Tripodal ligands possessing six convergent hydroxyl groups a novel family of iron sequestering agents based on o,o'-dihydroxybiphenyl subunits

Baret, Paul; Béguin, Claude; Gaude, Didier; Gellon, Gisèle; Mourral, C.; Pierre, Jean‐Louis; Serratrice, Guy; Favier, Alain

doi:10.1016/s0040-4020(01)85070-5

Cited by 22 publications

(10 citation statements)

References 24 publications

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“…Except for isonicotinoylhydrazones (which exhibit a higher denticity), the bidentate subunits mentioned above involve a five-membered chelating ring size, whose role will be discussed in the physicochemical part of this paper. Pyridinophenol subunits allow a sixmembered coordination ring with the same donor atoms as in the 8-hydroxyquinoline backbone whereas a seven-membered ring chelate can be achieved with o, o¢-dihydroxybiphenyl subunits (Baret et al 1994(Baret et al , 1998. The more usual bidentate groups encountered in tripodal ligands are depicted in Figure 2 often used for comparisons with the more efficient corresponding tripodal compound.…”

Section: The Nature Of the Chelating Subunitsmentioning

confidence: 99%

Design of Iron chelators: Syntheses and iron (III) complexing abilities of tripodal tris-bidentate ligands

et al. 2006

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The interest in synthetic siderophore mimics includes therapeutic applications (iron chelation therapy), the design of more effective agents to deliver Fe to plants and the development of new chemical tools in order to study iron metabolism and iron assimilation processes in living systems. The design of ligands needs a rational approach for the understanding of the metal ion complexing abilities. The octahedral arrangement of donor atoms is the most favourable geometry, allowing the maximum possible distance between their formal or partial negative charges. Hexadentate chelators, usually of the tris-bidentate type, can accommodate the metal coordination sphere and are well-suited to obtain high pFe values. The first part of this review is dedicated to selected synthetic routes, taking into account (i) the nature of the chelating subunits, connecting groups and spacers, (ii) the water-solubility and hydrophilic/lipophilic balance, (iii) the chirality and (iv) the possibility of grafting probes or vectors. In the second part, we discuss the role of the molecular design on complexing abilities (thermodynamics and kinetics). The bidentate 8-hydroxyquinoline moiety offers an alternative to the usual coordinating hydroxamic acids, catechols and/or alpha-hydroxycarboxylic acids groups encountered in natural siderophores. The promizing results obtained with the tris-hydroxyquinoline-based ligand O-TRENSOX are summarized. O-TRENSOX exhibits a high and selective affinity for Fe(III) complexation. Its efficiency in delivering Fe to plants, iron mobilization, cell protection, and antiproliferative effects has been evidenced. Other chelators derived from O-TRENSOX (mixed catechol/8-hydroxyquinoline ligands, lipophilic ligands) are also described. Some results question the relevance of partition coefficients to foresee the activity of iron chelators. The development of probes (fluorescent, radioactive, spin labelled) based on the O-TRENSOX backbone is in progress in order to get insights in the complicated iron metabolism processes.

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Section: The Nature Of the Chelating Subunitsmentioning

confidence: 99%

Design of Iron chelators: Syntheses and iron (III) complexing abilities of tripodal tris-bidentate ligands

et al. 2006

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“…The method involves skillful design and uses inexpensive reagents than the method reported by Kelly. One of the hydroxy groups in 13 was etherified with allyl bromide in anhydrous DMF in the presence of potassium carbonate, 15 and the other hydroxy group in 13 was transesterified simultaneously in one-pot. 16 The yield of 14 was improved by controlling the molar ratio of reagents (13/allyl bromide/potassium carbonate = 1:1.2:1.5) and the reaction temperature (60°C).…”

Section: Methodsmentioning

confidence: 99%

Facile and Efficient Total Synthesis of Taspine

Cheng¹,

Zhang²,

Zhu³

et al. 2009

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The facile and efficient total synthesis of taspine was achieved in 10 steps in high yield (16.5% overall) from commercially available isovanillin. Key steps in the synthesis are preparation of a symmetrical homodimer employing a classical Ullmann coupling reaction, and introduction of an allyl substituent by the Claisen rearrangement reaction. Significantly, the facile synthetic scheme proposed in this work has the characteristics of mild reaction conditions, inexpensive reagents, higher yield, and simple operation.

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“…244 Furthermore, derivatives bearing siderophore units different from DHB have been extensively studied by different research groups. In 1994, a series of TREN-based iron chelators bearing 2,2′-dihydroxybiphenyl moieties (o-TRENBIPHENS) 281, 282, and 283 (Figure 7, grey box) were reported by Baret and co-workers, 245 all exhibiting significantly weaker Fe(III) complexes compared to TRENCAM and showing only moderate water solubility. The corresponding m-TRENBIPHENS 287 (Figure 7, grey box) introduced by This document was downloaded for personal use only.…”

Section: Review Synthesismentioning

confidence: 99%

“…In 1994, Serratrice and co-workers synthesized SERBI-PHEN 382 (Figure 13) bearing 2,2′-dihydroxybiphenyl moieties as chelating units, however, no further information on iron complexing properties were reported. 245 In 2006, Raymond and co-workers reported the synthesis of a series of spermidine-based siderophores (3,4-Li(1-Me-3,2-HOPO 383, 384, and 385 and 3,4-LiTAM 386, Figure 13, grey box) bearing 3-hydroxy-1-methyl-2-oxopyridine-4-carboximide and terephthalamide as chelating units. 303 They demonstrated that these ligands effectively bind Fe(III) and that the ligands acidity is reduced while the affinity for Fe(III) is simultaneously increased with every additional terephthalamide (TAM) unit.…”

Section: Review Synthesismentioning

confidence: 99%

Advances in the Synthesis of Enterobactin, Artificial Analogues, and Enterobactin-Derived Antimicrobial Drug Conjugates and Imaging Tools for Infection Diagnosis

2022

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Iron is an essential growth factor for bacteria, but although highly abundant in nature, its bioavailability during infection in the human host or the environment is limited. Therefore, bacteria produce and secrete siderophores to ensure their supply with iron. The tris-catecholate siderophore enterobactin and its glycosylated derivatives, the salmochelins, play a crucial role for iron acquisition in several bacteria. As these compounds can serve as carrier molecules for the design of antimicrobial siderophore drug conjugates as well as siderophore-derived tool compounds for the detection of infections with bacteria, their synthesis and the design of artificial analogues is of interest. In this review, we give an overview on the synthesis of enterobactin, biomimetic as well as totally artificial analogues and related drug-conjugates covering up to 12/2021.

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Tripodal ligands possessing six convergent hydroxyl groups a novel family of iron sequestering agents based on o,o'-dihydroxybiphenyl subunits

Cited by 22 publications

References 24 publications

Design of Iron chelators: Syntheses and iron (III) complexing abilities of tripodal tris-bidentate ligands

Design of Iron chelators: Syntheses and iron (III) complexing abilities of tripodal tris-bidentate ligands

Facile and Efficient Total Synthesis of Taspine

Advances in the Synthesis of Enterobactin, Artificial Analogues, and Enterobactin-Derived Antimicrobial Drug Conjugates and Imaging Tools for Infection Diagnosis

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