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Kenji Aoki – One of the best experts on this subject based on the ideXlab platform.

Shinji Takenaka – One of the best experts on this subject based on the ideXlab platform.

  • Constitutive Synthesis of Enzymes Involved in 2Aminophenol Metabolism and Inducible Synthesis of Enzymes Involved in Benzoate, p-Hydroxybenzoate, and Protocatechuate Metabolism in Pseudomonas sp. Strain AP-3
    Bioscience biotechnology and biochemistry, 2005
    Co-Authors: Shinji Takenaka, Shuichiro Murakami, Young-ju Kim, Endang Setyorini, Kenji Aoki
    Abstract:

    Pseudomonas sp. strain AP-3 grows on benzoate, p-hydroxybenzoate, protocatechuate, and 2Aminophenol as sole carbon and energy source. This strain converted benzoate and p-hydroxybenzoate to catechol and protocatechuate respectively, which were metabolized via the ortho-cleavage pathway. The enzymes responsible for these reactions were shown to be inducible. In contrast, strain AP-3 constitutively expresses the enzymes involved in the metabolism of 2Aminophenol.

  • Complete nucleotide sequence and functional analysis of the genes for 2Aminophenol metabolism from Pseudomonas sp. AP-3.
    Archives of microbiology, 2000
    Co-Authors: Shinji Takenaka, Shuichiro Murakami, Young-ju Kim, Kenji Aoki
    Abstract:

    A 13.9-kb region, which contained the 2Aminophenol 1,6-dioxygenase genes (amnBA) reported before, was cloned from the 2Aminophenol-assimilating bacterium Pseudomonas sp. AP-3. The complete nucleotide sequence of this region was determined and six genes were found downstream of amnBA. The eight genes together were designated amnBACFEDHG. Each gene was similar to the corresponding gene operating in the meta-cleavage pathway, except for amnB, amnA, and amnD. The four 2Aminophenol-metabolizing enzymes, 2-aminomuconic 6-semialdehyde dehydrogenase, 2-aminomuconate deaminase, 4-oxalocrotonate decarboxylase, and 2-oxopent-4-enoate hydratase, were purified and characterized. NH2-terminal amino acid sequences of each purified enzyme agreed with those deduced from amnC, amnF, amnE, and amnD, respectively. These genes were therefore assigned as the genes encoding these respective proteins. The tight clustering of the amn genes, which were all transcribed in the same direction, raised the possibility that these genes formed a single operon. The organization of the amn genes was entirely different from that of the atd, dmp, and xyl genes reported in the meta-cleavage pathway, although these latter genes clustered similarly.

  • Metabolism of 2Aminophenol by Pseudomonas sp. AP-3: modified meta-cleavage pathway.
    Archives of microbiology, 1998
    Co-Authors: Shinji Takenaka, Shuichiro Murakami, Ryu Shinke, Kenji Aoki
    Abstract:

    A novel pathway for 2Aminophenol metabolism by Pseudomonas sp. AP-3 is proposed. The proposed pathway is similar to that known for meta-cleavage of catechol except that one of the hydroxyl groups on the metabolites is replaced by an amino group. During the degradation of 2Aminophenol, 2-amino-2,4-pentadienoic acid is the last metabolite containing an amino group. We, therefore, propose a modified meta-cleavage pathway for the 2Aminophenol metabolism.

Shuichiro Murakami – One of the best experts on this subject based on the ideXlab platform.

  • Constitutive Synthesis of Enzymes Involved in 2Aminophenol Metabolism and Inducible Synthesis of Enzymes Involved in Benzoate, p-Hydroxybenzoate, and Protocatechuate Metabolism in Pseudomonas sp. Strain AP-3
    Bioscience biotechnology and biochemistry, 2005
    Co-Authors: Shinji Takenaka, Shuichiro Murakami, Young-ju Kim, Endang Setyorini, Kenji Aoki
    Abstract:

    Pseudomonas sp. strain AP-3 grows on benzoate, p-hydroxybenzoate, protocatechuate, and 2Aminophenol as sole carbon and energy source. This strain converted benzoate and p-hydroxybenzoate to catechol and protocatechuate respectively, which were metabolized via the ortho-cleavage pathway. The enzymes responsible for these reactions were shown to be inducible. In contrast, strain AP-3 constitutively expresses the enzymes involved in the metabolism of 2Aminophenol.

