93839-89-5

Basic information

• Product Name: ADENOSINE 5'-O-(3-THIOTRIPHOSPHATE), TETRALITHIUM SALT
• Synonyms: adenosine-5’-o-(3-thiotriphosphate)(atp-g-s),sodiumsalt;ADENOSINE 5'-(3-THIOTRIPHOSPHATE) TETRALITHIUM SALT;ADENOSINE-5'-O-(3-THIOTRIPHOSPHATE) LITHIUM SALT;ADENOSINE-5'-O-(3-THIOTRIPHOSPHATE) SODIUM SALT;ADENOSINE 5'-O-(3-THIOTRIPHOSPHATE), TETRALITHIUM SALT;ADENOSINE-5'-O-(3-THIOPHOSPHATE) LI4;ADENOSINE-5'-O-(3-THIOTRIPHOSPHORIC ACID), SODIUM;ADENOSINE-5'-O-(3-THIOTRIPHOSPHORIC ACID), TETRALITHIUM
• CAS NO: 93839-89-5
• Molecular Formula: C10H12Li4N5O12P3S
• Molecular Weight: 546.98
• EINECS: 298-862-8
• Mol File: 93839-89-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 940.5 °C at 760 mmHg
• Flash Point: 522.6 °C
• Appearance: white/powder
• Storage Temp.: −20°C
• Solubility: H2O: 25 mg/mL
• Stability: Moisture Sensitive
• BRN: 6265083
• CAS DataBase Reference: ADENOSINE 5'-O-(3-THIOTRIPHOSPHATE), TETRALITHIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: ADENOSINE 5'-O-(3-THIOTRIPHOSPHATE), TETRALITHIUM SALT(93839-89-5)
• EPA Substance Registry System: ADENOSINE 5'-O-(3-THIOTRIPHOSPHATE), TETRALITHIUM SALT(93839-89-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 93839-89-5(Hazardous Substances Data)

Usage

Description

ADENOSINE 5'-O-(3-THIOTRIPHOSPHATE), TETRALITHIUM SALT, also known as ATP-γ-S, is a modified form of adenosine triphosphate (ATP) with a sulfur atom replacing the terminal phosphate group. This white solid is a useful reagent in various biochemical applications due to its unique chemical properties.

Uses

Used in Biochemical Research:
ADENOSINE 5'-O-(3-THIOTRIPHOSPHATE), TETRALITHIUM SALT is used as a reagent in the synthesis of DNA N-acetylglucosamine analogs, which are important for studying the structure and function of nucleic acids and their interactions with proteins.
Used in Plant Biology:
In plant biology, ATP-γ-S is used to treat pollen grains to determine the inhibitory effect of ATP or its hydrolysis product on pollen germination and tube growth. This helps researchers understand the role of ATP in plant reproduction.
Used in Protein Phosphorylation Studies:
ATP-γ-S is used as a substrate and inhibitor of ATP-dependent enzyme systems, particularly protein kinases. Due to its slow hydrolysis by phosphatases and ATPases, it allows for the selective thiophosphorylation of target proteins, which can provide insights into protein function and regulation.
Used in Enzyme Inhibition:
Once thiophosphorylated, proteins are resistant to protein phosphatases, making ATP-γ-S a valuable tool for studying enzyme inhibition and the role of protein phosphorylation in various cellular processes.

Biological Activity

atpγs tetralithium salt is an analogue of atp, acting as a potent agonist of g protein-coupled p2y2 and p2y11 receptors (pec50 = 5.52 for p2y11) [1].the p2y receptors consist of 8 human subtypes, i.e. p2y1, p2y2, p2y4, p2y6, p2y11, p2y12, p2y13, and p2y14, coupled to g protein-dependent and -independent signaling pathways, including ion channels. the p2y receptors are involved in controlling levels of extracellular nucleotides and nucleosides, and intracellular signaling pathways [1].in pc 12 cells, preincubation of the cells with norepinephrine (ne) and atpγs tetralithium salt (1 μm) resulted in a persistent increase in uptake of ne, whilst similar pretreatment with atp did not show this increase. in the presence of atp, the activation effect produced by atpγs tetralithium salt on ne uptake was blocked [2]. in tea3a1 cells, atpγs tetralithium salt (0 ~ 200 μm) increased ca2+ influx in a dose-dependent manner, with ed50 value of about 50 μm. a maximum level of ca2+ influx was observed when cells were treated with atpγs tetralithium salt at concentrations above 100 μm. similar dose-dependent increases in the production of prostaglandin e2 (pge2) were also observed after atpγs tetralithium salt treatment [3].[1]. jacobson k a, ivanov a a, de castro s, et al. development of selective agonists and antagonists of p2y receptors. purinergic signal, 2009, 5(1): 75-89.[2]. hardwick j c, ehrlich y h, hendley e d. extracellular atp stimulates norepinephrine uptake in pc12 cells. journal of neurochemistry, 1989, 53(5):1512-1518.[3]. liu p, lalor d, bowser s s, et al. regulation of arachidonic acid release and prostaglandin e2 production in thymic epithelial cells by atpgammas and transforming growth factor-alpha. cellular immunology, 1998, 188(2): 81-88.

Biochem/physiol Actions

Adenosine 5′-[γ-thio]triphosphate (ATP-γ-S) is widely used as a non-hydrolyzed ATP analogue for studies on the effects of ATP binding to ATP sites in a wide range of processes including extracellular functions. ATP- γ-S is a P2 purinergic agonist which increases the activity of Ca2+-activated K+ channels. ATP- γ-S can substitute for ATP in kinase reactions yielding thiophosphorylated proteins that are resistant to protein phosphatases and modulate the ATP-dependent steps in the binding of ubiquitin conjugates to the 26S proteasome. ATP-γ -S differentially modulates Toll-like receptor 4-mediated cell survival and death.