Synthesis of nitric oxide probes with fluorescence lifetime sensitivity

Zhegalova, Natalia G.; Gonzales, Garrett; Berezin, Mikhail Y.

doi:10.1039/c3ob41498a

Cited by 17 publications

(7 citation statements)

References 50 publications

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“…In the last decade work in the NIR technology opened a variety of new ways in industrial, scientific, military and medical applications with new optical devices, 39, 40, 92 imaging techniques 41, 42 contrast agents, 43, 44 and sensors. 45, 46 As a result of advances of new technology, a diverse set of photoluminescent compounds, emitting in the NIR region from small molecules to nanoparticles and larger aggregates, has emerged.…”

Section: Introductionmentioning

confidence: 99%

Shortwave infrared luminescent Pt-nanowires: a mechanistic study of emission in solution and in the solid state

et al. 2017

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Several complexes of “PtL2” composition containing two cyanoxime anions – 2-oximino-2-cyano-N-piperidineacetamide (PiPCO−) and 2-oximino-2-cyano-N-morpholylacetamide (MCO−) have been obtained and characterized both in solutions and in solid state. Complexes exist as two distinct polymorphs: monomeric yellow complexes, and dark-green [PtL2]n 1D polymers, while for the MCO− anion a red, solvent containing dimeric [Pt(MCO)2xDMSO]2 complex also has been isolated. The interconversion of polymorphs was investigated. The monomeric PtL2 units are arranged into the anisotropic extended solid [PtL2]n polymers with the help of Pt—Pt metallophilic interactions. Crystal structures of monomeric PtL2 (L= PiPCO−, MCO−) and red dimeric [Pt(MCO)2xDMSO]2 complexes were determined and revealed the cis-arrangement of cyanoxime anions. The Pt-Pt distance in the “head-to-tail” red dimer was found to be 3.133 Å. The structure of polymeric [Pt(PiPCO)2]n compound was elucidated using the EXAFS method and evidenced the formation of the Pt-wire with ~3.15 Å intermetallic separations. The EPR spectra of both 1D polymers at variable temperatures indicate the absence of Pt(III) species. Both pure dark-green [PtL2]n polymers showed considerable room temperature electrical conductivity of 20–30 S/cm, which evidences the formation of mixed valence Pt(II)/Pt(IV) system. We discovered that these 1D polymeric [PtL2]n complexes show an intense NIR fluorescence beyond 1000 nm, while yellow monomeric PtL2 complexes are not emissive at all. The room temperature excitation spectra of 1D polymeric [PtL2]n complexes demonstrated their strong emission beyond 1000 nm regardless of the used excitation wavelength between 350 and 800 nm, which is typical of systems with delocalized charge carriers. For the first time the formation of mixed valence “metal wire” assembled by metallophilic interactions is directly linked both with an intense fluorescence in the NIR region of spectrum and the electrical conductivity. The effect of concentration of [PtL2]n complexes dispersed in the dielectric salt matrix on the photoluminescence wavelength and intensity was investigated. Both polymers show a remarkably high for this region of spectrum quantum yield reaching ~2%. Variable temperature emission of polymeric [PtL2]n in the −190 - +60°C range was studied as well.

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Section: Introductionmentioning

confidence: 99%

Shortwave infrared luminescent Pt-nanowires: a mechanistic study of emission in solution and in the solid state

et al. 2017

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“…A range of Mg 2+ lifetime probes has also been tested, but again without imaging (Szmacinski and Lakowicz, 1996). However, phosphate ions have been mapped in living cells using FLIM (Paredes et al, 2013), and nitric oxide lifetime probes have been reported, but without use in FLIM as yet (Zhegalova et al, 2013).…”

Section: Flim To Map Ion Concentrationsmentioning

confidence: 97%

Fluorescence lifetime imaging (FLIM): Basic concepts and some recent developments

et al. 2015

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“…1 (11). Isothiocyanatobenzene (0.20 mL, 0.23 mmol) and EDC (0.56 g, 2.9 mmol) were added to a stirred solution of N 1 -methyl-4-(4,4,5,5tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,2-diamine ( 15) 56 in dry THF (16 mL) at rt. The mixture was heated to 50 °C for 16 h. The mixture was concentrated and the residue was partitioned between water (30 mL) and EtOAc (30 mL).…”

Section: -Chloro-n-(cyclopropylmethyl)-3-(1h-indazol-5-yl)imidazo[12b...mentioning

confidence: 99%

Binding to an Unusual Inactive Kinase Conformation by Highly Selective Inhibitors of Inositol-Requiring Enzyme 1α Kinase-Endoribonuclease

et al. 2019

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A series of imidazo[1,2- b ]pyridazin-8-amine kinase inhibitors were discovered to allosterically inhibit the endoribonuclease function of the dual kinase-endoribonuclease inositol-requiring enzyme 1α (IRE1α), a key component of the unfolded protein response in mammalian cells and a potential drug target in multiple human diseases. Inhibitor optimization gave compounds with high kinome selectivity that prevented endoplasmic reticulum stress-induced IRE1α oligomerization and phosphorylation, and inhibited endoribonuclease activity in human cells. X-ray crystallography showed the inhibitors to bind to a previously unreported and unusually disordered conformation of the IRE1α kinase domain that would be incompatible with back-to-back dimerization of the IRE1α protein and activation of the endoribonuclease function. These findings increase the repertoire of known IRE1α protein conformations and can guide the discovery of highly selective ligands for the IRE1α kinase site that allosterically inhibit the endoribonuclease.

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Synthesis of nitric oxide probes with fluorescence lifetime sensitivity

Cited by 17 publications

References 50 publications

Shortwave infrared luminescent Pt-nanowires: a mechanistic study of emission in solution and in the solid state

Shortwave infrared luminescent Pt-nanowires: a mechanistic study of emission in solution and in the solid state

Fluorescence lifetime imaging (FLIM): Basic concepts and some recent developments

Binding to an Unusual Inactive Kinase Conformation by Highly Selective Inhibitors of Inositol-Requiring Enzyme 1α Kinase-Endoribonuclease

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