Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery

• Jan Hoyer,
• Ulrich Schatzschneider,
• Michaela Schulz-Siegmund and
• Ines Neundorf

Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204

• kDa antimicrobial protein), which is found in rabbit leukocytes and was shown to bind to negatively charged lipopolysaccharides of Gram-negative bacteria to inhibit their pathogenic activity [9]. We were able to successfully apply sC18 for tumor imaging by conjugation with a metal chelator and a tumor

Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups

• H. Bauke Albada,
• Alina-Iulia Chiriac,
• Michaela Wenzel,
• Maya Penkova,
• Julia E. Bandow,
• Hans-Georg Sahl and
• Nils Metzler-Nolte

Beilstein J. Org. Chem. 2012, 8, 1753–1764, doi:10.3762/bjoc.8.200

• activity of WRWRW-peptides against Gram-positive and Gram-negative bacteria. MIC values of 2–6 µM for RcCO-W(RW)2 and 1–11 µM for (RW)3 were determined. Interestingly, W(RW)2-peptides derivatized with ferrocene were significantly less active than those derivatized with ruthenocene which have similar

• with different N- and C-terminal substituents, which showed low micromolar antibacterial activity against various strains of Gram-positive bacteria and moderate activity against Gram-negative bacteria. Interestingly, head-to-tail cyclized RW-based synAMPs with clustered functionalities increased the

• constructs [33]. Our group has previously shown that the covalent attachment of metal complexes to RW-based synAMPs yields more active derivatives with a changed activity profile for Gram-positive and Gram-negative bacteria. In this work, the attachment of the neutral ferrocenoyl group (ferrocene

Partial thioamide scan on the lipopeptaibiotic trichogin GA IV. Effects on folding and bioactivity

• Marta De Zotti,
• Barbara Biondi,
• Cristina Peggion,
• Matteo De Poli,
• Haleh Fathi,
• Simona Oancea,
• Claudio Toniolo and
• Fernando Formaggio

Beilstein J. Org. Chem. 2012, 8, 1161–1171, doi:10.3762/bjoc.8.129

• Peptide antibacterial activity was tested against Gram-positive and Gram-negative bacteria by the standardized disk diffusion Bauer–Kirby method [75] using the Müller–Hinton culture medium at pH 7.2–7.4 as recommended by the National Committee for Clinical Laboratory Standards [76]. The antibacterial

Synthesis of fluorinated maltose derivatives for monitoring protein interaction by ¹⁹F NMR

• Michaela Braitsch,
• Hanspeter Kählig,
• Georg Kontaxis,
• Michael Fischer,
• Toshinari Kawada,
• Robert Konrat and
• Walther Schmid

Beilstein J. Org. Chem. 2012, 8, 448–455, doi:10.3762/bjoc.8.51

• involved in active transport processes of small molecules into gram-negative bacteria through their function as an initial high-affinity binding component; furthermore, these proteins participate as sensors for signaling during chemotaxis [14]. MBP binds maltodextrin and linear oligosaccharides of up to

Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline

• Karel Křenek,
• Petr Šimon,
• Lenka Weignerová,
• Barbora Fliedrová,
• Marek Kuzma and
• Vladimír Křen

Beilstein J. Org. Chem. 2012, 8, 428–432, doi:10.3762/bjoc.8.48

• capsular polysaccharides in Gram-negative bacteria. N-Acetyl-D-mannosamine (ManNAc) has been found to be, presumably, the strongest monosaccharidic ligand for the natural killer cells (NK-cells) activating protein NKR-P1 [1], and some ManNAc-containing oligosaccharides (e.g., GlcpNAc-β-(1→4)ManpNAc) have

Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

• Hany M. Mohamed,
• Ashraf H. F. Abd EL-Wahab,
• Ahmed M. EL-Agrody,
• Ahmed H. Bedair,
• Fathy A. Eid,
• Mostafa M. Khafagy and
• Kamal A. Abd-EL-Rehem

Beilstein J. Org. Chem. 2011, 7, 1688–1696, doi:10.3762/bjoc.7.199

• activity, better than the standard ampicillin, against two species of Gram-positive bacteria, Staphylococcus aureus (NCTC-7447), Bacillus cereus (ATCC-14579) and two Gram-negative bacteria, Escherichia coli (NCTC-10410) and Serratia marcescens (IMRU-70), while the same compounds showed moderate antifungal

• bacteria, namely Staphylococcus aureus (NCTC-7447), Bacillus cereus (ATCC-14579), and two Gram-negative bacteria, namely Escherichia coli (NCTC-10410), Serratia marcescens (IMRU-70); and against two species of fungi, namely Aspergillus fumigatus (MTCC-3008) and Candida albicans (MTCC-227). The tested

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

• Lucie Brulikova and
• Jan Hlavac

Beilstein J. Org. Chem. 2011, 7, 678–698, doi:10.3762/bjoc.7.80

• tested for their antimicrobial activity against standard reference gram-positive and gram-negative bacterial strains such as Enterococcus faecalis CCM 4224, Staphylococcus aureus CCM 3953, Escherichia coli CCM 3954 and Pseudomonas aeruginosa CCM 3955 and against gram-positive and gram-negative bacteria

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

Pyridinium based amphiphilic hydrogelators as potential antibacterial agents

• Sayanti Brahmachari,
• Sisir Debnath,
• Sounak Dutta and
• Prasanta Kumar Das

Beilstein J. Org. Chem. 2010, 6, 859–868, doi:10.3762/bjoc.6.101

• antibacterial activity against both Gram-positive and Gram-negative bacteria with minimum inhibitory concentration (MIC) values as low as 0.4 μg/mL. Cytotoxicity tests using MTT assay showed 50% NIH3T3 cell viability with hydrogelating amphiphile 2 up to 100 μg/mL. Keywords: antibacterial; bilayer structure

• killing bacteria with MIC values of 0.4–2.0 μg/mL for Gram-positive bacteria and 5.0–20.0 μg/mL for Gram-negative bacteria. However, 2 was found to have slightly better antibacterial activity than 1 with MIC values of only 0.4 μg/mL for Gram-positive Micrococcus luteus and 10 μg/mL for Gram-negative

• Escherichia coli. Interestingly, the pyridinium based amphiphilic hydrogelators showed antibacterial activity against both type of bacteria which is in contrast to the antibacterial activity of conventional quaternary cationic amphiphiles which are, in general, ineffective against Gram-negative bacteria. The

Synthesis of 6-PEtN-α-D-GalpNAc-(1–>6)-β-D-Galp-(1–>4)-β-D-GlcpNAc-(1–>3)-β-D-Galp-(1–>4)-β-D-Glcp, a Haemophilus influenzae lipopolysacharide structure, and biotin and protein conjugates thereof

• Andreas Sundgren,
• Martina Lahmann and
• Stefan Oscarson

Beilstein J. Org. Chem. 2010, 6, 704–708, doi:10.3762/bjoc.6.80

• the title compound have been constructed to allow further use in biological experiments. Keywords: conjugate vaccines; glycoconjugates; Haemophilus influenzae; lacto-N-neotetraose; oligosaccharide synthesis; thioglycosides; Introduction Haemophilus influenzae are Gram-negative bacteria divided into