FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W4283026131> ?p ?o ?g. }

• W4283026131 endingPage "110460" @default.
• W4283026131 startingPage "110460" @default.
• W4283026131 abstract "In this work, two new phenothiazinium dyes containing N -piperidinyl-carbinol auxochrome units have been designed, synthesized and investigated in vitro for ovarian cancer cell fluorescence imaging and cytotoxicity. A solvent free mechanochemical procedure is described as a greener alternative to the previously reported synthetic methodology applied in the preparation of methylene blue analogues by the substitution of the phenothiazinium tetraiodide substrate with nucleophilic secondary amines in solution. The optical properties of the new dyes were evaluated by UV–vis absorption/emission spectroscopy which revealed maxima situated in the red region (λ max absorption = 668-664 nm and λ max emission = 715-698 nm) with large molar extinction coefficients (log ε = 4.5–5.1) and bathochromic shifts of 314–383 cm −1 occurring upon switching from less polar to more polar solvents . The theoretical DFT computational study performed in order to clarify the obtained data indicated that the vertical TD-DFT calculations (typically applied for simulating UV–vis spectra) were within ∼150 nm of the experimental data, but a better agreement with experiment was obtained by using the vibronic corrections which revealed a dominant vibronic component not only for the main absorption/emission maxima, but also for the displayed shoulders which are rather the effects of the vibronic coupling between S 0 and S 1 electronic states. The new dyes presented a hydrophilic character (logP n -octanol/water = −1.15 and −1.29 respectively) comparable to the parent methylene blue and no aggregation tendency was observed in aqueous solution at concentration range 75–150 μM used in this study. Cellular imaging experiments displayed the new dyes' ability to selectively stain the cytoplasm of tumoral OVCAR-3 and A2780 fixed cells. The evaluation of their biological activity encompassed cell grow inhibitory potential (dose-response activity and half maximal inhibitory concentration IC 50 ), as well as their capacity to influence the tumoral OVCAR-3, A2780 and healthy BJ ovarian cells’ metabolic activity . Dye 2 exhibited moderate cytotoxicity against human ovarian cancer cell lines, being the most active against the A2780 ovarian adenocarcinoma cells where its cellular uptake was noteworthy and displayed a deeper influence on the chemoresistant, highly malignant OVCAR-3 cells function by modulating FOLR1, ICAM-1 and VCAM-1 proteins with role in the growth and migration of cancer cells. • New symmetrical Phenothiazinium dyes containing N-piperidinyl-carbinol auxochrome. • Solvent free mechanochemical procedure for the synthesis of MB analogues. • Optical properties enlightened by theoretical TD-DFT calculations with vibronic correction. • In vitro cytoplasmatic accumulation and staining of ovarian tumor cell lines. • Cytotoxicity and multitarget influence on ovarian tumor cell's functions." @default.
• W4283026131 created "2022-06-18" @default.
• W4283026131 creator A5016084974 @default.
• W4283026131 creator A5023707007 @default.
• W4283026131 creator A5024200295 @default.
• W4283026131 creator A5027865946 @default.
• W4283026131 creator A5029326151 @default.
• W4283026131 creator A5035275284 @default.
• W4283026131 creator A5037442423 @default.
• W4283026131 creator A5040864132 @default.
• W4283026131 creator A5062211071 @default.
• W4283026131 creator A5064239145 @default.
• W4283026131 creator A5068452701 @default.
• W4283026131 creator A5068629446 @default.
• W4283026131 creator A5081415056 @default.
• W4283026131 date "2022-09-01" @default.
• W4283026131 modified "2023-10-18" @default.
• W4283026131 title "New methylene blue analogues with N-piperidinyl-carbinol units: Synthesis, optical properties and in vitro internalization in human ovarian cancer cells" @default.
• W4283026131 cites W1548267815 @default.
• W4283026131 cites W1979412076 @default.
• W4283026131 cites W1979576753 @default.
• W4283026131 cites W1982243918 @default.
• W4283026131 cites W1987831003 @default.
• W4283026131 cites W1994319018 @default.
