Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic

Research output: Contribution to journal › Journal article › Research › peer-review

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Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic. / Persson, Tobias; Hansen, Thomas H; Rasmussen, Thomas B; Skindersø, Mette E; Givskov, Michael; Nielsen, John.

In: Organic & Biomolecular Chemistry, Vol. 3, No. 2, 2004, p. 253-62.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Persson, T, Hansen, TH, Rasmussen, TB, Skindersø, ME, Givskov, M & Nielsen, J 2004, 'Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic', Organic & Biomolecular Chemistry, vol. 3, no. 2, pp. 253-62. https://doi.org/10.1039/b415761c

APA

Persson, T., Hansen, T. H., Rasmussen, T. B., Skindersø, M. E., Givskov, M., & Nielsen, J. (2004). Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic. Organic & Biomolecular Chemistry, 3(2), 253-62. https://doi.org/10.1039/b415761c

Vancouver

Persson T, Hansen TH, Rasmussen TB, Skindersø ME, Givskov M, Nielsen J. Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic. Organic & Biomolecular Chemistry. 2004;3(2):253-62. https://doi.org/10.1039/b415761c

Author

Persson, Tobias ; Hansen, Thomas H ; Rasmussen, Thomas B ; Skindersø, Mette E ; Givskov, Michael ; Nielsen, John. / Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic. In: Organic & Biomolecular Chemistry. 2004 ; Vol. 3, No. 2. pp. 253-62.

Bibtex

@article{5611bfd0fcef11ddb219000ea68e967b,
title = "Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic",
abstract = "Parallel solution-phase synthesis of sulfide AHL analogues (10a-s) by one-pot or a sequential approach is reported. The corresponding sulfoxides 13a-e and sulfones 14a-e were prepared to expand the diversity of the 19-member array of sulfides . Likewise, dithianes 12a-c were prepared with similarity both to sulfides 10a-s and to bioactive structures from garlic. Design and biological screening of all compounds presented in this work targeted inhibition of quorum-sensing comprising competitive inhibition of transcriptional regulators LuxR and LasR. The design was based on critical interactions within the binding-site and structural motifs in molecular components isolated from garlic, 7 and 8, shown to be quorum-sensing inhibitors but not antibiotics. A potent quorum-sensing inhibitor N-(heptylsulfanylacetyl)-l-homoserine lactone (10c) was identified. Together with data collected for the other analogues, the resulting structure-activity relationship led to a hypothesis in which competitive binding was assumed.",
author = "Tobias Persson and Hansen, {Thomas H} and Rasmussen, {Thomas B} and Skinders{\o}, {Mette E} and Michael Givskov and John Nielsen",
note = "Keywords: 4-Butyrolactone; Biological Products; Drug Design; Garlic; Microbial Sensitivity Tests; Molecular Structure; Pseudomonas aeruginosa; Structure-Activity Relationship",
year = "2004",
doi = "10.1039/b415761c",
language = "English",
volume = "3",
pages = "253--62",
journal = "Organic & Biomolecular Chemistry",
issn = "1470-4358",
publisher = "Royal Society of Chemistry",
number = "2",

}

RIS

TY - JOUR

T1 - Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic

AU - Persson, Tobias

AU - Hansen, Thomas H

AU - Rasmussen, Thomas B

AU - Skindersø, Mette E

AU - Givskov, Michael

AU - Nielsen, John

N1 - Keywords: 4-Butyrolactone; Biological Products; Drug Design; Garlic; Microbial Sensitivity Tests; Molecular Structure; Pseudomonas aeruginosa; Structure-Activity Relationship

PY - 2004

Y1 - 2004

N2 - Parallel solution-phase synthesis of sulfide AHL analogues (10a-s) by one-pot or a sequential approach is reported. The corresponding sulfoxides 13a-e and sulfones 14a-e were prepared to expand the diversity of the 19-member array of sulfides . Likewise, dithianes 12a-c were prepared with similarity both to sulfides 10a-s and to bioactive structures from garlic. Design and biological screening of all compounds presented in this work targeted inhibition of quorum-sensing comprising competitive inhibition of transcriptional regulators LuxR and LasR. The design was based on critical interactions within the binding-site and structural motifs in molecular components isolated from garlic, 7 and 8, shown to be quorum-sensing inhibitors but not antibiotics. A potent quorum-sensing inhibitor N-(heptylsulfanylacetyl)-l-homoserine lactone (10c) was identified. Together with data collected for the other analogues, the resulting structure-activity relationship led to a hypothesis in which competitive binding was assumed.

AB - Parallel solution-phase synthesis of sulfide AHL analogues (10a-s) by one-pot or a sequential approach is reported. The corresponding sulfoxides 13a-e and sulfones 14a-e were prepared to expand the diversity of the 19-member array of sulfides . Likewise, dithianes 12a-c were prepared with similarity both to sulfides 10a-s and to bioactive structures from garlic. Design and biological screening of all compounds presented in this work targeted inhibition of quorum-sensing comprising competitive inhibition of transcriptional regulators LuxR and LasR. The design was based on critical interactions within the binding-site and structural motifs in molecular components isolated from garlic, 7 and 8, shown to be quorum-sensing inhibitors but not antibiotics. A potent quorum-sensing inhibitor N-(heptylsulfanylacetyl)-l-homoserine lactone (10c) was identified. Together with data collected for the other analogues, the resulting structure-activity relationship led to a hypothesis in which competitive binding was assumed.

U2 - 10.1039/b415761c

DO - 10.1039/b415761c

M3 - Journal article

C2 - 15632967

VL - 3

SP - 253

EP - 262

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1470-4358

IS - 2

ER -

ID: 10614975