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Special Issue "Photoresponsive Drugs"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (15 September 2016)

Special Issue Editor

Guest Editor
Dr. Wiktor Szymański

Department of Radiology, Universitair Medisch Centrum Groningen, Groningen, The Netherlands
Website | E-Mail
Interests: photopharmacology; photochromism; molecular medical imaging; photocaged drugs; wavelength-selective uncaging

Special Issue Information

Dear Colleagues,

 

With the advent of theranostics and personalized medicine, chemists are challenged to provide molecular solutions for locally activated pharmacological treatment. Supported by recent developments in molecular medical imaging, which provide information on the localization of the pathology, one can envision fascinating prospects for focusing the activity of the drug on the disease spot. Bioactive molecules (drugs), whose activity can be externally regulated, could help to tackle important societal problems, including drug side-effects, emergence of resistance and environmental toxicity. There is also a need for externally-regulated bioactive molecules in research, where it allows precisely controlled regulation of the activity of receptor ligands, enzyme inhibitors, and others.

In recent years, and thanks to several proof-of-principle studies, light has emerged as a promising external control element for drug activity (photopharmacology). Light is a privileged stimulus, as it is allows for non-invasive treatment and can be delivered with very high spatiotemporal precision and control over intensity and wavelength. Furthermore, photons do not contaminate the patient’s body and have low (wavelength-dependent) cytotoxicity.

The developing field of photoresponsive drugs is in constant need of molecular designs and therapeutic targets. Of crucial importance are also new photoswitches and caging groups, that can be addressed with bio-compatible light of longer wavelengths in one and two-photon processes. Finally, the developments in the delivery of light to tissues, inspired by solutions in photodynamic therapy, are also in high demand. This Special Issue aims at offering the space in which recent research in the above-described topics could be communicated.

Dr. Wiktor Szymański
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.


 

Keywords

  • photocaged drugs
  • photopharmacology
  • visible and near-IR light photoswitching and uncaging
  • light delivery to tissues
  • two-photon switching and uncaging of photoactive drugs
  • light-controlled drug delivery

Published Papers (3 papers)

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Research

Open AccessArticle Red Light Activation of Ru(II) Polypyridyl Prodrugs via Triplet-Triplet Annihilation Upconversion: Feasibility in Air and through Meat
Molecules 2016, 21(11), 1460; doi:10.3390/molecules21111460
Received: 5 October 2016 / Revised: 24 October 2016 / Accepted: 26 October 2016 / Published: 1 November 2016
PDF Full-text (3669 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Triplet-triplet annihilation upconversion (TTA-UC) is a promising photophysical tool to shift the activation wavelength of photopharmacological compounds to the red or near-infrared wavelength domain, in which light penetrates human tissue optimally. However, TTA-UC is sensitive to dioxygen, which quenches the triplet states needed
[...] Read more.
Triplet-triplet annihilation upconversion (TTA-UC) is a promising photophysical tool to shift the activation wavelength of photopharmacological compounds to the red or near-infrared wavelength domain, in which light penetrates human tissue optimally. However, TTA-UC is sensitive to dioxygen, which quenches the triplet states needed for upconversion. Here, we demonstrate not only that the sensitivity of TTA-UC liposomes to dioxygen can be circumvented by adding antioxidants, but also that this strategy is compatible with the activation of ruthenium-based chemotherapeutic compounds. First, red-to-blue upconverting liposomes were functionalized with a blue-light sensitive, membrane-anchored ruthenium polypyridyl complex, and put in solution in presence of a cocktail of antioxidants composed of ascorbic acid and glutathione. Upon red light irradiation with a medical grade 630 nm PDT laser, enough blue light was produced by TTA-UC liposomes under air to efficiently trigger full activation of the Ru-based prodrug. Then, the blue light generated by TTA-UC liposomes under red light irradiation (630 nm, 0.57 W/cm2) through different thicknesses of pork or chicken meat was measured, showing that TTA-UC still occurred even beyond 10 mm of biological tissue. Overall, the rate of activation of the ruthenium compound in TTA-UC liposomes using either blue or red light (1.6 W/cm2) through 7 mm of pork fillet were found comparable, but the blue light caused significant tissue damage, whereas red light did not. Finally, full activation of the ruthenium prodrug in TTA-UC liposomes was obtained under red light irradiation through 7 mm of pork fillet, thereby underlining the in vivo applicability of the activation-by-upconversion strategy. Full article
(This article belongs to the Special Issue Photoresponsive Drugs)
Figures

Open AccessArticle Photoactivatable Caged Prodrugs of VEGFR-2 Kinase Inhibitors
Molecules 2016, 21(5), 570; doi:10.3390/molecules21050570
Received: 16 March 2016 / Revised: 20 April 2016 / Accepted: 21 April 2016 / Published: 29 April 2016
Cited by 1 | PDF Full-text (3580 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
In this study, we report on the design, synthesis, photokinetic properties and in vitro evaluation of photoactivatable caged prodrugs for the receptor tyrosine kinase VEGFR-2. Highly potent VEGFR-2 inhibitors 1 and 3 were caged by introduction of a photoremovable protecting group (PPG) to
[...] Read more.
In this study, we report on the design, synthesis, photokinetic properties and in vitro evaluation of photoactivatable caged prodrugs for the receptor tyrosine kinase VEGFR-2. Highly potent VEGFR-2 inhibitors 1 and 3 were caged by introduction of a photoremovable protecting group (PPG) to yield the caged prodrugs 4 and 5. As expected, enzymatic and cellular proliferation assays showed dramatically diminished efficacy of caged prodrugs in vitro. Upon ultraviolet (UV) irradiation of the prodrugs original inhibitory activity was completely restored and even distinctly reinforced, as was the case for the prodrug 4. The presented results are a further evidence for caging technique being an interesting approach in the protein kinase field. It could enable spatial and temporal control for the inhibition of VEGFR-2. The described photoactivatable prodrugs might be highly useful as biological probes for studying the VEGFR-2 signal transduction. Full article
(This article belongs to the Special Issue Photoresponsive Drugs)
Figures

Open AccessArticle Cellular Uptake and Photo-Cytotoxicity of a Gadolinium(III)-DOTA-Naphthalimide Complex “Clicked” to a Lipidated Tat Peptide
Molecules 2016, 21(2), 194; doi:10.3390/molecules21020194
Received: 12 December 2015 / Revised: 1 February 2016 / Accepted: 2 February 2016 / Published: 5 February 2016
Cited by 1 | PDF Full-text (2002 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new bifunctional macrocyclic chelator featuring a conjugatable alkynyl-naphthalimide fluorophore pendant group has been prepared and its Gd(III) complex coupled to a cell-penetrating lipidated azido-Tat peptide derivative using Cu(I)-catalysed “click” chemistry. The resulting fluorescent conjugate is able to enter CAL-33 tongue squamous carcinoma
[...] Read more.
A new bifunctional macrocyclic chelator featuring a conjugatable alkynyl-naphthalimide fluorophore pendant group has been prepared and its Gd(III) complex coupled to a cell-penetrating lipidated azido-Tat peptide derivative using Cu(I)-catalysed “click” chemistry. The resulting fluorescent conjugate is able to enter CAL-33 tongue squamous carcinoma cells, as revealed by confocal microscopy, producing a very modest anti-proliferative effect (IC50 = 93 µM). Due to the photo-reactivity of the naphthalimide moiety, however, the conjugate’s cytotoxicity is significantly enhanced (IC50 = 16 µM) upon brief low-power UV-A irradiation. Full article
(This article belongs to the Special Issue Photoresponsive Drugs)
Figures

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