
• Sota Sato,
• Saori Maki-Yonekura,
• Kiyofumi Takaba,
• Jungmin Kang,
• Kensuke Tono,
• Koji Yonekura and
• Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

• avenues for the development of fluorescent probes based on the bis-THIQ alkaloidal scaffold. Further efforts to develop a concise and modular synthetic process for saframycins are currently underway. Representative bis-tetrahydroisoquinoline (THIQ) alkaloids and their analogues. Oxygen atoms on both the A

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• fluorescent chemosensors and probes [4][5][6], as well as materials for applications in organic light-emitting diodes (OLEDs) [7][8][9], organic field-effect transistors (OFETs) [10], and perovskite solar cells [11]. In this respect, replacing either one or more of the carbons or rings of a fluoranthene with

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• applied in various fields, including organometallic catalysis, dye-sensitized solar cells, sensing, artificial olfactory systems, photodynamic therapy (PDT), anticancer drugs, biochemical probes, and electrochemical devices. Relevant examples of these two pyrrolic macrocycles as metal-free organocatalysts

Chemical structure metagenomics of microbial natural products: surveying nonribosomal peptides and beyond

• Thomas Ma and
• John Chu

Beilstein J. Org. Chem. 2024, 20, 3050–3060, doi:10.3762/bjoc.20.253

• traditional medicine formulations [2]. Modern science has found that natural products are uniquely suited as the starting point for the development of new drugs [3][4]. They may serve as chemical probes and help confirm laboratory findings [5]; furthermore, entirely new physical and chemical principles are

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

• Anastasia I. Ershova,
• Sergey V. Fedoseev,
• Konstantin V. Lipin,
• Mikhail Yu. Ievlev,
• Oleg E. Nasakin and
• Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

• ], positron emission tomography (PET) imaging [24], fluorescent probes and labels [25][26][27] detecting H2S in foodstuff, water, and living cells [28], Fe3+ ions [29], Hg2+ ions [30], and cyanide anions [31], for acid–base vapor sensing [32], and as candidate material for photonics devices, optical switches

Investigation of a bimetallic terbium(III)/copper(II) chemosensor for the detection of aqueous hydrogen sulfide

• Parvathy Mini,
• Michael R. Grace,
• Genevieve H. Dennison and
• Kellie L. Tuck

Beilstein J. Org. Chem. 2024, 20, 2818–2826, doi:10.3762/bjoc.20.237

• not exhibit any discernible increase in luminescence. As far as we are aware, there are only three reports of lanthanide-based probes for the detection of gaseous hydrogen sulfide. Two are the europium(III) complexes from our group ([Eu(triazole-DPA)3·Cu]3+ and [Eu(DO2A)(triazole-DPA)·Cu]+), which are

Young investigators in natural products chemistry, biosynthesis, and enzymology

• Jeffrey D. Rudolf,
• Lena Barra and
• Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 2720–2721, doi:10.3762/bjoc.20.229

• clusters, and enzymes, development of chemical probes, biocatalysis and chemoenzymatic total synthesis, enzymatic mechanisms, and computational investigations of chemical structures and reactions. All of the major classes of natural products are represented here: nonribosomal peptides, ribosomally

Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels

• Connor R. M. MacDonald and
• Emily R. Draper

Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220

• use of fluorescence probes should be used in tandem with CLSM. For example, Raeburn et al. showed that the addition of molecular rotors and fluorescent dyes affects the bulk network of self-assembled materials using rheology. The co-packing was observed to alter rheological properties of the materials

• arising, for example, from differences in the rate of fibre growth and entanglements. The change in rheological properties when comparing the material and its co-assembly with the probe shows that addition of such probes may lead to measurements which do not truly represent the system of interest [19

• proportions of fluorescent probes in the self-assembled material will be much smaller than the example discussed here, it is important to use appropriate methods to show that the addition of any co-assembling component does not impact the nanoscale structure and bulk network. To our knowledge there are very

Improved deconvolution of natural products’ protein targets using diagnostic ions from chemical proteomics linkers

• Andreas Wiest and
• Pavel Kielkowski

Beilstein J. Org. Chem. 2024, 20, 2323–2341, doi:10.3762/bjoc.20.199

• study several small molecule probes were used including propargylamine, a glutamine derivative, N6-propargyladenosine and a tyrosine derivative to document the thiotriazole formation during CuAAC. The two selected examples of adenosine and glutamine-derived diagnostic ions are shown in Figure 8E. Since

