62669-70-9 Usage
Description
Rhodamine 123 is a membrane-permeable cationic dye that is readily accumulated within living cells. It is a substrate for the efflux pump P-glycoprotein (P-gp; also known as multidrug resistance protein 1 and ABCB1) and is rapidly exported from cells with functional P-gp. As P-gp is expressed on a population of stem cells known as the side population, rhodamine 123 is used to detect this group of stem cells. Rhodamine 123 also accumulates within mitochondria due to its positive charge and can inhibit oxidative phosphorylation. Rhodamine 123 has excitation/emission maxima of 507/529 nm.
Chemical Properties
red-brown to brown or dark green powder
Uses
Different sources of media describe the Uses of 62669-70-9 differently. You can refer to the following data:
1. Rhodamine derivative, a fluoresent dye-labeled compound.
2. Fluorescent dye most commonly used as functional reporter in flow cytometry.
3. Rhodamine-123
lycoprotein (P-gp) functional efflux activity in vivo. Rhodamine-123
PE-Cy5 and AMCA (7-amino-4-methylcoumarin-3-acetic acid).
4. Useful as a laser dye and to have selective cell growth effects. Mitochondrial specific fluorescent dye and substrate for P-glycoprotein.
5. Rhodamine-123 is a fluorescent dye most commonly used in flow cytometry as functional reporter for Pgp. Rhodamine 123 (R123), as a typical of P-glycoprotein substrate, was widely used to quantify P-glycoprotein (P-gp) functional efflux activity in vivo. Rhodamine-123 can be used in multiparameter analyses without fluorescence interference in combination with common protein labeling dyes such as PE-Cy5 and AMCA (7-amino-4-methylcoumarin-3-acetic acid).
in vitro
rhodamine 123, which was identified as a member of the rhodamine family of flurone dyes, was used to examine membrane transport by the abcb1 gene product, mdr1. previous study determined the λmax for excitation and emission for rhodamine 123 in commonly used solvents and extraction buffers, indicating that the fluorescence of rhodamine 123 was highly dependent on the chemical environment. the optimal parameters are 1% methanol in hbss. in addition, the uptake of rhodamine 123 into cells was via both passive and active processes, and this occurred mainly by oatp1a2-mediated transport. furthermore, this previous study quantified the intracellular sequestration and metabolism of rhodamine 123, showing that these were both cell line-dependent factors that might influence the interpretation of transport assays [1].
references
[1] samantha forster et al. characterization of rhodamine-123 as a tracer dye for use in in vitro drug transport assays. plos one. 2012; 7(3): e33253.
Check Digit Verification of cas no
The CAS Registry Mumber 62669-70-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,2,6,6 and 9 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 62669-70:
(7*6)+(6*2)+(5*6)+(4*6)+(3*9)+(2*7)+(1*0)=149
149 % 10 = 9
So 62669-70-9 is a valid CAS Registry Number.
InChI:InChI=1/C21H17N2O3.ClH/c1-25-21(24)15-5-3-2-4-14(15)20-16-8-6-12(22)10-18(16)26-19-11-13(23)7-9-17(19)20;/h2-11H,22-23H2,1H3;1H/q+1;/p-1
62669-70-9Relevant articles and documents
Phototoxicity of some bromine-substituted rhodamine dyes: synthesis, photophysical properties and application as photosensitizers.
Pal,Zeng,Durocher,Girard,Li,Gupta,Giasson,Blanchard,Gaboury,Balassy,Turmel,Laperriere,Villeneuve
, p. 161 - 168 (1996)
The synthesis of some bromine-substituted rhodamine derivatives viz., 4,5-dibromorhodamine methyl ester (dye 2) and 4,5-dibromorhodamine n-butyl ester (dye 3) are reported. These dyes were synthesized to promote a more efficient cancer cell photosensitizer for potential use in in vitro bone marrow purging in preparation for autologous bone marrow transplantation. Spectroscopic and photophysical characterization of these dyes together with rhodamine 123 (dye 1) are reported in water, methanol, ethanol and also in a microheterogeneous system, sodium dodecyl sulfate. The possible mechanism of photosensitization is characterized in terms of singlet oxygen efficiency of these dyes. Singlet oxygen quantum yields for bromine-substituted dyes are in the range of 0.3-0.5 depending on the solvent. For dye 1 no singlet oxygen production is found. The photodynamic actions of these dyes in different cell lines are tested. It was found that dye 2 and dye 3 are efficient photosensitizers and mediate eradication of K562, EM2, myeloid cell lines (CML) and the SMF-AI rhabdomyosarcoma line.
Does Perthionitrite (SSNO-) Account for Sustained Bioactivity of NO? A (Bio)chemical Characterization
Wedmann, Rudolf,Zahl, Achim,Shubina, Tatyana E.,Dürr, Maximilian,Heinemann, Frank W.,Bugenhagen, Bernhard Eberhard Christian,Burger, Peter,Ivanovic-Burmazovic, Ivana,Filipovic, Milos R.
, p. 9367 - 9380 (2015)
Hydrogen sulfide (H2S) and nitric oxide (NO) are important signaling molecules that regulate several physiological functions. Understanding the chemistry behind their interplay is important for explaining these functions. The reaction of H2S with S-nitrosothiols to form the smallest S-nitrosothiol, thionitrous acid (HSNO), is one example of physiologically relevant cross-talk between H2S and nitrogen species. Perthionitrite (SSNO-) has recently been considered as an important biological source of NO that is far more stable and longer living than HSNO. In order to experimentally address this issue here, we prepared SSNO- by two different approaches, which lead to two distinct species: SSNO- and dithionitric acid [HON(S)S/HSN(O)S]. (H)S2NO species and their reactivity were studied by 15N NMR, IR, electron paramagnetic resonance and high-resolution electrospray ionization time-of-flight mass spectrometry, as well as by X-ray structure analysis and cyclic voltammetry. The obtained results pointed toward the inherent instability of SSNO- in water solutions. SSNO- decomposed readily in the presence of light, water, or acid, with concomitant formation of elemental sulfur and HNO. Furthermore, SSNO- reacted with H2S to generate HSNO. Computational studies on (H)SSNO provided additional explanations for its instability. Thus, on the basis of our data, it seems to be less probable that SSNO- can serve as a signaling molecule and biological source of NO. SSNO- salts could, however, be used as fast generators of HNO in water solutions.
