Rhodamine 6G

Names

[ CAS No. ]:
989-38-8

[ Name ]:
Rhodamine 6G

[Synonym ]:
fanal pink gfk
Rhodamine 590 chloride
Rhodamine 5GDN
rhodamin6g
Aizen Rhodamine 6GCP
Basic rhodamine yellow
rh6g
rhodamine 4gh
calcozine red 6g
rhodamine 6gb
Rhodamine 6GDN Extra
Basic Rhodaminic Yellow
Rhodamine 6JH-SA Extra 1150
Mitsui Rhodamine 6GCP
cibasicred1
Rhodamine 6G Extra
Basonyl Red 483
CI Basic Red 1
Basonyl Red 482
Rhodamine 6GBN
Nyco Liquid Red GF
Basic red 1
Rhodamine 5GL
Ethyl 2-[(3Z)-6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]benzoate hydrochloride (1:1)
Rhodamine 6JH
Flexo Red 482
Rhodamine 5GDN Extra
Eljon Pink Toner
Rhodamine F 5GL
fanalpinkb
Rhodamine F 5G
Rhodamine GDN Extra
Rhodamine 6G Extra Base
Rhodamine 6GCP
Fanal Pink B
red169
Calcozine Rhodamine 6GX
rhodaminej
Heliostable Brilliant Pink B Extra
Vali Fast Red 1308
Rhodamine 6G
rhodamine 3B hydrochloride
MFCD00012665
ethyl 2-[(3Z)-6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]benzoate hydrochloride
Benzoic acid, 2-[(3Z)-6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]-, ethyl ester, hydrochloride (1:1)
Rhodamine 6GD
rhodamine y 20-7425
Mitsui Rhodamine
N-[(3Z)-9-[2-(Ethoxycarbonyl)phenyl]-6-(ethylamino)-2,7-dimethyl-3H-xanthen-3-ylidene]ethanaminium chloride
Rhodamine 4GD
silosuper pink b
Rhodamine 6Zh-DN
benzoic acid, 2-[(3Z)-6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]-, ethyl ester, monohydrochloride
Rhodamine 6GDN
Rh 6G
Elcozine Rhodamine 6GDN
Rhodamine 6GO
Rhodamine 6GH
rhodaminezh
rhodamine 6gex ethyl ester
EINECS 213-584-9
Fanal Red 25532
rhodamine gdn
rhodamine 6gx
Rhodamine 6G chloride
rhodamine ZH

Biological Activity

[Description]:

Rhodamine 6G is a rhodamine analog useful in Pgp efflux assays. It can be used in characterizing the kinetics of MRP1- mediated efflux, and as a laser dye and potential mitochondrial probe.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Dye Reagents

Research Areas >> Others

[In Vitro]

Rhodamine 6G, also known as Rhodamine 590, is widely used as a lasing medium and as a fluorescence tracer. For use in dye lasers, it is dissolved in methanol, ethanol and a variety of other organic solvents. In environmental flow studies, the tracer medium is typically water. In ethanol, the absorption of rhodamine 6G ranges between 440 nm and 570 nm, with the peak at 530 nm. It is thus ideally suited for pumping by frequency doubled Nd:YAG lasers at 532 nm, copper vapor lasers at 511 nm, and argon-ion lasers at 514 nm. The resulting emission spectrum varies from about 510 nm to around 710 nm with the peak at 550 nm depending on the solvent and the dye concentration. However, the laser emission range is much narrower, from around 560 nm to 610 nm with the peak wavelength around 575 nm. Energy conversion efficiencies greater than 50% are achievable. In order to select the optimal solvent and dye concentration, good knowledge of their effects is a pre-requisite. Rhodamine 6G in DMSO shows a distinct behavior exhibiting only 41% of the fluorescence intensity of the methanol case with an 11 nm red-shifted wavelength. Relatively small changes of the fluorescence spectrum are observed for the different solvents; the highest fluorescence intensity is observed for methanol and lowest for DMSO. The shortest peak wavelength is found in methanol (568 nm) and the longest in DMSO (579 nm). Changing the dye concentration provides tunability between 550 nm in the dilute case and 620 nm at high concentration, at which point the fluorescence spectrum indicates the formation of rhodamine 6G aggregates[1]. Rhodamine 6G is a fluorescent dye capable of penetrating a living cell. Upon entering the cell, Rhodamine 6G binds to the inner membranes of mitochondria. Based on these observations, it has been proposed that Rhodamine dyes may be used for producing fluorescent images of mitochondria with low background noise and high resolution. Extremely low concentrations of Rhodamine 6G appear to selectively destroy malignant cells in culture, sparing the normal cell populations[2].