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• ][12][13]. The most promising applications of truxene-based systems have been found in organic photovoltaics (OPVs), dye‐sensitized solar cells (DSSCs), fluorescent probes, organic thin‐film transistors (OTFTs), lasers, organic light emitting diodes (OLEDs), liquid crystals, non-linear optical (NLO

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

• Pengcheng Lu,
• Luis Juarez,
• Paul A. Wiget,
• Weihe Zhang,
• Krishnan Raman and
• Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

• spectra were acquired on Bruker 300 MHz spectrometers equipped with 5 mm BBFO probes. HRMS data were acquired using an Agilent 6530 LC/Q-TOF using a Dual AJS/ESI ion source, and the isotope 79 was used for HRMS analysis for any bromine-containing compounds. Synthesis All procedures and spectra can be

A new platform for the synthesis of diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions

• Vitor A. S. Almodovar and
• Augusto C. Tomé

Beilstein J. Org. Chem. 2024, 20, 1933–1939, doi:10.3762/bjoc.20.169

• used in a wide range of applications, namely as organic semiconductors [8], acceptors for organic solar cells [9][10], as fluorescent probes [11][12][13], or as photosensitizers for photodynamic therapy and antimicrobial photodynamic therapy [14][15][16][17]. DPP derivatives with improved performance

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

A Diels–Alder probe for discovery of natural products containing furan moieties

• Alyssa S. Eggly,
• Namuunzul Otgontseren,
• Carson B. Roberts,
• Amir Y. Alwali,
• Haylie E. Hennigan and
• Elizabeth I. Parkinson

Beilstein J. Org. Chem. 2024, 20, 1001–1010, doi:10.3762/bjoc.20.88

• -based probes; Introduction To date, natural products and their derivatives have served as the foundation of many pharmaceuticals used today. These compounds have activity against various diseases such as cancer, bacterial infections, and fungal infections, as well as other indications [1]. Specifically

• the MMFs specifically, we have developed a chemical probe that is capable of covalently binding to natural products containing furan moieties. Molecular probes are molecules that covalently bind to a compound of interest in order to make them easier to identify from the complex milieu of the cell

• supernatant. There are two main types of molecular probes based on their detection methods: imaging and UV–vis (Figure 2A). An imaging probe contains a mass spectrometry (MS) tag, oftentimes a halogen with a distinct isotopic ratio such as chlorine or bromine. A UV–vis probe contains a UV-tag, such as an

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

• Victoria M. Alpatova,
• Evgeny G. Rys,
• Elena G. Kononova and
• Valentina A. Ol'shevskaya

Beilstein J. Org. Chem. 2024, 20, 767–776, doi:10.3762/bjoc.20.70

• biosensors, bioimaging probes, and especially as photosensitizers (PSs) in photodynamic therapy (PDT) [2]. PDT is a treatment modality that uses the combination of a non-toxic PS, oxygen, and light to treat diseases ranging from cancer to age-related macular degeneration and antibiotic-resistant infections

Development of a chemical scaffold for inhibiting nonribosomal peptide synthetases in live bacterial cells

• Fumihiro Ishikawa,
• Sho Konno,
• Hideaki Kakeya and
• Genzoh Tanabe

Beilstein J. Org. Chem. 2024, 20, 445–451, doi:10.3762/bjoc.20.39

• previously described an activity-based protein profiling (ABPP) strategy for NRPSs using ABPs that target A-domains (Figure 2b) [13][14][15]. The probes comprise an aminoacyl-AMS ligand and a photoaffinity group with clickable alkyne functionality appended to the 2′-OH group of adenosine. A complex structure

• probes (AA-AMS-BPyne) can selectively label the A-domains corresponding to the amino acid of the ligand in both recombinant enzymes and proteomes. We recently reported that these probes can be used to label the A-domains of endogenous NRPSs in live bacterial cells [17][18][19]. The intracellular labeling

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

• Eugeny Ivakhnenko,
• Vasily Malay,
• Pavel Knyazev,
• Nikita Merezhko,
• Nadezhda Makarova,
• Oleg Demidov,
• Gennady Borodkin,
• Andrey Starikov and
• Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

• probes, organic light-emitting diodes, and organic solar cells [2][7][8][9]. The principal way for the preparation of these heterocycles involves the coupling of 3H-phenoxazin-3-ones with variously functionalized aromatic amines. This is followed by the cyclization of the initially formed adducts [10][11

