New potential antitumoral di(hetero)arylether derivatives in the thieno[3,2-b]pyridine series: Synthesis and fluorescence studies in solution and in nanoliposomes

• Type: Article in International Scientific Journal
• Date: 2012

Authors

Maria Joao R P Queiroz (Author) Other; Sofia Dias (Author) Other; Daniela Peixoto (Author) Other; Ana Rita O Rodrigues (Author) Other; Andreia D S Oliveira (Author) Other; Paulo J G Coutinho (Author) Other; Luis A Vale Silva (Author) Other; Eugenia Pinto (Author) FFUP; Elisabete M S Castanheira (Author) Other

Journal

Title: Journal of Photochemistry and Photobiology A: Chemistry

Vol. 238

Pages: 71-80

ISSN: 1010-6030

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 16 Citations

Scopus - 16 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-002-8Z8

DOI: 10.1016/j.jphotochem.2012.04.007

Abstract (EN): New fluorescent methoxylated di(hetero)arylethers in the thieno[3,2-b]pyridine series were prepared by a copper-catalyzed Ullmann-type C-O coupling of the methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate with ortho, meta and para-methoxyphenols, using N,N-dimethylglycine as the ligand and Cs2CO3 as the base. The compounds obtained were tested for their inhibitory growth activity in three human tumor cell lines MCF-7 (breast adenocarcinoma), A375-05 (melanoma), NCI-H460 (non-small cell lung cancer). The di(hetero)arylethers bearing a methoxy group in the ortho and meta positions showed very low GI(50) values (1.1-2.5 mu M) in all the three tumor cell lines. Their fluorescence properties in solution and when encapsulated in different nanoliposome formulations, composed either by egg-yolk phosphatidylcholine (Egg-PC), dipalmitoyl phosphatidylcholine (DPPC), dimyristoyl phosphatidylglycerol (DMPG), dioctadecyldimethylammonium bromide (DODAB), distearoyl phosphatidylcholine (DSPC), with or without cholesterol (Ch), or distearoyl phosphatidylethanolamine-(polyethylene glycol)2000 (DSPE-PEG), were studied. All compounds can be carried in the hydrophobic region of the liposome membrane. The liposomes with incorporated compounds are nanometric in size (diameter lower than 150 nm) and have generally low polydispersity.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10