One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline

• Jiawei Niu,
• Yuhui Wang,
• Shenghu Yan,
• Yue Zhang,
• Xiaoming Ma,
• Qiang Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2024, 20, 912–920, doi:10.3762/bjoc.20.81

• [10][11] (Figure 1). The tetrazole ring can also be found in functional materials for photography, imaging, and military applications [12][13][14][15][16][17]. The hydroisoquinoline core, such as 1,2,3,4-tetrahydroisoquinoline and pyrazino[2,1-a]isoquinolinone, is also a privileged heterocycle which

Synthesis and characterization of water-soluble C₆₀–peptide conjugates

• Yue Ma,
• Lorenzo Persi and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2024, 20, 777–786, doi:10.3762/bjoc.20.71

• photodynamic therapy photosensitizers (PDT PSs) [41] and magnetic resonance imaging contrast agents (MRI CAs) [42], which are the most relevant topics in fullerene biological studies. Aggregated fullerenes in the micelle structure may cause self-quenching of the excited state of PS fullerenes or may inhibit

Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

• Julika Schlosser,
• Olga Fedorova,
• Yuri Fedorov and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11

• compounds, which have been employed in biomedical imaging and as potential DNA-targeting anticancer agents [14][15][16][17]. More recently, a benzoquinolizinium-based fluorescent dye was reported to be used as imaging agent for inflammation and for the evaluation of the physiological response to anti

Electron-beam-promoted fullerene dimerization in nanotubes: insights from DFT computations

• Laura Abella,
• Gerard Novell-Leruth,
• Josep M. Ricart,
• Josep M. Poblet and
• Antonio Rodríguez-Fortea

Beilstein J. Org. Chem. 2024, 20, 92–100, doi:10.3762/bjoc.20.10

• molecules on surfaces like graphene or carbon nanotubes have allowed the scientific community to visualize at atomic resolution the structural changes of molecules in situ by single-molecule atomic-resolution real-time TEM imaging (SMART-TEM) [1][2][3][4][5]. Since the initial discovery [2], many movies

Optimizing reaction conditions for the light-driven hydrogen evolution in a loop photoreactor

• Pengcheng Li,
• Daniel Kowalczyk,
• Johannes Liessem,
• Mohamed M. Elnagar,
• Dariusz Mitoraj,
• Radim Beranek and
• Dirk Ziegenbalg

Beilstein J. Org. Chem. 2024, 20, 74–91, doi:10.3762/bjoc.20.9

• voltage of 15 kV. To prepare the sample for SEM imaging, a few milligrams of the Pt-PCN material were dispersed in 1.0 mL of ethanol using sonication for 5 min. Subsequently, a thin film of the sample was obtained by drop-casting a few microliters of the suspended sample onto a conductive Cu foil

• substrate and allowed to dry at room temperature. To improve the conductivity and achieve higher resolution SEM imaging, a 20 nm thick layer of Au was sputtered onto the sample surface. For EDS mapping, the samples were not sputtered with Au to avoid interference during the determination of Pt. UV–vis

Unprecedented synthesis of a 14-membered hexaazamacrocycle

• Anastasia A. Fesenko and
• Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

• agents for magnetic resonance imaging, radiopharmaceuticals, sensors, NMR shift reagents, luminescent materials, catalysis, etc. To date, a large variety of PAMs with various ring sizes, number and location of nitrogen atoms, levels of unsaturation, etc. have been prepared and studied. Nevertheless, the

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• bio-imaging purposes [144]. In 1995, Mauleón et al. [145], extended this study by reporting the incorporation of a phenyl group in ω-position or by adding an alkyl group, a ketone or an alcohol function as illustrated in Figure 33. The idea of

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

• based on TBTQ with fluorescent imaging modules that are stable in acidic environments and collapse/swell in alkaline environments. The development of nanoscale drug delivery systems equipped with synchronized fluorescent imaging modules has attracted significant interest in recent years. However

• , conventional fluorescent dyes exhibit aggregation-caused quenching (ACQ) when introduced into nanoparticles at high loads, resulting in poor fluorescence imaging quality. In recent years, tetraphenylethylene (TPE)-based dyes have been frequently used to overcome the ACQ problem due to their unique aggregation

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

• Josipa Matić,
• Tana Tandarić,
• Marijana Radić Stojković,
• Filip Šupljika,
• Zrinka Karačić,
• Ana Tomašić Paić,
• Lucija Horvat,
• Robert Vianello and
• Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

• . The dye Phen-Py-1 was added to the cells at a final concentration of 1 × 10−6 M, an hour before confocal imaging. Computational details: In order to sample the conformational flexibility of investigated systems and probe their intrinsic dynamics in the aqueous solution, classical molecular dynamics

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• well as optical properties. Moreover, the versatility of coumarin hybrids finds numerous applications including fluorescent brightening agents [16], optical sensors [17], organic light emitting diodes [18][19], light harvesting materials [20] and fluorescent probes in biological imaging [21]. Therefore

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• interaction in the control group was not observed in the groups treated with nanoparticles. Similarly, it was determined that incubation with nanoparticles caused a change in the colonization of CT26 cells. Based on the results of both mitochondrial functional activity and microscopic imaging analyses

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• images were viewed with the Soft Imaging Program AnalySIS [49]. Thermogravimetric analysis (TGA): TGA analyses were performed on the TA-Q500 (Texas Instruments) with Universal Analysis 2000 software. Sample preparation involved rapidly removing the crystals from their mother liquor and subsequently

Computational model predicts protein binding sites of a luminescent ligand equipped with guanidiniocarbonyl-pyrrole groups

