Selenorhodamine photosensitizers with the Texas-red core for photodynamic therapy of cancer cells

Kryman, Mark W.; Davies, Kellie S.; Linder, Michelle K.; Ohulchanskyy, Tymish Y.; Detty, Michael R.

doi:10.1016/j.bmc.2015.06.006

Cited by 17 publications

(15 citation statements)

References 22 publications

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“…Their practical application in medicine for the treatment of tumors and cancers is a subject of current intense interest . In addition, selenium‐containing heterocycles are promising photosensitizers for photodynamic therapy of cancers . They also have valuable applications in material science, where they are used in organic conductors, semiconductors, and optoelectronics .…”

Section: Introductionmentioning

confidence: 99%

An Easy Synthetic Approach to Construct Some Ebselen Analogues and Benzo[b]selenophene Derivatives: Their Antioxidant and Cytotoxic Assessment

Elsherbini

Hamama

Zoorob

2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com). 2-(Chloroseleno)benzoyl chloride serves as a versatile building block for the synthesis of novel ebselen (2-phenyl-1,2-benzisoselenazol-3(2H)-one) analogues and benzo[b]selenophen-3(2H)-one derivatives. The antioxidant activity and cytotoxic evaluation of the newly synthesized compounds were implemented. Among all the synthesized compounds, 1-(3-hydroxybenzo[b]selenophen-2-yl)ethanone oxime (9) was the most potent antioxidant and the most cytotoxic compound as well.

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Section: Introductionmentioning

confidence: 99%

An Easy Synthetic Approach to Construct Some Ebselen Analogues and Benzo[b]selenophene Derivatives: Their Antioxidant and Cytotoxic Assessment

Elsherbini

Hamama

Zoorob

2018

Journal of Heterocyclic Chem

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“…These ratios can be compared to the ratios of uptake +VER/−VER for 3 – 6 in P-gpexpressing Colo-26 cells of 1.9 and 5.1 for 3 and 4 , respectively, 18 and 2.9 and 7.6 for 5 and 6 , respectively. 19 Additionally, as shown in Figure 3, 5 and 6 are comparably phototoxic to HUT-78 cells over a range of photosensitizer concentrations and light doses. These results indicate that uptake of selenorhodamine photosensitizers in Sezary cells is minimally influenced by P-gp ATPase stimulation, and that P-gp stimulation does not protect malignant T cells against phototoxicity using these agents.…”

Section: Discussion Of Biological Resultsmentioning

confidence: 83%

“…The syntheses of 9-(5-(piperidylcarbamothioyl)thiophen-2-yl)-2,3,6,7,12,13,16,17-octahydro-[1 H ,5 H ,11 H ,15 H ]-10-selenoxantheno[2,3,4-ij:5,6,7-i′j′]diquinolizin-18-ium chloride ( 5 ) and 9-(5-(piperidylcarbamoyl)thiophen-2-yl)-2,3,6,7,12,13,16,17-octa-hydro[1 H ,5 H ,11 H ,15 H ]-10-selenoxantheno-[2,3,4-ij:5,6,7-i′j′]diquinolizin-18-ium chloride ( 6 ) have been previously described 19 and a similar synthetic approach was employed for the synthesis of 7 – 10 . Xanthones 11 and 12 were prepared as previously described.…”

Section: Resultsmentioning

confidence: 99%

“…To investigate mitochondrial targeting of HUT-78 cells by 3 – 6 , ImageStream multispectral imaging flow cytometry was employed using MitoTracker Green ( 16 , MTG), MitoTracker Red ( 17 , MTR), and LysoTracker ( 18 , LYS) for reference (Chart 4). 18,19 …”

Section: Resultsmentioning

confidence: 99%

“…Selenorhodamines 3 – 6 18,19 and selenoxanthones 11 and 12 20 were prepared by literature methods. Fluorescence quantum yields ( Φ FL ) 16 and quantum yields for the generation of singlet oxygen [ Φ ( 1 O 2 )] 20 were measured as previously described.…”

