TAMRA alkyne, 6-isomer

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TAMRA alkyne, 6-isomer

TAMRA alkyne, 6-isomer | 1352649-44-5

Catalog Number R02-0037
Category Alkynes
Molecular Formula C28H25N3O4
Molecular Weight 467.52
Catalog Number Size Price Quantity
R02-0037 -- $--

Product Introduction

Tetramethylrhodamine (TAMRA) alkyne, pure 6-isomer. TAMRA is a popular dye that is used in qPCR and other applications. It forms a FRET pair with FAM (serving as an acceptor). This product is a terminal alkyne for copper-catalyzed Click chemistry. It can be conjugated with azide groups using CuAAc reaction.

Chemical Information

Synonyms 2-(3,6-Bis(dimethylamino)xanthylium-9-yl)-4-(prop-2-yn-1-ylcarbamoyl)benzoate; 6-Carboxytetramethylrhodamine, propargylamide
Purity NMR 1H, HPLC-MS (95%)
IUPAC Name 2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]-4-(prop-2-ynylcarbamoyl)benzoate
Canonical SMILES CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=CC(=C4)C(=O)NCC#C)C(=O)[O-]
InChI InChI=1S/C28H25N3O4/c1-6-13-29-27(32)17-7-10-20(28(33)34)23(14-17)26-21-11-8-18(30(2)3)15-24(21)35-25-16-19(31(4)5)9-12-22(25)26/h1,7-12,14-16H,13H2,2-5H3,(H-,29,32,33,34)
InChI Key ZKVFIMYNEWHSCO-UHFFFAOYSA-N
Solubility good in DMF, DMSO, alcohols
Appearance dark colored solid
  • Product Specification
  • Application
ε, L⋅mol-1⋅cm-1 84000
Fluorescence Quantum Yield 0.1
Excitation 541
Emission 567
Storage 24 months after receival at -20°C in the dark. Transportation: at room temperature for up to 3 weeks. Avoid prolonged exposure to light. Desiccate.

Fluorescent Labeling for Biomolecular Imaging: TAMRA alkyne, 6-isomer, is widely used in the field of biomolecular imaging due to its strong fluorescent properties. Its alkyne group allows for facile conjugation with various biomolecules through copper-catalyzed azide-alkyne cycloaddition (CuAAC), commonly known as click chemistry. This conjugation technique is particularly valuable for tagging proteins, nucleic acids, and other cellular components, enabling researchers to visualize dynamic biological processes in real-time. The high quantum yield and photostability of TAMRA make it an ideal choice for applications requiring long-term imaging and high sensitivity.

Development of Fluorescent Probes for Enzyme Activity: TAMRA alkyne, 6-isomer, is frequently used to design fluorescent probes that monitor enzyme activity. By conjugating TAMRA to specific substrates that are cleaved or modified by target enzymes, researchers can observe changes in fluorescence that directly correspond to enzymatic activity. This approach is particularly useful in drug discovery and enzyme kinetics studies, where accurate and high-throughput measurement of enzyme activity is crucial. The versatility of the alkyne group facilitates the attachment of various enzyme-specific recognition elements, making TAMRA-based probes adaptable to a wide range of enzymatic assays.

Quantitative Analysis of Biomolecular Interactions: The ability to quantitatively analyze biomolecular interactions is essential in fields such as molecular biology, pharmacology, and diagnostics. TAMRA alkyne, 6-isomer, is often employed in fluorescence resonance energy transfer (FRET) and fluorescence anisotropy assays to study the interactions between proteins, DNA, and small molecules. When coupled with appropriate acceptor dyes, TAMRA's fluorescence can be used to measure distances and conformational changes at the molecular level, providing insights into binding affinities and interaction dynamics. This capability is critical for understanding complex biological systems and developing novel therapeutics.

Cellular Uptake and Localization Studies: Understanding how molecules enter cells and where they localize is fundamental to fields such as drug delivery and cell biology. TAMRA alkyne, 6-isomer, can be conjugated to a variety of small molecules, peptides, and nanoparticles to study their cellular uptake and distribution. The bright fluorescence of TAMRA enables precise localization of conjugated molecules within cells, facilitating the study of intracellular trafficking pathways and the optimization of delivery systems. This application is particularly valuable in the development of targeted therapies and nanomedicine, where efficient cellular delivery and precise localization are crucial for therapeutic efficacy.

Computed Properties

XLogP3 3.1
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 5
Rotatable Bond Count 4
Exact Mass 467.18450629 g/mol
Monoisotopic Mass 467.18450629 g/mol
Topological Polar Surface Area 84.7Ų
Heavy Atom Count 35
Formal Charge 0
Complexity 1000
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes
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