Photocatalyzed elaboration of antibody-based bioconjugates

• Marine Le Stum,
• Eugénie Romero and
• Gary A. Molander

Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49

• applied to ADCs [34][35][36], the discussion below focuses on photocatalytic approaches that have been used to date to elaborate antibodies, providing insight into those methods that aim to revolutionize approaches to cancer treatment and other medical applications via the use of synthetically

Cryptophycin unit B analogues

• Thomas Schachtsiek,
• Jona Voss,
• Maren Hamsen,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2025, 21, 526–532, doi:10.3762/bjoc.21.40

• ongoing challenge. Cryptophycins are a class of cyclic depsipeptides renowned for their high cytotoxicity in the picomolar range often combined with efficacy against multidrug-resistant tumour cell lines. However, cryptophycins failed as stand-alone drugs in cancer treatment, and their naturally occurring

• particularly effective against multidrug-resistant cancers. Keywords: cancer treatment; cryptophycins; drug conjugates; payload; targeted delivery; Introduction Cryptophycins emerged as highly potent cytotoxins for the use in targeted cancer therapy [1]. Originally discovered over three decades ago by

Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

• Cesia M. Aguilar-Morales,
• América A. Frías-López,
• Nadia V. Emilio-Velázquez,
• Alejandro Islas-Jácome,
• Angelica Judith Granados-López,
• Jorge Gustavo Araujo-Huitrado,
• Yamilé López-Hernández,
• Hiram Hernández-López,
• Luis Chacón-García,
• Jesús Adrián López and
• Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

• bioactivity study was proposed based on observations that indole-coumarin-thiadiazole hybrid compounds described by Kamath et al. [44], as well as indole-benzimidazole hybrids reported by Singla et al. [45] have shown potential as therapeutic agents for breast cancer treatment. Thereby, we hypothesized that

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

• (TNF-related apoptosis-inducing ligand). The death ligand TRAIL is a promising strategy for cancer treatment. In contrast to non-glycosylated thioindirubin 35, a significant activity was observed also for non-glycosylated selenoindirubin 40h. This might be due to the fact that selenoindirubin-N

• moiety. It was demonstrated that 3-alkylideneoxindole-N-glycosides 46 show a significant antitumor activity against melanoma human cell lines SK-Mel-147 and A-375 [46]. As mentioned above, the death ligand TRAIL is a promising strategy for cancer treatment. Unfortunately, melanoma cells show both

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

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

• culture study. As previously noted, CDs have a known affinity for cell membrane structures and components, and they are used for this purpose in the literature. The cholesterol affinity of CD derivatives has been used in the literature for a variety of applications in cancer treatment. Cholesterol

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

• potential uses can be either for oral delivery targeting intestine [33] or for an anti-skin cancer treatment [35], for example. This complexation step is also interesting for the synthesis of molecular imprinted polymers containing cyclodextrin [36]. In previous works, we have produced crosslinked

A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction

• Ksenia Malkova,
• Andrey Bubyrev,
• Vasilisa Krivovicheva,
• Dmitry Dar’in,
• Alexander Bunev and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1636–1641, doi:10.3762/bjoc.18.175

• fragments in the structure of compound 5a) include compound 6 for the treatment of cognitive impairment [7], BET bromodomain inhibitors 7 [8] and 8 [9] for cancer treatment, σ1 receptor modulator 9 for diverse disorders [10] and bacterial regulatory RNA binder 10 [11] (scaffold A) as well as antidiuretic 11

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• cancer treatment [1][2]. Many types of chemotherapeutic drugs have been commonly used in clinical practice, including doxorubicin (DOX) [3], chlorambucil [4], oxaliplatin [5], etc. However, the use of most chemotherapeutic agents is often challenged by their poor water solubility and non-selective

