Synthesis and characterization of a isothiouronium-calix[4]arene derivative: self-assembly and anticancer activity

• Giuseppe Granata,
• Loredana Ferreri,
• Claudia Giovanna Leotta,
• Giovanni Mario Pitari and
• Grazia Maria Letizia Consoli

Beilstein J. Org. Chem. 2025, 21, 2535–2541, doi:10.3762/bjoc.21.195

• , it is generally accepted that values higher than ±40 mV are associated with strong stability by repulsion, preventing further aggregation phenomena. Cytotoxicity and cancer cell selectivity Thiouronium-containing molecules can inhibit cancer cells, inducing apoptosis or necrosis, by different

Rotaxanes with integrated photoswitches: design principles, functional behavior, and emerging applications

• Jullyane Emi Matsushima,
• Khushbu,
• Zuliah Abdulsalam,
• Udyogi Navodya Kulathilaka Conthagamage and
• Víctor García-López

Beilstein J. Org. Chem. 2025, 21, 2345–2366, doi:10.3762/bjoc.21.179

• generate singlet oxygen (¹O2), which can be controlled through dithienylethene photoisomerization. Therefore, the authors investigated these nanoparticles for bioimaging and apoptosis of HeLa cells. When the dithienylethene is in the open form, the nanoparticles have relatively high cytotoxicity due to the

Convenient alternative synthesis of the Malassezia-derived virulence factor malassezione and related compounds

• Karu Ramesh and
• Stephen L. Bearne

Beilstein J. Org. Chem. 2025, 21, 1730–1736, doi:10.3762/bjoc.21.135

• others (11–19) (see Figure 1), which may serve as virulence factors [8][9][10][11][12][13]. Most significantly, some of these indoles have been shown to be potent aryl hydrocarbon receptor (AHR) ligands [8][9][14][15], which can lead to induction of melanocyte apoptosis and inhibition of neutrophil

Heterologous biosynthesis of cotylenol and concise synthesis of fusicoccane diterpenoids

• Ye Yuan,
• Zhenhua Guan,
• Xue-Jie Zhang,
• Nanyu Yao,
• Wenling Yuan,
• Yonghui Zhang,
• Ying Ye and
• Zheng Xiang

Beilstein J. Org. Chem. 2025, 21, 1489–1495, doi:10.3762/bjoc.21.111

• that cotylenin A and its aglycone, cotylenol (3), induce differentiation in murine and human myeloid leukemia cells [13]. Cotylenin A and fusicoccin A also act synergistically with interferon-α or rapamycin to induce apoptosis in cancer cell lines [14][15][16]. However, cotylenin A cannot be produced

4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Luc Van Meervelt,
• Do Thi Thao and
• Nguyen Minh Thong

Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65

• response, respiratory, vasodilation, apoptosis, tumor growth, and cardiovascular system [1][2]. Nitric oxide (NO) is released as product of the NADPH and oxygen-dependent oxidation of ʟ-arginine to ʟ-citrulline under the catalysis of the enzyme nitric oxide synthase (NOS) [3]. There are three distinct

Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

• Ayesha Saeed,
• Shahana Ehsan,
• Muhammad Zia-ur-Rehman,
• Erin M. Marshall,
• Sandra Loesgen,
• Abdus Saleem,
• Simone Giovannuzzi and
• Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

• prepared in DMSO and cancer cells were treated with 10 μM doses of compounds using the apoptosis inducing standard mensacarcin (10 μM) as a positive control [56]. Only compound 7l decreased cell viability to 63%, while the rest of the compounds showed very low to no significant decrease in cell viability

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

• collaboration with Manfred Kunz (University of Leipzig), it was shown that all four compounds exhibit excellent antiproliferative activity against the malignant melanoma cell lines MeI-19, SK-MeI-29, SK-MeI-103, and SK-MeI-147. The compounds also induce apoptosis of the cancer cell lines which was investigated

• carbohydrate moiety is later hydrolytically cleaved in the cell to release the indirubin which then acts as a CDK inhibitor. A synergistic effect of plasma-activated medium (PAM) and β-33b on human skin cancer cells was observed [32][33]. With regard to viability, adhesion capacity, apoptosis and G2/M cell

