Intracellular oxygen-sensitive phosphorescent probes based on cell-penetrating peptides

Dmitriev, Ruslan I.; Zhdanov, Alexander V.; Ponomarev, G. V.; Yashunski, Dmitri; Papkovsky, Dmitri B.

doi:10.1016/j.ab.2009.10.048

Cited by 64 publications

(99 citation statements)

References 32 publications

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“…DNA synthesis), which was observed for the fragment [5,8]. The short (15)(16)(17)(18)(19)(20)(21)(22)(23)(24) fragment contains five prolines of 10 residues and, when carrying a small (fluorescein isothiocyanate, FITC) or even large (60-kDa NeutrAvidin) cargo, is able to penetrate mammalian cells with an efficiency comparable with that of the TAT peptide [5].…”

Section: Introductionmentioning

confidence: 83%

“…The targeted delivery of porphyrins and, in particular, their metal complexes in subcellular compartments has been hindered by their significant size and hydrophobicity [17][18][19]. However, porphyrin photosensitizer conjugates with cell-penetrating peptides have been described and have shown potential for in vivo applications, such as prostate cancer therapy [9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…MitoXpress possesses useful features; however, the slow (24-28 h), cell-specific loading limits its use and analytical performance [20,22]. Recently, we have described a panel of conjugates of PtCP with cell-penetrating peptides, and have studied the influence of the charge of the porphyrin moiety and peptide structure [19]. The uncharged (esterified) PtCP derivatives conjugated to TAT and nonaarginine peptides show significant improvement in cell loading compared with those based on negatively charged dye analogues with three carboxylic groups.…”

Section: Introductionmentioning

confidence: 99%

“…In this article, we describe a novel phosphorescent oxygen-sensitive probe for intracellular use which comprises a bactenecin 7 peptide fragment (15)(16)(17)(18)(19)(20)(21)(22)(23)(24) conjugated with the uncharged monofunctional derivative of Pt(II) coproporphyrin I (PEPP0). This probe provides efficient loading of various mammalian cells, including PC12, HCT116, SH-SY5Y and HeLa, via cell-type-dependent uptake mechanisms.…”

Section: Introductionmentioning

confidence: 99%

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Bactenecin 7 peptide fragment as a tool for intracellular delivery of a phosphorescent oxygen sensor

et al. 2010

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Research on cell‐penetrating peptides for the intracellular delivery of porphyrin compounds has mainly focused on the use of trans‐activator of transcription (TAT)‐derived peptides and, to a lesser extent, on proline‐rich peptides and phosphorescent metalloporphyrins. In this article, we describe a novel phosphorescent oxygen‐sensitive probe for intracellular use which comprises a bactenecin 7 peptide fragment (15–24) conjugated with the uncharged monofunctional derivative of Pt(II) coproporphyrin I (PEPP0). This probe provides efficient loading of various mammalian cells, including PC12, HCT116, SH‐SY5Y and HeLa, via cell‐type‐dependent uptake mechanisms. The conjugate displays a similar distribution in cytoplasm and mitochondria which allows local oxygen levels to be monitored. Respiratory responses of PC12 cells loaded with the conjugate, measured on a time‐resolved fluorescent reader, showed significant cell deoxygenation in response to uncoupling by carbonyl cyanide 4‐(trifluoromethoxy)phenylhydrazone and external hypoxia. Treatment with mitochondrial inhibitors led to a decrease in cell deoxygenation. Although the biophysical properties of this conjugate are similar to those of the phosphorescent intracellular oxygen‐sensitive probes described previously, it possesses a number of advantages, including ease of synthesis, high loading efficiency and reliability in physiological experiments with cells. This intracellular probe can be employed for the measurement of intracellular O2 levels in samples containing mammalian cells using the phosphorescence quenching technique. In addition, the responses to metabolic stimuli can be assessed in a wide range of cells, as can the levels of relative cell oxygenation under external hypoxia.

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Section: Introductionmentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bactenecin 7 peptide fragment as a tool for intracellular delivery of a phosphorescent oxygen sensor

et al. 2010

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“…Another class of cell-penetrating dyes which rely on an endocytic mechanism of cell entry is represented by the derivative of tetracarboxylic Pt(II)-coproporphyrin I (PtCP) [58,174]. Such conjugates were successfully tested to measure intracellular O 2 concentration in live cells, giving informationrich data on cellular function and metabolism.…”

Section: Intra and Extracellular O 2 Imaging And Do In Tissuementioning

confidence: 99%

Indicators for optical oxygen sensors

Borisov¹,

Quaranta²,

Klimant³

2012

Advances in Chemical Bioanalysis

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Continuous monitoring of oxygen concentration is of great importance in many different areas of research which range from medical applications to food packaging. In the last three decades, significant progress has been made in the field of optical sensing technology and this review will highlight the one inherent to the development of oxygen indicators. The first section outlines the bioanalytical fields in which optical oxygen sensors have been applied. The second section gives the reader a comprehensive summary of the existing oxygen indicators with a critical highlight on their photophysical and sensing properties. Altogether, this review is meant to give the potential user a guide to select the most suitable oxygen indicator for the particular application of interest.

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Multifunctional Phosphorescent Conjugated Polymer Dots for Hypoxia Imaging and Photodynamic Therapy of Cancer Cells

et al. 2015

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Molecular oxygen (O2) plays a key role in many physiological processes, and becomes a toxicant to kill cells when excited to 1O2. Intracellular O2 levels, or the degree of hypoxia, are always viewed as an indicator of cancers. Due to the highly efficient cancer therapy ability and low side effect, photodynamic therapy (PDT) becomes one of the most promising treatments for cancers. Herein, an early‐stage diagnosis and therapy system is reported based on the phosphorescent conjugated polymer dots (Pdots) containing Pt(II) porphyrin as an oxygen‐responsive phosphorescent group and 1O2 photosensitizer. Intracellular hypoxia detection has been investigated. Results show that cells treated with Pdots display longer lifetimes under hypoxic conditions, and time‐resolved luminescence images exhibit a higher signal‐to‐noise ratio after gating off the short‐lived background fluorescence. Quantification of O2 is realized by the ratiometric emission intensity of phosphorescence/fluorescence and the lifetime of phosphorescence. Additionally, the PDT efficiency of Pdots is estimated by flow cytometry, MTT cell viability assay, and in situ imaging of PDT induced cell death. Interestingly, Pdots exhibit a high PDT efficiency and would be promising in clinical applications.

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Intracellular oxygen-sensitive phosphorescent probes based on cell-penetrating peptides

Cited by 64 publications

References 32 publications

Bactenecin 7 peptide fragment as a tool for intracellular delivery of a phosphorescent oxygen sensor

Bactenecin 7 peptide fragment as a tool for intracellular delivery of a phosphorescent oxygen sensor

Indicators for optical oxygen sensors

Multifunctional Phosphorescent Conjugated Polymer Dots for Hypoxia Imaging and Photodynamic Therapy of Cancer Cells

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