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

• for compounds that act directly on specific molecules). Imoto and colleagues constructed a reverse screening system that targets a malignant factor of prostate cancer and thereby identified several novel compounds from actinomycete strains [16][17][18][19]. Many researchers have focused on identifying

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

• prostate cancer. The same apoptotic function can be observed in colon and pancreatic cancer, since BIMs (specifically DIM-C-pPhOCH3 (5)) can act as a Nur77 (Nuclear Receptor 4A1) antagonist, which modulates the life cycle of cells [6]. The correlation between lower lung cancer risk and the consumption of

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

• (231MFP), melanoma (C8161) and prostate cancer (PC3) cells compared with less aggressive cancer cells (MCF7, MUM2C, and LNCaP, respectively) suggesting that AGPS is an important player in the aggressiveness of cancers [17]. It was also suggested to use ELs as biomarkers for some human diseases like

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• (L929) (IC50 = 15.2 µM), breast cancer cells (MCF-7) (17.6 µM), and prostate cancer cells (PC-3) (18.9 µM). Discussion The introduction of a hydroxy group at C-2 rendered forpinioside C (2) inactive in antimicrobial assays compared to forpinioside B (1), however; both compounds were not active in the

• prostate cancer cells PC-3) were obtained from the DSMZ collection (Braunschweig, Germany). Chemical structures of compounds 1–4. Key 1H,1H COSY, HMBC, and ROESY correlations of compounds 1 and 2. 1H and 13C NMR data of compounds 1 and 2 in methanol-d4. Supporting Information Supporting Information File

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• ] showed a good cytotoxic effect against the prostate cancer cell line PC-3 (Figure 2). When the spacer of I was increased from C6 to C11, the antimicrobial potential dramatically decreased [11]. In order to extend the compound platform, the synthesis of 3-azidocholest-5-ene was addressed [10]. Starting

Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• that saponins possess anticancer properties, by limiting proliferation and metastasis. This has been tested on different cancers such as leukemia [16], breast cancer [17] or prostate cancer to cite only a few of them [18]. They also present antimicrobial, antioxidant, anti-inflammatory, antidiabetic

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

• , fragmentation of the mitochondrial tubular network, chromosome misalignment, and cell cycle arrest in mitosis in LNCaP prostate cancer cells [38]. The bastadin structure class is well-documented within the literature for their cytotoxic activity [37][39][40][41], with both bastadins 4 and 8 exhibiting in vitro

Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction

• Dušan Đ. Škorić,
• Olivera R. Klisurić,
• Dimitar S. Jakimov,
• Marija N. Sakač and
• János J. Csanádi

Beilstein J. Org. Chem. 2021, 17, 2611–2620, doi:10.3762/bjoc.17.174

• six human tumor cell lines (MCF-7 estrogen receptor positive breast adenocarcinoma, MDA-MB-231 estrogen receptor negative breast adenocarcinoma, PC-3 prostate cancer, HeLa cervix carcinoma, HT-29 colon adenocarcinoma, and A549 adenocarcinomic human alveolar basal epithelial cells). Standard MTT assay

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

• assay against the cell proliferation of the human hormone-refractory prostate cancer cell line (PC-3). Mohapatra’s strategy to brevipolide H (8) As part of the interest in synthesizing biologically active cyclopropane-containing natural products, Mohapatra and co-workers in 2015 started their attempt to

A systems-based framework to computationally describe putative transcription factors and signaling pathways regulating glycan biosynthesis

• Theodore Groth,
• Rudiyanto Gunawan and
• Sriram Neelamegham

Beilstein J. Org. Chem. 2021, 17, 1712–1724, doi:10.3762/bjoc.17.119

• -value = 0.039) may regulate the type 1 and 2 LacNAc pathways. CREB3L4 is known to primarily be expressed in the prostate and some breast cancer cell lines and has been linked to diverse roles involving chromatin organization in spermiogenesis, adipocyte regulation, and dysregulation in prostate cancer

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

Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati,
• Andhika B. Mahardhika,
• Lukas L. Wendt and
• Christa E. Müller

