Amphiphilic perfluoroalkyl carbohydrates as new tools for liver imaging

Richard, Cyrille; Chaumet-Riffaud, Philippe; Belland, A.; Parat, Audrey; Contino‐Pépin, Christiane; Bessodes, Michel; Scherman, Daniel; Pucci, Bernard; Mignet, Nathalie

doi:10.1016/j.ijpharm.2009.05.045

Cited by 12 publications

(5 citation statements)

References 26 publications

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“…The number of applications of NPs is increasing rapidly, especially in the biomedical field for drug-delivery purposes [7]. If we just consider polymer NPs, there are many examples of their use in therapies for cancer [8,9], HIV [10][11][12], malaria [13] and Chagas disease [14], siRNA delivery [15], image-guided drug delivery [16], imaging agents [17], sensors and self-healing systems [18]. The applicability of those systems is related to the nature, the morphology, and the size of the nanocarriers and their structural control is essential.…”

Section: Introductionmentioning

confidence: 99%

Single-chain polymer nanoparticles

Aiertza

Odriozola

Cabañero

et al. 2011

Cell. Mol. Life Sci.

115

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The synthesis of polymer nanoparticles (NPs) with controlled characteristics has become an appealing research topic lately. Nanomedicine, and especially drug delivery and imaging, are fields that require particles of a controlled size and with a tailored arrangement of functional groups. Intramolecular cross-linking or collapse of single polymer chains has emerged as an efficient alternative for the synthesis of well-defined polymer NPs. This technique allows the generation of 1.5-20 nm particles with a wide variety of chemical compositions and functionalities. This review begins by gathering synthetic strategies described in the literature and groups them into four main synthetic methods: homo-functional collapse, hetero-functional collapse, crosslinker-mediated collapse, and one-block collapse of diblock or triblock copolymers. Afterwards, the main characterization techniques and physical properties of single-chain polymer NPs (SCPNs) are exposed. Finally, several applications in nanomedicine are mentioned followed by some future perspectives.

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Section: Introductionmentioning

confidence: 99%

Single-chain polymer nanoparticles

Aiertza

Odriozola

Cabañero

et al. 2011

Cell. Mol. Life Sci.

115

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“…Amphiphilic compounds possessing both hydrophilic and lipophilic groups could exhibit improved cellular permeability, and therefore, several amphiphilic derivatives of PBN such as the fluorinated amphiphilic PBN conjugate FAPBN (Figure ) have been developed as potential therapeutic agents , , or modification of these amphiphiles with technetium-chelating sites has found application as nonproteic probes for hepatocyte PET imaging . However, amphiphilic compounds with a long hydrogenated tail (i.e., 8 carbons or more) are detergent by nature and lead to disruption of cell membranes when used above their critical micellar concentration (cmc).…”

Section: Introductionmentioning

confidence: 99%

Spin Trapping and Cytoprotective Properties of Fluorinated Amphiphilic Carrier Conjugates of Cyclic versus Linear Nitrones

Durand

Prosak

Han

et al. 2009

Chem. Res. Toxicol.

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Nitrone spin traps have been employed as pharmacological agent against neurodegenerative diseases and ischemia-reperfusion induced injury. The structure-activity relationship was explored for the two types of nitrones, i.e., cyclic (DMPO) and linear (PBN), which are conjugated to a fluorinated amphiphilic carrier (FAC) for their cytoprotective properties against hydrogen peroxide (H 2 O 2 ), 3-morpholinosynonimine hydrochloride (SIN-1) and 4-hydroxynonenal (HNE) induced cell death on bovine aortic endothelial cells. The compound FAMPO was synthesized and characterized, and its physical-chemical and spin trapping properties were explored. Cytotoxicity and cytoprotective properties of various nitrones either conjugated and non-conjugated to FAC (i.e., AMPO, FAMPO, PBN and FAPBN) were assessed using 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium (MTT) reduction assay. Results show that of all the nitrones tested, FAPBN is the most protective against H 2 O 2 , but FAMPO and to a lesser extent its unconjugated form, AMPO, are more protective against SIN-1 induced cytotoxicity. However, none of the nitrones used protect the cells from HNE-induced cell death. The difference in the cytoprotective properties observed between the cyclic and linear nitrones may arise from the differences in their intrinsic antioxidant properties and localization in the cell.

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“…The modification of carbohydrates with perfluoroalkylated chains brings about significantly improved properties and new applications of these compounds compared with their nonperfluoroalkylated analogs, with relevance in diverse fields such as supramolecular chemistry, [5] glycoconjugation, liquid crystals, [6] and surfactant developments. [7,8] Carbohydrate-based perfluoroalkylated amphiphiles are more effective surfactants [9,10] than their hydrocarbon counterparts and tend to form ordered supramolecular assemblies more easily. [11] Perfluoroalkylated single-tailed sugar amphiphiles form more stable liquid-crystalline phases than their carbon analogs, [5,12] and can be considered potential alterna-tives for utilization in wetting, [13] antifreeze, [14] or coating applications.…”

Section: Introductionmentioning

confidence: 99%

“…Carbohydrate‐based perfluoroalkylated amphiphiles are more effective surfactants [9, 10] than their hydrocarbon counterparts and tend to form ordered supramolecular assemblies more easily [11] . Perfluoroalkylated single‐tailed sugar amphiphiles form more stable liquid‐crystalline phases than their carbon analogs, [5, 12] and can be considered potential alternatives for utilization in wetting, [13] antifreeze, [14] or coating applications [8] …”

Section: Introductionmentioning

confidence: 99%

Approaches to the Synthesis of Perfluoroalkyl‐Modified Carbohydrates and Derivatives: Thiosugars, Iminosugars, and Tetrahydro(thio)pyrans

Uhrig

Flores

Postigo

2021

Chemistry A European J

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Fluoroalkyl-substituted carbohydrates play relevant roles in diverse areas such as supramolecular chemistry, glycoconjugation, liquid crystals, and surfactants, with direct applications as wetting, antifreeze, and coating agents. In light of these promising applications, new methodologies for the late-stage incorporation of fluoroalkyl R F groups into carbohydrates and derivatives are herein presented as they are relevant to the synthetic carbohydrate community. Previously reviewed protocols for the installation of R F groups onto carbohydrates and derivatives will be succinctly summarized in the light of the new achievements. Fluoroalkylsubstituted iminosugars, on the other hand, are also interesting glycomimetic derivatives with prominent roles as glycosidases and glycosyltransferases inhibitors, as has recently been demonstrated. Also, they positively contribute to the study of sugar-protein interactions and enzyme mechanisms. New advances in the syntheses of fluoroalkyl-substituted iminosugars will also be presented here.

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Amphiphilic perfluoroalkyl carbohydrates as new tools for liver imaging

Cited by 12 publications

References 26 publications

Single-chain polymer nanoparticles

Single-chain polymer nanoparticles

Spin Trapping and Cytoprotective Properties of Fluorinated Amphiphilic Carrier Conjugates of Cyclic versus Linear Nitrones

Approaches to the Synthesis of Perfluoroalkyl‐Modified Carbohydrates and Derivatives: Thiosugars, Iminosugars, and Tetrahydro(thio)pyrans

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