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Design and Synthesis of Fluorescent Pilicides and Curlicides : Bioactive Tools to Study Bacterial Virulence Mechanisms

Chorell, Erik (author)
Umeå universitet,Kemiska institutionen
Pinkner, Jerome S (author)
Bengtsson, Christoffer (author)
Umeå universitet,Kemiska institutionen
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Edvinsson, Sofie (author)
Umeå universitet,Kemiska institutionen
Cusumano, Corinne K (author)
Rosenbaum, Erik (author)
Umeå universitet,Kemiska institutionen
Johansson, Lennart B-Å (author)
Umeå universitet,Kemiska institutionen
Hultgren, Scott J (author)
Almqvist, Fredrik (author)
Umeå universitet,Kemiska institutionen,Umeå Centre for Microbial Research (UCMR)
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 (creator_code:org_t)
2012-03-16
2012
English.
In: Chemistry - A European Journal. - Berlin : Wiley-VCH Verlagsgesellschaft. - 0947-6539 .- 1521-3765. ; 18:15, s. 4522-4532
  • Journal article (peer-reviewed)
Abstract Subject headings
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  • Pilicides and curlicides are compounds that block the formation of the virulence factors pili and curli, respectively. To facilitate studies of the interaction between these compounds and the pili and curli assembly systems, fluorescent pilicides and curlicides have been synthesized. This was achieved by using a strategy based on structure-activity knowledge, in which key pilicide and curlicide substituents on the ring-fused dihydrothiazolo 2-pyridone central fragment were replaced by fluorophores. Several of the resulting fluorescent compounds had improved activities as measured in pili- and curli-dependent biofilm assays. We created fluorescent pilicides and curlicides by introducing coumarin and 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) fluorophores at two positions on the peptidomimetic pilicide and curlicide central fragment. Fluorescence images of the uropathogenic Escherichia coli (UPEC) strain UTI89 grown in the presence of these compounds shows that the compounds are strongly associated with the bacteria with a heterogeneous distribution.

Subject headings

NATURVETENSKAP  -- Kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Keyword

antivirulence
biological activity
coumarin
fluorescence
structure–activity relationships

Publication and Content Type

ref (subject category)
art (subject category)

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