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Enhanced photochemical nitric oxide release from a flutamide derivative incorporated in Pluronic F127 micelles

Paper ID Volume ID Publish Year Pages File Format Full-Text
25887 43907 2014 7 PDF Available
Title
Enhanced photochemical nitric oxide release from a flutamide derivative incorporated in Pluronic F127 micelles
Abstract

•We synthesized N-(3-aminopropyl)-3-(trifluoromethyl)-4-nitrobenzenamine (ATN).•ATN was shown to release NO upon irradiation with visible light.•ATN was incorporated in Pluronic F127, a PEO–PPO–PEO triblock copolymer.•The micellar F127/ATN environment enhanced the photochemical NO release from ATN.•Micellar F127/ATN solutions are promising for topical photochemical NO delivery.

The incorporation of nitric oxide (NO) photodonors into nontoxic vehicles may allow for the tunable control of topical NO release to treat pathological conditions associated with the impairment of NO production in the dermal vasculature. Pluronic F127 is a PEO–PPO–PEO triblock copolymer that is used as a nontoxic vehicle that undergoes thermally reversible micellization and gelation. In this study, we synthesized a thermally stable flutamide derivative, N-(3-aminopropyl)-3-(trifluoromethyl)-4-nitrobenzenamine (ATN), which is capable of releasing NO upon irradiation with visible light, as shown by real-time chemiluminescence NO detection. We demonstrated that the incorporation of ATN into the hydrophobic nuclei of F127 micelles leads to an enhancement of its photochemical NO release, which is consistent with the photodecomposition route associated with the nitro-to-nitrite photorearrangement of ATN. This mechanism underscores a new role of the F127 micelles as concentrating “nanoreactors” for hydrophobic NO releasing drugs. In this case, this effect may represent a new strategy for enhancing photochemical NO release from ATN, which makes the micellar F127/ATN solutions promising for topical NO application.

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Keywords
Nitric oxide; Flutamide; PEO–PPO–PEO; Photochemical NO release
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Enhanced photochemical nitric oxide release from a flutamide derivative incorporated in Pluronic F127 micelles
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 293, 1 November 2014, Pages 65–71
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us