Polyene antibiotic-sterol interactions in membranes of Acholeplasma laidlawii cells and lecithin liposomes. III. Molecular structure of the polyene antibiotic-cholesterol complexes

Kruijff, Ben de; Demel, R.A.

doi:10.1016/0005-2736(74)90332-0

Cited by 602 publications

(342 citation statements)

References 19 publications

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“…Similar interactions stabilized to some extent the binary complex; nevertheless the sterol had almost complete conformational freedom there [13]. As presupposed in the hypothetical [5], confirmed in the computational models of other authors [19,22,23] and in our study, the additional stabilizing factors were van der Waals intermolecular forces between AmB and a sterol. Their positioning properties for the sterol molecule arise from its presence in the groove between chromophore systems of AmBs.…”

Section: Discussionsupporting

confidence: 90%

“…The most comprehensive one was created by deKruijff and Demel in the early 1970s [5]. According to this model the channel structure is circular and consists of 8 AmB molecules interdigitated by 8 sterol molecules.…”

Section: Introductionmentioning

confidence: 99%

“…In the earliest proposal put forward by Herve et al the sterol hydroxyl group is bound to the charged fragments of the antibiotic molecule [10]. Mazerski and coworkers [8] postulate that the primary complex could be a part or the complete structure of the deKruijff's channel [5]. They specify three types of interactions responsible for the complex existence: binding forces between hydrophobic parts of the molecules, stabilizing ones between charged groups of adjacent AmB molecules, and orienting forces between the sterol hydroxyl group and an unidentified polar fragment of the antibiotic molecule.…”

Section: Introductionmentioning

confidence: 99%

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Molecular modeling of amphotericin B–ergosterol primary complex in water II

Baran

Borowski²,

Mazerski³

2009

Biophysical Chemistry

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The work presented is a part of our continual study on the behavior of the polyene macrolide antibiotic amphotericin B (AmB) complexes with sterols on the molecular level. In contrast to the previously researched AmB-ergosterol binary complex, the AmB-ergosterol-AmB aggregates simulated of 2:1 stoichiometry retain significantly higher stability and relatively rigid, "sandwich" geometry. Van der Waals forces with a considerable share of the electrostatic interactions are responsible for such behavior. System of the intermolecular hydrogen bonds also seems to be of notable importance for the complex's structure preservation. The most energetically favored geometries match fairly close the geometric criteria and the network of interactions postulated in the contemporary hypothetical and computational models of antibiotic-sterol complexes. On the basis of works previously published and the present study novel hypotheses on the AmB selectivity towards sterols varying in chemical structure and on the possible mechanisms of channel structure formation were presented.A

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Section: Discussionsupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Molecular modeling of amphotericin B–ergosterol primary complex in water II

Baran

Borowski²,

Mazerski³

2009

Biophysical Chemistry

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“…Both filipin and methyl-β-cyclodextrin (MCD) affect cholesterol in the membrane, however in different ways [9,10]. We showed that MCD treatment lead to failure of CCR5 to inhibit forskolin-stimulated accumulation of cAMP and it also changed the potency of CCL3 for intracellular calcium release, however cholesterol depletion had no effect on receptor internalisation.…”

Section: Introductionmentioning

confidence: 95%

Distinct modes of molecular regulation of CCL3 induced calcium flux in monocytic cells

Cardaba

Müeller

2009

Biochemical Pharmacology

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.Page 1 of 32A c c e p t e d M a n u s c r i p t 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 by MCD addition, which shows that the cholesterol content in the membrane is only one factor in determining the amount of receptor response. We show that CCR5signalling is dependant on thapsigargin-sensitive Ca 2+ stores and on activation of ryanodine receptors as well as InsP3 receptors or store-operated channels.Cholesterol depletion with MCD changes the thapsigargin sensitivity in THP-1 cells * ManuscriptPage 2 of 32 A c c e p t e d M a n u s c r i p t 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 2 and also alters receptor-G-protein coupling towards pertussis toxin (PTX) independent G-proteins. Cholesterol removal by MCD in THP-1 cells has far reaching consequences for receptor activation and signalling and emphasises the need for a clearer understanding of how membrane fluidity affects receptor signalling events.

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“…Therefore, we have constructed model membranes containing either 13% or 30% of a sterol (ergosterol or cholesterol) and a model phospholipd (saturated: DPPC and unsaturated: DOPC). The knowledge of the interactions between phospholipids and cholesterol/ergosterol may have significant implications in the mode of action of the polyene antifungal antibiotics, which are believed to form channels in cellular membranes, due to their interactions with sterols, which are responsible for the leakage of vital cellular components, leading to the cell death [19]. Therefore, because phospholipids comprise ca.…”

mentioning

confidence: 99%

Interactions between membrane sterols and phospholipids in model mammalian and fungi cellular membranes — A Langmuir monolayer study

Miñones

País

Conde

et al. 2009

Biophysical Chemistry

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To cite this version:J. Miñones, S. Pais, O. Conde, P. Dynarowicz-Łątka. Interactions between membrane sterols and phospholipids in model mammalian and fungi cellular membranes -A Langmuir monolayer study. Biophysical Chemistry, Elsevier, 2009, 140 (1-3) This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. A C C E P T E D

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Polyene antibiotic-sterol interactions in membranes of Acholeplasma laidlawii cells and lecithin liposomes. III. Molecular structure of the polyene antibiotic-cholesterol complexes

Cited by 602 publications

References 19 publications

Molecular modeling of amphotericin B–ergosterol primary complex in water II

Molecular modeling of amphotericin B–ergosterol primary complex in water II

Distinct modes of molecular regulation of CCL3 induced calcium flux in monocytic cells

Interactions between membrane sterols and phospholipids in model mammalian and fungi cellular membranes — A Langmuir monolayer study

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