Beilstein J. Org. Chem. 2021, 17, 1464–1475, doi:10.3762/bjoc.17.102

• treatment of prostate cancer [16] and showed promise for the treatment of cervical dysplasia [17]. The related trisindoline (II) was reported to possess antibiotic activity [18], while DIM derivatives III and IV also showed anticancer activities (Figure 1). Owing to their exciting biological activities, DIM

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• cytotoxicity, proliferation and growth of HT-29 (human colon adenocarcinoma cell line), PC-3 (human prostate cancer cell line) and L-929 cells (mouse fibroblast cell line). The results obtained from the MTT assay revealed that the tested phthalazinone derivatives were cytotoxic towards the tested cell lines in

Progress in the total synthesis of inthomycins

• Bidyut Kumar Senapati

Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

• biosynthesis [1][4], in vitro antimicrobial activity [4][5], and anticancer activity against human prostate cancer cell lines [6][7]. A recent study suggested that the close analogue (+)-11 of inthomycin C was found to exhibit proteasome inhibition activity [8]. The skeletal structures of inthomycins A–C (1–3

Syntheses of spliceostatins and thailanstatins: a review

• William A. Donaldson

Beilstein J. Org. Chem. 2020, 16, 1991–2006, doi:10.3762/bjoc.16.166

• of 77 with Kitahara’s sulfone 119, proceeded less efficiently (22% yield). In a subsequent assay for repressed cell proliferation against the human prostate cancer cell lines LNCaP, LNCaP95, and CWR22Rv, these authors reported IC50 values of 63, 175, and 93 nM, respectively, for 124. These can be

Design and synthesis of diazine-based panobinostat analogues for HDAC8 inhibition

• Sivaraman Balasubramaniam,
• Sajith Vijayan,
• Liam V. Goldman,
• Xavier A. May,
• Kyra Dodson,
• Sweta Adhikari,
• Fatima Rivas,
• Davita L. Watkins and
• Shana V. Stoddard

Beilstein J. Org. Chem. 2020, 16, 628–637, doi:10.3762/bjoc.16.59

• interests are Class I HDAC isozymes, HDAC2 and HDAC8, which are important targets in cancer models as both are associated with high risk diseases such as prostate cancer and neuroblastoma [6][7][8]. Compounds such as vorinostat, givinostat and panobinostat have been successfully applied as HDAC inhibitors

Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

• Thomas J. Cogswell,
• Craig S. Donald and
• Rodolfo Marquez

Beilstein J. Org. Chem. 2020, 16, 135–139, doi:10.3762/bjoc.16.15

• be cytotoxic against human leukaemia, kidney, ovarian and prostate cancer cell lines (IC50 = 25 µM, U251 cell line) [14][15][16]. In an attempt to increase the bioavailability of (R)-(+)-goniothalamin 2, aza-goniothalamin 1 was designed and synthesised; however, aza-goniothalamin 1 was found to have

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

• Lei Zhang,
• Greta Linden and
• Olalla Vázquez

Beilstein J. Org. Chem. 2019, 15, 2500–2508, doi:10.3762/bjoc.15.243

• envision a minimal model based on the previously reported accessible mRNA region of the class I histone deacetylase HDAC-1: 5’-GUGAGCCAAGAAACACUGCCU-3’ to investigate our photoswitchable PNAs [38]. Importantly, HDAC-1 is frequently overexpressed in tumors and particularly, in prostate cancer [39]. Results

Heck- and Suzuki-coupling approaches to novel hydroquinone inhibitors of calcium ATPase

• Robert J. Kempton,
• Taylor A. Kidd-Kautz,
• Soizic Laurenceau and
• Stefan Paula

Beilstein J. Org. Chem. 2019, 15, 971–975, doi:10.3762/bjoc.15.94

• convey specificity for prostate cancer cells. Keywords: calcium ATPase inhibitors; Heck- and Suzuki-coupling reactions; hydroquinones; prostate cancer; tethered amino acid; Introduction Sarco/endoplasmic reticulum calcium ATPase (SERCA) is an integral protein that resides in the membrane of the

• cytotoxic agent. The problem of concomitant toxicity to healthy cells has been circumvented by attaching a short peptide (His-Ser-Ser-Lys-Leu-Gln-Leu) to a tether at TG’s C-8 position (1b). This modification renders the inhibitor inactive [3]. Prostate cancer cells produce on their surface the serine

