Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA

• Yu Fan,
• Ahmed El Rhaz,
• Stéphane Maisonneuve,
• Emilie Gillon,
• Maha Fatthalla,
• Franck Le Bideau,
• Guillaume Laurent,
• Samir Messaoudi,
• Anne Imberty and
• Juan Xie

Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132

• formation is one of main causes of bacterial antimicrobial resistance infections. It is known that the soluble lectins LecA and LecB, produced by Pseudomonas aeruginosa, play a key role in biofilm formation and lung infection. Bacterial lectins are therefore attractive targets for the development of new

• ; lectin A; photoswitchable ligands; Introduction Bacterial infection is a growing health problem due to antimicrobial resistance (AMR) among others. AMR causes approximately 33,000 deaths per annum in Europe only [1], and costs between €1.5 and €9 billion in healthcare and associated activities. Many

• the leading cause of morbidity and mortality in cystic fibrosis and immunocompromised patients and as one of the leading causes of nosocomial infections [1]. Due to the existence of numerous molecular mechanisms conferring resistance to multiple classes of antibiotics, therapeutic options are

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

• Lu Li,
• Na Li,
• Xiao-Tian Mo,
• Ming-Wei Yuan,
• Lin Jiang and
• Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

• -substituent as compared to their ortho- or meta-substituted counterparts. It might be explained by the less obvious steric resistance of the former in the process of Schiff base formation. In addition, an alkylidenyl-equipped 3-cyclohexanone was found to be incompatible with the current reaction system, only

Kinetically stabilized 1,3-diarylisobenzofurans and the possibility of preparing large, persistent isoacenofurans with unusually small HOMO–LUMO gaps

• Qian Liu and
• Glen P. Miller

Beilstein J. Org. Chem. 2024, 20, 1099–1110, doi:10.3762/bjoc.20.97

• . We previously studied substituent effects in acenes and reported that several substituents promote photooxidative resistance in pentacenes [5] and larger acenes including heptacene [6] and nonacene [7]. One or more substituents that promote photooxidative resistance by quenching singlet oxygen could

• photooxidative resistance, especially along the acene-like segment, plus a strong measure of kinetic stabilization at the 1,3-carbons of the furan ring. As described here, there are compelling reasons to contemplate the synthesis of large, persistent isoacenofurans with unusually small HOMO–LUMO gaps. In this

• resistance to the most reactive 1,3-carbons of the furan ring. A combination of experimental and computational studies clarifies the impacts of these sterically congesting substituents on each molecule’s electronic structure. We further studied the reaction rates of 1,3-diarylisobenzofurans with the strong

Synthesis of 1,4-azaphosphinine nucleosides and evaluation as inhibitors of human cytidine deaminase and APOBEC3A

• Maksim V. Kvach,
• Stefan Harjes,
• Harikrishnan M. Kurup,
• Geoffrey B. Jameson,
• Elena Harjes and
• Vyacheslav V. Filichev

Beilstein J. Org. Chem. 2024, 20, 1088–1098, doi:10.3762/bjoc.20.96

• , biochemical and structural studies support a model in which this A3-mediated mutagenesis promotes tumour evolution and strongly influences disease trajectories, including the development of drug resistance and metastasis [18][19][20][21][22][23]. Of the seven A3 enzymes, three (A3A, A3B and A3H) are at least

• with reduced tamoxifen sensitivity of tumours in those patients [19] and poor survival rates for estrogen receptor-positive (ER+) breast cancer patients [21][29]. In line with these observations, A3B overexpression accelerates the development of tamoxifen resistance in murine xenograft with ER+ breast

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• transport. On the other hand, unipolar electron transport could be facilitated in the case of DCPQs 1a–6a given their extremely deep HOMO energy levels. Deep HOMO levels are important for optimal device performance and resistance to oxidation [34]. Compounds with deep LUMO energy levels are essential for

Methodology for awakening the potential secondary metabolic capacity in actinomycetes

