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Antimicrobial peptides (AMPs) work as a primary defense against pathogenic microorganisms. BP100, (KKLFKKILKYL-NH), a rationally designed short, highly cationic AMP, acts against many bacteria, displaying low toxicity to eukaryotic cells. Previously we found that its mechanism of action depends on membrane surface charge and on peptide-to-lipid ratio. Here we present the synthesis of two BP100 analogs: BP100‑alanyl‑hexadecyl‑1‑amine (BP100-Ala-NH-CH) and cyclo(1‑4)‑d‑Cys, Ile, Leu, Cys-BP100 (Cyclo(1‑4)‑cILC-BP100). We examined their binding to large unilamellar vesicles (LUV), conformational and functional properties, and compared with those of BP100. The analogs bound to membranes with higher affinity and a lesser dependence on electrostatic forces than BP100. In the presence of LUV, BP100 and BP100-Ala-NH-CH acquired α-helical conformation, while Cyclo(1‑4)‑cILC-BP100) was partly α-helical and partly β-turn. Taking in conjunction: 1. particle sizes and zeta potential, 2. effects on lipid flip-flop, 3. leakage of LUVs internal contents, and 4. optical microscopy of giant unilamellar vesicles, we concluded that at high concentrations, all three peptides acted by a carpet mechanism, while at low concentrations the peptides acted by disorganizing the lipid bilayer, probably causing membrane thinning. The higher activity and lesser membrane surface charge dependence of the analogs was probably due to their greater hydrophobicity. The MIC values of both analogs towards Gram-positive and Gram-negative bacteria were similar to those of BP100 but both analogues were more hemolytic. Confocal microscopy showed Gram-positive B. subtilis killing with concomitant extensive membrane damage suggestive of lipid clustering, or peptide-lipid aggregation. These results were in agreement with those found in model membranes.

Os compostos utilizados pelo percevejo da soja Piezodorus guildinii como feromônio de alarme foram caracterizados através da análise da composição química das secreções da glândula metatorácica dos insetos adultos. Além dos hidrocarbonetos característicos, (E)-2-hexenal e (E)-4-oxo-2-hexenal foram detectados como constituintes majoritários. Tais compostos já foram previamente descritos como feromônio de alarme em outras espécies de pentatomídeos.The compounds utilized by the soybean stink bug Piezodorus guildinii as alarm pheromone were characterized by analysis of the chemical composition of the metathoracic scent gland secretions from adult bugs. In addition to characteristic hydrocarbons, (E)-2-hexenal and (E)-4-oxo-2-hexenal were detected as major constituents. These compounds were previously described as alarm pheromone in several other pentatomid species.

A series of optically active helical copolymers of phenylacetylenes are prepared by the rhodium-catalyzed copolymerization of the imidazolidinone-linked, catalytically active achiral phenylacetylenes and catalytically inactive chiral phenylacetylenes. The obtained chiral/achiral copolymers exhibit an induced circular dichroism in the UV-vis regions of the copolymer backbones resulting from a preferred-handed helical conformation biased by the chiral imidazolidinone units incorporated in the copolymers. The copolymers are found to catalyze the asymmetric Diels-Alder reaction and produce the products with a moderate enantioselectivity in spite of the fact that the catalytically active units of the copolymers are achiral, indicating that the observed enantioselectivity totally originates from the helical chirality dynamically induced by the optically active, but catalytically inactive imidazolidinone units incorporated in the copolymers.

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