Pyronin Y

Names

[ CAS No. ]:
92-32-0

[ Name ]:
Pyronin Y

[Synonym ]:
N-[6-(dimethylamino)-3H-xanthen-3-ylidene]-N-methylmethanaminium chloride
Pyronine Y
Tetramethyl pyronin
EINECS 202-147-8
Ammonium, [6-(dimethylamino)-3H-xanthen-3-ylidene]dimethyl-, chloride
N-[6-(Dimethylamino)-3H-xanthene-3-ylidene]-N-methylmethanaminium Chloride
Pyronine
Methanaminium, N-[6-(dimethylamino)-3H-xanthen-3-ylidene]-N-methyl-, chloride (1:1)
Pyroniny(G)
Methyl pyronin
Pyronin G
Pyronine G chloride
Pyronine ZH
MFCD00011725
[6-(dimethylamino)xanthen-3-ylidene]-dimethylazanium,chloride
pyronine G hydrochloride
xanthylium, 3,6-bis(dimethylamino)-, chloride (1:1)
Xanthylium, 3,6-bis(dimethylamino)-, chloride
Pyronin Y
6-(Dimethylamino)-N,N-dimethyl-3H-xanthen-3-iminium chloride
Pyronine G
Pyronin Yellow
3,6-Bis(dimethylamino)xanthenium chloride
[6-(Dimethylamino)-3H-xanthen-3-ylidene]dimethylammonium Chloride
tetramethyldiaminoxanthylium chloride

Biological Activity

[Description]:

Pyronin Y is an intercalating cationic dye that shows specificity towards RNA.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Dye Reagents

Research Areas >> Others

[In Vitro]

Pyronin Y forms fluorescent complexes with double-stranded nucleic acids, especially RNA, enabling semi-quantitative analysis of cellular RNA in flow cytometry, to estimate the RNA content per cell in formalin fixed EL4 leukosis tumor cells, enzyme dispersed R3327-G rat prostatic adenocarcinoma cells, mouse spleen cells stimulated with concanavalin A, and human peripheral blood lymphocytes stimulated with phytohemagglutinin[1]. A fluorescent staining procedure based on pyronin Y is described. The technique has been used to stain RNA in human reticulocytes for subsequent flow analysis and sorting[2]. In viable cells this dye also accumulates in mitochondria. At a concentration of 1.7 to 3.3 μM, pyronin Y is localized almost exclusively in mitochondria of cultured cells, similar to another mitochondria! probe, rhodamine 123. At that concentration PY is not toxic but suppressed cell growth, arresting cells[3]. Pyronin Y has long been used, in combination with other dyes such as Methyl Green, as a differential stain for nucleic acids in paraffin tissue sections. In sections stained with Methyl Green-pyronin Y, red blood cells, elastic fibre of blood vessels, zymogen granules of pancreatic acinar cells, surface membrane of heptocytes and kidney tubular cells showed strikingly strong green and/or red fluorescence, while the nuclei of cells appeared non-fluorescent[4].

[Cell Assay]

The cells are resuspended and stained for 30 min in 1.0 mL of 0.01% pyronin Y in sodiumacetate buffer (1.0 M, pH 4.7). For this purpose 1.0 g of pyronin Y is dissolved in 100 mL distilled water and this solution is purified by chloroform extraction (three fractions of 100 mL). The purified pyronin Y solution is diluted with 1.0 M sodiumacetate buffer pH 4.7 to the appropriate concentration and filtered through paper filters before use. Stained cell samples are studied by fluorescence microscopy (excitation filters SP 560 and LP 515, chromatic beam splitter at 580 nm, barrier filter LP 580) or by flow cytometry[2].

[References]

[1]. Pollack A, et al. Flow cytometric analysis of RNA content in different cell populations using pyronin Yand methyl green. Cytometry. 1982 Jul;3(1):28-35.

[2]. Tanke HJ, et al. Flow cytometry of human reticulocytes based on RNA fluorescence. Cytometry. 1981 Mar;1(5):313-20.

[3]. Darzynkiewicz Z, et al. Cytostatic and cytotoxic properties of pyronin Y: relation to mitochondrial localization of the dye and its interaction with RNA. Cancer Res. 1986 Nov;46(11):5760-6.

[4]. Li B, et al. Pyronin Y as a fluorescent stain for paraffin sections. Histochem J. 2002 Jun-Jul;34(6-7):299-303.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
250-260ºC(lit.)

[ Molecular Formula ]:
C₁₇H₁₉ClN₂O

[ Molecular Weight ]:
302.799

[ Exact Mass ]:
302.118591

[ PSA ]:
19.39000

[ Storage condition ]:
Store at RT.

[ Water Solubility ]:
Soluble in water; sparingly soluble in ethanol, ethylene glycol, methyl cellosolve | Soluble in water. Also soluble in methyl cellosolve (9 mg/mL) and ethanol (3 mg/mL).

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: BQ1450000

CHEMICAL NAME :: Ammonium, (6-(dimethylamino)-3H-xanten-3-ylidene)dimethyl-, chloride

CAS REGISTRY NUMBER :: 92-32-0

LAST UPDATED :: 199701

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C17-H19-N2-O.Cl

MOLECULAR WEIGHT :: 302.83

WISWESSER LINE NOTATION :: T C666 BO EYJ EUK1&1 MN1&1 &G

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 179 mg/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

MUTATION DATA

TEST SYSTEM :: Insect - Drosophila melanogaster

DOSE/DURATION :: 1000 ppm

REFERENCE :: AMNTA4 American Naturalist. (Univ. of Chicago Press, Journals Div., POB 37005, Chicago, IL 60637) V.1- 1867- Volume(issue)/page/year: 87,295,1953 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X7179 No. of Facilities: 63 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 1056 (estimated) No. of Female Employees: 810 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R68

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
BQ1450000

[ HS Code ]:
2921199090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2921199090

[ Summary ]:
2921199090 other acyclic monoamines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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