Ground-State Proton-Transfer (GSPT)-Assisted Enhanced Two-Photon Uncaging from a Binol-based AIE-Fluorogenic Phototrigger

Mengji

et al. 2021

Preprint

Self Cite

In recent times, organelle-targeted drug delivery systems gained tremendous attention due to the site specific delivery of active drug molecules resulting in enhanced bioefficacy. In this context, the phototriggered drug delivery system (DDS) for releasing an active molecule is superior as it provides spatial and temporal control over the release. So far, near infrared (NIR) light responsive organelle targeted DDS has not yet been developed. Hence, we introduced a two-photon NIR-light responsive lysosome targeted ʽAIE + ESIPTʼ active single component DDS based on naphthalene chromophore. The Two-photon absorption cross-section of our DDS is 142 GM at 850 nm. The DDS was converted into pure organic nanoparticles for biological applications. Our nano-DDS is capable of selective targeting, AIE-luminogenic imaging, and drug release within the lysosome. In vitro studies using cancerous cell lines showed that our single component photoresponsive nanocarrier exhibited enhanced cytotoxicity and real-time monitoring ability of the drug release.

Section: Introductionmentioning

confidence: 69%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

NIR-Responsive Lysosomotropic Phototrigger: ʽAIE + ESIPTʼ Active Naphthalene Based Single Component Photoresponsive Nanocarrier with Two-Photon Uncaging and Real-Time Monitoring Ability

Mengji

et al. 2021

Preprint

Self Cite

“…This phenomenon is known as a ground-state proton-transfer (GSPT) process, where solvent molecules assist the proton transfer, resulting in the redshift of absorption and emission maximum due to the formation of an anionic structure. 14 To confirm that our photocages are GSPT active, we recorded the absorption (Figure 1f) and emission spectra (Figure 1g) of all the photocages (5a-d) in dry DMSO and 1:1 DMSO: buffer (pH 7.4) mixture 14 . We noted that the addition of buffer solution enhanced the intensity of the absorption and the emission maximum of our photocages by ten folds with a slight blue-shift (~20 nm) of the absorption maximum (580 nm).…”

Section: Scheme 2 Synthesis Of Dcm-photocages (5a-d)mentioning

confidence: 77%

“…Herein, we developed an acyl group appended o-Hydroxystyryl dicyanomethylene-4H-pyran PRPG to release aliphatic and aromatic carboxylic acids in the 'phototherapeutic window' (Scheme 1b). Our newly developed DCM-PRPG exhibited exciting features like, (i) requires only three steps to synthesize the photocages starting from salicylaldehyde, (ii) good solubility in the aqueous medium (iii) exhibits ground state proton transfer (GSPT) phenomenon in the aqueous medium resulting in the increase in the intensity of absorption and emission 14 (iv) uncaging of carboxylic can be carried out with red-light (600 -650 nm) via single-photon excitation.…”

Section: Introductionmentioning

confidence: 99%

Red-Light Triggered Photouncaging from Dicyanomethylene-4H-pyran Phototrigger in Aqueous Solution: Applied as a Single Component Nano-Drug Delivery System for Cancer Therapy

Mengji

Kundu

et al. 2021

Preprint

Self Cite

The development of Photoremovable protecting groups (PRPGs), which can be activated in the ʽphototherapeutic windowʼ for biological applications, is highly challenging. Only PRPGs based on BODIPY dye have been developed so far, which can be excited ≥600 nm. Herein, we developed for the first time NIR dye hydroxystyryl dicyanomethylene-4H-pyran (DCM) as a PRPG that can be operated in the phototherapeutic window. Ours easily synthesized DCM photocages efficiently released aromatic and aliphatic carboxylic acids in an aqueous solution on irradiation using the light of wavelength ≥600 nm and 650 nm, separately. As an application, we used our DCM-PRPG as a single component nanocarrier drug delivery system (DDS) to uncage valproic acid (a known histone deacetylase inhibitor) for cancer treatment. In vitro studies revealed that our DDS, hydroxystyryl dicyanomethylene-4H-pyran valproic acid conjugate nanoparticles (DCM-VPA-NPs) exhibited good cellular internalization, biocompatibility, and enhanced cytotoxicity upon irradiation.

Two‐Photon Mediated Cancer Therapy: A Comprehensive Review on Two‐Photon Photodynamic Therapy and Two‐Photon‐Activated Therapeutic Delivery Systems

Soleimany,

Aghmiouni,

Amirikhah

et al. 2024

Adv Funct Materials

Two‐photon excitation (2PE) represents substantial advantages in biophotonics over traditional one‐photon excitation (1PE), offering enhanced spatial resolution and deeper tissue penetration capabilities. Since its introduction in the 1990s, two‐photon excited microscopy has spurred the rapid emergence of novel 2PE‐based applications, including photodynamic therapy (PDT) and the targeted release of biologically active agents. This review first elucidates the fundamental principles of 2PE before comprehensively examining the evolution of photosensitizers (PSs) for two‐photon PDT (2P‐PDT), covering both nanomaterials and small molecules, categorized based on their respective characteristics. Additionally, it explores advancements in PS development for integrating 2P‐PDT with other therapeutic modalities (e.g., photothermal therapy, chemotherapy, immunotherapy, gene therapy, etc.). Subsequent sections provide an overview of photoactivatable compounds with two‐photon absorption properties for the controlled release of various therapeutic agents (e.g., drugs, genes, and gasotransmitters), emphasizing their potential in anticancer applications. Last, a deep discussion deciphers the prospects and challenges of 2P‐mediated therapy in cancer treatment, particularly concerning their clinical translation.