Von Ein‐ zu Zwei‐Photonen‐Sonden: photoaktivierbare Reagentien, Aktuatoren und Photoschalter

Bort, Guillaume; Gallavardin, Thibault; Ogden, David; Dalko, Peter I.

doi:10.1002/ange.201204203

Cited by 38 publications

(10 citation statements)

References 141 publications

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“…Reported here are two new diketopyrrolopyrroleporphyrin conjugates as robust two-photon absorbing dyes with high two-photon absorption cross-sections within the therapeutic window. [2,5] Nevertheless, developing TP sensitizers which fulfill the specifications of PDT in terms of solubility, high singlet-oxygen production quantum yield, and low dark cytotoxicity is much more challenging. A preliminary study on cell culture showed efficient two-photon induced phototoxicity.…”

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confidence: 99%

“…In PDT, upon light excitation, a photosensitizer undergoes an efficient intersystem crossing that populates the triplet excited state which reacts with molecular oxygen, thus producing singlet oxygen and/or other cytotoxic reactive oxygen species. [2,5] Nevertheless, developing TP sensitizers which fulfill the specifications of PDT in terms of solubility, high singlet-oxygen production quantum yield, and low dark cytotoxicity is much more challenging. Light excitation is usually performed in the UV-visible region and its low penetration in tissues for wavelengths below l = 700 nm limits the treatment to superficial damage.…”

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confidence: 99%

“…[1] A major drawback of PDT performed in clinics concerns the accessibility of the photosensitizer to the light source. [2,5] Nevertheless, developing TP sensitizers which fulfill the specifications of PDT in terms of solubility, high singlet-oxygen production quantum yield, and low dark cytotoxicity is much more challenging. An emerging and promising development concerns two-photon PDT.…”

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confidence: 99%

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Diketopyrrolopyrrole‐Porphyrin Conjugates with High Two‐Photon Absorption and Singlet Oxygen Generation for Two‐Photon Photodynamic Therapy

et al. 2014

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Two-photon photodynamic therapy is a promising therapeutic method which requires the development of sensitizers with efficient two-photon absorption and singlet-oxygen generation. Reported here are two new diketopyrrolopyrrole-porphyrin conjugates as robust two-photon absorbing dyes with high two-photon absorption cross-sections within the therapeutic window. Furthermore, for the first time the singlet-oxygen generation efficiency of diketopyrrolopyrrole-containing systems is investigated. A preliminary study on cell culture showed efficient two-photon induced phototoxicity.

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Diketopyrrolopyrrole‐Porphyrin Conjugates with High Two‐Photon Absorption and Singlet Oxygen Generation for Two‐Photon Photodynamic Therapy

et al. 2014

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“…Unfortunately, nearly all lightactivatable prodrugs described to date respond to shortwavelength irradiation < 450 nm. [3] This limitation is respon-sible for the intense interest in two-photon [4] and up-converting [5] technologies. However, as discussed in recent reviews, [4,5] both technologies must overcome daunting challenges before potential therapeutic applications are realized.…”

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Cell‐Mediated Assembly of Phototherapeutics

et al. 2014

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Light-activatable drugs offer the promise of controlled release with exquisite temporal and spatial resolution. However, light sensitive pro-drugs are typically converted to their active forms using short wavelengths, which display poor tissue penetrance. We report herein erythrocyte-mediated assembly of long wavelength-sensitive phototherapeutics. The activating wavelength of the constructs is readily pre-assigned by using fluorophores with the desired λ ex . Drug release from the erythrocyte carrier was confirmed by standard analytical tools and by the expected biological consequences of the liberated drugs in cell culture: methotrexate, binding to intracellular dihydrofolate reductase; colchicine, inhibition of microtubule polymerization; dexamethasone, induced nuclear migration of the glucocorticoid receptor. KeywordsPhotochemistry; Drug Delivery; Cobalamins; Pro-drugs The use of light to activate therapeutic agents at disease sites offers the advantage of aggressive treatment with exquisite spatial control, thereby reducing potential deleterious side effects at unintended sites. An excellent example of this concept is photodynamic therapy, which employs the delivery of a photosensitizer to the tissue of interest. [1] Upon excitation with the appropriate wavelength of light and, in the presence of oxygen, cytotoxic reactive oxygen species are generated, resulting in destruction of the target cells. This minimally invasive procedure furnishes control over where and when the reactive oxygen species are produced. However, a more general strategy that can control the delivery of any drug could profoundly influence the treatment of a variety of disorders, including cancer, diabetes, and autoimmune and vascular diseases. A major challenge in this regard is the socalled "optical window of tissue", the wavelength of light that enjoys maximal tissue penetration, which lies in the range of 600 -900 nm. [2] Wavelengths less than <600 nm are absorbed by hemoglobin in the circulatory system and melanin in the skin whereas water interferes with light penetrance >900 nm. Unfortunately, nearly all light-activatable prodrugs described to date respond to short wavelengths <450 nm. [3] This limitation is responsible for the intense interest in two-photon [4] and up converting [5] technologies. However, as discussed in recent reviews, [4][5] both technologies must overcome daunting challenges before potential therapeutic applications are realized. We recently described the long wavelength (>600 nm) photolysis of alkylcobalamins (alkyl-Cbl). [6] We now report the cell-mediated assembly of lipid-Cbl-drug and lipid-fluorophore conjugates in which the latter serve as long wavelength-capturing antennas that promote drug release.Erythrocytes have been called the "champions of drug delivery" due to their biocompatibility, their long life span (120 days), and their size, which allows large quantities of drug to be conveyed relative to other carriers. [7] However, "practically useful controlled release from carrier RBC (red blo...

