Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

• Mathias B. Danielsen and
• Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

• ’-position (Table 5). Interestingly the resulting nucleotides were found to adopt a conformation which was, with respect to duplex stability, tolerated at terminal positions but not at internal positions [91]. The modified PS-ASOs were transfected into human-607B melanoma cells, and after 48 h, the B-cell

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

• disulfide linkages to transportan and penetratin peptides. The PNA–peptide conjugates were effectively internalized in human Bowes melanoma cells and in vivo in rats [171]. Transportan peptide localized the PNA in membranous structures of cells, while the penetratin conjugate preferred nuclear localization

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

• melanoma cells was increased by [4Lys(Ac)]-GnRH-III(Dau=Aoa), while the GnRH-III(Dau=Aoa) and [4Lys(Bu)]-GnRH-III(Dau=Aoa) decreased this activity. Conclusion: Internalization and cytotoxicity of the conjugates showed that GnRH-III peptides could guard Dau to melanoma cells and promote antitumor activity

• demonstrated in melanoma cell lines [25][26]. There are also evidences that the short-chain fatty acids, including sodium butyrate and valproic acid, could inhibit the proliferation of melanoma cells both in in vitro (e.g., A2058 [27], B16 cell lines [28]) and in vivo experiments [28][29] or could abrogate the

• anticancer drug resistance as they are co-administrated with other chemotherapeutics [29][30]. Nevertheless, there is some controversy about the effects of short-chain fatty acids on the metastatic ability of melanoma cells, since both pro-invasive [31] and anti-invasive [29][32] activities have been

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship

• Mohamed Yacine Ameur Messaoud,
• Ghenia Bentabed-Ababsa,
• Madani Hedidi,
• Aïcha Derdour,
• Floris Chevallier,
• Yury S. Halauko,
• Oleg A. Ivashkevich,
• Vadim E. Matulis,
• Laurent Picot,
• Valérie Thiéry,
• Thierry Roisnel,
• Vincent Dorcet and
• Florence Mongin

Beilstein J. Org. Chem. 2015, 11, 1475–1485, doi:10.3762/bjoc.11.160

• -(trifluoromethyl)phenyl)azole 1f or 2f (Figure 5) could be in relation with a reaction temperature (too high) not suitable to discriminate between similarly acidified positions. Antiproliferative activity in A2058 melanoma cells The N-arylated pyrroles and indoles exerted low to moderate antiproliferative activity

• in A2058 melanoma cells (Figure 6). The best result was obtained with 1f at 10−5 M, which induced 31.9 ± 0.1% growth inhibition in cells treated for 72 h. The linear N-arylated pyrroles 1b and 1e were poorly active. Arylation by a thiophene moiety (1a and 2a) moderately increased the

• previously [60]. A2058 cells are highly invasive human epithelial adherent melanoma cells, derived from lymph nodes metastatic cells obtained from a 43 year old male patient. They are tumorigenic at 100% frequency in nude mice, and considered as very resistant to anticancer drugs. All cell culture

Antioxidant potential of curcumin-related compounds studied by chemiluminescence kinetics, chain-breaking efficiencies, scavenging activity (ORAC) and DFT calculations

• Adriana K. Slavova-Kazakova,
• Silvia E. Angelova,
• Timur L. Veprintsev,
• Petko Denev,
• Davide Fabbri,
• Maria Antonietta Dettori,
• Maria Kratchanova,
• Vladimir V. Naumov,
• Aleksei V. Trofimov,
• Rostislav F. Vasil’ev,
• Giovanna Delogu and
• Vessela D. Kancheva

Beilstein J. Org. Chem. 2015, 11, 1398–1411, doi:10.3762/bjoc.11.151

• , dimers 6 and 7 are nontoxic to PC12 cells at a concentration of 40 μM and, contrary to curcumin, dimer 7 protects PC12 cells against MnCl2 damage [11]. When the phenol OH groups of dimer 8 were protected with methyl or phenyl groups, antiproliferative activity against malignant melanoma cells was

Glycodendrimers: tools to explore multivalent galectin-1 interactions

• Jonathan M. Cousin and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2015, 11, 739–747, doi:10.3762/bjoc.11.84

• ][25]. Synthetic multivalent ligands have been observed to enhance galectin-1 binding through the glycoside cluster effect by mediating the formation of cross-linked aggregates [26][27][28]. Tinari et al. observed galectin-1 augmentation of homotypic cellular aggregation in human melanoma cells (A375

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• a tetrasubstituted trans-cyclopropane subunit. The compound shows modest cytotoxic activity against murine melanoma cells [98][99]. The first enantioselective total synthesis of anthoplalone was achieved by Hanessian and co-workers and utilized their chloroallyl phosphonamide anion cyclopropanation

Human dendritic cell activation induced by a permannosylated dendron containing an antigenic GM₃-lactone mimetic

• Renato Ribeiro-Viana,
• Elena Bonechi,
• Javier Rojo,
• Clara Ballerini,
• Giuseppina Comito,
• Barbara Richichi and
• Cristina Nativi

Beilstein J. Org. Chem. 2014, 10, 1317–1324, doi:10.3762/bjoc.10.133

• the realm of immunotherapy [23][24][25]. GM3-ganglioside 1 (Figure 1), the major glycosphingolipid in normal melanocytes, is overexpressed in melanoma cells with metastatic potential [26][27]. It has been considered a carbohydrate melanoma-associated antigen and widely investigated as a key component

• of a potential vaccine against melanoma disease [28]. The GM3 metabolite, named GM3-lactone 2 (Figure 1) has also been found in melanoma cells as a minor component [29][30]. Although more immunogenic than GM3-ganglioside 1, GM3-lactone 2 failed as an immunostimulant because under physiological

An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells

• Grazia Marano,
• Claas Gronewold,
• Martin Frank,
• Anette Merling,
• Christian Kliem,
• Sandra Sauer,
• Manfred Wiessler,
• Eva Frei and
• Reinhard Schwartz-Albiez

Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89

• ), inhibited the activation of matrix-metalloproteinase-2 (MMP-2) as well as migration of the human melanoma cells of the lines WM-115 and WM-266-4 in a two-dimensional migration assay. GSF inhibited completely the adhesion of WM-115 cells to the extracellular matrix (ECM) proteins, fibrinogen and fibronectin

• (hydroxymethyl)furan and benzoylated galactose imidate, is nontoxic and antagonizes cell physiological processes in vitro that are important for the dissemination and growth of tumor cells in vivo. Keywords: angiogenesis; biomimetic synthesis; carbohydrates; in silico blind docking; melanoma cells

• -adhesive properties showed that 3,4-bis{[(β-D-galactopyranosyl)oxy]methyl}furan (BGF) could inhibit the adhesion of murine B16F10 melanoma cells to several ECM-proteins [15]. Probably, more important than uncharged saccharides are carbohydrates that contain acidic residues, such as sialic acids or sulfated