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

• . Nonspecific binding sites were blocked with 200 µL of 1% bovine serum albumin (BSA) solution in phosphate-buffered saline (PBS). To control for nonspecific adherence to the PVC surface, cell adhesion was also measured on noncoated PVC plates. Nearly confluent monolayers of WM-115 cells (48 h growth) were

• number of adherent cells relative to the 5 × 104 cells/well were calculated and related to the control incubations without test compounds. Standard deviations were calculated according to Bishop [54], taking the SD of the control into account. Cell migration (wound healing) assay: Intact cell monolayers

2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis

• Hemali D. Premathilake and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2012, 8, 597–605, doi:10.3762/bjoc.8.66

• can be reverted as needed (active–latent strategy). Direct conjugation of the AP moiety to biomolecules, monolayers, arrays, etc., should be possible by executing thiol–ene chemistry [43], ozonolysis/reductive amination [44][45][46], or other ligation protocols [47][48]. Experimental General remarks

Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

• Friederike I. Nollmann,
• Andrea Dowling,
• Marcel Kaiser,
• Klaus Deckmann,
• Sabine Grösch,
• Richard ffrench-Constant and
• Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60

• adhere. The monolayers were washed with GIM before the addition of GIM containing 100, 10 or 1 µg/mL of each of the compounds, which were co-incubated with the hemocytes for 4 h. Following incubation, the GIM and compounds mixture was aspirated and replaced with GIM containing 500 nM Mitotracker CMH2XRos

• for 45 min at 28 °C (Molecular Probes, Invitrogen). Hemocyte monolayers were washed with 1× PBS and fixed with 4% paraformaldehyde for 15 min before permeabilizing with 0.2% Triton X-100 in PBS for 10 min. Cells were stained with FITC-conjugated phalloidin and Hoechst 33258 and finally washed with PBS

Syntheses and properties of thienyl-substituted dithienophenazines

• Annemarie Meyer,
• Eva Sigmund,
• Friedhelm Luppertz,
• Gregor Schnakenburg,
• Immanuel Gadaczek,
• Thomas Bredow,
• Stefan-S. Jester and
• Sigurd Höger

Beilstein J. Org. Chem. 2010, 6, 1180–1187, doi:10.3762/bjoc.6.135

• functional theory at the B3LYP/TZVP level and verify the experimental data. Adsorption of the dithienophenazines on highly ordered pyrolytic graphite (HOPG) was investigated by scanning tunneling microscopy, showing that one of the compounds forms highly organized self-assembled monolayers. Keywords

• : oligothiophenes; phenazines; scanning tunneling microscopy; self-assembled monolayers; TD-DFT calculations; Introduction Thiophene based oligomers and polymers have drawn considerable interest as active materials in various fields of organic electronics such as organic light-emitting diodes (OLEDs), organic thin

• and HOMO-1 in 17a are nearly the same (ΔEHOMO,HOMO-1 =0.02 eV), while in 13 the energy difference between HOMO and HOMO-1 is larger than 0.6 eV [35]. STM study All synthesized thiophene oligomers 12–18 were investigated concerning their ability to form self-assembled monolayers (SAMs) at the HOPG/TCB

Towards racemizable chiral organogelators

• Jian Bin Lin,
• Debarshi Dasgupta,
• Seda Cantekin and
• Albertus P. H. J. Schenning

Beilstein J. Org. Chem. 2010, 6, 960–965, doi:10.3762/bjoc.6.107

• with the synthesis of the starting materials and X. Lou for the help with the chiral HPLC measurements. This research was supported by a Small Scale Collaborative Project grant: Bottom-up Resolution of Functional Enantiomers from Self-Organised Monolayers (Project acronym: RESOLVE) seventh framework

Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines

• Adam W. Franz,
• Svetlana Stoycheva,
• Michael Himmelhaus and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2010, 6, No. 72, doi:10.3762/bjoc.6.72

• relevance in the miniaturization of electronic devices particularly since they could serve as molecular switches, wires, and transistors [2][3][4][5]. As a consequence, the molecule-based bottom-up approach to nanodimensional structured self-assembled monolayers (SAMs) on well-defined metal surfaces has

• conformation of phenothiazines [36], with a folding angle of 158.5°, represents an intriguing new aspect for the formation of self-assembled monolayers (SAMs) of this class of compounds. Furthermore, the transformation of phenothiazines into stable planar radical cations with excellent delocalization [37

• preferential {111} orientation [55]. The thickness of the layer was determined by ellipsometry as described above. As an estimate for the molecular dimensions of the monolayers, the structures of the (oligo)phenothiazines 2 and 4 were computed at the MM2 and DFT levels of theory (Table 2) [56]. To minimize

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

Influence of spacer chain lengths and polar terminal groups on the mesomorphic properties of tethered 5-phenylpyrimidines

• Gundula F. Starkulla,
• Elisabeth Kapatsina,
• Angelika Baro,
• Frank Giesselmann,
• Stefan Tussetschläger,
• Martin Kaller and
• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 63, doi:10.3762/bjoc.5.63

• is 26 Å, which is clear evidence for the presence of monolayers. This leads to the assumption that the molecules might be aligned antiparallel within each smectic layer (Figure 9). Packing the molecules in this array prevents close contacts between the polar regions of the rigid core and the terminal

1-(4-Alkyloxybenzyl)-3-methyl-1H-imidazol-3-ium organic backbone: A versatile smectogenic moiety

• William Dobbs,
• Laurent Douce and
• Benoît Heinrich

Beilstein J. Org. Chem. 2009, 5, No. 62, doi:10.3762/bjoc.5.62

• mesogens impose a bilayer (N = 2) type of organisation on these sublayers, consisting of two head-to-head facing ionic monolayers. The resulting variations of S versus temperature T within the analogous series of various anions but constant chain length (see Figure 7) consist of steep increases

Stereoselective synthesis of (2S,3S,4Z)-4-fluoro- 1,3-dihydroxy- 2-(octadecanoylamino)octadec- 4-ene, [(Z)-4-fluoroceramide], and its phase behavior at the air/water interface

• Gergana S. Nikolova and
• Günter Haufe

Beilstein J. Org. Chem. 2008, 4, No. 12, doi:10.3762/bjoc.4.12

• observed in compressed monolayers of ethyl (Z)-2-fluorooctadec-2-enoate [29] and ethyl (2E,4Z)-4-fluorooctadeca-2,4-dienoate [43]. Moreover, a very short C–H···F–C distance (2.30 Å) was observed in crystalline state for (Z)-2-amino-4-fluorododec-4-enecarboxylic acid [44]. Conclusion In this paper a short

Themed series in organo- fluorine chemistry

• David O'Hagan

Beilstein J. Org. Chem. 2008, 4, No. 11, doi:10.3762/bjoc.4.11

• ]. Organo-fluorine compounds have also found a significant role in soft materials chemistry such as liquid crystals, photoresist polymers and self assembling monolayers [3]. Allied to this breadth of activity is a steady development in the number and range of fluorination reagents and methodologies. DAST