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“…Zudem entfallen weitere Inkubations-oder Waschschritte. Kürzlich wurden lichtempfindliche Verbindungen zur Manipulation von biologischen Systemen, [2] wie reversible Photoschalter [3] oder gerichtete Trigger, [4] so genannte photoaktivierbare Verbindungen, beschrieben. [5] Zweidimensionale (2D-)Strukturen werden durch lithographische Techniken generiert, [6] wogegen eine 3D-Strukturierung besonders durch den nichtlinearen Zwei-Photonen-Effekt mçglich wird.…”

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Dreidimensionale Proteinnetzwerke durch Zwei‐Photonen‐ Aktivierung

et al. 2014

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Die präzise räumliche und zeitliche Steuerung biologischer Prozesse spielt eine Schlüsselrolle in den Lebens-und Materialwissenschaften. Wir haben ein photoaktivierbares Glutathion (GSH) synthetisiert, um seine Interaktion mit der Glutathion-S-Transferase (GST) lichtgesteuert mit hoher räumlich-zeitlicher Auflçsung zu induzieren. Diese zweiPhotonen-aktivierbare Verbindung zeigt eine schnelle und definierte Umwandlung zu bioaktivem GSH, das in der Folge mit verschiedenen GST-markierten Proteinen interagieren kann. Die Affinität der GSH/GST-Interaktion wird durch Licht über mehrere Grçßenordnungen bis in den nanomolaren Bereich erhçht. In situ kçnnen durch fs-gepulste Zwei-Photonen-Anregung gleichzeitig vielfältige, dreidimensionale Proteinnetzwerke generiert werden. Die Zwei-Photonen-Aktivierung ermçglicht ein "Schreiben" von dreidimensionalen Proteinstrukturen in Echtzeit mit bisher unerreichter räumlich-zeitlicher Auflçsung und çffnet somit neue weitreichende Anwendungen in den Lebens-und Materialwissenschaften.Ein Ziel der chemischen Biologie besteht darin, Proteininteraktionen oder zelluläres Verhalten durch externe Stimuli zu steuern.[ oder gerichtete Trigger, [4] so genannte photoaktivierbare Verbindungen, beschrieben. [5] Zweidimensionale (2D-)Strukturen werden durch lithographische Techniken generiert, [6] wogegen eine 3D-Strukturierung besonders durch den nichtlinearen Zwei-Photonen-Effekt mçglich wird.[7] Im letztgenannten Fall absorbiert das Zielmolekül gleichzeitig Abbildung 1. Lichtinduzierte GSH/GST-Interaktion. An GST gebundenes GSH (PDB-Code: 1UA5; Schistosoma japonicum) wird als Oberflä-chendarstellung (oben) und Interaktionsdiagramm (unten) gezeigt. Das neue zwei-Photonen-aktivierbare GSH NDBF kann durch Ein-oder Zwei-Photonen-Aktivierung bei 365 bzw. 730 nm in bioaktives GSH umgewandelt werden. Das Thiol, hier durch den Rest R repräsentiert, wird zur Modifikation mit Fluorophoren oder zur Anheftung an 2D-oder 3D-Matrices verwendet.

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Von Ein‐ zu Zwei‐Photonen‐Sonden: photoaktivierbare Reagentien, Aktuatoren und Photoschalter

Cited by 38 publications

References 141 publications

Diketopyrrolopyrrole‐Porphyrin Conjugates with High Two‐Photon Absorption and Singlet Oxygen Generation for Two‐Photon Photodynamic Therapy

Diketopyrrolopyrrole‐Porphyrin Conjugates with High Two‐Photon Absorption and Singlet Oxygen Generation for Two‐Photon Photodynamic Therapy

Cell‐Mediated Assembly of Phototherapeutics

Dreidimensionale Proteinnetzwerke durch Zwei‐Photonen‐ Aktivierung

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