119191-33-2Relevant academic research and scientific papers
Molecular docking studies of (1E,3E,5E )-1,6-bis(substituted phenyl)-hexa-1,3,5-triene and 1,4-bis(substituted trans-styryl)benzene analogs as novel tyrosinase inhibitors
Ha, Young Mi,Lee, Hye Jin,Park, Daeui,Jeong, Hyoung Oh,Park, Ji Young,Park, Yun Jung,Lee, Kyung Jin,Lee, Ji Yeon,Moon, Hyung Ryong,Chung, Hae Young
, p. 55 - 65 (2013/03/14)
We simulated the docking of the tertiary structure of mushroom tyrosinase with our compounds. From the structure-tyrosinase inhibitory activity relationship, it is notable that compounds 4, 8 and 11 showed similar or better activity rates than kojic acid which was used as a positive control. Compounds 17, 21, and 23 among benzene analogs that possess the same substituent showed significantly lower tyrosinase inhibitory effects. Therefore, we have confirmed that among the compounds showing better tyrosinase inhibitory effects than kojic acid, the compounds with triene analogs have better tyrosinase inhibitory effect than the compounds with benzene analogs. Docking simulation suggested the mechanism of compounds by several key residues which had possible hydrogen bonding interactions. The pharmacophore model underlined the features of active compounds, 4,4′-((1E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)diphenol, 5,5′-((1E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)bis(2-methoxy-phenol), and 5,5′-((1 E,3E,5E )-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,3-diol among triene derivatives which had several hydrogen bond groups on both terminal rings. The soundness of the docking results and the agreement with the pharmacophores suggest that it can be conveniently exploited to design inhibitors with an improved affinity for tyrosinase.
Copper(II) ion-sensing mechanism of oligo-phenylene vinylene derivatives: Syntheses and theoretical calculations
Tongkate, Pratoomrat,Phromyothin, Darinee,Sumranjit, Jitapa
experimental part, p. 3329 - 3335 (2012/07/03)
Oligo-phenylene vinylene (oligo-PV) with two picolinamide side-groups and six methoxy end-groups was synthesized in order to be a fluorescent sensing molecule. Various metal ion solutions (1.5×10-4 M) were added to the 1.5×10-6 M acetonitrile solution of the fluorescent molecule. The fluorescent emission spectra showed that, at about the same concentration (1.5×10-4 M), only Cu(II) ion can quench the fluorescent emission of the picolinamide-PV solution. Possible metal ion-sensing mechanisms could be either the binding at picolinamide side-groups or methoxy end-groups, or interchain-stacking driven by the metal ions. Hence, oligo-PVs with six methoxy end-groups but without substituted side-groups, and another oligo-PV with six methoxy end-groups and two ethoxy side-groups were synthesized for comparison. These molecules turned out to be inactive to any metal ion solutions. Moreover, quantum calculation was used to confirm the result. Binding energy and conformation were calculated and simulated. It could be concluded that nitrogen and oxygen atoms of the picolinamide group and one oxygen atom from the methoxy group are involved in the metal ion-binding process.
