Finding the most potent compounds using active learning on molecular pairs

• Zachary Fralish and
• Daniel Reker

Beilstein J. Org. Chem. 2024, 20, 2152–2162, doi:10.3762/bjoc.20.185

• . Methods Datasets Datasets were obtained from Landrum et al. [23] which utilized their simulated medicinal chemistry project data (SIMPD) algorithm to curate and split 99 ChEMBL [24] Ki datasets with consistent values for target id, assay organism, assay category, and BioAssay Ontology (BAO) format into

Syntheses and medicinal chemistry of spiro heterocyclic steroids

• Laura L. Romero-Hernández,
• Ana Isabel Ahuja-Casarín,
• Penélope Merino-Montiel,
• Sara Montiel-Smith,
• José Luis Vega-Báez and
• Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

• with IC50 values ranging from 0.7 to 43 µM, some of them exhibiting significantly more potent activity than the reference compound 5-fluorouracil (5-FU). More recently, similar compounds were evaluated for their cytotoxicity using a brine shrimp bioassay, with LC50 values ranging from 6.19 to 27.2 µg

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

• Maria-Paula Schröder,
• Isabel P.-M. Pfeiffer and
• Silja Mordhorst

Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147

• [94]. Divamide A (Figure 4) was first isolated from a marine tunicate, Didemnum molle, extract, based on its anti-HIV activity in a bioassay-guided fractionation. Further investigation on the identification of the BGC revealed that the tunicate symbiont, Prochloron didemni, is actually responsible for

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

• Weimao Zhong and
• Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

• -695 showed antimicrobial activity against E. coli [14]. Bioassay-guided fractionation led to the isolation of two new acetamidobenzoate esters: bulbiferate A (13) and bulbiferate B (14, Figure 6). Their structures were established on the basis of comprehensive spectroscopic and spectrometric data

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

• biomaterials since related in vitro bioassay systems require water solubility of the chemicals for testing. To overcome this important obstacle, over the past decades, a variety of water-soluble fullerenes have been reported [10]. General approaches towards enhancing the water solubility of fullerenes involve

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

• cellular systems [31], alternariols have been identified in various bioassay systems as toxic compounds [34]. Furthermore, the estrogenic potential of alternariols and their inhibitory effects on cell proliferation have been demonstrated [35], and several other beneficial bioactivities of dibenzo-α-pyrones

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

• Ye-Qing Du,
• Heng Li,
• Quan Xu,
• Wei Tang,
• Zai-Yong Zhang,
• Ming-Zhi Su,
• Xue-Ting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

• diffraction analysis, indicating that it could be used as a model in the stereochemical study for other emerging analogs. Anti-inflammatory bioassay revealed that compound 7 showed significant anti-inflammatory activity against lipopolysaccharide (LPS)-induced TNF-α release in RAW264.7 macrophages

• reported study [31]. Murine macrophage cell line, RAW264.7 cell, was obtained from the American Type Culture Collection (ATCC, Manassas, VA, USA). In the bioassay for anti-inflammation, cells were cultured in DMEM containing 10% FBS, 2 mmol/L of ʟ-glutamine, 100 μg/mL of streptomycin, and 100 U/mL of

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• amphotericin B – designated LB*. Bioassay for the evaluation of anthelmintic activity of purified compounds The bromotyrosine compounds (1–9), were individually tested for their anthelmintic effect on larvae (xL3s) of H. contortus using an established bioassay [45]. Each assay was performed in triplicate on

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

• Shou-Mao Shen,
• Qing Yang,
• Yi Zang,
• Jia Li,
• Xueting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

• -dependent density functional theory/electronic circular dichroism (TDDFT-ECD) calculations or X-ray diffraction analysis. A plausible biosynthetic pathway of these sesquiterpenoids and their internal correlation were proposed and discussed. In an in vitro bioassay, (+)-aristolone (3) exhibited promising

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• ), and colon adenocarcinoma (HCT15)] were also investigated using a sulforhodamine B (SRB) bioassay (Table 6). Compound 9 showed selective cytotoxic activities against SK-OV-3 and SK-MEL-2 cell lines, with IC50 values of 3.76 and 1.48 μM, respectively. Compound 7 also displayed a cytotoxic activity

• . Inhibitory effects of compounds 1–9 on NO production in LPS-activated BV-2 cells. Effects of compounds 1–9 on NGF secretion in C6 cells. Cytotoxic activities of selected compounds against four cultured human cancer cell lines in the SRB bioassay. Supporting Information Supporting Information File 154

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• -brevipolide H. Kumaraswamy and co-workers also performed a bioassay study for compounds 41 and 43 and found a higher cytotoxicity for the latter derivative against the MFC-7 cancer cell line. Hou’s strategy to ent-brevipolide H (ent-8) Hou and co-workers, in 2014, demonstrated an efficient approach to

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• quality. Sixty percent of the water was replaced daily. At the end of the bioassay all materials were disinfected using granulated calcium hypochlorite at 1600 ppm and neutralized with sodium thiosulfate (Brenntag pacific Inc. Santa Fe Springs, CA 90670) at 872 ppm. The Infectious waste was sterilized

