Cyanine Nanocages Activated by Near-Infrared Light for the Targeted Treatment of Traumatic Brain Injury

Black, Caroline E.; Zhou, Eugene; DeAngelo, Caitlin M.; Asante, Isaac; Louie, Stan G.; Petasis, Nicos A.; Humayun, Mark S.

doi:10.3389/fchem.2020.00769

Cited by 10 publications

(8 citation statements)

References 40 publications

(67 reference statements)

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“…carboxylates, amines. Their application in tumor [19, 20] and traumatic brain injury [21] treatments lends credibility to the use of singlet oxygen‐mediated processes in therapeutic settings. Winter and Weinstain independently reported BODIPY photocages with strong green absorption [22, 23] that have since been extensively optimized to improve the photoreleasing efficiencies [24, 25] and extend their absorption maxima towards the edge of the NIR region [26] .…”

Section: Methodsmentioning

confidence: 99%

Photouncaging of Carboxylic Acids from Cyanine Dyes with Near‐Infrared Light**

et al. 2022

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Near‐infrared light (NIR; 650–900 nm) offers unparalleled advantages as a biocompatible stimulus. The development of photocages that operate in this region represents a fundamental challenge due to the low energy of the excitation light. Herein, we repurpose cyanine dyes into photocages that are available on a multigram scale in three steps and efficiently release carboxylic acids in aqueous media upon irradiation with NIR light up to 820 nm. The photouncaging process is examined using several techniques, providing evidence that it proceeds via photooxidative pathway. We demonstrate the practical utility in live HeLa cells by delivery and release of the carboxylic acid cargo, that was otherwise not uptaken by cells in its free form. In combination with modularity of the cyanine scaffold, the realization of these accessible photocages will fully unleash the potential of the emerging field of NIR‐photoactivation and facilitate its widespread adoption outside the photochemistry community.

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Section: Methodsmentioning

confidence: 99%

Photouncaging of Carboxylic Acids from Cyanine Dyes with Near‐Infrared Light**

et al. 2022

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“…When the precursor solution containing drugs, cells and/or biomolecules is injected into the subcutaneous region of defective site, composite hydrogels can be quickly formed via the physically or chemically crosslinking reaction with close correlations to the surrounding environments (Yang J.A. et al, 2014;Cao et al, 2018;Wang et al, 2018a;Bao et al, 2019;Liu B.C. et al, 2020).…”

Section: Cs-based Hydrogelsmentioning

confidence: 99%

Recent Advances of Chitosan-Based Injectable Hydrogels for Bone and Dental Tissue Regeneration

Tang

Tan

Zeng

et al. 2020

Front. Bioeng. Biotechnol.

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Traditional strategies of bone repair include autografts, allografts and surgical reconstructions, but they may bring about potential hazard of donor site morbidity, rejection, risk of disease transmission and repetitive surgery. Bone tissue engineering (BTE) is a multidisciplinary field that offers promising substitutes in biopharmaceutical applications, and chitosan (CS)-based bone reconstructions can be a potential candidate in regenerative tissue fields owing to its low immunogenicity, biodegradability, bioresorbable features, low-cost and economic nature. Formulations of CS-based injectable hydrogels with thermo/pH-response are advantageous in terms of their highwater imbibing capability, minimal invasiveness, porous networks, and ability to mold perfectly into an irregular defect. Additionally, CS combined with other naturally-derived or synthetic polymers and bioactive agents has proven to be an effective alternative to autologous bone and dental grafts. In this review, we will highlight the current progress in the development of preparation methods, physicochemical properties and applications of CS-based injectable hydrogels and their perspectives in bone and dental regeneration. We believe this review is intended as starting point and inspiration for future research effort to develop the next generation of tissue-engineering scaffold materials.

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“…For instance, cyanines that are prone to aggregate due to poor solubility can be induced to form self-assembled particles that can be used as red-shifted imaging agents. , Likewise, the photoswitching behavior of cyanines that result from a thiol reversibly adding across the conjugated system is commonly employed for super-resolution microscopy . Moreover, fluorogenic probes for ratiometric detection of ROS such as O 2 •– , H 2 O 2 , ONOO – , ClO – , etc., have been developed by linking an unstable cyanine prone to oxidative cleavage to a reference dye that is resistant to ROS-mediated decomposition. ,, Lastly, Schnermann and co-workers have leveraged the photobleaching properties of heptamethine cyanine dyes to serve as NIR photocages, − which can release an appended molecule (e.g., gabapentin) through an intramolecular cyclization event after photolysis. However, it is notable that this uncaging strategy requires covalent appendage of the cargo to the cyanine photocage through a cleavable linker.…”

Section: Introductionmentioning

confidence: 99%

Repurposing Cyanine Photoinstability To Develop Near-Infrared Light-Activatable Nanogels for In Vivo Cargo Delivery

et al. 2022

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The favorable properties of cyanines (e.g., nearinfrared (NIR) absorbance and emission) have made this class of dyes popular for a wide variety of biomedical applications. However, many cyanines are prone to rapid photobleaching when irradiated with light. In this study, we have exploited this undesirable trait to develop NIR-nanogels for NIR light-mediated cargo delivery. NIR-nanogels feature a photolabile cyanine crosslinker (Cy780-Acryl) that can cleave via dioxetane chemistry when irradiated. This photochemical process results in the formation of two carbonyl fragments and concomitant NIR-nanogel degradation to facilitate cargo release. In contrast to studies where cyanines are utilized as photocages, our approach does not require direct chemical attachment to the cargo, thus expanding our ability to deliver molecules that cannot be covalently modified. We showcase this feature by encapsulating a palette of small-molecule chemotherapeutics that feature a structurally diverse chemical architecture. To demonstrate site-selective release in vivo, we generated a murine model of breast cancer. Relative to nonlight irradiated and drugfree controls, treatment with NIR-nanogels loaded with paclitaxel (a potent cytotoxic agent) and NIR light resulted in significant attenuation of tumor growth. Moreover, we show via histological staining of the vital organs that minimal off-target effects are observed.

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Cyanine Nanocages Activated by Near-Infrared Light for the Targeted Treatment of Traumatic Brain Injury

Cited by 10 publications

References 40 publications

Photouncaging of Carboxylic Acids from Cyanine Dyes with Near‐Infrared Light**

Photouncaging of Carboxylic Acids from Cyanine Dyes with Near‐Infrared Light**

Recent Advances of Chitosan-Based Injectable Hydrogels for Bone and Dental Tissue Regeneration

Repurposing Cyanine Photoinstability To Develop Near-Infrared Light-Activatable Nanogels for In Vivo Cargo Delivery

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