Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

• Julika Schlosser,
• Olga Fedorova,
• Yuri Fedorov and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11

• intercalators, and some currently applied anticancer drugs actually operate on the basis of intercalation [3]. Hence, several classes of compounds have been established, whose DNA-binding properties can be tailored and fine-tuned for that purpose, for example anthracyclines [5], indolocarbazoles [6], acridines

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

• ., cardiac disorders typical for anthracyclines) [12]. The adverse effects were supposed to be related to (i) doxorubicin released early from the conjugate because of the instability of the ester linkage and (ii) [D-6Lys]-GnRH-I induced endocrine side effects [8]. Therefore, recent strategies for the

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

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

• highlighted in Figure 4. Anthracyclines: Anthracyclines are among the main anti-cancer drugs that are applied in combinations with other chemotherapeutic agents. They are utilized against a variety of cancers including leukemias, lymphomas, breast, ovarian, bladder and lung. Daunorubicin (Dau) was the first

• anthracycline discovered that was extracted from Streptomyces peucetius, a species of actinobacteria, at the beginning of the 1960s. Shortly after, the isolation of doxorubicin (Dox) from a mutated Streptomyces strain was accomplished. Anthracyclines are consisted of a tetracyclin aglycon part and a daunosamine

• sugar moiety. The difference between Dau and Dox is a hydroxy group substituted at the C-14 carbon atom on Dox providing an extra conjugation site for ester linkage (Figure 6). The mechanism of action of anthracyclines is based on their intercalation to DNA inhibiting the macromolecular biosynthesis

Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

• Sabine Schuster,
• Beáta Biri-Kovács,
• Bálint Szeder,
• Viktor Farkas,
• László Buday,
• Zsuzsanna Szabó,
• Gábor Halmos and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

• , 9Pro-EA] and triporelin [6D-Trp], which are used as pharmaceutical peptides to treat inter alia hormone dependent prostate and/or breast cancer [7]. Since the mid-1980s cytotoxic GnRH-I derivatives were developed and investigated to treat tumor cells [4][5][8][9]. Anthracyclines such as doxorubicin

• (Dox), daunorubicin (Dau) or epirubicin are frequently used anticancer drugs. Their mode of action is based on a planar ring system which is important for intercalation into DNA [10]. In this way, anthracyclines can affect a broad range of DNA processes leading to an inhibited synthesis of

• macromolecules such as mRNA and DNA [10][11]. More precisely, anthracyclines act as topoisomerase II toxins inhibiting DNA transcription and replication. They stabilize a DNA topoisomerase-II intermediate in which the DNA strands are separated and a specific tyrosine residue of the topoisomerase II is covalently

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

• Markus Leibeling and
• Daniel B. Werz

Beilstein J. Org. Chem. 2013, 9, 2194–2201, doi:10.3762/bjoc.9.258

• different products and a broad range of structural diversity. Keywords: anthracyclines; carbohydrates; carbopalladation; catalysis; domino reaction; natural products; Introduction Anthracyclines are a widespread class of natural products which belong to the group of aromatic polyketides [1]. Most of them

• have been isolated from bacteria of the order Streptomycetales. The group of Brockmann, who first found anthracyclines in 1963, described them as red to orange dyes [2]. Their structure elucidation revealed a linear fourfold annulated ring system including two benzene units (A-ring and C-ring). The

• substitution pattern of the D-ring bares most of the functionalities, i.e., a secondary and a tertiary alcohol, the former of which is commonly glycosylated with 2,6-dideoxy sugars (Figure 1) [3]. These carbohydrates are of highest importance for the biological activity of anthracyclines and bind to the minor

Effect of transannular interaction on the redox- potentials in a series of bicyclic quinones

• Grigoriy Sereda,
• Jesse Van Heukelom,
• Miles Koppang,
• Sudha Ramreddy and
• Nicole Collins

Beilstein J. Org. Chem. 2006, 2, No. 26, doi:10.1186/1860-5397-2-26

• starting compound. Despite the neglected orbital relaxation that immediately follows the reduction, such correlations have proved to be an efficient tool for prediction of redox-potentials of anthracyclines [5], substituted anthracenes [6], and oligothiophenes [7]. For all chemical species, the