Hemicyanine‐Based Near‐Infrared Activatable Probes for Imaging and Diagnosis of Diseases

Zeng, Ziling; Liew, Si Si; Wei, Xin; Pu, Kanyi

doi:10.1002/ange.202107877

Cited by 42 publications

(10 citation statements)

References 130 publications

(74 reference statements)

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“…1a). P-CyPt comprises (1) a NIR merocyanine fluorophore (mCy) 26,27 capped with an ALP-recognition phosphate group (PO 3 H) 28 , (2) a GSH-reducible CDDP prodrug (Pt(IV)) 29,30 , and (3) a hydrophobic D -Phe-D -Phe (FF) dipeptide 31 , which shows low NIR FL, low PA signal and low cytotoxicity. After systemic administration, P-CyPt as a small molecule can extravasate and penetrate deeply into tumor tissues (Fig.…”

Section: Resultsmentioning

confidence: 99%

Controlled sequential in situ self-assembly and disassembly of a fluorogenic cisplatin prodrug for cancer theranostics

Wen

Zhang

et al. 2023

Nat Commun

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Temporal control of delivery and release of drugs in tumors are important in improving therapeutic outcomes to patients. Here, we report a sequential stimuli-triggered in situ self-assembly and disassembly strategy to direct delivery and release of theranostic drugs in vivo. Using cisplatin as a model anticancer drug, we design a stimuli-responsive small-molecule cisplatin prodrug (P-CyPt), which undergoes extracellular alkaline phosphatase-triggered in situ self-assembly and succeeding intracellular glutathione-triggered disassembly process, allowing to enhance accumulation and elicit burst release of cisplatin in tumor cells. Compared with cisplatin, P-CyPt greatly improves antitumor efficacy while mitigates off-target toxicity in mice with subcutaneous HeLa tumors and orthotopic HepG2 liver tumors after systemic administration. Moreover, P-CyPt also produces activated near-infrared fluorescence (at 710 nm) and dual photoacoustic imaging signals (at 700 and 750 nm), permitting high sensitivity and spatial-resolution delineation of tumor foci and real-time monitoring of drug delivery and release in vivo. This strategy leverages the advantages offered by in situ self-assembly with those of intracellular disassembly, which may act as a general platform for the design of prodrugs capable of improving drug delivery for cancer theranostics.

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Section: Resultsmentioning

confidence: 99%

Controlled sequential in situ self-assembly and disassembly of a fluorogenic cisplatin prodrug for cancer theranostics

Wen

Zhang

et al. 2023

Nat Commun

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“…While nanoparticle formulations can potentially offset these drawbacks, it is preferable to develop complementary SWIR dyes that do not require encapsulation for in vivo imaging. In this study, we strategically remodeled the hemicyanine dye (HD) 14,15 (a common NIR platform) for multimodal SWIR FL and PA imaging. Of note, complementary remodeling efforts have yielded PA and NIR-II analogs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of silicon-substituted hemicyanines for multimodal SWIR imaging

East

Lee

Smaga³

et al. 2022

Preprint

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SWIR dyes offer many advantages over their more common NIR congeners; however, the available options are limited. New SWIR imaging agents can be accessed by remodeling existing NIR molecules (i.e., hemicyanines (HD)). In this study, we syn-thesized SWIR-HD, a modified HD featuring silicon-dimethyl and benzo[cd]indolium groups that are designed to red-shift the absorbance and emission to 988 and 1126 nm, respectively. SWIR-HD was tested in three cell lines and shown to exhibit ex-cellent biocompatibility.

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“…Such hemicyanine-based probes have also been used in animal models and showed no cytotoxicity (Figure S4). 14,8,19…”

mentioning

confidence: 99%

Renal-Clearable Molecular Probe for Near-Infrared Fluorescence Imaging and Urinalysis of SARS-CoV-2

et al. 2021

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Despite the importance of rapid and accurate detection of SARS-CoV-2 in controlling the COVID-19 pandemic, current diagnostic methods are static and unable to distinguish between viable/nonviable virus or directly reflect viral replication activity. Real-time imaging of protease activity specific to SARS-CoV-2 can overcome these issues but remains lacking. Herein, we report a near-infrared fluorescence (NIRF) activatable molecular probe (SARS-CyCD) for detection of SARS-CoV-2 protease in living mice. The probe comprises a hemicyanine fluorophore caged with a protease peptide substrate and a cyclodextrin unit, which function as an NIRF signaling moiety and a renal-clearable enabler, respectively. The peptide substrate of SARS-CyCD can be specifically cleaved by SARS-CoV-2 main protease (M pro ), resulting in NIRF signal activation and liberation of the renal-clearable fluorescent fragment (CyCD). Such a design not only allows sensitive detection of M pro in the lungs of living mice after intratracheal administration but also permits optical urinalysis of SARS-CoV-2 infection. Thus, this study presents an in vivo sensor that holds potential in preclinical high-throughput drug screening and clinical diagnostics for respiratory viral infections.

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Hemicyanine‐Based Near‐Infrared Activatable Probes for Imaging and Diagnosis of Diseases

Cited by 42 publications

References 130 publications

Controlled sequential in situ self-assembly and disassembly of a fluorogenic cisplatin prodrug for cancer theranostics

Controlled sequential in situ self-assembly and disassembly of a fluorogenic cisplatin prodrug for cancer theranostics

Synthesis of silicon-substituted hemicyanines for multimodal SWIR imaging

Renal-Clearable Molecular Probe for Near-Infrared Fluorescence Imaging and Urinalysis of SARS-CoV-2

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