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

• oxonium species in the methylation step. Abiraterone acetate (53) is a drug used in cancer treatment [138]. The Mn-catalyzed methylation of an abiraterone analogue was achieved by replacing the fluorination step by mesylation in 15% of overall yield and only a single diastereoisomer was observed (Scheme

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

• Jana M. Boysen,
• Nauman Saeed and
• Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

• [72]. It was further shown to be cytotoxic and inhibiting cell cycle progression at G2/M phase [163]. Fumitremorgin C was shown to effect mammalian cells and inhibit the breast cancer resistance protein which imparts multidrug resistance and thus resistance to chemotherapeutics in breast cancer

• treatment [75][164]. Helvolic acid Helvolic acid (HA) (23) is a fusidane-type antibiotic that belongs to the triterpenoid class of secondary metabolites. Originally, it was discovered from A. fumigatus but later several other members of the sub phylum Pezizomycotina were also found to be HA producers [165

Fluorinated phenylalanines: synthesis and pharmaceutical applications

• Laila F. Awad and
• Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

• yields of 25–35% and with a radiochemical purity of more than 99%. The 18F-labeling of 4-borono-ᴅ,ʟ-phenylalanine (BPA) provided a potential tool for cancer treatment by boron neutron capture therapy [53] (Scheme 16). The syntheses of a variety of clinically relevant radiotracers including protected 4

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

• Valentina A. Ol’shevskaya,
• Elena G. Kononova and
• Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

• spectroscopy and mass spectrometry. These novel porphyrins and chlorins are expected to be efficient photosensitizers for cancer treatment. The presence of four maleimide groups in these compounds may provide improved binding with proteins in living systems. Synthesis of fluorinated maleimide-substituted

Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

• Daniela Imperio,
• Erika Del Grosso,
• Silvia Fallarini,
• Grazia Lombardi and
• Luigi Panza

Beilstein J. Org. Chem. 2019, 15, 1355–1359, doi:10.3762/bjoc.15.135

• ; Introduction Boron neutron capture therapy (BNCT) belongs to the so-called binary therapies for cancer treatment. It is based on the fission reaction after a low-energy neutron capture by a 10B atom. The neutron capture reaction gives rise to two high linear energy transfer (LET) particles (an α-particle and a

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

• on the biochemical, molecular biological and medicinal aspects of a broad range of tumor diseases, as well as progress in drug development technologies provided the basis for a fundamental paradigm shift in cancer treatment, away from non-selective cytotoxic chemotherapeutics towards specifically

• been identified as fast and efficiently internalizing GPCR in those cells upon agonist binding [29][30]. The NPY Y1 receptor subtype for these reasons is a very promising molecular target to be addressed by selective peptide–drug conjugates (PDCs), notably for cancer treatment or diagnosis. However

Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases

• Maroš Bella,
• Sergej Šesták,
• Ján Moncoľ,
• Miroslav Koóš and
• Monika Poláková

Beilstein J. Org. Chem. 2018, 14, 2156–2162, doi:10.3762/bjoc.14.189

• structure and related pyrrolidines are of particular interest as potential candidates for cancer treatment [26][27]. Our research interest has been focused on searching for efficient inhibitors of α-mannosidases from the GH38 family. Another important feature required for such a potential inhibitor is its

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

• lack of an enzymatically cleavable spacer resulted in conjugate 4 without toxic effects on any cardiac cell types. Because the oxime bond-linked Dau conjugates with or without spacers showed a similar antitumor effect on cancer cells, conjugate 4 could be the safest compound for cancer treatment. The

Development of novel cyclic NGR peptide–daunomycin conjugates with dual targeting property

• Andrea Angelo Pierluigi Tripodi,
• Szilárd Tóth,
• Kata Nóra Enyedi,
• Gitta Schlosser,
• Gergely Szakács and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 911–918, doi:10.3762/bjoc.14.78

• release; NGR peptides; oxime-linkage; targeted drug delivery; Introduction Targeted chemotherapy is one of the most promising approaches for selective cancer treatment that may decrease the toxic side effects of anticancer drugs. This therapeutic approach is based on the fact that tumor specific

