Ascorbate Analogs for Use in Medical Imaging: Synthesis and Radical Scavenging Activity of 5-O-(4'-Iodobenzyl)-L-ascorbic Acid

Kato, Hiroharu; Kino, Tomohiro; Yamamoto, Fujio; Kaneshiro, Tetsuo; Mukai, Takahiro; Maëda, Minoru

doi:10.1248/cpb.55.1700

Cited by 7 publications

(5 citation statements)

References 21 publications

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“…Earlier studies to generate ascorbic acid transporter-specific ligands have shown that the C5 and C6 positions are modifiable without significantly affecting the interaction with the transporter [227][228][229]. Additionally, the oxidized forms of these derived compounds showed no interaction with GLUT transporters GLUT1 or GLUT3, which transport DHA, confirming their specificity for SVCT transporters [227,228].…”

Section: Vitamin Transportersmentioning

confidence: 91%

Transporter-Mediated Drug Delivery

Gyimesi¹,

Hediger²

2022

Preprint

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Transmembrane transport of small organic and inorganic molecules is one of the cornerstones of cellular metabolism. Among transmembrane transporters, solute carrier (SLC) proteins form the largest, albeit very diverse, superfamily with over 400 members. It has been early on recognized that xenobiotics can directly interact with SLCs and that this interaction can fundamentally determine their efficacy, including bioavailability and intertissue distribution. Apart from the well-established prodrug strategy, the chemical ligation of transporter substrates to nanoparticles of various chemical composition has recently been used as a means to enhance their targeting or absorption. In this review, we summarize efforts in drug design exploiting interactions with specific SLC transporters to optimize their therapeutic effects. Furthermore, we describe current and future challenges as well as new directions for the advanced development of therapeutics that target SLC transporters.

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Section: Vitamin Transportersmentioning

confidence: 91%

Transporter-Mediated Drug Delivery

Gyimesi¹,

Hediger²

2022

Preprint

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“…Earlier studies to generate ascorbic acid transporter-specific ligands have shown that the C 5 and C 6 positions are modifiable without significantly affecting the interaction with the transporter [ 231 , 232 , 233 ]. Additionally, the oxidized forms of these derived compounds showed no interaction with GLUT1 and GLUT3, which transport DHA, confirming their specificity for SVCT transporters [ 231 , 232 ].…”

Section: Targeting Transportersmentioning

confidence: 99%

Transporter-Mediated Drug Delivery

Gyimesi

Hediger

2023

Molecules

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Transmembrane transport of small organic and inorganic molecules is one of the cornerstones of cellular metabolism. Among transmembrane transporters, solute carrier (SLC) proteins form the largest, albeit very diverse, superfamily with over 400 members. It was recognized early on that xenobiotics can directly interact with SLCs and that this interaction can fundamentally determine their efficacy, including bioavailability and intertissue distribution. Apart from the well-established prodrug strategy, the chemical ligation of transporter substrates to nanoparticles of various chemical compositions has recently been used as a means to enhance their targeting and absorption. In this review, we summarize efforts in drug design exploiting interactions with specific SLC transporters to optimize their therapeutic effects. Furthermore, we describe current and future challenges as well as new directions for the advanced development of therapeutics that target SLC transporters.

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“…Kato et al synthesized a 5- O -modified 4-iodobenzylated ASA derivative (Figure S3) with a radical scavenging activity in the DPPH assay similar to that of ASA, indicating its potential use in imaging of ascorbate bioactivity in the brain [76].…”

Section: Antioxidant Properties Of L-ascorbic Acid Derivativesmentioning

confidence: 99%

Therapeutic Perspective of Vitamin C and Its Derivatives

2019

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L-Ascorbic acid (ASA), vitamin C, is a ubiquitous carbohydrate-like compound that has an essential role in a number of cellular processes, such as collagen synthesis, cellular oxidation, and various hydroxylation reactions. ASA is a biomolecule of critical importance for protection of cellular components against oxidative damage caused by toxic free radicals and other reactive oxygen species (ROS) that are involved in the development of various types of chronic diseases. Vitamin C has a switchover role from being an antioxidant in physiological conditions to a prooxidant under pathologic conditions. Moreover, some l-ascorbic acid derivatives exhibit strong and selective antitumor and antiviral activity. This review emphasizes the advances on diverse and potent biological profiles of l-ascorbic acid and its derivatives, and their perspective in the development of new bioactive chemical entities in the future. The work is primarily addressed at antioxidant, anticancer, and antiviral potencies of l-ascorbic acid and compounds containing its butenolide structural motif.

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Ascorbate Analogs for Use in Medical Imaging: Synthesis and Radical Scavenging Activity of 5-O-(4'-Iodobenzyl)-L-ascorbic Acid

Cited by 7 publications

References 21 publications

Transporter-Mediated Drug Delivery

Transporter-Mediated Drug Delivery

Transporter-Mediated Drug Delivery

Therapeutic Perspective of Vitamin C and Its Derivatives

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