A Nonmetal‐Containing Nitric Oxide Donor Activated with Single‐Photon Green Light

Blangetti, Marco; Fraix, Aurore; Lazzarato, Loretta; Marini, Elisabetta; Rolando, Barbara; Sodano, Federica; Fruttero, Roberta; Gasco, Alberto; Sortino, Salvatore

doi:10.1002/chem.201701889

Cited by 35 publications

(29 citation statements)

References 24 publications

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“…The quantum yield for the NO photorelease of 1 and 2 , Φ NO , were 0.031±0.001 and 0.001±0.0002, respectively. Note that, the value observed for 1 is more than one order of magnitude larger than that observed for other organic NOPDs based on BODIPY derivatives –. Furthermore, the quantum efficiency, expressed as the product of ϵ max Φ NO , is approximately 2800, a value much more superior to those reported for other organic NOPDs –.…”

Section: Resultsmentioning

confidence: 65%

“…In this scenario BODIPY and Rhodamine derivatives are suitable chromogenic scaffolds to achieve NOPDs working under excitation with the more biocompatible green‐orange light, by virtue of their intense absorption and emission properties in this spectral range. However, despite some BODIPY‐based NOPDs exhibited good fluorescence emission, the NO photorelease quantum yield ( Φ NO ) was on the order of 10 −3 and the quantum efficiency ( ϵ max Φ NO ) did not exceed 550 –. On the other hand, in the case of Rhodamine‐based NOPDs the typical fluorescence emission of this fluorogenic unit is dramatically quenched before the NO photorelease takes place –…”

Section: Introductionmentioning

confidence: 99%

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Fluorescent Nitric Oxide Photodonors Based on BODIPY and Rhodamine Antennae

Parisi

Failla

Fraix

et al. 2019

Chemistry A European J

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Twon ovel NO photodonors (NOPDs) based on BODIPYa nd Rhodamine antennae activatable with the highly biocompatible green light are reported. Both NOPDs exhibitc onsiderable fluorescencee mission and release NO with remarkableq uantum efficiencies. Thec ombination of the photoreleasing and emissive performance for both compoundsi ss uperior to those exhibited by otherN OPDs based on similar light-harvesting centres,m aking them very intriguing for image-guided phototherapeutic applications.P reliminaryb iological data prove their easy visualizationi nc ell environment due to the intense green and orange-red fluorescence and their photodynamic action on cancerc ells due to the NO photo-liberated.

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Section: Resultsmentioning

confidence: 65%

Section: Introductionmentioning

confidence: 99%

Fluorescent Nitric Oxide Photodonors Based on BODIPY and Rhodamine Antennae

Parisi

Failla

Fraix

et al. 2019

Chemistry A European J

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“…Furthermore, UV can be harmful to normal cells of human, so NO releasing materials triggered by physiological friendly visible lights or near-infrared lights (NIR) would have more advantages in antibacterial therapy. Researchers have developed small molecule photoresponsive NO donors triggered by visible lights with wavelengths of 390 nm [127] (also reported with 380 nm [128]), 405 nm [73], 500 nm [129], 530–550 nm [130], and even NIR with wavelengths of 800 nm [131] and 980 nm [132] (partly presented in Figure 7).…”

Section: No Releasing Polymeric Materials For Antibacterial Applicmentioning

confidence: 99%

Nitric Oxide-Releasing Polymeric Materials for Antimicrobial Applications: A Review

et al. 2019

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Polymeric materials releasing nitric oxide have attracted significant attention for therapeutic use in recent years. As one of the gaseous signaling agents in eukaryotic cells, endogenously generated nitric oxide (NO) is also capable of regulating the behavior of bacteria as well as biofilm formation in many metabolic pathways. To overcome the drawbacks caused by the radical nature of NO, synthetic or natural polymers bearing NO releasing moiety have been prepared as nano-sized materials, coatings, and hydrogels. To successfully design these materials, the amount of NO released within a certain duration, the targeted pathogens and the trigger mechanisms upon external stimulation with light, temperature, and chemicals should be taken into consideration. Meanwhile, NO donors like S-nitrosothiols (RSNOs) and N-diazeniumdiolates (NONOates) have been widely utilized for developing antimicrobial polymeric agents through polymer-NO donor conjugation or physical encapsulation. In addition, antimicrobial materials with visible light responsive NO donor are also reported as strong and physiological friendly tools for rapid bacterial clearance. This review highlights approaches to delivery NO from different types of polymeric materials for combating diseases caused by pathogenic bacteria, which hopefully can inspire researchers facing common challenges in the coming ‘post-antibiotic’ era.

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“…The first examples required the use of damaging UV irradiation to release NO from caged diazeniumdiolates, 48 aryl N-nitrosamines, 49 and nitrobenzenes. 50,51 Molecules stimulated by visible [52][53][54][55][56] and two-photon NIR light 57,58 were soon realized to improve tissue penetration and biocompatibility.…”

Section: ■ Introductionmentioning

confidence: 99%

Near-Infrared Photoactivatable Nitric Oxide Donors with Integrated Photoacoustic Monitoring

et al. 2018

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Photoacoustic (PA) tomography is a noninvasive technology that utilizes near-infrared (NIR) excitation and ultrasonic detection to image biological tissue at centimeter depths. While several activatable small-molecule PA sensors have been developed for various analytes, the use of PA molecules for deep-tissue analyte delivery and monitoring remains an underexplored area of research. Herein, we describe the synthesis, characterization, and in vivo validation of photoNOD-1 and photoNOD-2, the first organic, NIR-photocontrolled nitric oxide (NO) donors that incorporate a PA readout of analyte release. These molecules consist of an aza-BODIPY dye appended with an aryl N-nitrosamine NO-donating moiety. The photoNODs exhibit chemostability to various biological stimuli, including redox-active metals and CYP450 enzymes, and demonstrate negligible cytotoxicity in the absence of irradiation. Upon single-photon NIR irradiation, photoNOD-1 and photoNOD-2 release NO as well as rNOD-1 or rNOD-2, PA-active products that enable ratiometric monitoring of NO release. Our in vitro studies show that, upon irradiation, photoNOD-1 and photoNOD-2 exhibit 46.6-fold and 21.5-fold ratiometric turn-ons, respectively. Moreover, unlike existing NIR NO donors, the photoNODs do not require encapsulation or multiphoton activation for use in live animals. In this study, we use PA tomography to monitor the local, irradiation-dependent release of NO from photoNOD-1 and photoNOD-2 in mice after subcutaneous treatment. In addition, we use a murine model for breast cancer to show that photoNOD-1 can selectively affect tumor growth rates in the presence of NIR light stimulation following systemic administration.

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A Nonmetal‐Containing Nitric Oxide Donor Activated with Single‐Photon Green Light

Cited by 35 publications

References 24 publications

Fluorescent Nitric Oxide Photodonors Based on BODIPY and Rhodamine Antennae

Fluorescent Nitric Oxide Photodonors Based on BODIPY and Rhodamine Antennae

Nitric Oxide-Releasing Polymeric Materials for Antimicrobial Applications: A Review

Near-Infrared Photoactivatable Nitric Oxide Donors with Integrated Photoacoustic Monitoring

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