Cell Viability Study of ZnCuInS/ZnS–TPPS4 Conjugates against Different Cell Lines as a Promising Fluorescent Probe (original) (raw)
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2018
New derivatives of tetrakis(4-carboxyphenyl) porphyrin were designed, synthesized and characterized by IR, proton NMR and mass spectroscopy. The ground and excited state nature of new derivatives were examined using UV-Vis. absorption and fluorescence spectroscopy, fluorescence quantum yield and fluorescence lifetime studies. The singlet oxygen quantum yield of each synthesized derivative of porphyrin was estimated for their further efficacy as potential photosensitizer in biological studies. The significant photophysical data of all synthesized derivatives was supplementary accessed to examine the cell imaging and cytotoxicity against two cancer cell lines viz. MBA-MD-231 and A375. The fluorescence lifetime, fluorescence quantum yield and efficiency of singlet oxygen generation suggests alkyl amine and alkyl hydrazide linked new porphyrin photosensitizers can be useful for PDT agent in cancer treatment.
Scientific Reports
The toxicity of heavy metals present in binary semiconductor nanoparticles also known as quantum dots (QDs) has hindered their wide applications hence the advent of non-toxic ternary quantum dots. These new group of quantum dots have been shown to possess some therapeutic action against cancer cell lines but not significant enough to be referred to as an ideal therapeutic agent. In this report, we address this problem by conjugating red emitting CuInS/ZnS QDs to a 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin -photosensitizer for improved bioactivities. The glutathione capped CuInS/ZnS QDs were synthesized in an aqueous medium using a kitchen pressure cooker at different Cu: In ratios (1:4 and 1:8) and at varied temperatures (95 °C, 190 °C and 235 °C). Optical properties show that the as-synthesized CuInS/ZnS QDs become red-shifted compared to the core (CuInS) after passivation with emission in the red region while the cytotoxicity study revealed excellent cell viability against nor...
2017
To assess the properties of pyridinium substituted porphyrins, new meso-porphyrinic derivative namely 5-mono-(4-pyridinum)10,15,20-tris-(4-carboxymethylphenyl)porphyrin MPyEt3 and 5-mono-(4pyridinum)-10,15,20-tris-(4-carboxymethylphenyl)-21,23-Zn(II)-porphine MPyEt3Zn were synthesized in high yields. The porphyrin ester PyEt3 was synthesized through a conventional method. Direct meso-substituted pyridyl derivatives of porphyrins prefer alkylation producing pyridinium ions for inducing water-solubility. The structures of the free-based porphyrin ligand and Zn(II) complex were confirmed through UV-Vis, emission, 1 HNMR, and ESI HRMS spectral data. The spectral absorption and emission properties of the ligand and complex were studied in organic solvents of different polarities, and the influence of solvent polarity on the wavelengths of the absorbance and fluorescence band maxima is described. Changes in fluorescence intensity, emission peak location and overall fluorescence line-shape...
International Journal of Nanomedicine
Background: Photodynamic therapy (PDT) is a non-invasive treatment modality that destroys abnormally growing cells or microorganisms. Porphyrins are used as photosensitizers in PDT; however, their clinical application has been limited by their poor water solubility, resulting in aggregation and low quantum yields of reactive oxygen species (ROS). Methods: To overcome these limitations and improve PDT efficacy, we herein report the conjugation of ZnCuInS/ZnS (ZCIS/ZnS) quantum dots (QDs) to 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin (mTHPP). The optimal conditions for QDs porphyrin conjugation formation were systematically evaluated. Discussion: This study further assessed the PDT efficacy and antibacterial potency of the synthesized ZCIS/ZnS-mTHPP conjugates. The PDT efficacy of the QDs, mTHPP, and conjugate was evaluated against the murine metastatic melanoma (B16 F10 Nex2) cell line. This was performed with and without LED irradiation. Results: The conjugate exhibited the highest reduction in cell viability following LED irradiation (72%) compared to the bare QDs (19%) and mTHPP (1%). Antimicrobial studies conducted on E. coli showed that the conjugation exhibits a higher antibacterial effect than the bare QDs, even without light. Conclusion: The results suggest that conjugate is a promising class of materials for anti-cancer and antimicrobial PDT.
Photochemistry and Photobiology, 2006
In the present study we investigated the photosensitizing properties of two novel mono-and bis-cyclodextrin tetrakis (pentafluorophenyl) porphyrin derivatives in several tumor cell lines and in BALBk mice bearing subcutaneously transplanted syngeneic mouse mammary carcinoma 4T1. Both studied sensitizers were localized mainly in lysosomes and were found to induce cell death by triggering apoptosis in human leukemic cells HL-60. In 4T1 and other cell lines both apoptotic and necrotic modes of cell death occurred depending on drug and light doses. Mono-cyclodextrin porphyrin derivative P(P-CD)l exhibited stronger in vitro phototoxic effect than bis-cyclodextrin derivative P(P-CD)2. However, in vivo P(fi-CD)2 displayed faster tumor uptake with maximal accumulation 6 h after application, leading to complete and prolonged elimination of subcutaneous tumors within 3 days after irradiation (100 J cm-*). In contrast, P(P-CD)l uptake was slower (48 h) and the reduction of tumor mass was only transient, reaching the maximum at the 12 h interval when a favorable tumor-to-skin ratio appeared. Thus, P@-CD)2 represents a new photosensitizing drug displaying fast and selective tumor uptake, strong antitumor activity and fast elimination from the body.