[In Vivo]

Melanoma-transplanted mice receiving Rhodamine 6G demonstrate prolonged survival, improved clinical parameters, inhibited tumor growth and metastases count, compared to their untreated counterparts. Twice-a-week 10-6M Rhodamine 6G regimen yield the most prominent results[2]. The Rhodamine-6G enters the circulatory system and labels leukocytes. It is possible to monitor changes in the interactions between leukocytes and the endothelium by determining the numbers of rolling and adhering leukocytes as well as the total flux of these cells[3].

[Cell Assay]

Malignant cells and normal control cultures are seeded in equal (protein adjusted) cell amounts into 6-well tissue culture plates. The cells are pulsed with 25µCi/mL of 3H-Thymidine and immediately treated with Rhodamine 6G at the fixed concentration of 1 μM for 24h, 48h, 72h or 5 days (120h). Following 24h, 48h, 72h or 5 days, the excessive radioactive material is ished out with PBS. The cell samples are transferred into polystyrene vials containing 4 ml scintillation liquid, and their radioactivity counted in a β-counter. Total cell protein is assessed by Bradford’s assay[2].

[Animal admin]

Mice: C57Bl mice are implanted with B16-F10 melanoma and treated with Rhodamine 6G (1, 0.1, 0.01 μM) at different dosage/time regimens. Viability and proliferation of cultured tumor cells are analyzed[2].

[References]

[1]. Zehentbauer FM, et al. Fluorescence spectroscopy of Rhodamine 6G: concentration and solvent effects. Spectrochim Acta A Mol Biomol Spectrosc. 2014;121:147-51.

[2]. Kutushov M, et al. Low concentrations of Rhodamine 6G selectively destroy tumor cells and improve survival of melanoma transplanted mice. Neoplasma. 2013;60(3):262-73.

[3]. Jain RK, et al. Measuring leukocyte-endothelial interactions in mice. Cold Spring Harb Protoc. 2013 Jun 1;2013(6):561-3.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.15g/cm3

[ Boiling Point ]:
<200ºC

[ Melting Point ]:
290 °C

[ Molecular Formula ]:
C₂₈H₃₁ClN₂O₃

[ Molecular Weight ]:
479.010

[ Flash Point ]:
318.6ºC

[ Exact Mass ]:
478.202332

[ PSA ]:
63.83000

[ LogP ]:
7.22550

[ Index of Refraction ]:
1.593

[ Water Solubility ]:
SOLUBLE

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DH0175000

CHEMICAL NAME :: Benzoic acid, o-(6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xant hen-9-yl)-, ethyl ester, monohydrochloride

CAS REGISTRY NUMBER :: 989-38-8

LAST UPDATED :: 199701

DATA ITEMS CITED :: 27

MOLECULAR FORMULA :: C28-H31-N2-O3.Cl

MOLECULAR WEIGHT :: 479.06

WISWESSER LINE NOTATION :: T C666 BO EYJ EUN2 F1 IR BVO2& L1 MN1&1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 125 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Cardiac - other changes Liver - other changes Blood - other hemolysis with or without anemia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6150 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2310 mg/kg/14D-C

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10192 mg/kg/13W-C

TOXIC EFFECTS :: Blood - changes in spleen

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 130 mg/kg/35D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - structural or functional change in trachea or bronchi Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 51 gm/kg/13W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7725 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg/1Y-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 4 mg/kg

SEX/DURATION :: female 7-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2 mg/kg

SEX/DURATION :: female 7-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2 mg/kg

SEX/DURATION :: female 7-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2 mg/kg

SEX/DURATION :: female 7-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 19900 ug/L

REFERENCE :: NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-364,1989 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 16,233,1978 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 16,233,1978 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M2209 No. of Facilities: 917 (estimated) No. of Industries: 20 No. of Occupations: 21 No. of Employees: 15041 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M2209 No. of Facilities: 2416 (estimated) No. of Industries: 27 No. of Occupations: 32 No. of Employees: 41538 (estimated) No. of Female Employees: 8238 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36/37/39-S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DH0175000

[ HS Code ]:
3204130000

Customs

[ HS Code ]: 2922199090

[ Summary ]:
2922199090. other amino-alcohols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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