A Model for Light‐Triggered Porphyrin Anticancer Prodrugs Based on an <i>o</i>‐Nitrobenzyl Photolabile Group

Lin, Weiying; Peng, Daiwei; Wang, Bin; Long, Lingliang; Guo, Can‐Cheng; Jie, Yuan

doi:10.1002/ejoc.200700972

Cited by 39 publications

(24 citation statements)

References 37 publications

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“…This photo-dependent enzyme inhibition was eliminated by the addition of thiols to the irradiated solution, but it is still commonly reported in the literature that this by-product may produce unwanted side effects in vivo [15]. However, there has been little reported evidence to support this claim and it is likely that the presence of reduced thiols in the cell protect them from damage [58,59]. Also, many of the photochemically triggered drug-delivery systems discussed in this section either require UV light or they are more efficiently actuated by UV light.…”

Section: Hydrogelsmentioning

confidence: 99%

Recent Advances in light-responsive on-demand drug-delivery Systems

2017

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The convergence of wearable sensors and personalized medicine enhance the ability to sense and control the drug composition and dosage, as well as location and timing of administration. To date, numerous stimuli-triggered smart drug-delivery systems have been developed to detect changes in light, pH, temperature, biomolecules, electric field, magnetic field, ultrasound and mechanical forces. This review examines the major advances within the last 5 years for the three most common light-responsive drug delivery-on-demand strategies: photochemical, photoisomerization and photothermal. Examples are highlighted to illustrate progress of each strategy in drug delivery applications, and key limitations are identified to motivate future research to advance this important field.

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Section: Hydrogelsmentioning

confidence: 99%

Recent Advances in light-responsive on-demand drug-delivery Systems

2017

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“…It is, however, arguable to what extent the growth inhibition of bacterial cells is representative for cytotoxic activity on human tumor cells. Another prodrug design based on 5-fluorouracil (5-FU) was published by Lin et al [86] Compound 54 ( Figure 23) is composed of three parts: the 5-fluorouracil prodrug (tegafur), [87] a porphyrin, and a linker based on the ONP scaffold. The porphyrin was included in the design because of its affinity for tumor cells.…”

Section: Antimetabolitesmentioning

confidence: 99%

Beyond Photodynamic Therapy: Light-Activated Cancer Chemotherapy

Reeßing

Szymański

2018

CMC

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“…11 Recently, photolabile o-nitrobenzyl linkers were utilized to design light-triggered anticancer pro-drugs which released the tegafur drug from porphyrins upon photolysis. 12 oNitrobenzyl linkers have advantages due to their compatibility with a variety of functional groups, ease of synthesis, stability under ambient light, clean cleavage and fast fragmentation upon photoirradiation. 13 In the present work, we develop the necessary synthetic methodologies for the construction of labile systems for porphyrin photosensitizers based on the o-nitrobenzyl linker group and selected bioconjugates.…”

Section: A C C E P T E D Article In Pressmentioning

confidence: 99%

Lead structures for applications in photodynamic therapy. Part 2: Synthetic studies for photo-triggered release systems of bioconjugate porphyrin photosensitizers

2009

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Please cite this article as: Bakar MB, Oelgemöller M, Senge MO. Lead structures for Applications in Photodynamic Therapy. 2. Synthetic studies for photo-triggered release systems of bioconjugate porphyrin photosensitizers, Tetrahedron (2009Tetrahedron ( ), doi: 10.1016Tetrahedron ( /j.tet.2009 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. M A N U S C R I P T A C C E P T E D ARTICLE IN PRESS Graphical AbstractTo create your abstract, type over the instructions in the template box below. Fonts or abstract dimensions should not be changed or altered. Abstract-Photodynamic therapy (PDT) selectivity and specificity can be improved by binding the photosensitizers to target receptors. One approach is to cross-link porphyrins to a biological target receptor via the photocleavable o-nitrobenzyl linker, where a controlled released of the porphyrin can be monitored upon irradiation. The synthetic pathways involved esterification of a porphyrin-carboxylic acid and a unit containing the o-nitrobenzyl alcohol moiety and the bioconjugate. Reactions of a model porphyrin and o-nitrobenzyl alcohol using the carbonyl activating carbodiimide reagent DCC gave a stable N-acyl urea porphyrin, whereas use of EDAC (1-ethyl-3-(3-dimethyl aminopropyl)carbodiimide hydrochloride) gave the desired compounds. Further studies were carried out on the attachment of carbohydrates (i.e. potentially receptor binding ligands) through such a linker to porphyrins. Preliminary irradiation experiments of such a compound show that upon UV irradiation (350nm) for 80 min, approximately 50% of the porphyrin was cleaved to release the carboxylic acid porphyrin photosensitizer indicating the utility of such systems as photosensitizers delivery systems. Lead Structures for applications in

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A Model for Light‐Triggered Porphyrin Anticancer Prodrugs Based on an o‐Nitrobenzyl Photolabile Group

Cited by 39 publications

References 37 publications

Recent Advances in light-responsive on-demand drug-delivery Systems

Recent Advances in light-responsive on-demand drug-delivery Systems

Beyond Photodynamic Therapy: Light-Activated Cancer Chemotherapy

Lead structures for applications in photodynamic therapy. Part 2: Synthetic studies for photo-triggered release systems of bioconjugate porphyrin photosensitizers

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