120690-80-4Relevant articles and documents
New 13-pyridinealkyl berberine analogues intercalate to DNA and induce apoptosis in HepG2 and MCF-7 cells through ROS mediated p53 dependent pathway: Biophysical, biochemical and molecular modeling studies
Chatterjee, Sabyasachi,Mallick, Sumana,Buzzetti, Franco,Fiorillo, Gaetano,Syeda, Tanjia Monir,Lombardi, Paolo,Saha, Krishna Das,Kumar, Gopinatha Suresh
, p. 90632 - 90644 (2015)
A new series of 13-pyridinealkyl berberine analogues was synthesized and their DNA binding efficacy studied by employing spectroscopic, calorimetric and molecular modeling techniques. Analogues with more than one CH2 group showed better intercalative binding than berberine. The analogue with one CH2 group bound DNA weaker than berberine. The binding of the analogue with single CH2 group was entropy driven, while those with more than one CH2 group was favoured by both entropy and enthalpy changes. Higher salt concentration and temperature destabilized the binding. A larger contribution from non-polyelectrolytic forces to the Gibbs energy and the involvement of strong hydrophobic interactions were inferred. Molecular modeling pin pointed the specific binding site and the non-covalent interactions in the association. The best DNA binding analogue (BER5) inhibited the growth of hepatocellular and breast carcinoma most efficiently. It induced apoptosis in HepG2 and MCF-7 cells with externalization of phosphatidylserine and reactive oxygen species generation with accumulation of cells in the G0/G1 phase. Furthermore, up regulation of p53 and p21 indicated the role of p53 in BER5 mediated apoptosis. The results suggested that 13-pyridinealkyl berberine analogues intercalated to DNA much stronger than berberine, the chain length of the linker plays an important role for the binding, and they induced ROS mediated apoptosis in HepG2 and MCF-7 cells by p53 modulation.
Synthesis and BK channel-opening activity of 2-amino-1,3-thiazole derivatives
Cui, Yong-Mei,Ji, Tong-Tong,Jo, Heeji,Lin, Hai-Xia,Park, Chul-Seung,Qi, Xiao-Lei,Wang, Xue-Ying
supporting information, (2021/05/19)
A series of 2-amino-5-arylmethyl- or 5-heteroarylmethyl-1,3-thiazole derivatives were synthesized and evaluated for BK channel-opening activities in cell-based fluorescence assay and electrophysiological recording. The assay results indicated that the activities of the investigated compounds were influenced by the physicochemical properties of the substituent at benzene ring.
Replacing triazole with diazole to optimize physicochemical properties of a click-based lead compound
Tian, Yinping,Lv, Wenhui,Meng, Qiuyue,Li, Xuewei,Zeng, Wei,Lu, Yaxin,Wang, Peng G.,Jin, Jin,Shen, Jie
, p. 2007 - 2014 (2017/08/03)
This work mainly demonstrated how the physicochemical properties of a click-based lead compound would be affected by the replacement of its triazole ring with a pyrazole or an imidazole ring. Compound A1, a click-based lead from our previous work, was a selective and moderate inhibitor against VEGFR2. Eight new derivatives of A1 were synthesized, from which a pyrazole derivative B2 was selected as a new lead. B2 maintained the in vitro activity of A1. The solubilities of B2 at pH 2.0 and pH 7.4 were enhanced to 1310 and 1.7 μg/mL, respectively. Its log D value of 3.4 would favor B2 to be modified with hydrophilic fragments to further improve intestinal solubility in our future work.