• collaboration with Jürgen Eberle and his team it was shown that selenoindirubin-N-glycosides β-38a–h showed antiproliferative activity against lung cancer cell lines H157 [38]. The antiproliferative activity against melanoma cells was accompanied by induced apoptosis in combination with the death ligand TRAIL

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

• turned out that induced cytotoxicity [75] is mediated by activation of the mitochondrial pathway of apoptosis in human colon carcinoma cells [76][77] and that cytotoxicity on HCT116 cells is increased, when AOH is combined with 9-O-methylalternariol (2, AME) [78]. AOH further showed to have a detrimental

• , preferentially affecting the IIα isoform [88], where on the other hand the damage turned out to be repaired in less than two hours [89]. Its induction of oxidative stress leading to DNA damage [90][91][92][93] and its causing cell cycle arrest, apoptosis, and changing the cell morphology further contribute to

• cells with ID50 values of 8 μg/mL [74], was a strong mutagen in Escherichia coli strain ND-160 [111], was maternally toxic and fetotoxic to Syrian golden hamsters [112], induced mitochondrial apoptosis in human colon carcinoma cells [113], induced cytochrome P450 1A1 formation and apoptosis in murine

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

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• -synuclein (αS), thereby alleviating the apoptosis of neuronal cells and cognitive impairment [30][31][32][33]. Lastly, the extract of C. sativus can also improve the chronic stress-induced loss of learning and memory by reducing the ROS level or regulating the synthesis of superoxide dismutase (SOD) and

• ]. Mollaei et al. observed an increased Bax/Bcl-2 ratio in crocin-treated cancer cells. Therefore, crocins are proposed to exert anticancer activity by promoting apoptosis of cancer cells [47]. This mechanism is consistent with the results of Hoshyar et al., who observed the apoptosis-promoting activity of

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

• general extends to other types of cancers as well, such as prostate cancer by being an androgen receptor (AR) agonist in LNCaP prostate cancer cells [6]. DIM controls cell growth rates in AR-negative cells, while also targeting the mitochondria inducing apoptosis, which alleviates some of the symptoms of

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

• biology, and biomedicine. These carbohydrate-binding proteins boast a range of functions, acting as recognition modules in cell–molecule and cell–cell interactions, thereby playing vital roles in immune defense, regulation of growth, and apoptosis [1]. In plants, they serve as essential components in

• realm of therapeutics, lectins such as mistletoe lectins have shown promise in cancer therapy, by virtue of their ability to induce apoptosis in malignant cells [7]. Further, the creation of lectin arrays [8][9], which employ a diverse set of characterized lectins, has enabled high-throughput glycan

Metal-catalyzed coupling/carbonylative cyclizations for accessing dibenzodiazepinones: an expedient route to clozapine and other drugs

• Amina Moutayakine and
• Anthony J. Burke

Beilstein J. Org. Chem. 2024, 20, 193–204, doi:10.3762/bjoc.20.19

• disorders (Figure 1) [1][2]. Dibenzodiazepinones were also found to exhibit significant anticancer properties [3], as they were found to effectively inhibit tumor invasion in vitro [4], and induce apoptosis among several cancer cell lines [5]. Additionally, several dibenzodiazepinone-based structures were

Visible-light-induced radical cascade cyclization: a catalyst-free synthetic approach to trifluoromethylated heterocycles

• Chuan Yang,
• Wei Shi,
• Jian Tian,
• Lin Guo,
• Yating Zhao and
• Wujiong Xia

Beilstein J. Org. Chem. 2024, 20, 118–124, doi:10.3762/bjoc.20.12

• compounds (Figure 1) [1][2][3], which exhibit a wide range of biological and pharmaceutical activities [4]. For example, mersicarpine has been found to inhibit protein translation and induce apoptosis [5] and vinburnine acts as a vasodilator for the treatment of cerebrovascular insufficiency [6][7]. Given

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

• Nadia Ledermann,
• Alae-Eddine Moubsit and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

• interest as indole-based blue emitters in solution and in the solid state. The expansion of this practical concise synthesis of indoles and azaindoles and their exploration as biologically active apoptosis inducers [37] and as functional blue emitters is currently underway. Experimental Consecutive four

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

• Feng Chen,
• Xiu-Hua Xu,
• Zeng-Hao Chen,
• Yue Chen and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2023, 19, 1372–1378, doi:10.3762/bjoc.19.98