• W4283026131 cites W2006024340 @default.
• W4283026131 cites W2014068089 @default.
• W4283026131 cites W2015369313 @default.
• W4283026131 cites W2024077985 @default.
• W4283026131 cites W2027537940 @default.
• W4283026131 cites W2036785982 @default.
• W4283026131 cites W2047297127 @default.
• W4283026131 cites W2047739340 @default.
• W4283026131 cites W2053839387 @default.
• W4283026131 cites W2058848030 @default.
• W4283026131 cites W2060882819 @default.
• W4283026131 cites W2066148764 @default.
• W4283026131 cites W2068259753 @default.
• W4283026131 cites W2078146328 @default.
• W4283026131 cites W2079488111 @default.
• W4283026131 cites W2085324825 @default.
• W4283026131 cites W2105017496 @default.
• W4283026131 cites W2111584125 @default.
• W4283026131 cites W2143981217 @default.
• W4283026131 cites W2167272563 @default.
• W4283026131 cites W2179141110 @default.
• W4283026131 cites W2397198015 @default.
• W4283026131 cites W2519382286 @default.
• W4283026131 cites W2524755676 @default.
• W4283026131 cites W2555960905 @default.
• W4283026131 cites W2676688063 @default.
• W4283026131 cites W2759226391 @default.
• W4283026131 cites W2765657675 @default.
• W4283026131 cites W2790127935 @default.
• W4283026131 cites W2794944537 @default.
• W4283026131 cites W2945537500 @default.
• W4283026131 cites W2951164998 @default.
• W4283026131 cites W2994771468 @default.
• W4283026131 cites W2995891414 @default.
• W4283026131 cites W2999417355 @default.
• W4283026131 cites W3015140753 @default.
• W4283026131 cites W3023388280 @default.
• W4283026131 cites W3095803259 @default.
• W4283026131 cites W3164111235 @default.
• W4283026131 cites W3188853621 @default.
• W4283026131 cites W3200238954 @default.
• W4283026131 cites W4205651038 @default.
• W4283026131 doi "https://doi.org/10.1016/j.dyepig.2022.110460" @default.
• W4283026131 hasPublicationYear "2022" @default.
• W4283026131 type Work @default.
• W4283026131 citedByCount "3" @default.
• W4283026131 countsByYear W42830261312022 @default.
• W4283026131 countsByYear W42830261312023 @default.
• W4283026131 crossrefType "journal-article" @default.
• W4283026131 hasAuthorship W4283026131A5016084974 @default.
• W4283026131 hasAuthorship W4283026131A5023707007 @default.
• W4283026131 hasAuthorship W4283026131A5024200295 @default.
• W4283026131 hasAuthorship W4283026131A5027865946 @default.
• W4283026131 hasAuthorship W4283026131A5029326151 @default.
• W4283026131 hasAuthorship W4283026131A5035275284 @default.
• W4283026131 hasAuthorship W4283026131A5037442423 @default.
• W4283026131 hasAuthorship W4283026131A5040864132 @default.
• W4283026131 hasAuthorship W4283026131A5062211071 @default.
• W4283026131 hasAuthorship W4283026131A5064239145 @default.
• W4283026131 hasAuthorship W4283026131A5068452701 @default.
• W4283026131 hasAuthorship W4283026131A5068629446 @default.
• W4283026131 hasAuthorship W4283026131A5081415056 @default.
• W4283026131 hasConcept C121608353 @default.
• W4283026131 hasConcept C126322002 @default.
• W4283026131 hasConcept C139770010 @default.
• W4283026131 hasConcept C1491633281 @default.
• W4283026131 hasConcept C155647269 @default.
• W4283026131 hasConcept C161790260 @default.
• W4283026131 hasConcept C185592680 @default.
• W4283026131 hasConcept C202751555 @default.
• W4283026131 hasConcept C21951064 @default.
• W4283026131 hasConcept C2777454769 @default.
• W4283026131 hasConcept C2779191827 @default.
• W4283026131 hasConcept C2780427987 @default.

• next