864745-80-2Relevant academic research and scientific papers
Furanoflavones pongapin and lanceolatin B blocks the cell cycle and induce senescence in CYP1A1-overexpressing breast cancer cells
Sharma, Rajni,Williams, Ibidapo S.,Gatchie, Linda,Sonawane, Vinay R.,Chaudhuri, Bhabatosh,Bharate, Sandip B.
, p. 6076 - 6086 (2018/11/23)
Expression of cytochrome P450-1A1 (CYP1A1) is suppressed under physiologic conditions but is induced (a) by polycyclic aromatic hydrocarbons (PAHs) which can be metabolized by CYP1A1 to carcinogens, and (b) in majority of breast cancers. Hence, phytochemicals or dietary flavonoids, if identified as CYP1A1 inhibitors, may help in preventing PAH-mediated carcinogenesis and breast cancer. Herein, we have investigated the cancer chemopreventive potential of a flavonoid-rich Indian medicinal plant, Pongamia pinnata (L.) Pierre. Methanolic extract of its seeds inhibits CYP1A1 in CYP1A1-overexpressing normal human HEK293 cells, with IC50 of 0.6 μg/mL. Its secondary metabolites, the furanoflavonoids pongapin/lanceolatin B, inhibit CYP1A1 with IC50 of 20 nM. Although the furanochalcone pongamol inhibits CYP1A1 with IC50 of only 4.4 μM, a semisynthetic pyrazole-derivative P5b, has ～10-fold improved potency (IC50, 0.49 μM). Pongapin/lanceolatin B and the methanolic extract of P. pinnata seeds protect CYP1A1-overexpressing HEK293 cells from B[a]P-mediated toxicity. Remarkably, they also block the cell cycle of CYP1A1-overexpressing MCF-7 breast cancer cells, at the G0-G1 phase, repress cyclin D1 levels and induce cellular-senescence. Molecular modeling studies demonstrate the interaction pattern of pongapin/lanceolatin B with CYP1A1. The results strongly indicate the potential of methanolic seed-extract and pongapin/lanceolatin B for further development as cancer chemopreventive agents.
Synthesis and anticancer effects of pongamol derivatives on mitogen signaling and cell cycle kinases
Rao, R. Ranga,Chaturvedi, Vishal,Babu, K. Suresh,Reddy, P. Prabhakar,Rao, V. Rama Subba,Sreekanth,Sreedhar,Madhusudana Rao
experimental part, p. 634 - 641 (2012/08/07)
A series of oxazole and pyrazole derivatives of pongamol (1) were designed and synthesized to examine their anti-cancer activity. The cytotoxicity of these compounds was examined in three different human tumor cell lines, IMR-32, HeLa and Jurkat. Although
An efficient route for commercially viable syntheses of furan- and thiophene-anellated β-hydroxychalcones
Yadav, Prem P.,Ahmad, Ghufran,Maurya, Rakesh
, p. 5621 - 5624 (2007/10/03)
An efficient route for the syntheses of β-hydroxychalcones containing benzofuran and benzothiophene rings is described. Isoxazolines obtained from oxime-olefin cycloadditions were reduced under pressure to a mixture of products. Isoxazoles obtained from C