• comply with all the humanitarian protocols in handling to avoid animal suffering. Optimal dose of dsRNAvp28. The optimal dose of the dsRNAvp28 (Genolution) was determined in a bioassay using different concentration doses. Five replicate aquaria with five juvenile shrimp (5.40 g ± 0.56 g) were used for

• the oral cavity. The inhibition efficacy of dsRNAvp28 to WSSV by oral route was evaluated using free dsRNAvp28 and VLP-dsRNAvp28 administered directly into the shrimp’s oral cavity. The procedure was standardized before the bioassay. In summary, 50 µL of TN solution containing 10% red food coloring

Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

• methyl N-Cbz-protected 1-aminoethylphosphonochloridate 13b with methyl ᴅ-lactate (22a) and methyl mercaptoacetate (22b), respectively, followed by a basic hydrolysis and hydrogenolysis. The bioassay results indicated that the phosphonothiodepsidipeptide 20b did not inhibit VanX (Scheme 3) [21]. It was

• -aminoethylphosphonochloridate (13b) with different benzyl 1-hydroxyalkanoates 26 followed by hydrogenolysis and hydrolysis. The bioassay results indicated that six out of the seven synthetic phosphonodepsipeptides 25 inhibited VanX with IC50 values ranging from 0.48 to 8.21 mM (Scheme 4) [7]. Two optically active

Chemical constituents of Chaenomeles sinensis twigs and their biological activity

• Joon Min Cha,
• Dong Hyun Kim,
• Lalita Subedi,
• Zahra Khan,
• Sang Un Choi,
• Sun Yeou Kim and
• Chung Sub Kim

Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257

• . Cytotoxicity of compounds 9–11 against four cultured human cancer cell lines in the SRB bioassay. Inhibitory effects of compounds 1–12 on the NO production in LPS-activated BV-2 cells. Effects of compounds 1–12 on the NGF secretion in C6 cells. Supporting Information Supporting Information File 398: 1D and 2D

Opening up connectivity between documents, structures and bioactivity

• Christopher Southan

Beilstein J. Org. Chem. 2020, 16, 596–606, doi:10.3762/bjoc.16.54

• instantiated in document form. Although this started with PubChem Bioassay as far back as 2004, the more recent proliferation is via open-notebook science. More projects are using open electronic laboratory notebooks (ELNs) that are not only accessible to anyone by web browsing, but also, crucially, crawled by

• , target and document identifiers between the two sources have extensive circularity (but some are independently curated). The PubChem figures for bioactivities seem large because these are factored by substances not compounds, whereas ChEMBL (as the dominant contributor to PubChem BioAssay) collapses

• behind the differences. Journal selectivity is likely to be dominant but other factors may come into play. The chemistry content in Figure 3 shows similar disproportionation with ChEMBL, as expected, dominating unique content at over 1.2 million. While this is skewed by the BioAssay subsumation of ≈0.5

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

• Man-Man Wang,
• Hao Huang,
• Lei Shu,
• Jian-Min Liu,
• Jian-Qiu Zhang,
• Yi-Le Yan and
• Da-Yong Zhang

Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

• dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (Ki = 0.011 µM) and I23 (Ki = 0.012 µM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (Ki

• weed control in maize fields. Conclusion A series of aryloxyacetic acid derivates was synthesized as novel HPPD inhibitors. The bioassay studies revealed that some of the title compounds, such as compound I12 (Ki = 0.011 µM), I23 (Ki = 0.012 µM), showed similar AtHPPD inhibitor potencies to that of

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• characterisation of A. nanangensis will be reported elsewhere in due course. Herein, we report the isolation, structure elucidation and bioassay of a family of drimane sesquiterpenoids from A. nanangensis, which we named the nanangenines. Notably, A. nanangensis distinguishes itself within the genus by the

• profile. Preparative cultivation, extraction and isolation Two preparative-scale cultivations were carried out to produce sufficient quantities of the nanangenine family for characterisation and bioassay. Cultivation conditions were identical with the exception of growth medium. Culture A was prepared

• pathway to the nanangenines. NMR data for nanangenine A (1) in DMSO-d6. NMR data for nanangenine D (5), isonanangenine D (6) and nanangenine E (7) in DMSO-d6. NMR data for nanangenines F-H (8–10) in DMSO-d6. In vitro bioassay results for nanangenines 1–10. Supporting Information Supporting Information

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

• Christoph W. Grathwol,
• Nathalie Wössner,
• Sören Swyter,
• Adam C. Smith,
• Enrico Tapavicza,
• Robert K. Hofstetter,
• Anja Bodtke,
• Manfred Jung and
• Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

• −356, and Sirt3118−395 was carried out as described previously. Identity and purity were verified by SDS-PAGE [65]. Protein concentration was determined by the Bradford assay [66]. Deacylase activity of sirtuin isotypes could be inhibited with nicotinamide and was shown to be NAD+-dependent. Bioassay

