871335-41-0

Upstream product

• 1772-65-2 (E)-4-(3-nitrophenyl)-2-oxo-3-butenoic acid 
• 26482-00-8 1-(2-oxo-2-(2-pyridyl)ethyl)pyridinium iodide 
• 1772-65-2 4-(3-nitrophenyl)-2-oxobut-3-enoic acid 
• 99-61-6 3-nitro-benzaldehyde 

Downstream Products

• 871335-42-1 3-([2,2′-bipyridin]-4-yl)aniline 
• 871335-44-3 4-[3''-(4'''-tolylazo)phenyl]-2,2'-bipyridine 
• 1363768-25-5 bis-{N-[3-(2,2'-dipyridin-4-yl)phenyl]}-9,18,-methano-1,8-naphthalimido[b,f][1,5]diazocene 
• 1363768-21-1 4-[N-(m-phenyl)-4-amino-1,8-napthalimide]-2,2'-bipyridine 
• 1363768-29-9 4-[N-phenyl-4-nitro-1,8-naphthalimide]-2,2’-bipyridine 

Relevant academic research and scientific papers

Synthesis, Characterization, and Biological Profiling of Ruthenium(II)-Based 4-Nitro- And 4-Amino-1,8-naphthalimide Conjugates

We report the synthesis, photophysical characterization, and biological evaluation of four DNA-binding ruthenium(II) polypyridyl 4-nitro- and 4-amino-1,8-naphthalimide conjugates. A meta arrangement around the ring connecting the 1,8-naphthalimide to a bipyridine ligand creates a cleft, the result of which renders the shape of the complex complementary to that of DNA. We have demonstrated that each complex exhibits water solubility and a distinctive set of photophysical properties that has allowed the nature of their interaction with DNA to be probed by various ground- and excited-state titrations. Furthermore, by varying the ancillary ligands, we also demonstrate their ability to act as DNA photocleavers, where all compounds have been found to cleave supercoiled DNA with high efficiency. Detailed cellular uptake experiments revealed that the conjugates accumulate in the cytoplasm and nucleus of HeLa cells, showing characteristic red metal-to-ligand charge-transfer emission, and also exhibit photoactivated cytotoxicity within the cells upon irradiation at 450 nm. A comparison between the meta and para arrangements of the 1,8-naphthalimide moiety relative to the Ru(II) center suggests increased DNA binding in the case of the meta arrangement; however, bipyridine-4-amino-1,8-naphthalimide conjugates appear to show superior phototoxicity in comparison to their 4-nitro derivatives.

Functionalisation of gold nanoparticles with ruthenium(ii) polypyridyl complexes for their application in cellular imaging

Two new dinuclear Ru(ii) polypyridyl complexes containing an alkyl disulphide functionalised bipyridine-based ligand and either 1,10-phenanthroline (phen) or 1,4,5,8-tetraazaphenanthrene (TAP) as ancillary ligands have been synthesised and characterised. Their attachment onto the surface of gold nanoparticles (AuNPs, average diameter of ca. 2.5 nm) resulted in the formation of two new water-soluble Ru(ii)-AuNP conjugates that combine the advantageous properties of both moieties. Both free complexes show the attractive photophysical properties of Ru(ii) polypyridyl complexes and a rapid cellular uptake in HeLa cervical cancer cells. However, their corresponding gold conjugates displayed lower quantum yields than those determined for the free complexes presumed to be due to an energy transfer quenching of the Ru(ii) luminescence by interaction with the gold surface. Despite their diminished luminescence, confocal fluorescence microscopy studies revealed that the Ru(ii)-AuNP conjugates are successfully internalised into HeLa cells and better tolerated than their free complex counterparts after 24 h incubation, which makes them potential luminescent nanomaterials for bioimaging applications.

Synthesis and photophysical evaluations of fluorescent quaternary bipyridyl-1,8-naphthalimide conjugates as nucleic acid targeting agents

A family of organic molecules containing the DNA intercalating chromophores, 4-nitro-and 4-amino 1,8-naphthalimide, conjugated to a diquat derivative by an orthogonal phenyl spacer have been prepared and characterised. Their binding interactions with double-stranded DNA were studied by a variety of spectroscopic techniques. These charged organic compounds are found to exhibit excellent binding affinities to DNA with binding constants comparable to those exhibited by metal complexes.

Photophysical and biological investigation of novel luminescent Ru(ii)-polypyridyl-1,8-naphthalimide Troeger's bases as cellular imaging agents

The synthesis and photophysical properties of 1 and 2, two Ru(ii)-polypyridyl based-1,8-naphthalimide Troeger's bases, are described; these were found to stabilize double stranded DNA, undergo rapid cellular uptake, displaying good luminescence without affecting cell viability even after 24 hours of incubation. This journal is The Royal Society of Chemistry 2012.

Photo-controllable tristability of a dithiolato-bipyridine-Pt(II) complex molecule containing two azobenzene moieties

A new platinum complex with both an azo-bound dithiolato ligand and an azobenzene-bound bipyridine ligand exhibits tristability reversibly controllable using different energy lights. The Royal Society of Chemistry 2005.