Small Two-Photon Organic Fluorogenic Probes: Sensing and Bioimaging of Cancer Relevant Biomarkers

Singh, Amit Kumar; Nair, Asha V.; Singh, N. D. Pradeep

doi:10.1021/acs.analchem.1c04306

Cited by 46 publications

(21 citation statements)

References 167 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, in pure ACN and f w < 70 vol %, no significant photodegradation of DPBF was found (Table S2). These results indicated that the 1 O 2 generation process was promoted by the aggregation of the (AIEgens) of the nanoDPPC-based PS. − …”

Section: Resultsmentioning

confidence: 87%

Dihydropyrrolo[3,2-b]pyrrole-3,6-dicarbaldehyde-Based Two-Photon-Responsive Nanoparticles for Effective Photodynamic Therapy

Shah

Singh

Banerjee

et al. 2022

ACS Appl. Nano Mater.

Self Cite

View full text Add to dashboard Cite

In recent times, photodynamic therapy (PDT) has emerged as an effective method to fight cancer. Hence, the search for efficient photosensitizers (PSs) to produce reactive oxygen species is rapidly growing. Herein, we present the development of a near-infrared (NIR)-responsive organic nanoparticle as a PS using dihydropyrrolo[3,2-b]pyrrole-3,6-dicarbaldehyde (DPPC) chromophore for effective PDT. The DPPC-based PS showed aggregation-induced emission (AIE), which improved singlet oxygen (1O2) generation in the aqueous medium. Incorporation of bromine atom into the DPPC chromophore enhanced the intersystem crossing efficiency due to the heavy-atom effect and facilitated weak intermolecular interactions between the halogen and carbaldehyde. Notably, the DPPC PS exhibited two-photon absorption within the phototherapeutic window (650–950 nm). With two-photon absorption cross-sections (δa) up to 102 GM, the DPPC-based PS generated significant 1O2 under two-photon excitation that is suitable for bioapplications. Furthermore, we formulated a DPPC-based PS as a nanoparticle. The nano-AIE luminogen of the DPPC-based PS was explored as an imaging agent for HeLa cells. In vitro studies showed that the nanoDPPC PS is a potent PDT agent because of its excellent ability to kill cancer cells only under light irradiation. This work provided a simple strategy for designing two-photon-responsive NIR-active nano-AIEgens to combat cancer.

show abstract

Section: Resultsmentioning

confidence: 87%

Dihydropyrrolo[3,2-b]pyrrole-3,6-dicarbaldehyde-Based Two-Photon-Responsive Nanoparticles for Effective Photodynamic Therapy

Shah

Singh

Banerjee

et al. 2022

ACS Appl. Nano Mater.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Further, we carried out in vitro studies of nano-DDS using HeLa cell lines. We observed that the nano-DDS was internalized inside the cancerous cells after 2 h of incubation, and the cells showed a reddish-orange color because of the cellular uptake of nano-DDS {Figure ia–iiia} . Interestingly, Figure ib,iib shows that after exposure to green light for 40 min, cellular morphology of the HeLa cells altered significantly with cell shrinkage and blebbing, indicating cellular death.…”

Section: Results and Discussionmentioning

confidence: 92%

“…We observed that the nano-DDS was internalized inside the cancerous cells after 2 h of incubation, and the cells showed a reddish-orange color because of the cellular uptake of nano-DDS {Figure 5ia− iiia}. 38 Interestingly, Figure 5ib,iib shows that after exposure to Results indicated that the cell viability of nano-DDS [DANbis(HO-Naph-VPA)] remained above 95% at different concentrations (0−50 μM), suggesting the biocompatibility of our DDS at the studied concentrations (Figure 6a). Additionally, we carried out a light exposure experiment on the HeLa cell lines.…”

Section: Photophysical Properties Of Dds [Dan-bis(ho-naph-vpa)]mentioning

confidence: 98%

Green Light-Activated Single-Component Organic Fluorescence-Based Nano-Drug Delivery System for Dual Uncaging of Anticancer Drugs

Singh

Banerjee

Nair

et al. 2022

ACS Appl. Bio Mater.