• tissues are avoided. Compound 1b was found to be selectively toxic to PSA-producing prostate cancer cells as well as in animal studies at submicromolar concentrations [3]. Unfortunately, TG has been difficult to obtain: extraction yields from natural sources are low and the total synthesis of TG required

Synthesis of a tubugi-1-toxin conjugate by a modulizable disulfide linker system with a neuropeptide Y analogue showing selectivity for hY1R-overexpressing tumor cells

• Rainer Kufka,
• Robert Rennert,
• Goran N. Kaluđerović,
• Lutz Weber,
• Wolfgang Richter and
• Ludger A. Wessjohann

Beilstein J. Org. Chem. 2019, 15, 96–105, doi:10.3762/bjoc.15.11

• tubugi-1–NPY conjugate), and native tubulysin A as reference were investigated by in vitro cell viability and proliferation screenings. The tumor cell lines HT-29, Colo320 (both colon cancer), PC-3 (prostate cancer), and in conjunction with RT-qPCR analyses of the hY1R expression, the cell lines SK-N-MC

Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer

• Sagnik Sengupta,
• Mena Asha Krishnan,
• Premansh Dudhe,
• Ramesh B. Reddy,
• Bishnubasu Giri,
• Sudeshna Chattopadhyay and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2018, 14, 2665–2679, doi:10.3762/bjoc.14.244

• tag; Fmoc-Lys-(Tfa)-OH; prostate cancer and ovarian cancer; solid-phase peptide synthesis; Introduction The understanding of cell processes is indispensable to devise new strategies for diagnosis and treatment of cancer and inflammatory diseases through targeted drug delivery techniques [1]. The

Microwave-assisted synthesis of biologically relevant steroidal 17-exo-pyrazol-5'-ones from a norpregnene precursor by a side-chain elongation/heterocyclization sequence

• Gergő Mótyán,
• László Mérai,
• Márton Attila Kiss,
• Zsuzsanna Schelz,
• Izabella Sinka,
• István Zupkó and
• Éva Frank

Beilstein J. Org. Chem. 2018, 14, 2589–2596, doi:10.3762/bjoc.14.236

• hormones, and therefore, in the development of prostate cancer [1]. According to extensive structure–activity relationship and docking studies, a potent steroidal inhibitor should possess certain structural characteristics for efficient P45017α inhibition [1][2][3], such as (i) a five or six-membered non

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• [4Lys(Ac)]-GnRH-III(Dau=Aoa) after 48 h or 72 h of incubation (Table 2). A similar enhanced antitumor activity was also detected for conjugates modified with acylated 4Lys in the HT-29 human colon [19], LNCaP [17] and DU145 [37] human prostate cancer cell lines compared to the conjugate containing

• responsiveness of A2058 cells. Our present results are in harmony with studies demonstrating the migration inhibitory effect of GnRH agonists on melanoma [25] and prostate cancer cell lines [54][55]. These studies also suggested that modulation of cell adhesion or actin cytoskeleton remodelling (morphological

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

• Livia Polgár,
• Eszter Lajkó,
• Pál Soós,
• Orsolya Láng,
• Marilena Manea,
• Béla Merkely,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

• ) showed a higher antitumor effect on MCF-7 human breast, HT-29 human colon and LNCaP human prostate cancer cells in vitro than that of conjugate 4, but not of conjugate 5. Conjugates 13 and 15 containing one Mtx and one Dau were more effective only on HT-29 cells in comparison with conjugate 4

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• ; Introduction Current cancer chemotherapy Cancer is one of the leading causes of death globally behind the heart and circulatory disorders based on statistics of World Health Organization (WHO) [1]. Among all different types of cancer, the most fatal for males are lung and prostate cancer, while for females are

• . The results demonstrated the stronger inhibition of AN-152 on the tumor with respect to the free DOX [126]. Similarly, in vivo experiments were conducted regarding AN-207 in nude mice bearing xenografts of MDA-PCa-2b prostate cancer cells, showing identical results like AN-152 [127]. Gründker et. al

• phase I and phase II studies (AN-152 was renamed to AEZS-108 for the clinical trials) of LHRH-R positive recurrent endometrial and ovarian cancers. The phase I/II study in castration-resistant prostate cancer (CRPC) and chemotherapy refractory bladder cancer also showed promising results. Due to the