Functionalised benzo[a]phenoxazine dyes as long-wavelength fluorescent probes for amino acids

Frade, Vânia H.J.; Coutinho, Paulo J. G.; Moura, João Martinho; Gonçalves, M. Sameiro T.

doi:10.1016/j.tet.2006.12.005

Cited by 57 publications

(28 citation statements)

References 14 publications

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“…Nile blue is also stable enough to undergo DCC coupling with amino acids directly to the dye core. They successfully conjugated the dyes to several amino acids via amide and ester linkages (Scheme ) …”

Section: Synthesis Of Nile Blue and Nile Red Analoguesmentioning

confidence: 99%

Nile Red and Nile Blue: Applications and Syntheses of Structural Analogues

Martinez

Henary

2016

Chemistry A European J

185

157

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Nile red and Nile blue are highly fluorescent and photostable organic dyes from the benzo[a]phenoxazine family. They have been used as histological stains for imaging lysosomes and lipids in vitro. The dyes' high quantum yields and solvent-dependent optical properties make them ideal scaffolds for the development of pH probes and local polarity indicators. Reviews of the literature in this area are scarce with only one review ever published in 2006. It has been 10 years since and the field has evolved. This review aims to expand upon topics covered by the previous reviewers and to report on recent advances in the literature. As authors, we hope to convey a sense of scope and to spark renewed interest in this useful niche of dye chemistry.

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Section: Synthesis Of Nile Blue and Nile Red Analoguesmentioning

confidence: 99%

Nile Red and Nile Blue: Applications and Syntheses of Structural Analogues

Martinez

Henary

2016

Chemistry A European J

185

157

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“…[27] A comparison between POZ-and PTZ-based sensitizers showed that the POZ-based dye TH301 gave an efficiency of 6.2 % and the structurally similar PTZ-based T2-1 showed an efficiency of 5.5 % under similar conditions. [25,26] POZ dyes have been used in other applications, such as laser dyes, [31] indicators, [32] biological stains, [33] anticancer agents, [34] hole-transporting materials, [35] and in host-guest systems. [36] There are some general considerations to take into account for the design of a sensitizer for DSCs: 1) strong and broad light absorption for efficient light harvesting, 2) appropriate energy levels for efficient electron injection and dye regeneration, and 3) easy and reliable synthesis with cheap, nontoxic materials suitable for future large-scale production.…”

Section: à2mentioning

confidence: 99%

Phenoxazine Dyes for Dye‐Sensitized Solar Cells: Relationship Between Molecular Structure and Electron Lifetime

Karlsson

Jiang

Eriksson

et al. 2011

Chemistry A European J

108

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A series of metal-free organic dyes with a core phenoxazine chromophore have been synthesized and tested as sensitizers in dye-sensitized solar cells. Overall conversion efficiencies of 6.03-7.40% were reached under standard AM 1.5G illumination at a light intensity of 100 mW cm(-2) . A clear trend in electron lifetime could be seen; a dye with a furan-conjugated linker showed a shorter lifetime relative to dyes with the acceptor group directly attached to the phenoxazine. The addition of an extra donor unit, which bore insulating alkoxyl chains, in the 7-position of the phenoxazine could increase the lifetime even further and, together with additives in the electrolyte to raise the conduction band, an open circuit voltage of 800 mV could be achieved. From photoelectron spectroscopy and X-ray absorption spectroscopy of the dyes adsorbed on TiO(2) particles, it can be concluded that the excitation is mainly of cyano character (i.e., on average, the dye molecules are standing on, and pointing out, from the surface of TiO(2) particles).

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“…2. The compound with a longer alkyl chain (FSd) is slightly red-shifted showing a higher fraction of a band near 500 nm, that corresponds to the neutral basic form [28,29]. Also, as expected, compound FSd has much less solubility in PBS aqueous buffer.…”

Section: Photosensitizersmentioning

confidence: 54%

“…The benzo[a]phenoxazinium chlorides termed N-(5-(3hydroxypropylamino)-10-methyl-9H-benzo[a]phenoxazin-9-ylidene)ethanaminium chloride -FSc and N-(5-(11-hydroxyundecylamino)-10-methyl-9H-benzo[a]phenoxazin-9-ylidene)ethanaminium chloride -FSd (Fig. 1) were previously synthetized in the Department of Chemistry of University of Minho [28,29] and the respective powders were solubilized in Dimethyl Sulfoxide (DMSO) to a final concentration of 10 mM. Then, the solutions were transferred to sterile amber microtubes (VWR International, LLC.…”

Section: Photosensitizersmentioning

confidence: 99%

Application of benzo[a]phenoxazinium chlorides in antimicrobial photodynamic therapy of Candida albicans biofilms

Lopes

Alves

Raju

et al. 2014

Journal of Photochemistry and Photobiology B: Biology

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The use of Antimicrobial Photodynamic Therapy (APDT) as a new approach to treat localized Candida infections is an emerging and promising field nowadays. The aim of this study was to verify the efficacy of photodynamic therapy using two new benzo[a]phenoxazinium photosensitizers against Candida albicans biofilms: N-(5-(3-hydroxypropylamino)-10-methyl-9H-benzo[a]phenoxazin-9-ylidene)ethanaminium chloride (FSc) and N-(5-(11-hydroxyundecylamino)-10-methyl-9H-benzo[a]phenoxazin-9-ylidene)ethanaminium chloride (FSd). The photodynamic activity of dyes against C. albicans biofilms was evaluated by incubating biofilms with dyes in the range of 100-300 μM for 3 or 18 h followed by illumination at 12 or 36 J cm(-2), using a xenon arc lamp (600 ± 2 nm). A total photoinactivation of C. albicans biofilm cells was achieved using 300 μM of FSc with 18 h of incubation, followed by illumination at 36 J cm(-2). Contrarily, FSd had insignificant effect on biofilms inactivation by APDT. The higher uptake of FSc than FSd dye by biofilms during the dark incubation may explain the greater photodynamic effectiveness achieved with FSc. The results obtained stresses out the FSc-mediated APDT potential use to treat C. albicans infections.

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Functionalised benzo[a]phenoxazine dyes as long-wavelength fluorescent probes for amino acids

Cited by 57 publications

References 14 publications

Nile Red and Nile Blue: Applications and Syntheses of Structural Analogues

Nile Red and Nile Blue: Applications and Syntheses of Structural Analogues

Phenoxazine Dyes for Dye‐Sensitized Solar Cells: Relationship Between Molecular Structure and Electron Lifetime

Application of benzo[a]phenoxazinium chlorides in antimicrobial photodynamic therapy of Candida albicans biofilms

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