Deciphering the fluorescence signature of daunomycin and doxorubicin

Karukstis, Kerry K.; Thompson, Elizabeth H.; Whiles, Jennifer A.; Rosenfeld, R.J.

doi:10.1016/s0301-4622(98)00150-1

Cited by 189 publications

(166 citation statements)

References 29 publications

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“…In a more general manner, the changes observed in the spectra in presence of oleates are consistent with a decrease of the dielectric constant of the molecular environment. 18) On the other hand, this interaction is observed with much higher oleate excess: one must reach the ratio Rϭ50 to observe a change in the fluorescence spectra. With RϾ50, the fluorescence quenching is rapidly supplanted by an intensity increase.…”

Section: Liquid-liquid Extraction Of Dox In Presence Of Oleate Ionsmentioning

confidence: 99%

“…[12][13][14][15] Fluorescence spectroscopy has been successfully used to study interactions between DOX and its surrounding, for instance when the drug intercalates DNA 16,17) or penetrates within membrane models or liposomal drug carriers. 18,19) Indeed, the dihydroanthraquinone moiety of DOX is a well known fluorophore excitable with visible light (absorption maxima at 480-500 nm). Fluorescence spectroscopy is particularly appropriate to our experimental conditions: i) in view of the experimental reasons described above, DOX-oleate molecular interactions should be studied at relatively low concentrations of both molecules; ii) much sensibility is required to highlight even weak interactions between DOX and OA Ϫ .…”

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confidence: 99%

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On the Interaction of Doxorubicin with Oleate Ions: Fluorescence Spectroscopy and Liquid-Liquid Extraction Study

Munnier

Tewes

Cohen-Jonathan

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Doxorubicin (DOX) is an antineoplastic agent of the anthracycline family used as a first-line treatment in numerous neoplastic diseases, particularly in breast cancer.1) The progression of tumor cell resistance, in particular multidrug resistance (MDR), is one of the main factors which limit its employment.2) MDR is generally associated with a decreased intracellular accumulation of drug related to a membrane glycoprotein, the P-gp that contributes to a rapid expelling of the drug from the cell.3) An interesting way to overcome this active efflux would be to support the drug accumulation into the cell, in particular by increasing its capacity to cross lipidic membranes. One can act upon the membrane fluidity or act upon the hydrophilic/lipophilic properties of the drug.DOX molecule (see structure on Fig. 1) is considered hydrophilic at physiological pH because it presents a positive charge on the sugar moiety. The more lipophilic molecular form of DOX is dominant at moderately alkaline pHs, between 8.2 and 9.5, the pK a values of the amine and the phenol in position 11 respectively.4) The hydrophilicity of DOX is also depending on the drug concentration, since beyond a concentration of 30 mM DOX molecules are prone to form less hydrophilic dimmers (stacking effect) which precipitate in aqueous solution. The increase of the pH, i.e. of the neutral form percentage, is in favor of the stacking phenomenon. 5,6) It has been recently shown that lipophilicity of cationic drugs 7,8) can be increased by association with an anion, namely with a long chain ion of a fatty acid.9,10) Nevertheless, no study is devoted to the molecular interaction between the drug and the ion. On the other hand, combined use of an anticancer drug, paclitaxel, with different fatty acids, has been shown to enhance mortality of cancer cells in vitro.11) It has not yet been established whether this gain in efficacy is dependent on an assembly between the drug and the fatty acid ion.Association DOX-fatty acid could be more lipophilic than DOX alone, and enter more efficiently into the cell. It could also facilitate drug encapsulation into pharmaceutical formulations based on hydrophobic polymers or liposomes. 7,9) Oleic acid is a good candidate for such an association within a feasibility study: it is the simplest of the w-9 fatty acid family (Fig. 1), and possesses a long hydrophobic chain that could contribute to a gain of lipophilicity of the association. Moreover, oleates are non-toxic and the behavior of oleic acid and its ion (oleate, OA Ϫ ) in aqueous solution is rather well studied. [12][13][14][15] Fluorescence spectroscopy has been successfully used to study interactions between DOX and its surrounding, for instance when the drug intercalates DNA 16,17) or penetrates within membrane models or liposomal drug carriers. 18,19) Indeed, the dihydroanthraquinone moiety of DOX is a well known fluorophore excitable with visible light (absorption maxima at 480-500 nm). Fluorescence spectroscopy Increase of lipophilicity of cationic doxorubicin (DO...