  • Complete nucleotide sequence and functional analysis of the genes for 2Aminophenol metabolism from Pseudomonas sp. AP-3.
    Archives of microbiology, 2000
    Co-Authors: Shinji Takenaka, Shuichiro Murakami, Young-ju Kim, Kenji Aoki
    Abstract:

    A 13.9-kb region, which contained the 2Aminophenol 1,6-dioxygenase genes (amnBA) reported before, was cloned from the 2Aminophenol-assimilating bacterium Pseudomonas sp. AP-3. The complete nucleotide sequence of this region was determined and six genes were found downstream of amnBA. The eight genes together were designated amnBACFEDHG. Each gene was similar to the corresponding gene operating in the meta-cleavage pathway, except for amnB, amnA, and amnD. The four 2Aminophenol-metabolizing enzymes, 2-aminomuconic 6-semialdehyde dehydrogenase, 2-aminomuconate deaminase, 4-oxalocrotonate decarboxylase, and 2-oxopent-4-enoate hydratase, were purified and characterized. NH2-terminal amino acid sequences of each purified enzyme agreed with those deduced from amnC, amnF, amnE, and amnD, respectively. These genes were therefore assigned as the genes encoding these respective proteins. The tight clustering of the amn genes, which were all transcribed in the same direction, raised the possibility that these genes formed a single operon. The organization of the amn genes was entirely different from that of the atd, dmp, and xyl genes reported in the meta-cleavage pathway, although these latter genes clustered similarly.

  • Metabolism of 2Aminophenol by Pseudomonas sp. AP-3: modified meta-cleavage pathway.
    Archives of microbiology, 1998
    Co-Authors: Shinji Takenaka, Shuichiro Murakami, Ryu Shinke, Kenji Aoki
    Abstract:

    A novel pathway for 2Aminophenol metabolism by Pseudomonas sp. AP-3 is proposed. The proposed pathway is similar to that known for meta-cleavage of catechol except that one of the hydroxyl groups on the metabolites is replaced by an amino group. During the degradation of 2Aminophenol, 2-amino-2,4-pentadienoic acid is the last metabolite containing an amino group. We, therefore, propose a modified meta-cleavage pathway for the 2Aminophenol metabolism.

Ryu Shinke – One of the best experts on this subject based on the ideXlab platform.

Oleg I. Shadyro – One of the best experts on this subject based on the ideXlab platform.

  • N-acyl derivatives of 4,6-di-tert-butyl-2Aminophenol protect neutrophils from halogenating stress
    Free Radical Biology and Medicine, 2018
    Co-Authors: Alena Kavalenka, G. N. Semenkova, Ivan Zholnerevich, G. A. Ksendzova, Victor L. Sorokin, Nadezda Amaegberi, Oleg I. Shadyro
    Abstract:

    Hypochlorous acid is an important microbicidal agent mainly formed by neutrophil myeloperoxidase (MPO), however HOCl hyperproduction leads to halogenating stress associated with different diseases. It is necessary to search for substances that can selectively prevent excessive HOCl generation. We synthesized a number of N-acyl derivatives of 4,6-di-tert-butyl-2Aminophenol which exhibit antiradical activity in cell free model systems. The aim of the work is to study the effect of (N-(4,6-di-tert-butyl-2Aminophenol)R, where R=-COCH3 (1), -COC2H5 (2), -COC3H7 (3) on ROS formation, secretory degranulation and viability of neutrophils exposed to HOCl. It has been shown that all compounds in micromolar concentrations reduce neutrophil ROS formation by 75% or more, inhibit MPO secretion and reduce HOCl production by MPO. It has been found that compounds 1–3 effectively intercept HOCl (up to 78%), but do not interact with H2O2. In concentrations of up to 1 μmol/l, compound 1 increases cell survival in the absence of exogenous HOCl, while compounds 2 and 3 do not influence it. Compound 1 in higher concentrations prevents destruction of neutrophils caused by addition of 300 μmol/l HOCl. Thus, compounds 1–3 can be considered as potential cytoprotectors under halogenating stress.