• Shun Saito and
• Midori A. Arai

Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69

• inducing resistance, and this approach has contributed to the isolation of many new compounds [47]. The ribosome engineering method is based on the principle that a mutation in the ribosomal S12 protein, which is associated with the acquisition of antibiotic resistance, activates secondary metabolism. The

Substrate specificity of a ketosynthase domain involved in bacillaene biosynthesis

• Zhiyong Yin and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2024, 20, 734–740, doi:10.3762/bjoc.20.67

• organism shares the same habitat with the predator Myxococcus xanthus that feeds on other bacteria including B. subtilis, and bacillaene is the primary factor conferring B. subtilis cells resistance to predation by M. xanthus [8]. The identification of its biosynthetic gene cluster (bae) revealed that the

Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

• Senze Qiao,
• Zhongyu Cheng and
• Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

• vancomycin-resistant S. aureus (VRSA). However, the recent discovery of daptomycin-resistant Enterococcus and S. aureus provided the impetus to develop novel derivatives that enable more comprehensive structure–activity relationship (SAR) and resistance mechanism studies. Multiple approaches have been

• exhibit a potent ability to induce tubulin depolymerization [77], originally isolated from the cyanobacteria Nostoc sp. ATCC 53789 [78]. Notably, the cryptophycins cannot serve as substrates for P-glycoprotein and multiple drug resistance-associated proteins, making them attractive as chemotherapeutic

New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• in Supporting Information File 1). To investigate whether the identified var biosynthetic gene cluster is responsible for variochelin production, we substituted varG encoding the polyketide synthase (PKS) module with a chloramphenicol resistance (cmR) gene cassette, using homologous recombination

• amplified by PCR, using Variovorax sp. H002 genomic DNA as the template. The chloramphenicol-resistance gene (cmR) and a linearized recipient plasmid pRED were amplified by PCR, using pRED as the template. The primer sets used to amplify the above-mentioned four fragments are listed in Table S2 (Supporting

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

• Michael O. Akintubosun and
• Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

• presence of a resistance gene within a biosynthetic gene cluster can indicate that it produces an antimicrobial compound [27]. We searched for annotated resistance genes in the surrounding genomic neighborhood of PF01408 sequences. We found 1,166 PF01408 sequences were associated with nearby glyoxalase

• /bleomycin resistance protein/dioxygenase superfamily (PF00903) sequences, 81 associated with CrcB-like protein, camphor resistance (PF02537) sequences, 22 associated with aminoglycoside antibiotic resistance kinase (PF04655) sequences, and 2 associated with putative multidrug resistance efflux protein

• pathways. Genome neighborhood analysis shows that many PF01408 sequences can be found near known biosynthetic enzymes, aminotransferases, and resistance genes suggesting that these enzymes may be promising candidates for targeted gene mining strategies to discover novel natural products. Experimental

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• (Figure 2). Furthermore, 7b, 7c, and 13b provided full control of ELEIN, one of the most difficult turfgrass weeds to control in the tropics and warmer temperate zones, emphasizing the potential of novel FAT inhibitors to contribute to integrated weed and resistance management. Conclusion The agrochemical

• (ALOMY_R, also known as slender foxtail or black twitch) and ryegrass (LOLSS_R). Remarkably, 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine 7b turned out to be superior to market standards (i.e., 1 and 2 in wheat) in terms of overall efficacy and resistance breaking potential. Halogen-free target compound 7c also

• structural scope of modern agrochemical research and to address sustainability goals, e.g., overcoming herbicide resistance and meeting demanding environmental safety goals. Experimental Synthesis Representative procedure for the synthesis of 6-bromo-5-(2-fluorophenyl)-2,3-dihydro[1,3]thiazolo[4,5-b]pyridine

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• clinical trials as neuroprotective agents, presenting an attractive alternative to traditional anti-inflammatory and anti-Parkinson’s disease drugs [7]. With the increased drug resistance of bacteria to modern medicine, BIMs have emerged as an interesting alternative, due to their antibacterial and

