Stimuli-responsive prodrug of non-steroidal anti-inflammatory drug diclofenac: self-immolative drug release with turn-on near-infrared fluorescence

Sufian, A. T.; Bhattacherjee, Debojit; Barman, Pallavi; Srivastava, Abhay; Thummer, Rajkumar P.; Bhabak, Krishna P.

doi:10.1039/d2cc02132c

Cited by 12 publications

(10 citation statements)

References 38 publications

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“…The emission intensity was measured from AM‐TCB in the absence of H 2 O 2 and in the lower concentration range of H 2 O 2 in determining the LOD (Figure 3B). The LOD of AM‐TCB was found to be 1.0 μM, indicating very good sensitivity of the prodrug towards H 2 O 2 (Figure S3, Table S1, Supporting Information) [25] . The trend of pH‐dependent drug uncaging from AM‐TCB (5 μM) with H 2 O 2 (200 μM) and the stability of the prodrug at various pH (4–10) of the medium was studied next.…”

Section: Resultsmentioning

confidence: 99%

“…The LOD of AM-TCB was found to be 1.0 μM, indicating very good sensitivity of the prodrug towards H 2 O 2 (Figure S3, Table S1, Supporting Information). [25] The trend of pH-dependent drug uncaging from AM-TCB (5 μM) with H 2 O 2 (200 μM) and the stability of the prodrug at various pH (4-10) of the medium was studied next. Although the emission was weak at lower pH range (4-5), it increased gradually over the pH 6-7 and became steady thereafter till pH 10 (Figure 3C).…”

Section: Analyte Selectivity and The Ph Dependencymentioning

confidence: 99%

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Dual‐Stimuli‐Activatable Hybrid Prodrug for the Self‐Immolative Delivery of an Anticancer Agent and Hydrogen Sulfide with Turn‐On Fluorescence

Sufian,

Badirujjaman,

Barman

et al. 2023

Chemistry A European J

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Stimuli‐responsive fluorogenic prodrugs are advantageous for the targeted drug delivery enabling real‐time non‐invasive monitoring with turn‐on fluorescence. We report herein the dual‐stimuli (ROS and CA)‐responsive thiocarbamate‐based prodrug (AM‐TCB) for the turn‐on fluorogenic delivery of the naphthalimide‐based anticancer agent amonafide along with the gasotransmitter hydrogen sulfide (H2S). A carbamate‐based prodrug AM‐CB was also designed, capable of releasing the anticancer agent amonafide without any H2S. The prodrugs were synthesized using multi‐step organic synthesis. UV‐Vis and fluorescence spectroscopic studies revealed selective reactivity of the boronate ester group of prodrugs towards ROS (primarily H2O2) with the release of amonafide and COS/CO2 via self‐immolative processes. Hydrolysis of the generated COS by carbonic anhydrase (CA) produces H2S. While the prodrug AM‐TCB retained the anticancer activity of free amonafide in cancer cells (MDA‐MB‐231 and HeLa), unlike amonafide, it enhanced the cellular viability of the non‐malignant cells (HEK‐293). Fluorescence imaging in HeLa cells revealed the simultaneous delivery of the anticancer agent and H2S from AM‐TCB with turn‐on fluorescence. Western blot studies further revealed the cytoprotective effects of the released H2S from AM‐TCB. The present adjuvant strategy therefore would be helpful in future for ameliorating the anticancer drug‐induced side‐effects.

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Section: Resultsmentioning

confidence: 99%

Section: Analyte Selectivity and The Ph Dependencymentioning

confidence: 99%

Dual‐Stimuli‐Activatable Hybrid Prodrug for the Self‐Immolative Delivery of an Anticancer Agent and Hydrogen Sulfide with Turn‐On Fluorescence