Imidazole-modified porphyrin as a pH-responsive sensitizer for cancer photodynamic therapy
Chemical Communications, 2011
All of the reagents and solvents were obtained commercially and used without further purification. meso-Tetra(4-carboxylphenyl) porphine (TCPP, 97%) and meso-Tetra(4sulfonatophenyl)porphine dihydrochloride (TSPP) were purchased from Frontier Scientific, Inc. 1-hydroxybenzotirazole hydrate (HOBT), 4-dimethylamino Pyridine (DMAP, Fluka), N-(3dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDCI, Fluka), histamine dihydrochloride, acetic acid, sodium hydroxide, hydrochloride acid, dimethylformamide (DMF) and deuterium oxide (D 2 O, 99% of D) were purchased from Sigma-Aldrich. Deionized water was obtained from a Nanopure Water System (Barnsted System, USA). A Q-switched Nd:YAG laser with pulse duration of 3-4 ns and a maximum energy of 30 mJ at 532 nm (Polaris II, Electro Scientific Industries, Inc.), equipped with a liquid N 2-cooled germanium photodetector (Applied Detector Corporation), was used for time-resolved 1 O 2 luminescence measurements. Steady-state photooxidation was conducted in oxygen-saturated solutions using a 150 W Xenon lamp (6255 Xenon lamp housed in 66907 Arc Lamp Source, Newport Oriel Instruments) equipped with a monochromator with primary wavelength region 450-2000 nm (77250 1/8 m Monochromator and 77305 Grating, Newport Oriel Instruments). A BioMate 3 UV-visible spectrophotometer (Thermo Scientific) and a Cary 300 UV-vis spectrophotometer (Varian, Inc.) were used for measuring absorbance and spectra. The fluorescence spectra were taken on a FluoroMax-2 spectrofluorometer. ESI MS spectra were obtained on a Finnigan LCQ Duo mass spectroscopy. A 300 MHz Bruker Spectrospin FT-NMR or a Varian Vnmrs 500 MHz NMR were also used for NMR spectra measurements. All of the measurements were carried out at ambient temperature. Samples were shielded from light using aluminum foil when not being irradiated. 2. Synthesis of 5,10,15,20-tetrakis(N-(2-(1H-imidazol-4-yl)ethyl)benzamide)porphyrin (TIEBAP, M.W.
Molecules (Basel, Switzerland), 2017
Abstract: We designed three unsymmetrical meso-tetrasubstituted phenyl porphyrins for further development as theranostic agents for cancer photodynamic therapy (PDT): 5-(4-hydroxy-3-methoxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin (P2.2), Zn(II)-5-(4-hydroxy-3-methoxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin (Zn(II)2.2) and Cu(II)-5-(4-hydroxy-3-methoxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl)porphyrin (Cu(II)2.2). The porphyrinic compounds were synthesized and their structures were confirmed by elemental analysis, FT-IR, UV-Vis, EPR and NMR. The compounds had a good solubility in polar/nonpolar media. P2.2 and, to a lesser extent, Zn(II)2.2 were fluorescent, albeit with low fluoresence quantum yields. P2.2 and Zn(II)2.2 exhibited PDT-acceptable values of singlet oxygen generation. A "dark" cytotoxicity study was performed using cells that are relevant for the tumor niche (HT-29 colon carcinoma cells and L929 fibroblasts) and for b...
Journal of Fluorescence, 2020
New porphyrin analogues have been designed and synthesized using pyrrole, various aldehydes and propionic acid. The formation of desired compounds was analyzed by utilizing the spectral analysis such as IR, NMR and Mass spectroscopy. The studies on absorption and fluorescence emission of synthesized porphyrins were used to evaluate photophysical characteristics such as molar excitation coefficient and Stokes shift. The estimated values of fluorescence lifetime and fluorescence quantum yield of synthesized porphyrins were found to be variable due to the presence of change in the electron donating and withdrawing characters. The efficiency of generation of singlet oxygen by each synthesized porphyrin as photosensitizer was measured in terms of singlet oxygen quantum yield through photooxidation of 9,10-dimethylantharacene. The obtained singlet oxygen quantum yield values were found to be higher in case of porphyrins those have more electron withdrawing characters rather than donating characters as compared to reference 5,10,15,20-tetraphenylporphyrin (H 2 TPP). The singlet oxygen quantum yield values of synthesized porphyrins varied from 0.52 to 0.66. Pleasingly, some of synthesized porphyrins are found to be photostable and competent to discover as PDT agents as compared to reference H 2 TPP.