3,3'-Dipentyloxacarbocyanine iodide - CAS 53213-81-3
Molecular Formula:
C27H33IN2O2
Molecular Weight:
544.47
COA:
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Application\Fluorophore:
Cell and Organelle Stains
Description:
3,3'-Dipentyloxacarbocyanine iodide is a lipophilic fluorescent stain for labeling membranes.
Synonyms:
DiOC5(3)
MSDS:
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InChIKey:
CDLMLYASVIQVPH-UHFFFAOYSA-M
InChI:
InChI=1S/C27H33N2O2.HI/c1-3-5-11-20-28-22-14-7-9-16-24(22)30-26(28)18-13-19-27-29(21-12-6-4-2)23-15-8-10-17-25(23)31-27;/h7-10,13-19H,3-6,11-12,20-21H2,1-2H3;1H/q+1;/p-1
Canonical SMILES:
CCCCCN1C2=CC=CC=C2OC1=CC=CC3=[N+](C4=CC=CC=C4O3)CCCCC.[I-]
1.Leishmania infantum promastigotes: flow cytometry as a possible tool for assessing the effects of drugs on cellular functions.
Azas N1, Di Giorgio C, Delmas F, Gasquet M, Timon-David P. Exp Parasitol. 1997 Sep;87(1):1-7.
The capacity of flow-cytometric techniques to detect drug-specific biochemical targets and side effects in Leishmania infantum promastigotes was estimated by assessing the effects of three antileishmanial drugs (pentamidine, allopurinol, and amphotericin B) on parasite metabolism. Cell cycle and total protein content were estimated by staining cells with propidium iodide and fluorescein isothiocyanate, nonprotein thiols were stained by mercury orange, and membrane potential was measured by the accumulation of 3,3'-dipenthyloxacarbocyanine iodide inside the cell. Results showed that dynamic studies in parasites treated with subtoxic concentrations of drugs allowed the detection of drug-specific targets: pentamidine primarily affected nonprotein thiol contents and DNA synthesis, allopurinol primarily affected intracellular protein contents, and amphotericin B primarily affected membrane potential. Moreover, the assessment of cellular functions in parasites treated with increasing concentrations of drugs certified the capacity of these techniques to establish dose-response curves and to permit the detection of side effects.
2.Neither lipophilicity nor membrane-perturbing potency of phenothiazine maleates correlate with the ability to inhibit P-glycoprotein transport activity.
Hendrich AB1, Wesołowska O, Poła A, Motohashi N, Molnár J, Michalak K. Mol Membr Biol. 2003 Jan-Mar;20(1):53-60.
Although phenothiazines are known as multidrug resistance modifiers, the molecular mechanism of their activity remains unclear. Since phenothiazine molecules are amphiphilic, the interactions with membrane lipids may be related, at least partially, to their biological effects. Using the set of phenothiazine maleates differing in the type of phenothiazine ring substitution at position 2 and/or in the length of the alkyl bridge-connecting ring system and side chain group, we investigated if their ability to modulate the multidrug resistance of cancer cells correlated with model membrane perturbing potency. The influence exerted on lipid bilayers was determined by liposome/buffer partition coefficient measurements (using the absorption spectra second-derivative method), fluorescence spectroscopy and calorimetry. Biological effects were assessed by a flow cytometric functional test based on differential accumulation of fluorescent probe DiOC(2)(3) by parental and drug-resistant cells.
3.Biophysical characterization of MDR breast cancer cell lines reveals the cytoplasm is critical in determining drug sensitivity.
Coley HM1, Labeed FH, Thomas H, Hughes MP. Biochim Biophys Acta. 2007 Apr;1770(4):601-8. Epub 2006 Dec 16.
Dielectrophoresis (DEP) was used to examine a panel of MCF-7 cell lines comprising parental MCF-7 cells and MDR derivatives: MCF-7TaxR (paclitaxel-resistant, P-glycoprotein (P-gp) positive), MCF-7DoxR (doxorubicin-resistant MRP2 positive) plus MCF-7MDR1 (MDR1 transfected, P-gp positive). MCF-7DoxR and MCF-7MDR1 were broadly cross-resistant to natural product anticancer agents, whereas MCF-7TaxR cells were not, contrary to P-gp expression. Whilst DEP revealed modest membrane changes in MDR sub-lines, we saw significant changes in their cytoplasmic conductivity: MCF-7TaxR<MCF-7<MCF-7MDR1<MCF-7DoxR (range 0.14-0.40 S/m). Cytoplasmic conductivity is affected by the movement of molecules e.g. as in intracellular trafficking MCF-7TaxR showed a reduced membrane potential, whereas MCF-7DoxR and MCF-7MDR1 showed an increase. Thus, altered membrane potential is associated with an MDR phenotype, but in a complex manner. DEP data suggest a model whereby relative increases in cytoplasmic conductivity are correlated with MDR, whilst relative decreases equate with a sensitised phenotype e.
4.Mechanism of cytotoxic action of perfluorinated acids. I. alteration in plasma membrane potential and intracellular pH level.
Kleszczyński K1, Składanowski AC. Toxicol Appl Pharmacol. 2009 Feb 1;234(3):300-5. doi: 10.1016/j.taap.2008.10.008. Epub 2008 Nov 5.
Perfluorinated (aliphatic) acids (PFAs) and congeners have many applications in various industrial fields and household for decades. Years later they have been detected in wildlife and this has spurred interest in environmental occurrence as well as influencing living organisms. PFAs were established as peroxisome proliferators and hepatocarcinogens. Amphipatic structure suggests that they may alter cell membrane potential (mbDeltaPsi) and/or induce changes in cytosolic pH (pHi). The aim of this study was to examine the correlation between changes of above parameters and PFAs structure (CF(6)-CF(12)) in human colon carcinoma HCT116 cells. mbDeltaPsi and pHi were measured by flow cytometry using fluorescence polarization of the plasma membrane probe 3,3'-dipentyloxacarbocyanine (DiOC(5)(3)) and fluorescein diacetate (FDA), respectively. Dose- and time-dependent manner analysis revealed relatively fast depolarization of plasma membrane and acidification of cytosol both positively correlated with fluorocarbon chain length.
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CAS 53213-81-3 3,3'-Dipentyloxacarbocyanine iodide

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