64505-68-6Relevant academic research and scientific papers
Fluorescent 1,4-Naphthoquinones to Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains
Neo Shin, Naewoo,Jeon, Hanna,Jung, Youngeun,Baek, Seungyeop,Lee, Sejin,Yoo, Hee Chan,Bae, Gi Hun,Park, Keunwan,Yang, Seung-Hoon,Han, Jung Min,Kim, Ikyon,Kim, Youngsoo
, p. 3031 - 3044 (2019)
Recent clinical approvals of brain imaging radiotracers targeting amyloid-β provided clinicians the tools to detect and confirm Alzheimer's disease pathology without autopsy or biopsy. While current imaging agents are effective in postsymptomatic Alzheimer's patients, there is much room for improvement in earlier diagnosis, hence prompting a need for new and improved amyloid imaging agents. Here we synthesized 41 novel 1,4-naphthoquinone derivatives and initially discovered 14 antiamyloidogenic compounds via in vitro amyloid-β aggregation assay; however, qualitative analyses of these compounds produced conflicting results and required further investigation. Follow-up docking and biophysical studies revealed that four of these compounds penetrate the blood-brain barrier, directly bind to amyloid-β aggregates, and enhance fluorescence properties upon interaction. These compounds specifically stain both diffuse and dense-core amyloid-β plaques in brain sections of APP/PS1 double transgenic Alzheimer's mouse models. Our findings suggest 1,4-naphthoquinones as a new scaffold for amyloid-β imaging agents for early stage Alzheimer's.
It takes two to tango: synthesis of cytotoxic quinones containing two redox active centers with potential antitumor activity
Almeida, Renata G.,Barbosa, Breno P. A.,Braga, Antonio L.,Costa, Pedro M. S.,Gatto, Claudia C.,Jacob, Claus,Jardim, Guilherme A. M.,Lima, Daisy J. B.,Pereira, Cynthia L. M.,Pessoa, Claudia,Santos, Augusto C. C.,Scheide, Marcos R.,de Carvalho, Guilherme G. C.,Valen?a, Wagner O.,da Silva Júnior, Eufranio N.
supporting information, p. 1709 - 1721 (2021/11/16)
We report the synthesis of 47 new quinone-based derivativesviaclick chemistry and their subsequent evaluation against cancer cell lines and the control L929 murine fibroblast cell line. These compounds combine two redox centers, such as anortho-quinone/para-quinone or quinones/selenium with the 1,2,3-triazole nucleus. Several of these compounds present IC50values below 0.5 μM in cancer cell lines with significantly lower cytotoxicity in the control cell line L929 and good selectivity index. Hence, our study confirms the use of a complete and very diverse range of quinone compounds with potential application against certain cancer cell lines.
General method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones (X = ferrocenyl, OMe, Me, I, Cl, and NO2) from 2-methoxy-1,4-naphthoquinone and investigation of H+ and Mg2+ catalysts with DFT calculations
Francisco, Acácio I.,Vargas, Maria D.,Carneiro, J. Walkimar de M.,Lanznaster, Maurício,Torres, José C.,Camara, Celso A.,Pinto, Angelo C.
experimental part, p. 228 - 232 (2009/04/13)
A rapid and simple method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones from 2-methoxy-1,4-naphthoquinone, in boiling MeOH, using MgCl2 and p-toluenesulfonic acid as catalysts is described. This methodology has been applied successfully to the synthesis of electron donor (4-OMe, 4-Me, 4-ferrocenyl) and electron withdrawing (4-I, 4-Cl, 4- and 3-NO2) aniline derivatives. The effect of both H+ and Mg2+ as catalysts was investigated using DFT calculations carried out at the B3LYP/6-31G(d) level. The electronic properties of the novel 2-(4-ferrocenylphenylene)amine-1,4-naphthoquinone 3b were investigated and show that the ferrocenyl and the methoxy group have similar electron donor properties in 2-(4-methoxy)amine-1,4-naphthoquinone 3a.