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• –vis spectrum, do not aggregate in solution. These dyes are expected to be developed into medical imaging probes. Phthalocyanine is expected to be used not only as a biological imaging agent but also in cancer treatment. Photodynamic therapy (PDT) is a laser cancer therapy that introduces organic dyes

• novel material in the future. Besides blue organic pigments such as ink and colorants, it is expected to be widely applied to electronic devices in the medical field such as color filters for liquid crystal screens [12][13], storage media [14], dye-sensitized solar cells [15][16], photodynamic cancer

• treatment method [17] and other applications. Incidentally, fluorine is one of the elements that is expected to improve the state-of-the-art science technology [18]. Fluorine is located at the top right of the periodic table of elements excluding the noble gas elements of group 18. The size of fluorine is

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

• Magdalena Ceborska,
• Magdalena Zimnicka,
• Aneta Aniela Kowalska,
• Kajetan Dąbrowa and
• Barbara Repeć

Beilstein J. Org. Chem. 2017, 13, 2252–2263, doi:10.3762/bjoc.13.222

• pharmacokinetic properties of the guest molecule, such as water solubility, bioavailability and stability [6][7]. In particular, many important drugs in cancer treatment are often toxic and/or sparingly soluble or even insoluble in water. Among other methods, reversible derivatization of these drugs into CD

Direct catalytic arylation of heteroarenes with meso-bromophenyl-substituted porphyrins

• Alexei N. Kiselev,
• Olga K. Grigorova,
• Alexei D. Averin,
• Sergei A. Syrbu,
• Oskar I. Koifman and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2017, 13, 1524–1532, doi:10.3762/bjoc.13.152

• fields of modern organic chemistry due to their unique structure and electronic properties. These molecules have already proved to be powerful tools in phototherapy, radioimmunotherapy and imaging [1], for cancer treatment [2], and actually sophisticated theranostic porphyrin-based nanodevices have been

Three-component synthesis of highly functionalized aziridines containing a peptide side chain and their one-step transformation into β-functionalized α-ketoamides

• Lena Huck,
• Juan F. González,
• Elena de la Cuesta and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2016, 12, 1772–1777, doi:10.3762/bjoc.12.166

• moieties occur in many natural products and are also encountered in unnatural biologically active compounds including drugs in clinical use, especially in the field of cancer treatment [1]. In the areas of medicinal chemistry and chemical biology, aziridines are of current interest as starting materials

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

• Antonio Dávila-Céspedes,
• Peter Hufendiek,
• Max Crüsemann,
• Till F. Schäberle and
• Gabriele M. König

Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96

• metastatic breast cancer treatment, demonstrating the therapeutic potential of myxobacterial secondary metabolites [29][30][31]. This drug has also been assessed as chemotherapeutic agent in pancreatic lymphoma showing promising results and tolerable toxicity [32]. Over time, different strategies have been

Smart molecules for imaging, sensing and health (SMITH)

• Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

• living subjects [18]. An eventual goal of this ongoing research project is to invent clinical imaging methods that will improve patient care by rapidly evaluating the efficacy of cancer treatment or the extent of cardiovascular disease. The capability of these ZnDPA probes to target anionic cell surfaces

Probing multivalency in ligand–receptor-mediated adhesion of soft, biomimetic interfaces

• Stephan Schmidt,
• Hanqing Wang,
• Daniel Pussak,
• Simone Mosca and
• Laura Hartmann

Beilstein J. Org. Chem. 2015, 11, 720–729, doi:10.3762/bjoc.11.82

• to identify the key principles of carbohydrate/protein receptor interaction and to utilize carbohydrate structures as drugs, e.g., in cancer treatment or pathogen-related diseases [2][3]. A well-established key principle of carbohydrate–receptor interactions is multivalency. Natural carbohydrate