• Neda Rafieiolhosseini,
• Matthias Killa,
• Thorben Neumann,
• Niklas Tötsch,
• Jean-Noël Grad,
• Alexander Höing,
• Thies Dirksmeyer,
• Jochen Niemeyer,
• Christian Ottmann,
• Shirley K. Knauer,
• Michael Giese,
• Jens Voskuhl and
• Daniel Hoffmann

Beilstein J. Org. Chem. 2022, 18, 1322–1331, doi:10.3762/bjoc.18.137

• overcome this issue is to use fluorescence emission as a read-out tool, such as an emission “on” or “off” behavior [15]. Selective and sensitive fluorescent ligands have been proven to be essential tools for the study of biological systems by biosensing and imaging [16]. There is an increasing demand for

• novel luminophores tailor-made for different applications. One unique, promising class of compounds, the so-called aggregation-induced emitters (AIE) have been used for a wide range of applications, e.g., in OLEDs, liquid crystals [17], stimuli responses, bioassays, protein and ion detection or imaging

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

• Ashish Kumar Mazumdar,
• Gyana Prakash Nanda,
• Nisha Yadav,
• Upasana Deori,
• Upasha Acharyya,
• Bahadur Sk and
• Pachaiyappan Rajamalli

Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

• thermally activated delayed fluorescence (TADF) characteristics are emerging due to the potential applications in optoelectronic devices, time-resolved luminescence imaging, and solid-phase sensing. Herein, we synthesized two (4-bromobenzoyl)pyridine (BPy)-based donor–acceptor (D–A) compounds with varying

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

• Laura Holzhauer,
• Chloé Liagre,
• Olaf Fuhr,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111

• diversity of metal complexes incorporating 1,2,3-triazoles as ligands have been reported [16][17][18]. Triazole ligands with N-heterocycles such as Pyta (4-(2-pyridyl)-1,2,3-triazole) and related structures were employed to obtain novel metal complexes as catalysts [19][20] and imaging probes [21], as well

• especially used as CO2 reduction catalysts [38][39][40] and noninvasive imaging probes [12][41]; examples for the application in organic light-emitting diodes [35] and as photoactive CO-releasing molecule [42][43] have been reported as well. For the complexation experiments, compounds with three different

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

• Durbis J. Castillo-Pazos,
• Juan D. Lasso and
• Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

• character – have been harnessed in a plethora of applications in modern life: Teflon in non-stick pans, fire-fighting foams, stain-resistant and weatherproof fabrics, etching of circuit boards, and even imaging agents [1]. Given their importance, multiple synthetic methodologies for the introduction of long

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

• Conrad Kuhwald,
• Sibel Türkhan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

• , they are less common due to their inherent toxicity and ease of oxidation. Another branch of research involving SPIONs focuses on developments in nanoscience, nanomedicine, and nanoparticle-assisted imaging, diagnosis, and drug delivery [4][5][6][7], an area that is not covered in this report. Review 1

Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

• Masayori Hagimori,
• Tatsusada Yoshida,
• Yasuhisa Nishimura,
• Yukiko Ogawa and
• Keitaro Tanaka

Beilstein J. Org. Chem. 2022, 18, 580–587, doi:10.3762/bjoc.18.60

• clinical applications such as cell imaging and cell sorting. To develop low-molecular-weight AIEE-based luminogens, we have synthesized a series of fluorescent compounds by the reaction of nucleophilic maleimides with 2-aminopyridines. This resulted in the development of a novel method to obtain

Synthesis and bioactivity of pyrrole-conjugated phosphopeptides

• Qiuxin Zhang,
• Weiyi Tan and
• Bing Xu

Beilstein J. Org. Chem. 2022, 18, 159–166, doi:10.3762/bjoc.18.17

• , such as intracellular phase transition [22], molecular imaging [23][24][25][26][27][28][29][30][31][32][33], anisotropic hydrogels [34][35], targeting subcellular organelles [36][37][38][39][40], elimination of pluripotent stem cells (PSC) [41][42], and cancer therapy [43][44][45][46][47][48][49][50

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

• Marco Keller,
• Karl Sauvageot-Witzku,
• Franz Geisslinger,
• Nicole Urban,
• Michael Schaefer,
• Karin Bartel and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

• adjusted to pH 9 with NaOH or neutral as mobile phase. Details of the syntheses and spectroscopic data are presented in Supporting Information File 1. Fluorometric Ca2+ measurements Concentration–response curves of 1-benzyltetrahydroisoquinolines were generated by using a custom-made fluorescence imaging

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

An initiator- and catalyst-free hydrogel coating process for 3D printed medical-grade poly(ε-caprolactone)

• Jochen Löblein,
• Thomas Lorson,
• Miriam Komma,
• Tobias Kielholz,
• Maike Windbergs,
• Paul D. Dalton and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2021, 17, 2095–2101, doi:10.3762/bjoc.17.136

• symmetrical stretching vibration [ν(C–O–C)] of ester groups (Figure 2C, blue and red circles). With Raman imaging and the corresponding spectra, the presence of PHEMA on the PCL MEW scaffolds was clearly verified (Figure 2C and Figure 2D), especially regarding the material spanning the boxes. Unfortunately

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• studies show that the γ-carbolines are highly toxic to cancer cells at micromolar concentrations similar to doxorubicin, whereas they are non-cytotoxic (Figure 6) to human macrophages or immune cells. At last, to evaluate cell uptake of the novel γ-carboline for fluorescence imaging, live-cell imaging

• Software, San Diego, CA). HeLa cell uptake study of γ-carboline 3ac A live-cell imaging experiment was performed with HeLa cells. The HeLa cells were placed in a 4-well confocal dish (cell count ≈ 100 cells per well) and incubated for 48 h at 37 °C under 5% CO2. After 3 h of incubation with carboline