The complete structure of the polyene macrolide antibiotic nystatin A1

Borowski, Edward; Zielinski, Jan M.; Falkowski, L.; Zimiński, T.; Golik, Jerzy; Kolodziejczyk, Pawel; Jereczek, E.; Gdulewicz, M.; Shenin, Yu. D.; Kotienko, T.

doi:10.1016/s0040-4039(01)96531-1

Cited by 48 publications

(8 citation statements)

References 8 publications

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“…The minor components of the antibiotic complex are nystatin A 2 and nystatin A 3. The composition and configuration of 1 have been elucidated (Fig. ).…”

Section: Introductioncontrasting

confidence: 99%

Intramolecular transformation of an antifungal antibiotic nystatin A₁ into its isomer, iso‐nystatin A₁ – structural and molecular modeling studies

Szwarc

Płosiński

Czerniejewska

et al. 2016

Magnetic Reson in Chemistry

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Nystatin A , a polyene macrolide antifungal antibiotic, in a slightly basic or acidic solution undergoes an intramolecular transformation, yielding a structural isomer, the translactonization product, iso-nystatin A with lactone ring diminished by two carbon atoms. Structural evidence is provided by advanced NMR and Mass Spectrometry (MS) studies. Molecular dynamics simulations and quantum mechanics calculations gave the insight into the course and mechanism of the transformation and its effect on the conformation of the subject molecule. Copyright © 2016 John Wiley & Sons, Ltd.

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“…The minor components of the antibiotic complex are nystatin A 2 and nystatin A 3. The composition and configuration of 1 have been elucidated (Fig. ).…”

Section: Introductioncontrasting

confidence: 99%

Intramolecular transformation of an antifungal antibiotic nystatin A₁ into its isomer, iso‐nystatin A₁ – structural and molecular modeling studies

Szwarc

Płosiński

Czerniejewska

et al. 2016

Magnetic Reson in Chemistry

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“…wt 922.1; Mechlinski et al, 1970) and nystatin (C47H75Q17N; mol. wt 9254 ; Borowski et al, 1971); this may account for the fact that resistance to filipin is less well developed than is resistance to the other two polyenes under consideration.…”

Section: Unabsorbed Absorbedmentioning

confidence: 99%

Physiological Properties Of Mutagen-Induced Variants Of Candida Albicans Resistant To Polyene Antibiotics

Hamilton‐Miller

1972

Journal of Medical Microbiology

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“…Nystatin A1 was the first polyene macrolide discovered [17]. Its covalent structure (without stereochemistry) was confirmed in 1970 [18] and 1971 [19]. Pimaricin, or natamycin [20], was isolated in 1957 [21] and its covalent structure was established by Golding et al .…”

mentioning

confidence: 99%

Solution NMR structure of five representative glycosylated polyene macrolide antibiotics with a sterol‐dependent antifungal activity

Volpon

Lancelin

2002

European Journal of Biochemistry

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Glycosylated polyene macrolide antibiotics, as nystatins and amphotericins, are amphiphilic structures known to exert antifungal activity by disrupting the fungal cell membrane, leading to leakage of cellular materials, and cell death. This membrane disruption is strongly influenced by the presence and the exact nature of the membrane sterols. The solution structures of five representative glycosylated members, three tetraenes (pimaricin, nystatin A1 and rimocidin) and two heptaenes (candidin and vacidin A) have been calculated using geometric restraints derived from 1 H-NMR data and random searches of their conformational space. Despite a different apparent structural order, the NMR solutions structure indicate that the hydroxyl groups all clustered on one side of the rod-shaped structures, and the glycosyl moieties are structurally conserved both in their conformation and their apparent order. The molecular structures afford an understanding of their selective interaction with the membrane sterols and the design of new polyene macrolides with improved activities.

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The complete structure of the polyene macrolide antibiotic nystatin A1

Cited by 48 publications

References 8 publications

Intramolecular transformation of an antifungal antibiotic nystatin A₁ into its isomer, iso‐nystatin A₁ – structural and molecular modeling studies

Intramolecular transformation of an antifungal antibiotic nystatin A₁ into its isomer, iso‐nystatin A₁ – structural and molecular modeling studies

Physiological Properties Of Mutagen-Induced Variants Of Candida Albicans Resistant To Polyene Antibiotics

Solution NMR structure of five representative glycosylated polyene macrolide antibiotics with a sterol‐dependent antifungal activity

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The complete structure of the polyene macrolide antibiotic nystatin A1

Cited by 48 publications

References 8 publications

Intramolecular transformation of an antifungal antibiotic nystatin A1 into its isomer, iso‐nystatin A1 – structural and molecular modeling studies

Intramolecular transformation of an antifungal antibiotic nystatin A1 into its isomer, iso‐nystatin A1 – structural and molecular modeling studies

Physiological Properties Of Mutagen-Induced Variants Of Candida Albicans Resistant To Polyene Antibiotics

Solution NMR structure of five representative glycosylated polyene macrolide antibiotics with a sterol‐dependent antifungal activity

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Product

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Intramolecular transformation of an antifungal antibiotic nystatin A₁ into its isomer, iso‐nystatin A₁ – structural and molecular modeling studies

Intramolecular transformation of an antifungal antibiotic nystatin A₁ into its isomer, iso‐nystatin A₁ – structural and molecular modeling studies