5603-15-6Relevant academic research and scientific papers
Discovery and investigation of anticancer ruthenium-arene Schiff-base complexes via water-promoted combinatorial three-component assembly
Chow, Mun Juinn,Licona, Cynthia,Yuan Qiang Wong, Daniel,Pastorin, Giorgia,Gaiddon, Christian,Ang, Wee Han
, p. 6043 - 6059 (2014/08/18)
The structural diversity of metal scaffolds makes them a viable alternative to traditional organic scaffolds for drug design. Combinatorial chemistry and multicomponent reactions, coupled with high-throughput screening, are useful techniques in drug discovery, but they are rarely used in metal-based drug design. We report the optimization and validation of a new combinatorial, metal-based, three-component assembly reaction for the synthesis of a library of 442 Ru-arene Schiff-base (RAS) complexes. These RAS complexes were synthesized in a one-pot, on-a-plate format using commercially available starting materials under aqueous conditions. The library was screened for their anticancer activity, and several cytotoxic lead compounds were identified. In particular, [(η6-1,3,5-triisopropylbenzene)RuCl(4-methoxy-N-(2- quinolinylmethylene)aniline)]Cl (4) displayed low micromolar IC50 values in ovarian cancers (A2780, A2780cisR), breast cancer (MCF7), and colorectal cancer (HCT116, SW480). The absence of p53 activation or changes in IC50 value between p53+/+ and p53-/- cells suggests that 4 and possibly the other lead compounds may act independently of the p53 tumor suppressor gene frequently mutated in cancer.
Designing a thiol specific fluorescent probe for possible use as a reagent for intracellular detection and estimation in blood serum: Kinetic analysis to probe the role of intramolecular hydrogen bonding
Das, Priyadip,Mandal, Amal Kumar,Reddy G., Upendar,Baidya, Mithu,Ghosh, Sudip K.,Das, Amitava
, p. 6604 - 6614 (2013/09/24)
A new and simple chemodosimetric probe L1 is utilized for the selective detection of biothiols in the presence of other relevant amino acids under physiological conditions (pH = 7.4). This eventually led to a turn-off luminescence response due to an effective photoinduced electron transfer based signaling mechanism. A comparison of the results of the fluorescence kinetic analysis and 1H NMR studies of the reaction between thiol and L 1 or the analogous compound L2 revealed the role of intramolecular hydrogen bonding in activating the imine functionality towards nucleophilic addition. Such an example is not common in contemporary literature. Conventional MTT assay studies revealed that this probe (L1) has low cytotoxicity. Results of the cell imaging studies revealed that this probe was cell membrane permeable and could detect the intracellular distribution of biothiols within living HeLa cells. Furthermore, our studies with human blood plasma demonstrated the possibility of using this reagent for the quantitative optical detection of total biothiols in biological fluid. Such an example for the detection of biothiols in real biological samples is rare in the contemporary literature. These results clearly demonstrate the possibility of using this reagent in medicinal biology and diagnostic applications.
A new facile method for preparation of heterocyclic α-iminonitriles and α-oxoacetic acid from heterocyclic aldehydes, p-aminophenol, and sodium cyanide
Jursic, Branko S.,Douelle, Frederic,Bowdy, Katherine,Stevens, Edwin D.
, p. 5361 - 5365 (2007/10/03)
Very efficient, simple, and high yield procedures for the transformation of heterocyclic aldehydes into heterocyclic methylidene-p-hydroxyanilines, heterocyclic α-iminonitriles, and finally into heterocyclic α-oxoacetic acids were described. Considering that many of these compounds have biological activity, the synthetic methodology was optimized using readily available, inexpensive starting materials, and the purification of the product involved only simple crystallization.