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• allowed precise control of the incident photon wavelength. To measure the photocurrent flowing in the circuit under illumination, a Keithley 6517B electrometer/high resistance meter was utilized, providing accurate and sensitive readings. An energy scan of the incident photons was performed by

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• the analysis procedure. AFM measurements of the organic films were performed using a Nanosurf EasyScan2 apparatus in tapping mode with a scanning rate of 1.0 Hz covering 512 × 512 lines. Hole-only devices were fabricated using indium tin oxide (ITO) coated glass plates (sheet resistance of about 15 Ω

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• limitations, as demonstrated by Elavarasan and colleagues. Their team synthesized TQT-C60 and anchored it to fullerene molecules (Figure 3) to prevent aggregation during thermal aging. The researchers found that TQT-C60 demonstrated enhanced morphological stability and thermal resistance compared to the

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• substrate with a sheet resistance of 12 Ω sq−1 was pre-cleaned carefully and cured with UV/O3 for 20 min. The OLED with an active diode area of 0.04 cm−2 was fabricated using a Kurt J. Lasker mini SPECTROS 100 thin film deposition system under vacuum conditions with a base pressure lower than 1 × 10−5 bar

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• conventional architecture devices with a layer stack of glass/ITO/PEDOT:PSS/PM6:Y6/CIL/Ag (Figure 5b). See Supporting Information File 1 for full device fabrication details. The BHJ materials, PM6:Y6 (Figure 5a), were selected due to their high photovoltaic performance and solvent resistance to ethyl acetate

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• type of post-polymerization modification introduces or removes functionalities at polymer chain ends [120]. 3.2 Chemical crosslinking of polymers Chemical crosslinking is a suitable approach to increase chemical resistance [121], mechanical strength [122], and other properties [123] of polymers. In

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis

• Bel Youssouf G. Mountessou,
• Élodie Gisèle M. Anoumedem,
• Blondelle M. Kemkuignou,
• Yasmina Marin-Felix,
• Frank Surup,
• Marc Stadler and
• Simeon F. Kouam

Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112

• ; endophytic fungi; hemiketal polyketide; Introduction Endophytic fungi are organisms that reside almost ubiquitously inside the fresh healthy tissue of plants, and they may increase the resistance of the host tropical trees to survive in extreme conditions [1]. As the global diversity of endophytic fungi is

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• have been found to possess antimicrobial resistance genes [6]. With the persistent increase in drug-resistant microbial strains, there is a pressing need to continuously explore new and alternative drug candidates. Plants naturally produce many compounds that can be used to treat a variety of human

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

• Oleksandr V. Kolomiiets,
• Alexander V. Tsygankov,
• Maryna N. Kornet,
• Aleksander A. Brazhko,
• Vladimir I. Musatov and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

• against E. coli was only observed at higher concentrations of 500 mg/L. This was also observed with the tested S. aureus strain. However, the Gram-negative bacterium P. aeruginosa showed resistance to a large number of synthesized compounds, with some compounds even promoting its growth and development at

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

• . These prepared porphyrin nanowires were subjected to surface microscopy and fluorescence energy transfer experiments, which elucidated their stability and resistance to disassembly. Conclusion Cu(I)-catalyzed “click chemistry” is a well-established protocol for the facile access of complexes from simple

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

• two different colon tumors to differ from each other is the origin of the cells. The genome-transcriptome mapping investigation revealed that despite having two separate origins, the CT26 cell has characteristics similar to human primary colorectal cancers in terms of drug resistance mechanisms, gene

• concentration has been related to cell membrane fluidity and rigidity, treatment resistance in cancer cells, and drug uptake through the cell membrane. Excipients such as methyl-β-CD are widely used to extract cholesterol from cancer cells such as melanoma and MCF7 cells in order to promote cellular uptake of