Synthesis, cellular uptake of, and cell photo-sensitization by a porphyrin bearing a quinoline group

Morlière, Patrice; Momenteau, M.; Candide, C.; Simonin, V.; Santús, René; Mazière, Jean‐Claude; Dubertret, Louis; Goldstein, Sonia; Hüppe, Gabriele

doi:10.1016/1011-1344(90)85005-h

Cited by 13 publications

(2 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…9–14 For example, most cancer cells show an increased uptake of low-density lipoprotein. Low-density lipoprotein’s capability to bind porphyrin molecules 13,15,16 may explain in part the selective uptake of most porphyrins by cancer cells. 13 Certain porphyrin compounds produce a characteristic fluorescence that can be used for cancer detection.…”

mentioning

confidence: 99%

Early Detection of Lung Cancer with Meso Tetra (4-Carboxyphenyl) Porphyrin-Labeled Sputum

Patriquin

Merrick

Hill

et al. 2015

Journal of Thoracic Oncology

View full text Add to dashboard Cite

Introduction Early detection of lung cancer in high-risk individuals reduces mortality. Low-dose spiral computed tomography (LDCT) is the current standard but suffers from an exceedingly high false-positive rate (>96%) leading to unnecessary and potentially dangerous procedures. We, therefore, set out to develop a simple, noninvasive, and quantitative assay to detect lung cancer. Methods This proof-of-concept study evaluated the sensitivity/specificity of the CyPath Early Lung Cancer Detection Assay to correctly classify LDCT-confirmed cohorts of high-risk control (n = 102) and cancer (n = 26) subjects. Fluorescence intensity parameters of red fluorescent cells (RFCs) from tetra (4-carboxyphe-nyl) porphyrin (TCPP)-labeled lung sputum samples and subjects’ baseline characteristics were assessed for their predictive power by multivariable logistic regression. A receiver operating characteristic curve was constructed to evaluate the sensitivity/specificity of the CyPath assay. Results RFCs were detectable in cancer subjects more often than in high-risk ones (p = 0.015), and their characteristics differed between cohorts. Two independent predictors of cancer were the mean of RFC average fluorescence intensity/area per subject (p < 0.001) and years smoked (p = 0.003). The CyPath-based classifier had an overall accuracy of 81% in the test population; false-positive rate of 40% and negative predictive value of 83%. Conclusions The tetra (4-carboxyphenyl) porphyrin-based CyPath assay correctly classified study participants into cancer or high-risk cohorts with considerable accuracy. Optimizing sputum collection, sample reading, and refining the classifier should improve sensitivity and specificity. The CyPath assay thus has the potential to complement LDCT screening or serve as a stand-alone approach for early lung cancer detection.

show abstract

mentioning

confidence: 99%

Early Detection of Lung Cancer with Meso Tetra (4-Carboxyphenyl) Porphyrin-Labeled Sputum

Patriquin

Merrick

Hill

et al. 2015

Journal of Thoracic Oncology

View full text Add to dashboard Cite

show abstract

“…Derivative 22 ( Figure 6) attached to a quinoline group showed various pharmaceutical activities, including anti-tumour activity, and meets several essential requirements of an ideal PS; for example, it produced 1 O 2 efficiently (U D ¼ 0.62) in tetrahydrofuran. The calculated value was above the range reported for most PSs employed in PDT 48,49 . Benzothiophene-containing porphyrin derivatives were found to selectively accumulate in the mitochondria and nucleus of MCF-7 cells.…”

Section: Functional Group-modified Porphyrin Derivativesmentioning

confidence: 41%

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

Lin

Zhou

Bai

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

With the development of photodynamic therapy (PDT), remarkable studies have been conducted to generate photosensitisers (PSs), especially porphyrin PSs. A variety of chemical modifications of the porphyrin skeleton have been introduced to improve cellular delivery, stability, and selectivity for cancerous tissues. This review aims to highlight the developments in porphyrin-based structural modifications, with a specific emphasis on the role of PDT in anticancer treatment and the design of PSs to achieve a synergistic effect on multiple targets.

show abstract

In vivo relaxometry of three brain tumors in the rat: Effect of Mn‐TPPS, a tumor‐selective contrast agent

Wilmes

Hoehn‐Berlage

Els

et al. 1993

Magnetic Resonance Imaging

View full text Add to dashboard Cite

T1 and T2 were determined simultaneously in vivo at 4.7 T in implanted rat brain tumors. Three different tumor cell lines were implanted in the right caudate nucleus: the F98 glioma, the E367 neuroblastoma, and the RN6 schwannoma. Their T1 and T2 values (mean +/- standard deviation [msec]), respectively, were 1,312 +/- 107 and 89 +/- 3 (glioma), 1,284 +/- 86 and 87 +/- 7 (neuroblastoma), and 1,338 +/- 85 and 86 +/- 9 (schwannoma). The T1 values (msec) of normal brain and muscle were 1,090 +/- 59 and 1,139 +/- 77, respectively, and the T2 values (msec) were 76 +/- 3 and 36 +/- 2, respectively. After injection of the contrast agent manganese (III) tetraphenylporphine sulfonate (TPPS) the T1 of all three tumors decreased by 30% and the T2 by 10%, whereas no such change in relaxivity was noted in normal brain. As a result, strong contrast enhancement of the three tumor types was seen on T1-weighted images. The tumor was clearly delineated and correlated with findings at histologic examination. This tumor enhancement was followed up for 4 days with quantitative relaxation time measurements, and the strong, selective reduction in T1 for all three tumor types after Mn-TPPS injection was preserved over the entire observation period.

show abstract

Synthesis, cellular uptake of, and cell photo-sensitization by a porphyrin bearing a quinoline group

Cited by 13 publications

References 26 publications

Early Detection of Lung Cancer with Meso Tetra (4-Carboxyphenyl) Porphyrin-Labeled Sputum

Early Detection of Lung Cancer with Meso Tetra (4-Carboxyphenyl) Porphyrin-Labeled Sputum

Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy

In vivo relaxometry of three brain tumors in the rat: Effect of Mn‐TPPS, a tumor‐selective contrast agent

Contact Info

Product

Resources

About