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Quinoline

About: Quinoline is a research topic. Over the lifetime, 14584 publications have been published within this topic receiving 176045 citations. The topic is also known as: benzo[b]pyridine & chinolin.


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Journal ArticleDOI
TL;DR: The compounds described are fluorescent Ca2+ indicators absorbing in the ultraviolet region; the very large spectral shifts observed on binding Ca2+, fit the prediction that complexation should hinder the conjugation of the nitrogen lone-pair electrons with the aromatic rings.
Abstract: A new family of high-affinity buffers and optical indicators for Ca2+ is rationally designed and synthesized. The parent compound is 1,2-bis(o-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA), a relative of the well-known chelator EGTA [ethylene glycol bis(beta-aminoethyl ether)-N,N,N',N'-tetraacetic acid] in which methylene links between oxygen and nitrogen are replaced by benzene rings. BAPTA and its derivatives share the high (greater than 10(5)) selectivity for Ca2+ over Mg2+ of EGTA but are very much less affected by pH changes and are faster at taking up and releasing Ca2+. The affinity of the parent compound for Ca2+ (dissociation constant 1.1 x 10(-7) M in 0.1 M KCl) may be strengthened or weakened by electron-releasing or -withdrawing substituents on the aromatic rings. The Ca2+ and Mg2+ affinities may further be altered by replacing the ether oxygens by heterocyclic nitrogen atoms. The compounds described are fluorescent Ca2+ indicators absorbing in the ultraviolet region; the very large spectral shifts observed on binding Ca2+ fit the prediction that complexation should hinder the conjugation of the nitrogen lone-pair electrons with the aromatic rings. Derivatives with quinoline nuclei are notable for their high sensitivity of fluorescent quantum yield to the binding of Ca2+ but not of Mg2+. Preliminary biological tests have so far revealed little or no binding to membranes or toxic effects following intracellular microinjection.

2,105 citations

Journal Article
TL;DR: The selectivity of this enzyme in the activation of a variety of environmental carcinogens and mutagens in Salmonella typhimurium TA1535/pSK1002 or NM2009 tester strains was examined using the SOS response as an end point of DNA damage.
Abstract: A human cytochrome P-450 (P450) 1B1 cDNA was expressed in Saccharomyces cerevisiae , and the microsomes containing P450 1B1 were used to examine the selectivity of this enzyme in the activation of a variety of environmental carcinogens and mutagens in Salmonella typhimurium TA1535/pSK1002 or NM2009 tester strains, using the SOS response as an end point of DNA damage. We also determined and compared these activities of P450 1B1 with those catalyzed by recombinant human P450s 1A1 and 1A2, which were purified from membranes of Escherichia coli . The carcinogenic chemicals tested included 27 polycyclic aromatic hydrocarbons and their dihydrodiol derivatives, 17 heterocyclic and aryl amines and aminoazo dyes, three mycotoxins, two nitroaromatic hydrocarbons, N -nitrosodimethylamine, vinyl carbamate, and acrylonitrile. Among the three P450 enzymes examined here, P450 1B1 was found to have the highest catalytic activities for the activation of 11,12-dihydroxy-11,12-dihydrodibenzo[ a,l ]pyrene, 1,2-dihydroxy-1,2-dihydro-5-methylchrysene, (+)-7,8-dihydroxy-7,8-dihydrobenzo[ a ]pyrene, 11,12-dihydroxy-11,12-dihydrobenzo[ g ]chrysene, 3,4-dihydroxy-3,4-dihydrobenzo[ c ]phenanthrene, 3-amino-1,4-dimethyl-5 H -pyrido[4,3- b ]indole, 2-aminoanthracene, 3-methoxy-4-aminoazobenzene, and 2-nitropyrene. P450 1B1 also catalyzed the activation of 2-amino-3,5-dimethylimidazo[4,5- f ]quinoline, 2-amino-3,8-dimethylimidazo[4,5- f ]quinoxaline, 2-amino-3-methylimidazo[4,5- f ]quinoline, 2-aminofluorene, 6-aminochrysene and its 1,2-dihydrodiol, (-)-7,8-dihydroxy-7,8-dihydrobenzo[ a ]pyrene, 1,2-dihydroxy-1,2-dihydrochrysene, 1,2-dihydroxy-1,2-dihydro-5,6-dimethylchrysene, 2,3-dihydroxy-2,3-dihydrofluoranthene, 3,4-dihydroxy-3,4-dihydro-7,12-dimethylbenz[ a ]anthracene, and 6-nitrochrysene to appreciable extents. However, P450 1B1 did not produce genotoxic products from benzo[ a ]pyrene, trans -3,4-dihydroxy-3,4-dihydrobenzo[ a ]anthracene, trans -8,9-dihydroxy-8,9-dihydrobenzo[ a ]anthracene, 7,12-dimethylbenz[ a ]anthracene and its cis -5,6-dihydrodiol, 5-methylchrysene, 11,12-dihydroxy-11,12-dihydro-3-methylcholanthrene, 1,2-dihydroxy-1,2-dihydro-6-methylchrysene, benzo[ c ]phenanthrene, 2-amino-6-methyldipyrido[1,2- a :3′,2′- d ]imidazole, 2-acetylaminofluorene, benzidine, 2-naphthylamine, aflatoxin B 1 , aflatoxin G 1 , sterigmatocystin, N -nitrosodimethylamine, vinyl carbamate, or acrylonitrile in this assay system. P450 1B1 is expressed constitutively in extrahepatic organs, including fetal tissue samples, and is highly inducible in various organs by 2,3,7,8-tetrachlorodibenzo- p -dioxin and related compounds in experimental animal models. Thus, activation of procarcinogens by P450 1B1 may contribute to human tumors of extrahepatic origin.