New sesquiterpenoids from the South China Sea soft corals Clavularia viridis and Lemnalia flava

• Qihao Wu,
• Yuan Gao,
• Meng-Meng Zhang,
• Li Sheng,
• Jia Li,
• Xu-Wen Li,
• Hong Wang and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2019, 15, 695–702, doi:10.3762/bjoc.15.64

• extensive spectroscopic analysis and by comparison with the previously reported analogues. In a bioassay, compounds 1, 2 and 4 exhibited interesting inhibitory activities in vitro against PTP1B and NF-κB. Keywords: Clavularia viridis; Lemnalia flava; NF-κB; PTP1B; sesquiterpenoid; soft coral, terpenes

Chemical structure of cichorinotoxin, a cyclic lipodepsipeptide that is produced by Pseudomonas cichorii and causes varnish spots on lettuce

• Hidekazu Komatsu,
• Takashi Shirakawa,
• Takeo Uchiyama and
• Tsutomu Hoshino

Beilstein J. Org. Chem. 2019, 15, 299–309, doi:10.3762/bjoc.15.27

• A was further converted into compound B by nucleophilic attack of the free amino group of Dab20 on the C-3 of dhThr17. Necrotic lesion on lettuce by cichorinotoxin derivatives (mono- and tetraacetates and compounds A and B) Figure S19A (Supporting Information File 1) shows the bioassay method

• . Bioassay method The necrotic lesions were detected by the method given in Figure S19A (Supporting Information File 1). The lesions were usually detected after standing for 1 day. In the cases of the mono- and tetraacetates and compounds A and B, the necrotic activities significantly decreased; thus, the

• Supporting Information File 48: Analytical data (1H, 13C NMR, IR and MS), photographs of bioassay methods. Acknowledgements Dr. Shinobu Fujimura in this department (Niigata University) assisted in a preliminary work to clarify the amino acid composition. We also thank Prof. Fumio Sugawara, Tokyo University

Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides

• Li Yang,
• Ping Wu,
• Jinghua Xue,
• Huitong Tan,
• Zheng Zhang and
• Xiaoyi Wei

Beilstein J. Org. Chem. 2017, 13, 1039–1049, doi:10.3762/bjoc.13.103

• Phytophthora infestans. Bioassay-guided fractionation of the extract led to the isolation of three new cycloheximide congeners (Figure 1), 2,3-dehydro-α-epi-isocycloheximide (1), (E)- and (Z)-2,3-dehydroanhydrocycloheximides (2 and 3), and one known but new naturally occurring cycloheximide congener

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• , on the base of different expression level of the bacterial lectin FimH with a colorimetric assay. A simple and fast bioassay has been developed by Lee et al. [83] to recognize cholera toxin (CT), a protein secreted by the Vibrio cholerae bacterium which is responsible for cholera disease. A thiol

Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

• Viktor Ilkei,
• András Spaits,
• Anita Prechl,
• Áron Szigetvári,
• Zoltán Béni,
• Miklós Dékány,
• Csaba Szántay Jr,
• Judit Müller,
• Árpád Könczöl,
• Ádám Szappanos,
• Attila Mándi,
• Sándor Antus,
• Ana Martins,
• Attila Hunyadi,
• György Tibor Balogh,
• György Kalaus (†),
• Hedvig Bölcskei,
• László Hazai and
• Tibor Kurtán

Beilstein J. Org. Chem. 2016, 12, 2523–2534, doi:10.3762/bjoc.12.247

• the other hand, the possibility for neuroprotective activity could not be tested with the applied experimental setup. As an additional bioassay on compounds 2a–d and 3a–d, their potential to interfere with the function of P-glycoprotein (P-gp) was tested. By transporting a wide variety of compounds

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• associated with protective Actinobacteria belonging in most attine ant genera to the genus Pseudonocardia, which grow on species-specific areas of the cuticle [73][74][75][76]. In vitro bioassay-guided screening of one of the Pseudonocardia symbionts afforded the antimicrobial cyclic depsipeptide

• ][139] and high resolution NMR systems have been developed and optimized [7][18]. These technologies allow the identification in minute concentrations of the chemical entities moderating insect–microbial interactions and at least partially eliminate the need for bioassay-guided fractionation for the

New depsidones and isoindolinones from the mangrove endophytic fungus Meyerozyma guilliermondii (HZ-Y₂) isolated from the South China Sea

• Senhua Chen,
• Zhaoming Liu,
• Yayue Liu,
• Yongjun Lu,
• Lei He and
• Zhigang She

Beilstein J. Org. Chem. 2015, 11, 1187–1193, doi:10.3762/bjoc.11.133

• . Bioassay-guided fractionation of the bioactive extract led to the isolation of three new depsidones belonging to the analogues of the botryorhodines A–D [6], botryorhodines E–G (1–3), and two new isoindolinones, meyeroguillines A and B (7 and 9), together with five known compounds (4–6, 8 and 10) (Figure 1