Tetramethylrhodamine - 70281-37-7

Tetramethylrhodamine

Catalog Number: EVT-292197
CAS Number: 70281-37-7
Molecular Formula: C24H23ClN2O3
Molecular Weight: 422.9 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.

Product Introduction

Description
Tetramethylrhodamine (TMR) is a fluorescent dye that is widely used in various fields of research, including medical, environmental, and industrial research. It is a member of the rhodamine family of dyes and is commonly used as a fluorescent probe for labeling biomolecules, such as proteins, nucleic acids, and lipids. TMR has a unique chemical structure that allows it to emit bright red fluorescence upon excitation with light of a specific wavelength. This property makes it an ideal tool for studying biological processes and environmental phenomena.
Applications in Various Fields
Tetramethylrhodamine has various applications in medical research, such as its role in drug development, clinical trials, and findings. Tetramethylrhodamine can be used to study the mechanism of action and biological targets of various drugs and toxins. It can also be used as a fluorescent probe for imaging and tracking cells and tissues in vivo. In environmental research, Tetramethylrhodamine can be used to study the effects of pollutants on ecosystems and to monitor the sustainability and environmental impact of various processes. In industrial research, Tetramethylrhodamine can be used to improve product quality and efficiency, as well as to ensure health and safety considerations.

Properties

CAS Number

70281-37-7

Product Name

Tetramethylrhodamine

IUPAC Name

[9-(2-carboxyphenyl)-6-(dimethylamino)xanthen-3-ylidene]-dimethylazanium;chloride

Molecular Formula

C24H23ClN2O3

Molecular Weight

422.9 g/mol

InChI

InChI=1S/C24H22N2O3.ClH/c1-25(2)15-9-11-19-21(13-15)29-22-14-16(26(3)4)10-12-20(22)23(19)17-7-5-6-8-18(17)24(27)28;/h5-14H,1-4H3;1H

InChI Key

WGTODYJZXSJIAG-UHFFFAOYSA-N

SMILES

CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=CC=CC=C4C(=O)O.[Cl-]

Synonyms

T 489
T-489
tetramethylrhodamine
tetramethylrhodamine maleimide

Canonical SMILES

CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=CC=CC=C4C(=O)O.[Cl-]
Method of Synthesis or Extraction
Tetramethylrhodamine can be synthesized using various methods, including the condensation of rhodamine B with formaldehyde and dimethylamine, or the reaction of rhodamine 6G with formaldehyde and dimethylamine. The efficiency and yield of each method depend on the reaction conditions, such as the concentration of reagents, temperature, and reaction time. The environmental and safety considerations of Tetramethylrhodamine synthesis are related to the use of toxic and flammable reagents, such as formaldehyde and dimethylamine. Therefore, proper safety measures and waste disposal procedures should be followed to minimize the environmental impact.
Chemical Structure and Biological Activity
Tetramethylrhodamine has a complex chemical structure that consists of a rhodamine core, four methyl groups, and a dimethylamino group. The unique arrangement of these groups allows Tetramethylrhodamine to exhibit strong fluorescence properties and high photostability. Tetramethylrhodamine is commonly used as a fluorescent probe for labeling biomolecules, such as proteins, nucleic acids, and lipids. It can also be used to study the mechanism of action and biological targets of various drugs and toxins. Tetramethylrhodamine has been shown to bind to specific sites on proteins and nucleic acids, which can affect their function and activity.
Biological Effects
Tetramethylrhodamine can affect cell function and signal transduction by binding to specific sites on proteins and nucleic acids. This can lead to changes in gene expression, protein activity, and cell signaling pathways. Tetramethylrhodamine has potential therapeutic and toxic effects, depending on the dose and duration of exposure. It has been shown to have anti-cancer properties by inhibiting the growth and proliferation of cancer cells. However, high doses of Tetramethylrhodamine can be toxic to cells and can cause cell death.
Future Perspectives and Challenges
The current limitations in the use and study of Tetramethylrhodamine include its toxicity at high doses and the need for more efficient and environmentally friendly synthesis methods. Possible solutions and improvements include the development of new synthesis methods that use non-toxic and renewable reagents, as well as the optimization of Tetramethylrhodamine labeling protocols for better sensitivity and specificity. Future trends and prospects in the application of Tetramethylrhodamine in scientific research include its use in advanced imaging techniques, such as super-resolution microscopy, and its integration with other fluorescent probes for multiplexed imaging and analysis.

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