791 citations

Journal ArticleDOI
TL;DR: Benzo[h]quinoline(bhqH) was metallated with iridium(III) to give [Ir(bq)2Cl]2 in which bhq is coordinated at 1-N and 10-C atoms.
Abstract: Benzo[h]quinoline(bhqH) is metallated with iridium(III) to give [Ir(bhq)2Cl]2 in which bhq is coordinated at 1-N and 10-C atoms. This complex reacts with a ligand(L) such as tri-n-butylphosphine and diethylsulfide to yield [Ir(bhq)2ClL].

741 citations

Journal ArticleDOI
TL;DR: Corrosion inhibition efficiencies of heterocyclic, unsaturated (aromatic and nonaromatic) compounds (pyrimidines, benzothiazole derivatives, amino acids containing an aromatic part, pyridi...
Abstract: Corrosion inhibition efficiencies of heterocyclic, unsaturated (aromatic and nonaromatic) compounds (pyrimidines, benzothiazole derivatives, amino acids containing an aromatic part, pyridi...

735 citations

Journal ArticleDOI
TL;DR: In this article, a donor-acceptor conjugated copolymer and a corresponding oligomer were synthesized and their solution and solid-state photophysics were investigated, and their optical band gaps were 2.35−2.64 eV.
Abstract: Alternating carbazole−quinoline and phenothiazine−quinoline donor−acceptor conjugated copolymers and a corresponding oligomer were synthesized, and their solution and solid-state photophysics were investigated. The new copolymers, poly(2,2‘-9-methyl-3,6-carbazolylene-6,6‘-bis(4-phenylquinoline)) and poly(2,2‘-10-methyl-3,7-phenothiazylene-6,6‘-bis(4-phenylquinoline)), had intrinsic viscosities of 11.2−22.0 dL/g, indicating very high molecular weights. The optical band gaps of the new copolymers were 2.35−2.64 eV, which are significantly smaller than the corresponding homopolymers. The absorption and emission spectra of the related donor−acceptor oligomers, 3,6-[bis(4-phenyl-2-quinolyl)]-9-methylcarbazole and 3,7-[bis(4-phenyl-2-quinolyl)]-10-methylphenothiazine, in solvents of varying polarity showed positive solvatochromism. An unusual dual fluorescence, with a blue emission band at 454 nm and an orange emission band at 584 nm, was observed in solid films of the carbazole-linked oligomer and related to i...

720 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
2023421
2022776
2021373
2020469
2019462
2018471