Microbial Transformation of Nitrogen Containing Heterocycles

Parshikov, Igor A.

doi:10.18411/978-1-68419-830-6

Cited by 3 publications

(3 citation statements)

References 109 publications

(153 reference statements)

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“…Fungi metabolize the piperazine ring by N-oxidation, dealkylation, N-acetylation, removal of two carbons, or total breakdown of the ring (Wetzstein et al, 1997;Parshikov, 2016;Parshikov, 2017). We have studied the transformation of fluoroquinolones by different strains of fungi, such as M. ramannianus R-56 (Parshikov et al, 2000) and Rh.…”

Section: Resultsmentioning

confidence: 99%

Fungal Transformation of Ofloxacin and Enrofloxacin

Parshikov¹,

Khasaeva²

2018

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Absrtact-The ability of Rhizoctonia solani VKM F-942 to regioselective metabolize the fluoroquinolones ofloxacin and enrofloxacin was investigated. The fungus was grown in sucrose/peptone broth at 28°C, dosed with 100 g/mL ofloxacin or enrofloxacin, and incubated with shaking for 18 days. The cultures were extracted with ethyl acetate, which was evaporated in vacuo. High-performance liquid chromatography showed that both drugs were transformed to single metabolites, which were identified by mass spectrometry and proton nuclear magnetic resonance spectrometry. The product from ofloxacin (40.0% of the total peak area at 280 nm) was ofloxacin N-oxide and the product from enrofloxacin (14.4% of the total peak area at 280 nm) was enrofloxacin N-oxide. INTRODUCTIONThe fluoroquinolones are synthetic antimicrobial agents that are active against a broad spectrum of pathogenic bacteria. Two of the widely used fluoroquinolones are ofloxacin and enrofloxacin; ofloxacin is used for treatment of various bacterial infections in humans (Monk and Campoli-Richards, 1987) but enrofloxacin is restricted to veterinary use (Brown, 1996). Both drugs are used in Japan to treat respiratory diseases of poultry (Nakamura, 1995).Ofloxacin is transformed in experimental animals to ofloxacin O-glucuronide, N-desmethyl-ofloxacin, and ofloxacin N-oxide (Sudo et al., 1986). Enrofloxacin is transformed in rats to enrofloxacin O-glucuronide and to desethyl-enrofloxacin (= ciprofloxacin) in several mammals (Heitzman, 1995;Mengozzi et al., 1996). In poultry, enrofloxacin metabolites are formed by deethylation and Nhydroxylation as well as by opening of the piperazine ring (Heitzman, 1995).Although the transformation of ofloxacin by fungi has not been reported, cultures of wooddecaying fungi have been shown to convert enrofloxacin to CO 2 and several other metabolites (Martens et al., 1996;Wetzstein et al., 1997). The fungus Mucor ramannianus transforms enrofloxacin to enrofloxacin N-oxide, desethylene-enrofloxacin, and N-acetylciprofloxacin (Parshikov et al., 2000). We now have investigated the transformation of fluoroquinolones by another fungus, Rhizoctonia solani VKM F-942. MATERIALS AND METHODSRhizoctonia solani VKM F-942 was from the AllRussian Microorganism Collection and maintained on agar slants (Modyanova et al., 1999; Khasaeva et al., 2016a,b). The mycelium was scraped from the surface of the agar, suspended in 5 mL of sterilized water, and used to inoculate 500 ml flasks. Each flask contained 100 mL of a medium containing (per liter): 30.0 g sucrose, 5.0 g peptone, 3.0 g NaCl, 3.0 g NaNO 3 , 5.0 g KH 2 PO 4 , 0.5 g MgSO 4 .7H 2 O, 0.5 g KCl, 0.1 g FeSO 4 , 1 mg MnSO 4 , and 1000 mL deionized water. The pH was adjusted to 5.0. Cultures were grown for 2 days on a rotary shaker at 28°C with shaking at 180 rpm.Ofloxacin and enrofloxacin were purchased from Sigma Chemical Co. These compounds were dissolved (at 10 mg mL -1 ) in 20 mM aqueous KOH and filter-sterilized; 1.0 mL was added to each flask to make the final concentrations 249 M ofl...

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Section: Resultsmentioning

confidence: 99%

Fungal Transformation of Ofloxacin and Enrofloxacin

Parshikov¹,

Khasaeva²

2018

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“…Stolyarov's 'V.I. Charnolusky -The Founder of Russian Pedagogical Bibliography' (Parshikov, Stolyarov, 2016) and T. Butorina and L. Ul'yanovskaya's 'The Issue of the Essence of Out-Of-School Education in the Works of V.I. Charnolusky' (Butorina, Ul'yanovskaya, 2015).…”

Section: Discussionmentioning

confidence: 99%

The Russian Prerevolutionary Periodical Press on Out-Of-School Education (1907–1917)

2023

European Journal of Contemporary Education

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This work examines the Russian prerevolutionary periodical press on out-of-school education. The study's source base was a diverse body of literature exploring the periodical press of the Russian Empire period. The use of the chronological method helped gain an insight into the impact of World War I on the nation's periodical press on out-of-school education, and the use of the content analysis method helped establish which of the journals were produced by individual publishers and which were published by academic societies.The study's findings revealed that out-of-school education was covered in prerevolutionary Russia by 12 academic pedagogical journals, which were produced from 1907 to 1917. Due to their distinctive nature, these journals were edited and published by private societies or private publishers. It was rare for most of them to be produced for a long time (e.g., Samoobrazovaniye and Izvestiya Samarskogo Obshchestva Narodnykh Universitetov were published from 1909 to 1917 and from 1910 to 1916, respectively). Half of the journals, 6 of the 12, lasted between 1 and 3 issues, which mainly was due to the outbreak of World War I and the use of tougher censorship measures.

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“…Некоторые хинолоны обладают противоопухолевой, антивирусной (против вирусов гепатита В и С, ВИЧ и вируса герпеса), антиаллергической, противотуберкулезной, иммуномодулирующей и антидиабетической активностью [Boteva, Krasnykh, 2009;Mugnaini et al, 2009;Kloskowski et al, 2010]. Хинолоны могут быть эффективными против различных типов возбудителей малярии [Mahmoudi et al, 2003;Banasik et al 1992;Waring et al 1975;Refaie et al 2005;Gomtsyan et al 2005;Taggart et al 1948;Guetzoyana et al 2009;Araújo et al 2009;Jones et al 2009;Kalkanidis et al 2002;Boibessot et al 2002;Boibessot et al 2002;Agarwal et al 2005;Kontnik, Clardy, 2008;Kaur et al 2009;Resnick et al 1993;Zefirov et al 1993;Parshikov et al 1994b;Kaiser et al 1996;Fetzner 1998;Willumsen et al 2005;Rajini et al 2011;Parshikov, Sutherland, 2012b].…”

Section: Introductionunclassified

Microorganisms in Chemistry of Nitrogenous Heterocycles

Parshikov¹

2017

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Microbial Transformation of Nitrogen Containing Heterocycles

Cited by 3 publications

References 109 publications

Fungal Transformation of Ofloxacin and Enrofloxacin

Fungal Transformation of Ofloxacin and Enrofloxacin

The Russian Prerevolutionary Periodical Press on Out-Of-School Education (1907–1917)

Microorganisms in Chemistry of Nitrogenous Heterocycles

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