New porphyrin derivatives for phosphate anion sensing in both organic and aqueous media

Rodrigues, João; Farinha, Andreia S.F.; Muteto, Paulino V.; Woranovicz-Barreira, Sandra M.; Paz, Filipe A. Almeida; Neves, Maria G. P. M. S.; Cavaleiro, José A. S.; Tomé, Augusto C.; Gomes, M. Teresa S.R.; Sessler, Jonathan L.; Tomé, João P. C.

doi:10.1039/c3cc47504b

Cited by 58 publications

(27 citation statements)

References 27 publications

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“…148,149 Diseases such as osteoporosis, Alzheimer’s, and cystic fibrosis are caused by perturbations in anion fluxes across cell membranes. 150-152 Anions including cyanide and arsenate are considered a threat when present in the environment, which leads to a need for systems capable of controlling and monitoring these species. 153 MetalloPors with metals such as zinc, rhodium, silver, gold or copper can be used as cyanide sensors because of the essential affinity of cyanide to these metals.…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

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Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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Porphyrinoids are robust heterocyclic dyes studied extensively for their applications in medicine and as photonic materials because of their tunable photophysical properties, diverse means of modifying the periphery, and the ability to chelate most transition metals. Commercial applications include their use as phthalocyanine dyes in optical discs, porphyrins in photodynamic therapy, and as oxygen sensors. Most applications of these dyes require exocyclic moieties to improve solubility, target diseases, modulate photophysical properties, or direct the self-organization into architectures with desired photonic properties. The synthesis of the porphyrinoid depends on the desired application, but the de novo synthesis often involves several steps, is time consuming, and results in low isolated yields. Thus, the application of core porphyrinoid platforms that can be rapidly and efficiently modified to evaluate new molecular architectures allows researchers to focus on the design concepts rather than the synthesis methods, and opens porphyrinoid chemistry to a broader scientific community. We have focused on several widely available, commercially viable porphyrinoids as platforms: meso-perfluorophenylporphyrin, perfluoro-phthalocyanine, and meso-perfluorophenylcorrole. The perfluorophenylporphyrin is readily converted to the chlorin, bacteriochlorin, and isobacteriochlorin. Derivatives of all six of these core platforms can be efficiently and controllably made via mild nucleophilic aromatic substitution reactions using primary S, N, and O nucleophiles bearing a wide variety of functional groups. The remaining fluoro groups enhance the photo and oxidative stability of the dyes and can serve as spectroscopic signatures to characterize the compounds or in imaging applications using 19F NMR. This review provides an overview of the chemistry of fluorinated porphyrinoids that are being used as a platform to create libraries of photo-active compounds for applications in medicine and materials.

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Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

“…TPPF 20 can be used as a platform to build new polyamine anion hosts that are effective receptors for dihydrogen phosphate in organic media. 152 Tomé and co-workers 152 have substituted various diamines onto the core TPPF 20 platform for the development of phosphate anion sensors (Fig. 23).…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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“…Anions are known to bind to the central protons of expanded free-base porphyrins and related macrocyclesi nt heir neutral form, [40][41][42][43][44][45][46][47] and one of our interests in the present study was to investigate how changes in the supporting electrolyte anion would affect both the measured reduction potentials and the stabilityo ft he porphyrin products formed in the first and/or second reduction on the electrochemical and spectroelectrochemical timescale. Examples of the electrochemical data are given in Figures S3 and S4, which illustrate cyclic voltammograms of H 2 TPP in the four solvents containing TBAX, where X = Cl À ,Br À ,I À ,and ClO 4 À .…”

Section: Effectsofs Olvent and Supporting Electrolyte On The Reductiomentioning

confidence: 99%

Tuning the Electrochemistry of Free‐Base Porphyrins in Acidic Nonaqueous Media: Influence of Solvent, Supporting Electrolyte, and Ring Substituents

et al. 2015

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International audienceA detailed study of reduction potentials, electroreduction mechanisms, and acid-base chemistry was carried out on two series of free-base porphyrins in nonaqueous media. The first series is represented by four -pyrrole-substituted tetraphenylporphyrin (TPP) derivatives, two of which are planar and two of which are nonplanar in their nonprotonated form. The second comprises porphyrins with 0-4 meso-phenyl groups on the macrocycle. Equilibrium constants for the conversion of each neutral porphyrin to its diprotic [H4P](2+) form were determined and the electrochemistry was then elucidated as a function of: 1)type of nonaqueous solvent, 2)anion of supporting electrolyte, 3)porphyrin ring substituents, and 4)concentration of acid added to solution. Spectroelectrochemistry was used to characterize absorption spectra of each electroreduced species and, when combined with results of the above studies, significantly improves our ability to tune redox reactivity of these types of compounds

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“…There has been a great deal of interest in the generation of selective anion sensors for use in aqueous environments [33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49], or which could be used directly upon biological samples; however this is a challenge due to the high hydration energies of the ions. The large size of the phosphate anion along with its high hydrophilicity, place it near the bottom of the Hofmeister selectivity series [50].…”

Section: Anion Sensingmentioning

confidence: 99%

The potential of ion mobility mass spectrometry for tuning synthetic host guest systems: A case study using novel zinc(II)dipicolylamine anion sensors

Nortcliffe

Migas

Liu

et al. 2015

International Journal of Mass Spectrometry

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Synthetic approaches to produce scaffolds that will act as efficient biosensors have been the subject of considerable research efforts in recent years. The preparation of host complexes which will specifically bind a given guest necessitates structural analysis of the potential complexes formed, as well as an assessment of the strength of the binding interaction. A challenge to the down-stream analytical scientist is to develop a rapid method that can probe the strength of binding, and the architecture of the complex. In this work we apply nano-ESI MS and Drift Tube ion mobility mass spectrometry (DT IM-MS) to examine host guest interactions. We present data on 5 cyclic peptide bis (Zn II -dipicolylamines) which have been systematically designed as potential molecular biosensors for pyrophosphate (PPi). The competition of the macrocycles for PPi compared with other small anions is investigated.Mass spectrometry provides the stoichiometry of the complex, and the proportion of complex preserved into the mass spectrometer correlates with solution phase data. We find the macrocycles have a higher affinity for PPi than for ATP or pyrocatechol violet (PV). The

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New porphyrin derivatives for phosphate anion sensing in both organic and aqueous media

Cited by 58 publications

References 27 publications

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Tuning the Electrochemistry of Free‐Base Porphyrins in Acidic Nonaqueous Media: Influence of Solvent, Supporting Electrolyte, and Ring Substituents

The potential of ion mobility mass spectrometry for tuning synthetic host guest systems: A case study using novel zinc(II)dipicolylamine anion sensors

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