Elucidating the glycan-binding specificity and structure of Cucumis melo agglutinin, a new R-type lectin

• Jon Lundstrøm,
• Emilie Gillon,
• Valérie Chazalet,
• Nicole Kerekes,
• Antonio Di Maio,
• Ten Feizi,
• Yan Liu,
• Annabelle Varrot and
• Daniel Bojar

Beilstein J. Org. Chem. 2024, 20, 306–320, doi:10.3762/bjoc.20.31

• garnered attention for their roles as laboratory probes and potential therapeutics. Here, we report the discovery and characterization of Cucumis melo agglutinin (CMA1), a new R-type lectin from melon. Our findings reveal CMA1’s unique glycan-binding profile, mechanistically explained by its 3D structure

• their non-reducing end and, thus, do not provide terminal GalNAc epitopes for binding. Further, while CMA1 did also bind to GalNAc-terminated GAGs (e.g., CSC-5, CSA-5), we measured higher binding to similar GAGs without the terminal GalNAc in several cases (Figure 2d,e). While some of the GAG probes

• , containing Fucα1-2Gal or GalNAc epitopes, were on average not bound by RCA1 (the exception being sequences in which there was an additional free Galβ terminus). Similarly, most chondroitin sulfate probes were not bound by RCA1. This gives rise to the conclusion that CMA1 does not merely tolerate but rather

Using the phospha-Michael reaction for making phosphonium phenolate zwitterions

• Matthias R. Steiner,
• Max Schmallegger,
• Larissa Donner,
• Johann A. Hlina,
• Christoph Marschner,
• Judith Baumgartner and
• Christian Slugovc

Beilstein J. Org. Chem. 2024, 20, 41–51, doi:10.3762/bjoc.20.6

• candidates as well. Ortho-hydroxy-substituted phosphines have been mainly used as chelating ligands for metal complexes until recently [16][17][18]. Further, ortho-hydroxy phosphines have been used for the synthesis of probes in metabolic labeling [19], as a photocatalyst in the defluoroalkylation of

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• extensively studied is 2-heptyl-4-quinolone (HHQ) and its oxygenated derivatives 2-heptyl-3-hydroxy-4-quionolone (PQS) and 4-hydroxy-2-heptylquinoline-N-oxide (HQNO) [27][36][37][38]. Considering the importance of 4-quinolones as potential drugs and biological probes, it is not surprising that the development

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• formulation, a solution containing only liposomes was used as the blank solution. The membrane permeability study by fluorescence spectroscopy The membrane permeability is commonly evaluated by following the leakage of self-quenching probes such as SRB from liposomes [14]. Indeed, a fluorescence auto

A fluorescent probe for detection of Hg²⁺ ions constructed by tetramethyl cucurbit[6]uril and 1,2-bis(4-pyridyl)ethene

• Xiaoqian Chen,
• Naqin Yang,
• Yue Ma,
• Xinan Yang and
• Peihua Ma

Beilstein J. Org. Chem. 2023, 19, 864–872, doi:10.3762/bjoc.19.63

• = 0.9926, and the limit of detection is 4.12 × 10−8 mol·L−1. The fluorescent probe can be used to detect the concentration of Hg2+ ions in aqueous solution, and provides a theoretical basis for the development of new fluorescent probes for detecting heavy metal ions. Keywords: 1,2-bis(4-pyridyl)ethane

• cucurbit[n]uril fluorescent probes has become increasingly mature [9][28][29][30][31]. For example, the host–guest fluorescent probe of cucurbit[10]uril (Q[10]) and the fluorescent dye acridine (AD) was used to identify the pesticide dodine (DD) [32]; a fluorescent probe of cucurbit[10]uril (Q[10]) and

• , which provides convenience for studying the host–guest chemistry of TMeQ[6] and constructing fluorescent probes in aqueous solution [37][38]. There is a π–π conjugation effect between the carbon–carbon double bond and the pyridine ring in 1,2-bis(4-pyridyl)ethene (G), which determines its ultraviolet

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• larger than those measured by TEM. This is because TEM probes samples in the dry state, while DLS examines samples in the solvated state, where the solvent molecules are associated with the nanoparticles. The zeta potentials of these three TBTQ-C6/CS-TPE nanoparticles were further measured to determine