Type 1 Phototherapeutic Agents. 2. Cancer Cell Viability and ESR Studies of Tricyclic Diarylamines

Rajagopalan, Raghavan; Lin, Tien‐Sung; Karwa, Amolkumar; Poreddy, Amruta R.; Asmelash, Bethel; Dorshow, Richard B.

doi:10.1021/ml200266v

Cited by 19 publications

(19 citation statements)

References 29 publications

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“…BMEMC alone and BMEMC with E. coli dissolved in PBS solution were exposed to the irradiation of the mercury lamp, yielding a similar signal (Figure a,c), which is in consistence with the previous report of nitride radicals in the literature . There is barely no signal for BMEPC with the E.…”

Section: Resultssupporting

confidence: 88%

“…BMEMC alone and BMEMC with E. coli dissolved in PBS solution were exposed to the irradiation of the mercury lamp, yielding a similar signal (Figure 5a,c), which is in consistence with the previous report of nitride radicals in the literature. 35 There is barely no signal for BMEPC with the E. coli suspension (Figure 5d), though, there is a strong signal under irradiation for BMEPC alone (Figure 5b). A reasonable assumption could be that the nitride radicals generated under irradiation have been consumed completely by E. coli.…”

Section: Epr Measurementmentioning

confidence: 96%

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Laser-Induced Antibacterial Activity of Novel Symmetric Carbazole-Based Ethynylpyridine Photosensitizers

Chen

Zheng

et al. 2018

ACS Omega

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In this study, two kinds of novel carbazole-based ethynylpyridine salts: 3,6-bis[2-(1-methylpyridinium)ethynyl]-9-pentyl-carbazole diiodide (BMEPC) and 3,6-bis[2-(1-methylpyridinium)ethynyl]-9-methyl-carbazole diiodide (BMEMC) have been employed as photosensitizers owing to their excellent antibacterial activity. These molecules possess symmetric A−π–D−π–A-type structures, which would bring in the unique optical properties. The inhibition zone measurement of a gradient concentration from 0 to 100 μM showed BMEPC and BMEMC photoinduced antibacterial activity against Escherichia coli. Diameters of zone of inhibition were up to 15 and 14 mm under laser irradiations. Under the exposure of the laser of 442 nm with a power density of 20 mW/cm2, the minimum inhibitory concentrations (MICs) of BMEPC on E. coli were between 3.5 and 6.9 μM and that of BMEMC were between 9.4 and 18.8 μM, respectively. In the dark experiments as a control, the MIC value is between 6.9 and 13.8 μM for BMEPC, whereas it is between 187.5 and 225.0 μM for BMEMC. By the comparison of the MIC values of BMEPC and BMEMC with laser irradiation and in dark, the laser-induced toxicity on bacteria is more evident, though both of the derivatives have dark toxicity. With the laser irradiation duration of 30 s and 10 min for BMEPC and BMEMC, respectively, the survival rate of E. coli approximates zero. An antibacterial mechanism has been proposed based on the electron paramagnetic resonance characterization, which indicates that a nitride radical is generated under laser irradiation. The carbazole-based ethynylpyridine photosensitizers would provide high potential for further applications in photodynamic therapy.

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Section: Resultssupporting

confidence: 88%

Section: Epr Measurementmentioning

confidence: 96%

Laser-Induced Antibacterial Activity of Novel Symmetric Carbazole-Based Ethynylpyridine Photosensitizers

Chen

Zheng

et al. 2018

ACS Omega

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“…Phenoxazines and phenothiazines (i.e., 1 and 2 , Figure ) figure prominently in medicinal chemistry, − and their photophysical properties have enabled their use in dye-sensitized solar cells, − organic light emitting diodes, − and as photoredox catalysts . Phenothiazines have also long been known to possess potent antioxidant activity and have been pursued as additives to protect petroleum-derived products, including lubricants, rubber, and fuels from (peroxyl) radical-mediated autoxidation.…”

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confidence: 99%

Diazaphenoxazines and Diazaphenothiazines: Synthesis of the “Correct” Isomers Reveals They Are Highly Reactive Radical-Trapping Antioxidants

Haidasz

Pratt

2017

Org. Lett.

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The preparation of 2,4-diazaphenothiazines and 2,4-diazaphenoxazines via a copper-catalyzed intramolecular amination is described. Literature approaches which utilize easily accessed (2′-aminophenyl) 4-pyri(mi)dyl sulfides undergo a Smiles rearrangement that gives rise to the 1,3-diaza derivatives instead, confirmed by X-ray crystallography. Inversion of the polarity of the cyclization avoids the rearrangement and affords the desired products. Preliminary kinetic studies suggest that 2,4diazaphenothiazines and diazaphenoxazines, but not the 1,3-diaza isomers, are remarkably potent radical-trapping antioxidants.

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“…Carbazole has diverse biological activities, including antitumor activities . It has been speculated that carbazole may intercalate into DNA helix, but carbazole itself has not been used as a DNA intercalating agent in our best knowledge . In addition, carbazole is less toxic (LD 50 >5,000 mg/kg) than most of the classical intercalators such as ethidium or acridine .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structure, and biological evaluation of a platinum‐carbazole conjugate

et al. 2017

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Cisplatin resistance is caused, in part, by the efficient removal of the helix-distorting cisplatin 1,2-intrastrand cross-links by nucleotide excision repair (NER) machinery.To make a platinum-DNA adduct that causes less helical distortion than the cisplatin 1,2-intrastrand adduct, we designed and synthesized a monofunctional platinumcarbazole conjugate (carbazoplatin). The 2.5 Å crystal structure of carbazoplatin-DNA adduct revealed both the monoplatination of the N7 of a guanine (G) base and the intercalation into two G:C base pairs, while causing a minor distortion of the DNA helix. A 50-mer dsDNA containing a single carbazoplatin lesion was poorly processed by UvrABC endonuclease, the prokaryotic NER machinery that detects helical distortion and performs dual incision around the lesion. Our cell viability assay indicated that the cytotoxic pathways of carbazoplatin might be different from those of cisplatin; carbazoplatin was 5-8 times more cytotoxic than cisplatin against PANC-1 and MDA-MB-231 cancer cell lines. K E Y W O R D Scancer therapy, cisplatin, DNA damage, nucleotide excision repair, X-ray crystallography

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Type 1 Phototherapeutic Agents. 2. Cancer Cell Viability and ESR Studies of Tricyclic Diarylamines

Cited by 19 publications

References 29 publications

Laser-Induced Antibacterial Activity of Novel Symmetric Carbazole-Based Ethynylpyridine Photosensitizers

Laser-Induced Antibacterial Activity of Novel Symmetric Carbazole-Based Ethynylpyridine Photosensitizers

Diazaphenoxazines and Diazaphenothiazines: Synthesis of the “Correct” Isomers Reveals They Are Highly Reactive Radical-Trapping Antioxidants

Synthesis, structure, and biological evaluation of a platinum‐carbazole conjugate

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