Antimalarial C-9 oxime derivatives from desmycosin, produced by click chemistry

Tsutsui, Atsuko; Hirose, Tomoyasu; Ishiyama, Aki; Iwatsuki, Masato; Yokota, Arisa; Maruyama, Hitomi; Matsui, Hidehito; Otoguro, Kazuhiko; Hanaki, Hideaki; Omacr, Satoshi; mura,; Sunazuka, Toshiaki

doi:10.1038/ja.2012.113

Cited by 9 publications

(3 citation statements)

References 18 publications

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“…Tylosin A and tylosin B have been shown to be effective against the malaria parasite P. falciparum [ 21 ]. In this study, we evaluated and compared the effects of the third-generation macrolide antibiotics tilmicosin and ATLL on T. gondii infection in vivo and in vitro.…”

Section: Discussionmentioning

confidence: 99%

“…Tilmicosin is referred to as a semi-synthetic macrolide extracted from the fermentation products of Streptomyces fradiae [ 20 ]. Previous studies have shown that tylosin A and tylosin B are active against the malaria parasite Plasmodium falciparum , which made us wander whether the upgraded macrolides have inhibitory effects against another Apicomplexan parasite T. gondii [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

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In Vitro and In Vivo Activities of Tilmicosin and Acetylisovaleryltylosin Tartrate against Toxoplasma gondii

Cao

Wang

et al. 2022

IJMS

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Toxoplasma gondii is a widespread intracellular pathogen that infects humans and a variety of animals. The current therapeutic strategy for human toxoplasmosis is a combination of sulphadiazine and pyrimethamine. However, this combination still has a high failure rate and is ineffective against chronic infections. Therefore, it is important to discover a new anti-T. gondii drug that is safer and more effective in both humans and animals. In this study, we describe the anti-T. gondii activities of the 16-membered macrolide tilmicosin and acetylisovaleryltylosin tartrate (ATLL). Both tilmicosin and ATLL potently inhibited T. gondii with a half-maximal effective concentration (EC50) of 17.96 μM and 10.67 μM, respectively. Interestingly, tilmicosin and ATLL had different effects on the parasites. ATLL exhibited a potent inhibitory effect on intracellular parasite growth, while tilmicosin suppressed parasites extracellularly. By studying the lytic cycle of T. gondii after treatment, we found that ATLL potently inhibited the intracellular proliferation of tachyzoites, while tilmicosin affected the invasion of tachyzoites. Immunofluorescence analysis using ATLL-treated T. gondii showed morphologically abnormal parasites, which may be due to the inhibition of tachyzoite proliferation and division. In addition, tilmicosin and ATLL significantly delayed the death of mice caused by acute toxoplasmosis. Our results suggest that ATLL has potent anti-Toxoplasma activity both in vitro and in vivo and may be an alternative to toxoplasmosis in the future.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In Vitro and In Vivo Activities of Tilmicosin and Acetylisovaleryltylosin Tartrate against Toxoplasma gondii

Cao

Wang

et al. 2022

IJMS

View full text Add to dashboard Cite

show abstract

“…McColm and McHardy reported in 1984 that tylosin A also has anti‐malarial activity against the Liverpool strain of P. falciparum (IC 50 = 0.1 µg mL −1 ). Novel C‐9 oximes of tylosin B also show anti‐malarial activity against chloroquine‐resistant P. falciparum K1 malaria parasites …”

Section: Introductionmentioning

confidence: 99%

Conformational study of tylosin A in water and full assignments of ¹H and ¹³C spectra of tylosin A in D₂O and tylosin B in CDCl₃

Arsić

Aguilar

Bryce

et al. 2016

Magnetic Reson in Chemistry

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Jietacins, azoxy antibiotics with potent nematocidal activity: Design, synthesis, and biological evaluation against parasitic nematodes

Sugawara

Kubo

Hirose

et al. 2018

European Journal of Medicinal Chemistry

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Antimalarial C-9 oxime derivatives from desmycosin, produced by click chemistry

Cited by 9 publications

References 18 publications

In Vitro and In Vivo Activities of Tilmicosin and Acetylisovaleryltylosin Tartrate against Toxoplasma gondii

In Vitro and In Vivo Activities of Tilmicosin and Acetylisovaleryltylosin Tartrate against Toxoplasma gondii

Conformational study of tylosin A in water and full assignments of ¹H and ¹³C spectra of tylosin A in D₂O and tylosin B in CDCl₃

Jietacins, azoxy antibiotics with potent nematocidal activity: Design, synthesis, and biological evaluation against parasitic nematodes

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Antimalarial C-9 oxime derivatives from desmycosin, produced by click chemistry

Cited by 9 publications

References 18 publications

In Vitro and In Vivo Activities of Tilmicosin and Acetylisovaleryltylosin Tartrate against Toxoplasma gondii

In Vitro and In Vivo Activities of Tilmicosin and Acetylisovaleryltylosin Tartrate against Toxoplasma gondii

Conformational study of tylosin A in water and full assignments of 1H and 13C spectra of tylosin A in D2O and tylosin B in CDCl3

Jietacins, azoxy antibiotics with potent nematocidal activity: Design, synthesis, and biological evaluation against parasitic nematodes

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Conformational study of tylosin A in water and full assignments of ¹H and ¹³C spectra of tylosin A in D₂O and tylosin B in CDCl₃