A new route to trihydroxamate-containing artificial siderophores and synthesis of a new fluorescent probe

Ouchetto, H.; Dias, Marylène; Mornet, R.; Lesuisse, Emmanuel; Camadro, Jean‐Michel

doi:10.1016/j.bmc.2004.11.053

Cited by 58 publications

(27 citation statements)

References 12 publications

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“…Table 1 summarizes applications of siderophores as imaging agents. They can be prepared either by the introduction of appropriate radiometal to the natural (iron-)siderophore complex via the exchange of iron or artificially by the modification of natural siderophore with a chromophore suitable for optical imaging [31][32][33][34]. Already in the 1970s and 1980s, first investigations of radiolabelled siderophores, including desferrioxamine (DFO), were already reported with gamma-emitting radionuclides- 67 Ga and 111 In [35][36][37][38].…”

Section: Siderophores For Molecular Imaging Of Infectionmentioning

confidence: 99%

“…Several groups have developed strategies of synthesizing siderophore-chromophore conjugates for optical imaging [31][32][33][55][56][57][58]. Siderophores (e.g.…”

Section: Siderophores For Molecular Imaging Of Infectionmentioning

confidence: 99%

“…Pseudomonas spp.) [31,32,58] and fungi (Ustilago maydis, Saccharomyces cerevisiae, Candida albicans and Rhizzopus arrhizus) [33,55,57]. The microbial activity was not altered by the attachment of various functionalities and fluorescent siderophore analogues became invaluable tools in the investigation of molecular mechanisms involved in microbial iron transport and acquisition.…”

Section: Siderophores For Molecular Imaging Of Infectionmentioning

confidence: 99%

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Siderophores for molecular imaging applications

Petřík

Zhai

Haas

et al. 2016

Clin Transl Imaging

110

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This review covers publications on siderophores applied for molecular imaging applications, mainly for radionuclide-based imaging. Siderophores are low molecular weight chelators produced by bacteria and fungi to scavenge essential iron. Research on these molecules has a continuing history over the past 50 years. Many biomedical applications have been developed, most prominently the use of the siderophore desferrioxamine (DFO) to tackle iron overload related diseases. Recent research described the upregulation of siderophore production and transport systems during infection. Replacing iron in siderophores by radionuclides, the most prominent Ga-68 for PET, opens approaches for targeted imaging of infection; the proof of principle has been reported for fungal infections using 68 Ga-triacetylfusarinine C (TAFC). Additionally, fluorescent siderophores and therapeutic conjugates have been described and may be translated to optical imaging and theranostic applications. Siderophores have also been applied as bifunctional chelators, initially DFO as chelator for Ga-67 and more recently for Zr-89 where it has become the standard chelator in Immuno-PET. Improved DFO constructs and bifunctional chelators based on cyclic siderophores have recently been developed for Ga-68 and Zr-89 and show promising properties for radiopharmaceutical development in PET. A huge potential from basic biomedical research on siderophores still awaits to be utilized for clinical and translational imaging.

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Section: Siderophores For Molecular Imaging Of Infectionmentioning

confidence: 99%

“…Several groups have developed strategies of synthesizing siderophore-chromophore conjugates for optical imaging [31][32][33][55][56][57][58]. Siderophores (e.g.…”

Section: Siderophores For Molecular Imaging Of Infectionmentioning

confidence: 99%

Section: Siderophores For Molecular Imaging Of Infectionmentioning

confidence: 99%

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Siderophores for molecular imaging applications

Petřík

Zhai

Haas

et al. 2016

Clin Transl Imaging

110

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“…A wealth of literature pertaining to the design, synthesis, and application of siderophore analogs exists, [59][60][61][62][63][64][65][66][67][68][69][70][71][72] some of which has been reviewed recently, 18 and we note that a number of these molecules are fluorescent Fe(III) sensors. [65][66][67][68][69][70][71][72] …”

Section: Introductionmentioning

confidence: 99%

Siderophore-based detection of Fe(iii) and microbial pathogens

Zheng

Nolan

2012

Metallomics

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Siderophores are low-molecular-weight iron chelators that are produced and exported by bacteria and fungi during periods of nutrient deprivation. The structures, biosynthetic logic, and coordination chemistry of these molecules have fascinated chemists for decades. Studies of such fundamental phenomena guide the use of siderophores and siderophore conjugates in a variety of medicinal applications that include iron-chelation therapies and drug delivery. Sensing applications constitute another important facet of siderophore-based technologies. The high affinities of siderophores for both ferric ions and siderophore receptors, proteins expressed on the cell surface that are required for ferric siderophore import, indicate that these small molecules may be employed for the selective capture of metal ions, proteins, and live bacteria.This minireview summaries progress in methods that utilize native bacterial siderophore scaffolds for the detection of Fe(III) or microbial pathogens.2

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“…A quick glance at the literature reveals numerous works focusing on selective and sensitive detection of transition metal ions such as Cu 2+ , Zn 2+ , Pb 2+ , Fe 3+ and Hg 2+ have been reported, [11][12][13][14][15][16] highlighting the importance and interest in this area of research. However, due to the paramagnetic nature of Fe 3+ , its presence is most often signaled by fluorescence quenching, [17][18][19] which may limit the application of probes. [20] Thus, developing a turn-on fluorescent probe for Fe 3+ has drawn increasing attention in recent years.…”

Section: Introductionmentioning

confidence: 99%

A New Schiff Base Chemodosimeter for Fluorescent Imaging of Ferric Ions in Living Cells

Chen¹,

Bhorge²,

Pape³

et al. 2015

J Fluoresc

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A new and efficient chemodosimeter for ferric ions has been developed. The visual and fluorescent behaviors of the compound toward various metal ions were investigated: ferric ions are distinguished from other cations by selective color change and unusual fluorescence enhancement in mixed aqueous solution. Fluorescence microscopy experiments showed that this receptor is effective for detection of Fe(3+) in vitro, developing a good image of the biological organelles. The sensing mechanism is shown to involve a hydrolysis process.

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A new route to trihydroxamate-containing artificial siderophores and synthesis of a new fluorescent probe

Cited by 58 publications

References 12 publications

Siderophores for molecular imaging applications

Siderophores for molecular imaging applications

Siderophore-based detection of Fe(iii) and microbial pathogens

A New Schiff Base Chemodosimeter for Fluorescent Imaging of Ferric Ions in Living Cells

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