Fluorescence properties and partitioning behaviour of esterified and unesterified rhodamines

Baraka, Mohamed El; Deumié, Michel; Viallet, Pierre; Lampidis, Theodor J.

doi:10.1016/1010-6030(91)87020-v

Cited by 22 publications

(14 citation statements)

References 29 publications

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“…Structure function analysis with these rhodamine analogs led to the observation that only those rhodamines that carried a delocalized positive charge were accumulating specifically in mitochondria [10, 11]. These rhodamine analogs are a subset of DLCs which contain an esterified carboxyl group and a positive charge over the molecule that does not interfere with the lipophilic nature of the dye [12]. They differ from the neutral rhodamine analogs which carry a free unesterified carboxyl group and are therefore amphoteric.…”

Section: Rhodamine 123 and Other Dlcs Preferentially Accumulate In mentioning

confidence: 99%

“…The free amino group in the glycosidic portion of the anthracyclines appears to be a key determinant for actual covalent bonding to nuclear DNA while the delocalized positive charge of the DLCs does not favor this kind of bonding to DNA. Thus, it appears that the nature of the positive charge (localized vs. delocalized) plays an important role in determining nuclear versus mitochondrial localization although the degree of lipophilicity has also been shown to affect the intracellular localization of analogs within each family of compounds [12]. 3 Positively charged anthracyclines and delocalized lipophilic cations accumulate preferentially in carcinoma versus normal epithelial cells…”

Section: Rhodamine 123 and Other Dlcs Preferentially Accumulate In MImentioning

confidence: 99%

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From delocalized lipophilic cations to hypoxia: Blocking tumor cell mitochondrial function leads to therapeutic gain with glycolytic inhibitors

Kurtoğlu

Lampidis²

2008

Molecular Nutrition Food Res

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An unexpected similarity between cancer and cardiac muscle cells in their sensitivity to anthracyclines and delocalized lipophilic cations (DLC) prompted a series of studies in which it was shown that the positive charge of these compounds is central to their selective accumulation and toxicity in these two distinct cell types. An initial finding to explain this phenomenon was that cancer and cardiac muscle cells exhibit high negative plasma membrane potentials resulting in increased uptake of these agents. However, the p-glycoprotein efflux pump was shown to be another factor underlying differential accumulation of these compounds, since it recognizes positively charged drugs and thereby actively reduces their intracellular concentrations. The delocalized positive charge and lipophilicity of DLCs leads to their retention and inhibition of ATP synthesis in mitochondria. Years later it was realized that cancer cells in the hypoxic portions of solid tumors were similar to those treated with DLCs in relying mainly on anaerobic metabolism for survival and could thus be targeted with a glycolytic inhibitor, 2-deoxy-D-glucose (2-DG). This hypothesis has lead to a Phase I clinical trial in which 2-DG is used to selectively kill the hypoxic tumor cell population which are resistant to standard chemotherapy or radiation.

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Section: Rhodamine 123 and Other Dlcs Preferentially Accumulate In mentioning

confidence: 99%

Section: Rhodamine 123 and Other Dlcs Preferentially Accumulate In MImentioning

confidence: 99%

From delocalized lipophilic cations to hypoxia: Blocking tumor cell mitochondrial function leads to therapeutic gain with glycolytic inhibitors

Kurtoğlu

Lampidis²

2008

Molecular Nutrition Food Res

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“…A possible explanation, but not the only one, for this accumulation is the phenomon known as ion-trapping (Peterson 1979). Indeed rhod a m~n e B exists in water as cationic, zwltterionic and lactonic molecular structure (Elbaraka et al 1991). When it enters the acidic environment of the lysosomes, however, it would be converted into membrane impermeable cations that would then accumulate.…”

mentioning

confidence: 99%

Rhodamine B accumulation and MXR protein expression in mussel blood cells:effects of exposure to vincristine

Minier¹,

Mn²

1996

Mar. Ecol. Prog. Ser.

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ABSTRACT. Mussel hemocytes accumulate rhodamine B within their lysosomal compartment. This intracellular retention, detected and quantified by computerised confocal microscopy, is enhanced by the presence of verapamil. Study of 2 different populations showed alteration in rhodamine B retention and simultaneous differential expression levels of proteins immunorelated to the multidrug resistance (MDR) transporter in relation to their environment. Chronic exposure of animals to the Vinca antitumor alkaloid vincristine causes the hemocytes to accumulate less rhodamine B, to be more sensitive to verapamil and to express more MDR-related proteins. These data add consistency to prevlous results on multixenobiotic resistance in mussels.

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“…The cation monomers of rhodamines 110 and 123 are reported to exhibit an absorption peak at 499 and 500 nm in neutral aqueous solutions, respectively. 36 The absorptance of these bands increased with an increase in the dye content. The spectra were broader than those of their cation species in aqueous solutions due to the ionic interaction with the titanium species.…”

Section: 33mentioning

confidence: 99%

Dimerization of xanthene dyes in sol–gel titania films

Nishikiori

Setiawan

Kawamoto

et al. 2013

Catal. Sci. Technol.

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Dye-dispersing titania gel films were prepared by the sol−gel method using the titanium alkoxide solutions containing the xanthene dyes; i.e., fluorescein, eosin Y, rhodamine 110, and rhodamine 123.Dimerization of the xanthene dyes in the films, depending on their concentrations, and their photoinduced electron transfer processes to the titania gels were investigated by spectroscopic and photoelectric techniques. The dye having a higher dimerization constant in solution formed a higher amount of the dimer in the titania gel.There was only a slight difference between the photoelectric conversion efficiencies of the monomer and dimer. The titanium species were coordinated to the carboxylate of the dyes.The dimers as well as the monomers were encapsulated in the narrow spaces of the gel films and strongly interacted with the surrounding titania matrix in the dye-dispersing titania gel films. The dye having a more nucleophilic carboxylate oxygen was easier to form the coordination complex with the titanium species. The dye-titania interaction played an important role in the injection from the dye to the titania conduction band.

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Fluorescence properties and partitioning behaviour of esterified and unesterified rhodamines

Cited by 22 publications

References 29 publications

From delocalized lipophilic cations to hypoxia: Blocking tumor cell mitochondrial function leads to therapeutic gain with glycolytic inhibitors

From delocalized lipophilic cations to hypoxia: Blocking tumor cell mitochondrial function leads to therapeutic gain with glycolytic inhibitors

Rhodamine B accumulation and MXR protein expression in mussel blood cells:effects of exposure to vincristine

Dimerization of xanthene dyes in sol–gel titania films

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