Oxetanocin, a novel nucleoside from bacteria.

Shimada, Nobuyoshi; Hasegawa, Shigeru; Harada, Takashi; Tomisawa, Takayuki; Fujii, Akio; Takita, Tomohisa

doi:10.7164/antibiotics.39.1623

Cited by 230 publications

(71 citation statements)

References 1 publication

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“…The structure was discovered earlier as a semisynthetic derivative of the natural anti-viral oxetanocin from Bacillus megaterium. 5,7 The IC 50 of 2¢-desmethoxy oxetanocin A (1) against HIV was approximately 10-fold better than that of oxetanocin A. However, subsequent synthetic efforts indicated that carbocylic analogs of oxetanocin were more potent anti-viral agents than analogs with an oxetanosyl N-glycoside; 8-10 therefore, 1 was not investigated further.…”

Section: Discussionmentioning

confidence: 99%

Albucidin: a novel bleaching herbicide from Streptomyces albus subsp. chlorinus NRRL B-24108

et al. 2009

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A novel nucleoside phytotoxin, albucidin (1), was isolated from the culture broth of Streptomyces albus subsp. chlorinus NRRL B-24108 using bioassay directed fractionation. The structure of the new natural product, albucidin, was determined by NMR and MS; however, the compound has been reported earlier in the literature following synthetic modification of oxetanocin. This is the first report of herbicidal activity for compounds of this structural type. Albucidin shows high levels of broad spectrum activity following post-emergence applications as well as moderate levels of pre-emergence activity. Accordingly, albucidin could be an important new lead for herbicide discovery.

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Section: Discussionmentioning

confidence: 99%

Albucidin: a novel bleaching herbicide from Streptomyces albus subsp. chlorinus NRRL B-24108

et al. 2009

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“…Further, it is used for the production of pyruvate, vitamin B 12 (Raux et al 1998;Wolf and Brey 1986), fungicidal toxins, and oxetanocin, a viral inhibitor active on HIV (Human immunodeficiency virus), hepatitis B virus, and herpes simplex corneal ulcers (Morita et al 1999;Shimada et al 1986;Shiota et al 1996;Tseng et al 1991). Many of its industrial applications have been reviewed in detail (Vary 1992;Vary 1994).…”

Section: Phage T (Lwoff and Gutmann 1950)mentioning

confidence: 99%

“…Now, we are on our way to a systems biotechnology approach to further systematically enhance biotechnological potential of this Nagao et al 1992) Neutral protease Leather industry (Kühn and Fortnagel 1993;Meinhardt et al 1994;Millet et al 1969) Oxetanocin production Inhibits HIV, hepatitis B virus, cytomegalovirus, herpes virus (Kohlbrenner et al 1990;Morita et al 1999;Shimada et al 1986;Shiota et al 1996;Tseng et al 1991) Penicillin amidase Construction of synthetic penicillins (Martin et al 1995;Suga et al 1990) Toxic waste cleanup Herbicides, C-P bond lysis (Quinn et al 1989) Vitamin B 12 production Aerobic and anaerobic Vitamin B 12 producer (Raux et al 1998;Wolf and Brey 1986) 5 10 Fig. 4 Analysis of UV sensitivity.…”

Section: Conclusion 10mentioning

confidence: 99%

Bacillus megaterium—from simple soil bacterium to industrial protein production host

Vary

Biedendieck

Fuerch

et al. 2007

Appl Microbiol Biotechnol

231

134

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“…For example, complex nucleosides exhibit antibacterial activity by specific inhibition of cell-wall peptidoglycan biosynthesis (Kimura & Bugg, 2003), certain bacterial enzymes, such as purine nucleoside phosphorylases (Bzowska et al, 2000), and DNA ligases (Mills et al, 2011). In particular, adenosine analogues such as cordycepin (Ahn et al, 2000), 29-amino-29-deoxyadenosine and oxetanocin (Shimada et al, 1986), formycins (Bzowska et al, 2000), toyocamycin and its derivatives (Kimura & Bugg, 2003) and some purine derivatives (Tunçbilek et al, 2009) showed biological activity including antibiotic properties. More detailed investigations on the antimicrobial activity of various classes of still untested nucleoside derivatives need to be conducted in order to maximize the potential for developing nucleoside analogues for the treatment of bacterial infections.…”

Section: Introductionmentioning

confidence: 99%

In vitro antibacterial activity of different adenosine analogues

Vitali

Petrelli

Lambertucci

et al. 2012

Journal of Medical Microbiology

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Nucleoside analogues may represent good candidates for the discovery of new antibacterial agents, therefore, a library of adenosine analogues was assessed for their antibacterial activity, and the relationship between the structure and activity of these molecules was outlined. Antibacterial activity was evaluated against that of reference strains of Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, Escherichia coli and Pseudomonas aeruginosa. We tested 54 adenosine analogues, modified both at ribose and base moieties, including adenine and 1/3-deazaadenine derivatives substituted in the 2-and/or N 6 -positions and bearing N-9 sugar moieties, such as ribose, 29-deoxyribose, 39-deoxyribose, 29,39-dideoxyribose or cycloalkyl groups like cyclopentane. The data obtained, MIC and minimal bactericidal concentrations demonstrated that the presence of bulky substituents such as cycloheptyl and cyclooctyl rings on the N 6 -amino, together with a chlorine atom in the 2-position, conferred antibacterial activity against the Gram-positive group with MIC values ranging from 16 to 128 mg l "1 . The intact sugar moiety seemed to be not essential for antimicrobial activity and nucleosides bearing deoxyribose or cyclopentyl groups associated with bulky substituents in N 6 -position showed good antimicrobial properties. Furthermore, N-1 proved to be non-crucial and the 2-chloro-N 6 -cyclooctyl-1-deaza-39-deoxyadenosine and 29,39-dideoxyadenosine compounds were among the more active in the series with an MIC of 32 mg l "1 against Staph. aureus and Strep. pneumoniae. None of the analogues was active against the two Gram-negative species tested. Hence, adenosine derivatives bearing bulky substituents in the N 6 -position may represent good lead compounds for the future discovery of a novel series of antibacterial agents.

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Oxetanocin, a novel nucleoside from bacteria.

Cited by 230 publications

References 1 publication

Albucidin: a novel bleaching herbicide from Streptomyces albus subsp. chlorinus NRRL B-24108

Albucidin: a novel bleaching herbicide from Streptomyces albus subsp. chlorinus NRRL B-24108

Bacillus megaterium—from simple soil bacterium to industrial protein production host

In vitro antibacterial activity of different adenosine analogues

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