108530-10-5Relevant articles and documents
Activatable fluorescent probes for hydrolase enzymes based on coumarin-hemicyanine hybrid fluorophores with large Stokes shifts
Fujioka, Hiroyoshi,Johnsson, Kai,Kamiya, Mako,Kojima, Ryosuke,Uno, Shin-Nosuke,Urano, Yasuteru
, p. 5617 - 5620 (2020)
We show that the equilibrium of intramolecular spirocyclization of coumarin-hemicyanine hybrid fluorophores can be finely tuned by means of chemical modifications. We used this scaffold to develop activatable fluorescent probes with large Stokes shifts for γ-glutamyltranspeptidase and esterase.
Synthesis and antiproliferative activity of 3- and 7-styrylcoumarins
Herrera-R, Angie,Castrillón, Wilson,Otero, Elver,Ruiz, Esneyder,Carda, Miguel,Agut, Raúl,Naranjo, Tonny,Moreno, Gustavo,Maldonado, Maria Elena,Cardona-G, Wilson
, p. 1893 - 1905 (2018)
A series of styrylcoumarins were obtained via Mizoroki-Heck reactions between 3-bromo-4-methyl-7-(octyloxy)-2H-chromen-2-one or 2-oxo-2H-chromen-7-yl trifluoromethanesulfonate and functionalized styrenes. The structures of the products were elucidated by spectroscopic analysis. All compounds were evaluated against SW480 and CHO-K1 cell lines. A number of hybrids showed good antiproliferative activity. Among the tested compounds, hybrids 6e, 10c, and 10d, exhibited the highest activity (IC50- SW480/48h = 6,92; 1,01 and 5,33 μM, respectively) and selectivity (IS48h = >400; 67,8 and 7,2, respectively). In addition, these compounds were able to preserve their activities over time. The results achieved by these hybrids were even better than the lead compounds (coumarin and resveratrol) and the standard drug (5-FU). As regards structure-activity relationship it seems that the location of the styryl group on the coumarin structure and the presence of the hydroxyl group on the phenyl ring were determinant for the activity.
Mechanism-based inactivation of cytochrome P450 2B1 by 7- ethynylcoumarin: Verification of apo-P450 adduction by electrospray ion trap mass spectrometry
Regal, Kelly A.,Schrag, Michael L.,Kent, Ute M.,Wienkers, Larry C.,Hollenberg, Paul F.
, p. 262 - 270 (2000)
7-Ethynylcoumarin was synthesized as a potential mechanism-based inhibitor, and it was found to be an effective inactivator of 7-ethoxy-4- (trifluoromethyl)coumarin (7EFC) O-deethylation catalyzed by purified, reconstituted P450 2B1. In contrast, 7-ethynylcoumarin demonstrated minimal inactivation of P450 2A6-mediated 7-hydroxycoumarin formation. The inactivation of P450 2B1 demonstrated pseudo-first-order kinetics and was NADPH- and inhibitor-dependent. The maximal rate constant for the inactivation of 2B1 was 0.39 min-1 at 30 °C, and thus, the time required to inactivate 50% of the P450 2B1 that was present (t( 1/2 )) was 1.8 min. The estimated concentration which led to half-maximal inactivation (K(I)) was 25 μM. No protection from inactivation was seen in the presence of nucleophiles (glutathione and sodium cyanide), an iron chelator (deferroxamine), or superoxide dismutase and catalase. Addition of the substrate (7EFC) protected P450 2B1 from inactivation, in a concentration-dependent manner. The partition ratio for P450 2B1 was 25; i.e., the number of metabolic events was 25-fold higher than the number of inactivating events. Incubations of 7- ethynylcoumarin with P450 2B1 for 10 min resulted in an 80% loss in enzymatic activity, while 90% of the ability to form a reduced-CO complex remained. This activity loss was not recovered following dialysis, indicative of irreversible inactivation. Covalent attachment of the entire inhibitor and oxygen to apo-P450 2B1, in a 1:1 ratio, was shown via electrospray ion trap mass spectrometry. This method also verified the absence of modification to the heme or the cytochrome P450 reductase. Taken together, the characterization of the inhibition seen with P450 2B1 and 7-ethynylcoumarin was consistent with all of the criteria required to distinguish a mechanism- based inactivator. In addition, electrospray ion trap mass spectrometry has the potential to be applied to protein adducts above and beyond those associated with the mechanism-based inactivation of cytochrome P450s.
Synthesis and antimycobacterial activity of 1-(β-D-Ribofuranosyl)-4-coumarinyloxymethyl- / -coumarinyl-1,2,3-triazole
Srivastava, Smriti,Bimal, Devla,Bohra, Kapil,Singh, Balram,Ponnan, Prija,Jain, Ruchi,Varma-Basil, Mandira,Maity, Jyotirmoy,Thirumal,Prasad, Ashok K.
, p. 268 - 281 (2018)
A series of β-D-ribofuranosyl coumarinyl-1,2,3-triazoles have been synthesized by Cu-catalyzed cycloaddition reaction between azidosugar and 7-O-/7-alkynylated coumarins in 62–70% overall yields. The in vitro antimycobacterial activity evaluation of the s
Coumarin Derivatives Exert Anti-Lung Cancer Activity by Inhibition of Epithelial–Mesenchymal Transition and Migration in A549 Cells
Barreto, Emiliano,Bourguignon, Jean-Jacques,Dos Santos Carmo, Julianderson de Oliveira,Filho, José Maria Barbosa,Mendon?a-Junior, Francisco Jaime Bezerra,Rodarte, Renato Santos,Schmitt, Martine,Silva, Simone Lara de Omena,Souza, Tayhana Priscila Medeiros,da Silva, Camila Radelley Azevedo Costa,de Aquino, Thiago Mendon?a,de Araújo, Rodrigo Santos Aquino,de Mélo, Natália Barbosa,de Moura, Ricardo Olímpio
, (2022/01/24)
A series of coumarin derivatives and isosteres were synthesized from the reaction of triflic intermediates with phenylboronic acids, terminal alkynes, and organozinc compounds through palladium-catalyzed cross-coupling reactions. The in vitro cytotoxic ef
