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Design and synthesis of fluorescent pilicides and curlicides: bioactive tools to study bacterial virulence mechanisms.

Chorell E, Pinkner JS, Bengtsson C, Edvinsson S, Cusumano CK, Rosenbaum E, Johansson LB, Hultgren SJ, Almqvist F - Chemistry (2012)

Bottom Line: 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.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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Umeå University, 90187 Umeå, Sweden.

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The UPEC strain UTI89 grown for 24 h with and without 100 μM of dual pilicide-curlicide 34 and 28. Blue is DAPI-nuclear stain, green is the compound. A) Bacteria grown in the presence of 100 μM of compound 34. B) Bacteria grown in the presence of 100 μM of compound 28. C) Bacteria grown without any added compound (scale bar is 2 μm).
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fig02: The UPEC strain UTI89 grown for 24 h with and without 100 μM of dual pilicide-curlicide 34 and 28. Blue is DAPI-nuclear stain, green is the compound. A) Bacteria grown in the presence of 100 μM of compound 34. B) Bacteria grown in the presence of 100 μM of compound 28. C) Bacteria grown without any added compound (scale bar is 2 μm).

Mentions: Finally, to study the compounds distribution in a bacterial population, UPEC strain UTI89 was grown under pili-producing conditions (24 h at 37 °C static) with compounds 28 and 34 and examined by fluorescence microscopy (Figure 2). Compounds 28 and 34 appeared to bind bacteria differently, with 34 appearing more punctate and 28 appearing more diffuse. Further experiments are working to examine the reason for these observed differences. We know that even under pilus-inducing conditions, not all bacteria are expressing pili. Thus it is likely that the pilicide is only binding bacteria expressing pili. Experiments are underway to confirm this hypothesis.


Design and synthesis of fluorescent pilicides and curlicides: bioactive tools to study bacterial virulence mechanisms.

Chorell E, Pinkner JS, Bengtsson C, Edvinsson S, Cusumano CK, Rosenbaum E, Johansson LB, Hultgren SJ, Almqvist F - Chemistry (2012)

The UPEC strain UTI89 grown for 24 h with and without 100 μM of dual pilicide-curlicide 34 and 28. Blue is DAPI-nuclear stain, green is the compound. A) Bacteria grown in the presence of 100 μM of compound 34. B) Bacteria grown in the presence of 100 μM of compound 28. C) Bacteria grown without any added compound (scale bar is 2 μm).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3569613&req=5

fig02: The UPEC strain UTI89 grown for 24 h with and without 100 μM of dual pilicide-curlicide 34 and 28. Blue is DAPI-nuclear stain, green is the compound. A) Bacteria grown in the presence of 100 μM of compound 34. B) Bacteria grown in the presence of 100 μM of compound 28. C) Bacteria grown without any added compound (scale bar is 2 μm).
Mentions: Finally, to study the compounds distribution in a bacterial population, UPEC strain UTI89 was grown under pili-producing conditions (24 h at 37 °C static) with compounds 28 and 34 and examined by fluorescence microscopy (Figure 2). Compounds 28 and 34 appeared to bind bacteria differently, with 34 appearing more punctate and 28 appearing more diffuse. Further experiments are working to examine the reason for these observed differences. We know that even under pilus-inducing conditions, not all bacteria are expressing pili. Thus it is likely that the pilicide is only binding bacteria expressing pili. Experiments are underway to confirm this hypothesis.

Bottom Line: 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.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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Umeå University, 90187 Umeå, Sweden.

Show MeSH
Related in: MedlinePlus