Disease relevance of diazene

• Reduction of cyclic and acyclic diazene derivates by Azotobacter vinelandii nitrogenase: diazirine and trans-dimethyldiazene [1].

High impact information on diazene

• The nanoparticles consist of an organic photoisomerizable dye, spiropyran, as an optically responsive component and another fluorescent dye, perylene diimide, as a high-energy emitter [2].
• The absorption band of the merocyanine matches well the fluorescence bands of perylene diimide (at 535 and 575 nm), and therefore fluorescence resonance energy transfer (FRET) converts the high-energy green emission of the perylene into low-energy red emission when the merocyanine form is present [2].
• Flavin-catalyzed generation of diimide: an environmentally friendly method for the aerobic hydrogenation of olefins [3].
• We tested the following design criteria: (i) binding of the diazene and subsequent reactive diyl to the DNA, (ii) sequence selectivity in the ligand binding and (iii) prevention of diyl dimerization [4].
• RESULTS: 1H-NMR structural studies of Compound 1 bound to d(CGGTACCG)(2) confirmed a threading mode of intercalation, with four base pairs between the diimide units [5].

Biological context of diazene

• Stopped-flow kinetics experiments demonstrate that the diimide both associates and dissociates from DNA more slowly than classical intercalators with similar binding constants [6].
• Reduction and de-excitation then yield the corresponding diazene complex; its generation represents the essential step in a nitrogen fixation and reduction protocol [7].
• The structure-activity relationships among three noncyclic diimide ionophores, designed to be Li+ carriers, were studied in lipid bilayer membranes [8].
• There was no cleavage of caspase-3 in RL-337-treated samples, and the majority of cells died 6 h after the treatment through necrosis (previously, apoptosis-like cell death was detected for diazene JK-279) [9].
• The binding affinities of N-[3-(dimethylamino)propyl amine]-1,8-naphthalenedicarboxylic imide (N-DMPrNI) and N,N'-bis [3,3'-(dimethylamino)propylamine]-naphthalene-1,4,5,8-tetracarboxylic diimide (N-BDMPrNDI) for natural DNAs of differing base composition were determined spectroscopically and by equilibrium dialysis [10].

Anatomical context of diazene

• Naphthalene diimide derivative 1 carrying ferrocenyl moieties at the termini of imide substituents binds intact calf thymus DNA 4 times more strongly than the denatured DNA, and its complex with the intact DNA dissociates 80 times more slowly than that with the denatured DNA [11].
• Effect of thioloxidant diazene dicarboxylic acid bis-(N'-methylpiperazide) (DIP) on 45Ca2+ net uptake into rat pancreatic islets [12].
• Glutathione. X. Human erythrocyte membrane diffusion coefficients for diazene derivatives of the DIP series via intracellular thiol oxidation [13].
• The naphthalenetetracarboxylic diimide derivatives were found to be inactive against mammalian cell lines, making them excellent antimicrobial candidates [14].
• Diazene RL-337 was cytotoxic against all three human tumor cell lines, being more cytotoxic to HeLa cells than diazene JK-279 [9].

Associations of diazene with other chemical compounds

• Herein we report the synthesis, intercalating properties, and analytical applications of an imidazole-substituted naphthalene diimide, N,N'-bis(3-propylimidazole)-1,4,5,8-naphthalene diimide (PIND), functionalized with electrocatalytic redox moieties [15].
• A similar diazene to iron charge-transfer band is found following the reaction of diazene with ferric horseradish peroxidase and with hemin chloride but not with met-myoglobin [16].
• The bisporphyrin host ZnH was synthesized, and its complexation with two aromatic diimide guest molecules, bis(pyridyl)naphthalenediimide NIN and bis(pyridyl)phenyldiimide PIN, was investigated by (1)H NMR and UV/Vis spectroscopy [17].
• These titrations show that 1,4,5,8-naphthalenetetracarboxylic diimide and 1,5-dinitronaphthalene derivatives are weaker pi-acceptors than viologens, which make good pi-acceptor cyclophanes [18].
• Immobilization of glucoamylase by adsorption, glutaraldehyde crosslinking, and covalent attachment to carbon activated by water-soluble diimide or diazotization have been examined [19].

Gene context of diazene

• Inhibition of unwinding of G-quadruplex structures by Sgs1 helicase in the presence of N,N'-bis[2-(1-piperidino)ethyl]-3,4,9,10-perylenetetracarboxylic diimide, a G-quadruplex-interactive ligand [20].
• Flow cytometry analysis showed that diazene JK-279 induces G(2)/M phase arrest, mediated by the increase in p21 expression, and accompanied by an alteration in the expression of survivin [21].
• Electrochemical telomerase assay with ferrocenylnaphthalene diimide as a tetraplex DNA-specific binder [22].
• By means of scanning tunneling microscopy (STM), the self-assembly of two organic donor-acceptor-donor triads (donor=oligo(p-phenylene vinylene) (OPV); acceptor=perylene diimide (PDI)) and their mixtures has been investigated at the liquid/solid interface [23].
• Diazene reacts rapidly with cytochrome c oxidase to reduce cytochrome a and CuA and to form a charge-transfer complex with ferric cytochrome a3; the diazene may serve to bridge the heme iron of this cytochrome and CuB [16].

Analytical, diagnostic and therapeutic context of diazene

• It was identified by UV-vis, RR, and (15)NMR spectroscopies as the diazene-bound [Fe(II)(CN)(5)N(2)H(2)](3)(-) ion and is formed in a competitive process with the radical path, still under the fast regime [24].
• Evaluation of binding of perylene diimide and benzannulated perylene diimide ligands to DNA by electrospray ionization mass spectrometry [25].
• DNA duplex regions of the spots on a DNA microarray were successfully visualized by scanning electrochemical microscopy (SECM) in the electrolyte containing ferrocenyl naphthalene diimide as a hybridization indicator [26].
• TAS+ salts (TAS = (Me2N)3S) of the sulfur diimide anions Me3XNSN- (X = C (1a), Si (1b)) were prepared by Si-N bond cleavage from the corresponding sulfur diimides Me3XNSNSiMe3 and TAS-fluoride ((Me2N)3S+Me3SiF2-) and characterized by X-ray crystallography and multinuclear NMR spectroscopy [27].
• Eight 5,10,15,20-tetrakis[3- or 4-(beta-D-glycopyranosyloxy)phenyl]chlorins were synthesized by means of the Whitlock method with diimide reduction and purified by reversed-phase thin layer chromatography (RP-TLC) [28].

References