Self Cite

View full text Add to dashboard Cite

Developing green or red light-activated drug delivery systems (DDSs) for cancer treatment is highly desirable. Herein, we have reported a green light-responsive single component-based organic fluorescence nano-DDS by simply anchoring 2-hydroxy-6-naphthacyl (phototrigger) on both sides of the 1,5-diaminonaphthalene (DAN) chromophore. This green light (λ ≥ 500 nm)-activated DDS released two equivalents of the anticancer drug (valproic acid) in a spatio-temporally controlled manner. Our photoresponsive DDS [DAN-bis(HO-Naph-VPA)] exhibited interesting properties such as excited-state intramolecular proton transfer (ESIPT) accompanied with aggregation-induced emission (AIE) phenomena. AIE initiated the photorelease, and ESIPT enhanced the rate of the photorelease. Further, in vitro studies revealed that our green light-activated nano-DDS exhibited good cytocompatibility, excellent cellular internalization, and effective cancer cell killing ability.

show abstract

“…Biomarkers can not only be used to diagnose diseases but will also reflect the occurrence and development of tumors. − α-Fetoprotein (AFP), one of the most important biomarkers, which has many important physiological functions, including transport function, bidirectional regulation function for growth, immunosuppression, and lymphocyte apoptosis induction, has been selected as a typical target for many ECL systems. − However, studies on the detection of AFP by ECL sensors using potassium persulfate (K 2 S 2 O 8 ) as the coreactant are relatively few, and promising ferrocene-containing ECL emitters are seldom reported. To this end, the suitable designation of sensitive and effective ECL emitter units such as ferrocene-functionalized porphyrins to coreact with K 2 S 2 O 8 is of great necessity for the development of ECL-sensing platforms for AFP in clinical diagnosis and cancer monitoring.…”

Section: Introductionmentioning

confidence: 99%

Nanoluminophores Composed of 1,1′-Ferrocenedicarboxylic Acid and Tetrakis-(4-carboxyphenyl) Porphyrin for Electrochemiluminescence Sensing

Zhao

et al. 2022

ACS Appl. Nano Mater.

View full text Add to dashboard Cite

Development of nanoluminophores with high efficiency, good stability, and excellent electronic transfer ability is one of the key challenges in electrochemiluminescence (ECL). Here, a porphyrin-based nanomaterial named Fc-TCPP was synthesized by self-assembly of 1,1′-ferrocenedicarboxylic acid (Fc(COOH)2) and tetrakis-(4-carboxyphenyl) porphyrin (TCPP) under infrared heating light. By tuning the ratio of the precursors, the morphology of Fc-TCPP can be regulated from primitive nanospheres to thorn-ball flowers decorated with branches and particles, and the possible formation mechanism was proposed. Nano-boron carbide (B4C) with carbon defect sites further boosts the ECL performance of Fc-TCPP, and thereby, an ECL biosensor for AFP was constructed innovatively. This study provides a simple and effective strategy for the preparation of ECL nanoluminophores taking the advantages of ferrocene and TCPP, opening a new horizon to design porphyrin-based nanomaterials with various structures and expanding their application in biosensing and disease diagnosis.

show abstract

Small Two-Photon Organic Fluorogenic Probes: Sensing and Bioimaging of Cancer Relevant Biomarkers

Cited by 46 publications

References 167 publications

Dihydropyrrolo[3,2-b]pyrrole-3,6-dicarbaldehyde-Based Two-Photon-Responsive Nanoparticles for Effective Photodynamic Therapy

Dihydropyrrolo[3,2-b]pyrrole-3,6-dicarbaldehyde-Based Two-Photon-Responsive Nanoparticles for Effective Photodynamic Therapy

Green Light-Activated Single-Component Organic Fluorescence-Based Nano-Drug Delivery System for Dual Uncaging of Anticancer Drugs

Nanoluminophores Composed of 1,1′-Ferrocenedicarboxylic Acid and Tetrakis-(4-carboxyphenyl) Porphyrin for Electrochemiluminescence Sensing

Contact Info

Product

Resources

About