Section: Methodsmentioning

confidence: 99%

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Selective photodepletion of malignant T cells in extracorporeal photopheresis with selenorhodamine photosensitizers

McIver

Kryman

Choi

et al. 2016

Bioorganic & Medicinal Chemistry

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Extracorporeal photopheresis (ECP) has been used successfully in the treatment of erythrodermic cutaneous T cell lymphoma (CTCL), and other T cell-mediated disorders. Not all patients obtain a significant or durable response from ECP. The design of a selective photosensitizer that spares desirable lymphocytes while targeting malignant T cells may promote cytotoxic T cell responses and improve outcomes after ECP. A series of selenorhodamines built with variations of the Texas red core targeted the mitochondria of malignant T cells, were phototoxic to malignant T cells presumably via their ability to generate singlet oxygen, and were transported by P-glycoprotein (P-gp). To determine the selectivity of the photosensitizers in the ECP milieu, staphylococcal enterotoxin B (SEB)-stimulated and non-stimulated human lymphocytes were combined with HUT-78 cells (a CTCL) to simulate ECP. The amide-containing analogues of the selenorhodamines were transported more rapidly than the thioamide analogues in monolayers of MDCKII-MDR1 cells and, consequently, were extruded more rapidly from P-gp-expressing T cells than the corresponding thioamide analogues. Selenorhodamine 6 with the Texas red core and a piperidylamide functionality was phototoxic to >90% of malignant T cells while sparing >60% of both stimulated and non-stimulated T cells. In the resting T cells, (63 ± 7)% of the CD4+ T cell compartment, and (78 ± 2.5)% of the CD8+ cytotoxic T cell population were preserved, resulting in an enrichment of healthy and cytotoxic T cells after photodepletion.

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6‐Endo‐dig versus 5‐exo‐dig: Exploring Radical Cyclization Preference with First‐, Second‐, and Third‐row Linkers using High‐level Quantum Chemical Methods

2023

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As an expansion upon Baldwin rules, the cyclization reactions of hex‐5‐yn‐1‐yl radical systems with different first‐, second‐, and third‐row linkers are explored at the CCSD(T) level via means of the SMD(benzene)‐G4(MP2) thermochemical protocol. Unlike C, O, and N linkers, systems with B, Si, P, S, Ge, As, and Se linkers are shown to favor 6‐endo‐dig cyclization. This offers fundamental insights into the rational synthetic design of cyclic compounds. A thorough analysis of stereoelectronic effects, cyclization barriers, and intrinsic barriers illustrates that structural changes alter the cyclization preference by mainly impacting 5‐exo‐dig reaction barriers. Based on the high‐level computational modeling, we proceed to develop a new tool for cyclization preference prediction from the correlation between cyclization barriers and radical structural parameters (e. g., linker bond length and bond angle). A strong correlation is found between the radical attack trajectory angle and the reaction barrier heights, i. e., cyclization preference. Finally, the influence of stereoelectronic effects on the two radical cyclization pathways is further investigated in stereoisomers of hypervalent silicon system, which provides novel insight into cyclization control.

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Selenorhodamine photosensitizers with the Texas-red core for photodynamic therapy of cancer cells

Cited by 17 publications

References 22 publications

An Easy Synthetic Approach to Construct Some Ebselen Analogues and Benzo[b]selenophene Derivatives: Their Antioxidant and Cytotoxic Assessment

An Easy Synthetic Approach to Construct Some Ebselen Analogues and Benzo[b]selenophene Derivatives: Their Antioxidant and Cytotoxic Assessment

Selective photodepletion of malignant T cells in extracorporeal photopheresis with selenorhodamine photosensitizers

6‐Endo‐dig versus 5‐exo‐dig: Exploring Radical Cyclization Preference with First‐, Second‐, and Third‐row Linkers using High‐level Quantum Chemical Methods

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