In the present study, novel dermacozine-1-carboxamides (8a-8n) were synthesized and screened for their in vitro cytotoxic activity against three different cancer cell lines: MCF-7 (breast cancer), A-549 (lung cancer) and DU145 (prostate cancer). All the compounds showed more efficiency against the DU145 cell line than against the MCF-7 and A-549 cell lines. Furthermore, 8a (CTC50: 7.02 µM) and 8l (CTC50: 6.32 µM) have been found to be more effective against the DU145 cells as they arrest the cell cycle at the G2/M phase by interfering with tubulin polymerization; these results indicate that these compounds act as potential anti-cancer agents by inhibiting tubulin polymerization.
[structure: see text] The recognition of dopamine in water has been achieved with tripodal oxazoline-based artificial receptors, capable of providing a preorganized hydrophobic environment by rational design, which mimics a hydrophobic pocket predicted for a human D2 receptor. The receptors show an amphiphilic nature owing to the presence of hydrophilic sulfonate groups at the periphery of the tripodal oxazoline ligands, which seems to contribute in forming the preorganized hydrophobic environment. The artificial receptors recognized dopamine hydrochloride in water with reasonable selectivity among various organoammonium guests examined. The observed binding behavior of the receptors was explained by evoking guest inclusion in the preorganized hydrophobic pocket-like environment and not by simple ion-pairing interactions. The rationally predicted 1:1 inclusion binding mode was supported by binding studies such as with a reference receptor that cannot provide a similar binding pocket, Job and VT-NMR experiments, electrospray ionization mass analysis, and guest selectivity data. This study implies that an effective hydrophobic environment can be generated even from an acyclic, small molecular artificial receptor. Such a preorganized hydrophobic environment, as being utilized in biological systems, can be effectively used as a complementary binding force for the recognition of organoammonium guests such as dopamine hydrochloride in water.
Biomimetic Materials/chemical synthesis , Biomimetic Materials/metabolism , Dopamine/metabolism , Receptors, Dopamine/chemistry , Receptors, Dopamine/metabolism , Biomimetic Materials/chemistry , Hydrophobic and Hydrophilic Interactions , Ions/chemistry , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular Conformation , Quaternary Ammonium Compounds/chemistry , Spectrometry, Mass, Electrospray Ionization , Titrimetry , Water
Fluorescence signaling in anion binding is modulated from quenching to enhancement by intramolecular H-bonding stabilization of anion-ionophore adducts; the intramolecular H-bonding is suggested to suppress the quenching processes otherwise possible and increase the conformational rigidity of the anionic adducts, leading to fluorescence enhancement in a selective fashion towards cyanide ion, among the various anions examined.
Dansyl Compounds/chemistry , Anions/chemical synthesis , Anions/chemistry , Cyanides/chemistry , Dansyl Compounds/chemical synthesis , Fluorescence , Hydrogen Bonding , Molecular Structure , Sensitivity and Specificity , Stereoisomerism
