Release and Report:  A New Photolabile Caging System with a Two-Photon Fluorescence Reporting Function

Majjigapu, Janaki R. R.; Kurchan, Alexei N.; Kottani, Rudresha; Gustafson, Tiffany P.; Kutateladze, Andrei G.

doi:10.1021/ja053654m

Cited by 50 publications

(32 citation statements)

References 13 publications

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“…439 As compared to molecular photorelease, delivery vehicles based on UCNPs have additional benefits in biological applications: the surface modification of UCNPs with hydrophilic ligands can be easily done to render them soluble in aqueous environments; and the luminescence emitted by UCNPs can be used to monitor the delivery, featuring upconverting nanocarriers with "release and report" functions. 491,492 Strategies for the photoactivation of caged prodrugs that are covalently grafted to the photolabile protecting group (uncaging) and the photorelease of drugs loaded in the carriers through noncovalent interactions can be categorized according to the type of the process that the photoresponsive functional group undergoes to initiate the release or activation of therapeutics upon NIR stimulation: (a) chemical bond cleavage, leading to the decomposition of the matrix carrying the drug, or (b) photoisomerization to generate in situ "photomechanical stirring" force. 4.8.2.1.…”

Section: Upconversion Nanoparticles For Drug Delivery and Chemotherapymentioning

confidence: 99%

Lanthanide Nanoparticles: From Design toward Bioimaging and Therapy

et al. 2015

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Section: Upconversion Nanoparticles For Drug Delivery and Chemotherapymentioning

confidence: 99%

Lanthanide Nanoparticles: From Design toward Bioimaging and Therapy

et al. 2015

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“…This general design logic is extremely versatile and can easily be adapted to most of the main families of fluorescent probes with the aid of chemical synthesis. Indeed, photoactivatable acridinone [46], anthracene [47], benzofurazan [48], borondipyrromethene [49], chromone [50], coumarin [51][52][53][54][55][56], dihydrofuran [57][58][59], fluorescein [60][61][62][63][64][65][66][67], naphthalene [68], pyranine [69], pyrazolines [70], resorufin [71], rhodamine [66,[72][73][74][75][76], thioxanthone [77] and xanthone [78] derivatives have been developed on the basis of these operating principles. Furthermore, this general strategy has been adapted to activate also the luminescence of conjugated oligomers [79] and semiconductor quantum dots [80,81].…”

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

Photoactivatable Fluorophores

Raymo

2012

ISRN Physical Chemistry

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Photoactivatable fluorophores switch from a nonemissive to an emissive state upon illumination at an activating wavelength and then emit after irradiation at an exciting wavelength. The interplay of such activation and excitation events can be exploited to switch fluorescence on in a defined region of space at a given interval of time. In turn, the spatiotemporal control of fluorescence translates into the opportunity to implement imaging and spectroscopic schemes that are not possible with conventional fluorophores. Specifically, photoactivatable fluorophores permit the monitoring of dynamic processes in real time as well as the reconstruction of images with subdiffraction resolution. These promising applications can have a significant impact on the characterization of the structures and functions of biomolecular systems. As a result, strategies to implement mechanisms for fluorescence photoactivation with synthetic fluorophores are particularly valuable. In fact, a number of versatile operating principles have already been identified to activate the fluorescence of numerous members of the main families of synthetic dyes. These methods are based on either the irreversible cleavage of covalent bonds or the reversible opening and closing of rings. This paper overviews the fundamental mechanisms that govern the behavior of these photoresponsive systems, illustrates structural designs for fluorescence photoactivation, and provides representative examples of photoactivatable fluorophores in actions.

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“…We believe that this dual strategy is of particular value for those therapeutic applications that require non-invasive and spatiotemporal drug activation. Future efforts to enhance the scope of potential in vivo applications will focus on investigating the use of longer wavelength light and two-photon excitation 14,15,27…”

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Light-controlled release of caged doxorubicin from folate receptor-targeting PAMAM dendrimer nanoconjugate

et al. 2010

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We report the synthesis and in vitro evaluation of folate receptor-targeted nanoconjugate that releases its therapeutic payload via a photochemical mechanism.The targeted delivery of therapeutic and imaging agents using nanoconjugates is a burgeoning field. [1][2][3][4] Strategies to develop cancer-cell specific nanoconjugates vary, but all attempts to selectively deliver therapeutics to cells use nanoscale carriers such as dendritic macromolecules, 2 liposomes, 5 polymers, 6 metal nanoparticles 3 or viruses 7 that include targeting and therapeutic agents. The desired result is less side toxicity in normal cells and more effective tumoricidal activity. Nanoconjugates also can be designed such that the therapeutic agents are released, and therefore active, only under particular conditions. The release mechanisms currently being explored are based primarily on reactions catalyzed by endogenous physiological factors such as reduction, 1 low pH, 3 and hydrolytic enzymes. 4 This communication describes a photochemical-based approach to release targeted drugs after delivery. In this scenario, the targeted drug conjugate is first placed on a surface, such as skin, or lung/gastrointestinal tract epithelium. After the exposure, the nanoconjugate drug is specifically taken up by the tumor cells and is washed away from the normal tissue; light is then applied from a laser device attached to an endoscope to specifically target the cancer cells. The strategy presented may be broadly applied to other cell targeting systems, particularly those that require time-and tissue-dependent control of drug activation.Photocaging refers to the temporary inactivation of a biologically active molecule using a protective photocleavable group. Upon UV irradiation of the photocleavable group, the active form of the caged molecule is irreversibly released. 8 Photocaging has been frequently applied in vitro towards the spatiotemporal control of biological processes 9-11 and the light-triggered payload release from nanoscale materials. 12,13 However, it has only been rarely applied in in vivo experiments 14,15 because of the low level tissue penetration and phototoxicity associated with short wavelength UV light.Recent advances in two-photon excitation 14,15 and optical fiber technology, however, have made it possible to cleave photocaged compounds by irradiation in the near-IR (720-800 nm 14 ). Because of this potential for higher level tissue penetration, we have applied the † Electronic supplementary information (ESI) available: Experimental details for synthesis and characterization of 1-9; details for photocleavage experiments of 3 and 7. See DOI: 10.1039/b927215cFax: (734) 615-0621; Tel: (734) 615-0618. NIH Public Access Author ManuscriptChem Commun (Camb). Author manuscript; available in PMC 2010 July 12. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author Manuscript photocaging approach towards the targeted delivery of doxorubicin, 16 an anticancer drug that inhibits DNA replication through intercalation (Fig. 1).In ...

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Release and Report: A New Photolabile Caging System with a Two-Photon Fluorescence Reporting Function

Cited by 50 publications

References 13 publications

Lanthanide Nanoparticles: From Design toward Bioimaging and Therapy

Lanthanide Nanoparticles: From Design toward Bioimaging and Therapy

Photoactivatable Fluorophores

Light-controlled release of caged doxorubicin from folate receptor-targeting PAMAM dendrimer nanoconjugate

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