  • INTRAMOLECULAR INTERACTIONS IN ANTIVIRAL DERIVATIVES OF 4,6-DI-tert-BUTYL-2Aminophenol
    Journal of Applied Spectroscopy, 2009
    Co-Authors: M. V. Belkov, G. A. Ksendzova, G. I. Polozov, I. V. Skornyakov, V. L. Sorokin, G. B. Tolstorozhev, Oleg I. Shadyro
    Abstract:

    We have used Fourier transform IR (FTIR) spectroscopy to study intramolecular interactions in solutions of 4,6-di-tert-butyl-2Aminophenol in n-hexane. When the hydroxyl group in the molecule is ortho to the amino group, an O-H⋅⋅⋅N intramolecular hydrogen bond is formed in the 4-6-di-tert-butyl-2Aminophenol derivatives, where the strength of the hydrogen bond depends on the type of substituent at the para position of the phenyl ring. If there are electron-donor groups on the phenyl ring, then a stronger O-H⋅⋅⋅N bond is formed in the 4,6-di-tert-butyl-2Aminophenol derivatives than in molecules containing electron-acceptor Cl and Br atoms. Formation of the above-indicated intramolecular hydrogen bond affects the course of radiation-induced reac- tions occurring in n-hexane with participation of these compounds and also affects their antiviral activity. Introduction. The ability of viruses to acquire drug resistance is why it is necessary to develop effective new antiviral agents. Attempts have been made to create viral inhibitors with therapeutic action based on successive change in the interactions between the virus and the cell, accompanied by incorporation of anomalous nucleotides formed into the growing viral nucleic acid chain (1). But along with virus-inhibiting properties, these drugs have toxic effects due to possible action on the genetic apparatus of the “host cell”. Accordingly, it is important to search for substances that can inhibit viral multiplication in stages unconnected with processes involving encoding and implementation of genetic information. Compounds able to control the prob- ability and direction of free-radical processes in biosystems may have such properties. Research in the field of free- radical virology has begun only recently, but already it has been shown that production of active forms of oxygen and activation of lipid peroxidation accompany the course of various viral infections, including rhinovirus, HIV, influenza, and various neuroviral infections, and chronic viraviral hepatitis infections (2). Therefore study of the possibility of using antioxidants for prophylaxis and treatment of viral diseases deserves attention in pharmacology. Some derivatives of Aminophenols (AP) having antioxidant properties have already found application as antivi- ral drugs for treatment of herpes infection (3-6). Steady-state radiolysis and IR specspectroscopy have also been used to establish that the antioxidant properties of these Aminophenols are enhanced when there are hydroxyl groups in the free state in the molecules, and such properties are diminished when intramolecular hydrogen bonds of the type O-H⋅⋅⋅N or O-H⋅⋅⋅O=C are formed (7). Nevertheless, data available so far do not allow us to establish a clear connection between the effect of the substances on free-radical processes and their antiviral activity. Establishment of such dependences is complicated because of the unclear role of free-radical processes in development of viral pathology. Reactions with participation of activated forms of oxygen generally are nonselective, and such reactions can lead to damage to both the cells themselves and to the viruses incorporated within them. Therefore the unanswered question is what kind of substances, when introduced into biosystems, can change the direction of free-radical reactions to ensure preferable de- velopment of an antiviral effect.

  • Synthesis and Antiviral Activity of N-Acyl Derivatives of 4,6-Di-( tert -butyl)-2Aminophenol
    Pharmaceutical Chemistry Journal, 2002
    Co-Authors: Oleg I. Shadyro, G. A. Ksendzova, G. I. Polozov, V. L. Sorokin, S. N. Nikolaeva, N. I. Pavlova, O. V. Savinova, E. I. Boreko
    Abstract:

    In recent years, the results of a number of experimental and clinical investigations have shown that antioxidants are promising candidates in the group of drugs used for the treatment of viral pathologies. The inhibiting action of antioxidants with respect to viral replication was reported for herpes simplex virus (HSV), hepatitis C, Epstein – Barr virus, cytomegalic inclusion virus, etc. [1]. It was also demonstrated that phenolic antioxidants of plant origin reduce HIV expression in tests on cell cultures [2]. In this context, we have undertaken the search for viral inhibitors among Aminophenol derivatives known to be capable of controlling the generation and utilization of free radicals [3]. Previously [4], we described the synthesis of N-acyl-substituted 4,6-di-tert-butyl-2Aminophenols and reported on the results of pharmacological tests revealing sufficiently high anti-HSV activity in some of the synthesized compounds. In continuation of this search for new antiviral agents in the class of spatially constrained o-Aminophenol, we have synthesized a series of N-aryl and N-cycloalkyl derivatives of 4,6-di-tert-butyl-2Aminophenol and tested these compounds for antiviral activity with respect to HSV and influenza species in cell cultures. The target compounds (I – VI) were synthesized by treating 3,5-di-tert-butylpyrocatechol with aniline, its derivatives, and cyclohexylamine in petroleum ether or methanol.