• experiments showed that trifluoromethyl acyloins can selectively induce apoptosis in human oral cancer cells [22][23] and have therefore attracted much more attention. However, trifluoromethyl acyloins were not widely used due to the challenge associated with their synthesis. Certain progress has been made in

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

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

• Jorge de Lima Neto and
• Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

• . After binding to tubulin, they act as stabilizing agents, allowing the formation of microtubules in the early stages, but preventing their disassembly in the final stages of cell division, thus leading to apoptosis [15][55][74] in a mechanism similar to taxol® [76]. However, it is worth to note that

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

• reported that depletion of cholesterol by methyl-β-cyclodextrin could inhibit EGFR signals, induce apoptosis, and suppress tumor growth in colon tumor-induced mice [57]. Shimolina et al. evaluated membrane fluidity in CT26 and HeLa Kyoto cells treated with cisplatin in a monolayer conventional cell culture

• . It was emphasized that the increased plasma membrane fluidity due to the decrease of lipid rafts and, moreover, cholesterol in the biological membrane plays a role in inducing apoptosis [58]. When the literature information and the findings are evaluated, it can be said that the use of CD

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

• enormous number of interactions with other proteins. Currently, more than 200 interacting proteins are known. 14-3-3 proteins play a significant role in cell signaling [2][3] and they were found to be essential in processes such as differentiation, apoptosis, or migration [4]. 14-3-3 proteins also play a

Synthesis and HDAC inhibitory activity of pyrimidine-based hydroxamic acids

• Virginija Jakubkiene,
• Gabrielius Ernis Valiulis,
• Markus Schweipert,
• Asta Zubriene,
• Daumantas Matulis,
• Franz-Josef Meyer-Almes and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 837–844, doi:10.3762/bjoc.18.84

• . This function is essential in the transcription of DNA, as histones with acetyl groups do not interact as strongly with DNA, which opens the chromatin for transcription. HDACs also interact with other cellular proteins to regulate vital functions such as cell differentiation or apoptosis. They have

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• (DNA and RNA), enzymes, structural proteins, and cell membrane lipids. These effects can lead to dysfunctions that activate the apoptosis process resulting in cell death [42][43][44][45][46]. In addition to participating in redox cycles as biomolecules in various biochemical processes, the 1,4

Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

• Rodolfo H. V. Nishimura,
• Thiago dos Santos,
• Valter E. Murie,
• Luciana C. Furtado,
• Leticia V. Costa-Lotufo and
• Giuliano C. Clososki

Beilstein J. Org. Chem. 2021, 17, 2968–2975, doi:10.3762/bjoc.17.206

• apoptosis [7]. Figure 1 highlights the structures of three EGFR inhibitors approved by the United States Food and Drug Administration (FDA) and one known tubulin inhibitor: erlotinib (1), gefitinib (2), lapatinib (3), and MPC-6827 – verubulin (4) [5][7]. Given that 4-anilinoquinazolines are potential

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

• after substraction of the basal value. Flow cytometry P-glycoprotein activity was assessed using the reporter dye calcein acetoxymethyl ester (AM) as described previously [59]. To assess apoptosis, VCR-R CEM cells were seeded at 0.125 × 106 cells/well, incubated for 4 h and stimulated as indicated for

• 48 h. Apoptosis was analyzed by propidium iodide staining and flow cytometry as described by Nicoletti et al. [60]. All flow cytometry experiments were conducted on a BD FACS Canto II (BD Biosciences). Prominent synthetic approaches to 1-benzyltetrahydroisoquinolines: Bischler–Napieralski, Pictet

• significance was determined by ordinary one-way ANOVA and Dunnett’s post test. ****p < 0.0001. D) Combination treatment of benzylisoquinolines and vincristine. VCR-R CEM cells were treated with 0.1 or 1 µM vincristine for 48 h in presence or absence of the respective benzylisoquinoline (10 µM). Apoptosis was

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

• , entries 1–7). A very low ED50 value of 8.5 nM was obtained for brevipolide C (3) (Table 2, entry 3) [4], making it a very potent lead compound for anticancer candidates related to mitochondrial dysfunction effect. A reduction in the mitochondrial membrane potential (MMP) could also indicate apoptosis [20