Sufian,

Badirujjaman,

Barman

et al. 2023

Chemistry A European J

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“…Moreover, it can be derived that the diclofenac-treated group has more significant changes than the aspirin group, implying a stronger anti-inflammatory effect. The main reason may be attributed to the better selectivity of diclofenac for cyclooxygenase-2 (COX-2), 54 which effectively inhibits the synthesis of prostaglandins (PGS), a key mediator in the development and progression of inflammation. These results indicate the MNs patch not only evaluates whether the drug has an antiperitonitis effect but also assesses the efficacy of different drugs.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Skin Interstitial Fluid-Based SERS Tags Labeled Microneedles for Tracking of Peritonitis Progression and Treatment Effect

et al. 2023

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Skin interstitial fluid (ISF)-based microneedle (MN) sensing has recently exhibited wide promise for the minimally invasive and painless diagnosis of diseases. However, it is still a great challenge to diagnose more disease types due to the limited in situ sensing techniques and insufficient ISF biomarker sources. Herein, ISF is employed to pioneer the tracking of acute peritonitis progression via surface-enhanced Raman scattering (SERS) tags labeled MNs patch technique. Densely deposited core-satellite gold nanoparticles and 3-mercaptophenylboronic acid as a Raman reporter enable the developed MNs patch with high sensitivity and selectivity in the determination of H2O2, an indicator of peritonitis development. Importantly, the MNs patch not only reliably tracks the different states of peritonitis but also evaluates the efficacy of drugs in the treatment of peritonitis, as evidenced by the altered SERS signal consistent with plasma pro-inflammatory factor (TNF-α) and peritoneum pathological manifestations. Interestingly, the major source of H2O2 in ISF of acute peritonitis investigated may not be through conventional blood capillary filtration pathway. This work provides a new route and technique for the early diagnosis of acute peritonitis and the evaluation of drug therapy effects. The developed MNs patch is promising to serve as a universal sensing tool to greatly enrich the variety and prospect of ISF-based disease diagnosis.

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“…Further animal-based studies confirmed that theranostic probe 27 provided for a distinct fluorescence enhancement (Cy7), which was taken as signaling CPT release, when subject to either intratumoral or intravenous administration. An ostensibly related NIR-based theranostic probe 28 was developed for H 2 O 2 -mediated release and monitoring of diclofenac (a nonsteroid anti-inflammatory drug, NSAID) delivery in inflammation-induced macrophages …”

Section: Theranostic Fluorescence Probes In Cancer Therapymentioning

confidence: 99%

Theranostic Fluorescent Probes

Sharma,

Verwilst,

et al. 2024

Chem. Rev.

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The ability to gain spatiotemporal information, and in some cases achieve spatiotemporal control, in the context of drug delivery makes theranostic fluorescent probes an attractive and intensely investigated research topic. This interest is reflected in the steep rise in publications on the topic that have appeared over the past decade. Theranostic fluorescent probes, in their various incarnations, generally comprise a fluorophore linked to a masked drug, in which the drug is released as the result of certain stimuli, with both intrinsic and extrinsic stimuli being reported. This release is then signaled by the emergence of a fluorescent signal. Importantly, the use of appropriate fluorophores has enabled not only this emerging fluorescence as a spatiotemporal marker for drug delivery but also has provided modalities useful in photodynamic, photothermal, and sonodynamic therapeutic applications. In this review we highlight recent work on theranostic fluorescent probes with a particular focus on probes that are activated in tumor microenvironments. We also summarize efforts to develop probes for other applications, such as neurodegenerative diseases and antibacterials. This review celebrates the diversity of designs reported to date, from discrete small-molecule systems to nanomaterials. Our aim is to provide insights into the potential clinical impact of this stillemerging research direction.

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Stimuli-responsive prodrug of non-steroidal anti-inflammatory drug diclofenac: self-immolative drug release with turn-on near-infrared fluorescence

Abstract: Reactive oxygen species (ROS)-responsive near infrared (NIR) fluorogenic prodrug DCI-ROS is developed for the self-immolative release of Diclofenac (DCF) with turn-on fluorescence. The non-toxic prodrug exhibited turn-on red fluorescence with...

Cited by 12 publications

References 38 publications

Dual‐Stimuli‐Activatable Hybrid Prodrug for the Self‐Immolative Delivery of an Anticancer Agent and Hydrogen Sulfide with Turn‐On Fluorescence

Dual‐Stimuli‐Activatable Hybrid Prodrug for the Self‐Immolative Delivery of an Anticancer Agent and Hydrogen Sulfide with Turn‐On Fluorescence

Skin Interstitial Fluid-Based SERS Tags Labeled Microneedles for Tracking of Peritonitis Progression and Treatment Effect

Theranostic Fluorescent Probes

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