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Section: Liquid-liquid Extraction Of Dox In Presence Of Oleate Ionsmentioning

confidence: 99%

mentioning

confidence: 99%

On the Interaction of Doxorubicin with Oleate Ions: Fluorescence Spectroscopy and Liquid-Liquid Extraction Study

Munnier

Tewes

Cohen-Jonathan

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Fluorescence spectroscopy has been frequently employed to study the interaction of doxorubicin (1), e.g., with DNA in the course of intercalation [11,12] or with lipid membranes [13]. We now measured the fluorescence spectra of the test compounds 1-3 in phosphate buffered saline (PBS; 5 µM) at pH 7.4.…”

Section: Fluorescence Spectroscopymentioning

confidence: 99%

Modification of uptake and subcellular distribution of doxorubicin by N-acylhydrazone residues as visualised by intrinsic fluorescence

Effenberger-Neidnicht

Breyer

Mahal

et al. 2011

Cancer Chemother Pharmacol

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Purpose: Doxorubicin (1) is commonly used in the treatment of a wide range of cancers. Some N-acylhydrazones of 1 were previously found to have an improved tumour and organ selectivity. In order to clarify the molecular basis for this effect, the cellular uptake into various cancer cells and the localisation in PtK 2 potoroo kidney cells of 1 and its N-acylhydrazones derived from heptadecanoic acid (2) and 11-(menthoxycarbonyl)undecanoic acid (3) were studied drawing on their intrinsic fluorescence.

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“…7B). DNM presents two major emission maxima at ϳ560 and ϳ592 nm (I 560 nm /I 592 nm ϭ 0.8) (Karukstis et al, 1998). The peak at ϳ592 nm dramatically increased in the DNM conjugates (the spectrum of PM-DNM in PBS is reported in Fig.…”

mentioning

confidence: 96%

TargetingMDR1Gene: Synthesis and Cellular Study of Modified Daunomycin-Triplex-Forming Oligonucleotide Conjugates Able to Inhibit Gene Expression in Resistant Cell Lines

Stierlé¹,

Duca²,

Halby³

et al. 2008

Mol Pharmacol

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Reversal of the multidrug-resistant (MDR) phenotype is very important for chemotherapy success. In fact, the expression of the MDR1 gene-encoded P-glycoprotein (P-gp) actively expels antitumor agents such as daunomycin (DNM) out of the cells, resulting in drug resistance. We show that upon conjugation to triplex-forming oligonucleotides, it is possible to address DNM in resistant cells (MCF7-R and NIH-MDR-G185). The oligonucleotide moiety of the conjugate changes the cellular penetra-

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Deciphering the fluorescence signature of daunomycin and doxorubicin

Cited by 189 publications

References 29 publications

On the Interaction of Doxorubicin with Oleate Ions: Fluorescence Spectroscopy and Liquid-Liquid Extraction Study

On the Interaction of Doxorubicin with Oleate Ions: Fluorescence Spectroscopy and Liquid-Liquid Extraction Study

Modification of uptake and subcellular distribution of doxorubicin by N-acylhydrazone residues as visualised by intrinsic fluorescence

TargetingMDR1Gene: Synthesis and Cellular Study of Modified Daunomycin-Triplex-Forming Oligonucleotide Conjugates Able to Inhibit Gene Expression in Resistant Cell Lines

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