Cas no 100020-57-3 (2-Methylthio-ATP tetrasodium)

2-Methylthio-ATP tetrasodium is a chemically modified adenosine triphosphate (ATP) analog, where a methylthio group replaces the oxygen at the 2-position of the adenine ring. This modification enhances its stability and resistance to enzymatic degradation compared to native ATP, making it particularly useful in biochemical and pharmacological research. The tetrasodium salt form ensures improved solubility in aqueous solutions, facilitating its application in cell-based assays and receptor studies. Its high affinity for P2 purinergic receptors allows it to serve as a potent agonist in studying ATP-mediated signaling pathways. This compound is widely utilized in investigations of neurotransmission, inflammation, and cardiovascular physiology due to its reliable bioactivity and prolonged half-life.
2-Methylthio-ATP tetrasodium structure
2-Methylthio-ATP tetrasodium structure
Product Name:2-Methylthio-ATP tetrasodium
CAS No:100020-57-3
MF:C11H14N5Na4O13P3S
MW:641.19992685318
CID:2090056
PubChem ID:16218831
Update Time:2025-05-22

2-Methylthio-ATP tetrasodium Chemical and Physical Properties

Names and Identifiers

    • 2-Methylthioadenosine triphosphate tetrasodium salt
    • 2-Methylthio-ATP tetrasodium
    • 2-(Methylthio)adenosine 5'-triphosphate tetrasodium salt
    • Adenosine 5'-(tetrahydrogen triphosphate), 2-(methylthio)-, tetrasodium salt (9CI)
    • Adenosine 5'-(tetrahydrogen triphosphate), 2-(methylthio)-, sodium salt (1:4)
    • 2-(Methylthio)adenosine 5'-triphosphate tetrasodium salt
    • 2-Methylthio-ATP tetrasodium
    • Inchi: 1S/C11H18N5O13P3S.4Na/c1-33-11-14-8(12)5-9(15-11)16(3-13-5)10-7(18)6(17)4(27-10)2-26-31(22,23)29-32(24,25)28-30(19,20)21;;;;/h3-4,6-7,10,17-18H,2H2,1H3,(H,22,23)(H,24,25)(H2,12,14,15)(H2,19,20,21);;;;/q;4*+1/p-4/t4-,6-,7-,10-;;;;/m1..../s1
    • InChI Key: UEEFBRHXFDJPTA-KWIZKVQNSA-J
    • SMILES: S(C)C1N=C(C2=C(N=1)N(C=N2)[C@H]1[C@@H]([C@@H]([C@@H](COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])O1)O)O)N.[Na+].[Na+].[Na+].[Na+]

Computed Properties

  • Exact Mass: 640.911245g/mol
  • Monoisotopic Mass: 640.911245g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 18
  • Heavy Atom Count: 37
  • Rotatable Bond Count: 8
  • Complexity: 825
  • Covalently-Bonded Unit Count: 5
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Molecular Weight: 641.2g/mol
  • Topological Polar Surface Area: 316?2

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Additional information on 2-Methylthio-ATP tetrasodium

2-Methylthio-ATP Tetrasodium: A Comprehensive Overview

2-Methylthio-ATP tetrasodium (CAS No. 100020-57-3) is a synthetic nucleotide analog that has garnered significant attention in the fields of biochemistry, pharmacology, and molecular biology. This compound is a modified version of adenosine triphosphate (ATP), where the sulfur atom in the thiol group replaces the oxygen atom in the hydroxyl group of the ribose sugar. This structural modification imparts unique chemical and biological properties to 2-Methylthio-ATP tetrasodium, making it a valuable tool in various research and therapeutic applications.

The synthesis of 2-Methylthio-ATP tetrasodium involves advanced chemical methodologies, including nucleophilic substitution and phosphorylation reactions. The tetrasodium salt form ensures stability and solubility in aqueous solutions, which is critical for its use in biological systems. Recent studies have highlighted its potential as a bioactive compound with applications in drug development, particularly in targeting ATP-dependent processes such as signal transduction, energy metabolism, and enzyme regulation.

One of the most promising areas of research involving 2-Methylthio-ATP tetrasodium is its role as an ATP analog in biochemical assays. Traditional ATP assays often suffer from interference due to endogenous ATP levels or enzymatic activity. However, 2-Methylthio-ATP tetrasodium provides a stable and specific substrate for luciferase-based assays, enabling precise measurement of ATP-dependent processes in vitro and in vivo. This has led to its widespread use in pharmacological screening, where it serves as a reliable tool for assessing the activity of kinase inhibitors and other ATP-binding proteins.

In addition to its role in biochemical assays, 2-Methylthio-ATP tetrasodium has been explored for its potential as a therapeutic agent. Preclinical studies have demonstrated its ability to modulate cellular energy metabolism by acting as an allosteric regulator of ATP-sensitive potassium channels (KATP). These channels play a critical role in maintaining cellular homeostasis, particularly in insulin secretion, vascular smooth muscle relaxation, and neuronal function. By targeting KATP channels, 2-Methylthio-ATP tetrasodium holds promise as a novel therapeutic for conditions such as diabetes, cardiovascular diseases, and neurodegenerative disorders.

Recent advancements in nanotechnology have further expanded the applications of 2-Methylthio-ATP tetrasodium. Researchers have successfully incorporated this compound into lipid nanoparticles (LNPs) for targeted drug delivery. The unique chemical properties of 2-Methylthio-ATP tetrasodium, including its stability and bioavailability, make it an ideal candidate for encapsulation within LNPs. This approach not only enhances the therapeutic efficacy but also reduces off-target effects, paving the way for personalized medicine.

The structural elucidation of 2-Methylthio-ATP tetrasodium has been facilitated by advanced analytical techniques such as X-ray crystallography and nuclear magnetic resonance (NMR) spectroscopy. These studies have provided insights into the three-dimensional arrangement of the molecule, revealing key interactions that contribute to its bioactivity. For instance, the methylthio group at position 5 of the ribose sugar forms critical hydrogen bonds with residues in the active site of KATP channels, thereby modulating channel activity.

Another area of active research is the investigation of 2-Methylthio-ATP tetrasodium's role in cellular signaling pathways. Emerging evidence suggests that this compound can influence downstream signaling cascades by interacting with purinergic receptors. Purinergic signaling, which involves extracellular nucleotides such as ATP and uridine triphosphate (UTP), plays a pivotal role in immune response, inflammation, and tissue repair. By modulating purinergic signaling, 2-Methylthio-ATP tetrasodium could serve as a novel therapeutic agent for inflammatory diseases such as arthritis and inflammatory bowel disease.

The development of biosensors based on 2-Methylthio-ATP tetrasodium represents another exciting frontier in its application. These sensors utilize the luminescent properties of luciferase enzymes to detect changes in ATP levels within living cells or tissues. The high specificity and sensitivity of these biosensors make them invaluable tools for real-time monitoring of cellular energy status during physiological or pathological conditions.

In conclusion, 2-Methylthio-ATP tetrasodium (CAS No. 100020-57-3) is a versatile compound with diverse applications across multiple disciplines. Its unique chemical properties, combined with recent advancements in synthesis and delivery technologies, position it as a promising candidate for both diagnostic and therapeutic applications. As research continues to uncover new insights into its mechanisms of action and potential uses, 2-Methylthio-ATP tetrasodium is poised to play an increasingly important role in advancing our understanding of cellular energetics and disease pathophysiology.

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