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F9128

5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride

Name: 5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride
Brand: SIGMA

Synonym(s):

Adenosine-5′-(4-fluorosulfonylbenzoate) hydrochloride, FSBA

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About This Item

Empirical Formula (Hill Notation):

C₁₇H₁₆FN₅O₇S · HCl

CAS Number:

78859-42-4

Molecular Weight:

489.86

Beilstein:

8178939

MDL number:

MFCD00043258

UNSPSC Code:

41106305

PubChem Substance ID:

24894988

NACRES:

NA.51

biological source

synthetic (organic)

Quality Level

200

Assay

≥95% (TLC)

form

powder

solubility

methanol: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Cl[H].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COC(=O)c4ccc(cc4)S(F)(=O)=O)[C@@H](O)[C@H]3O

InChI

1S/C17H16FN5O7S.ClH/c18-31(27,28)9-3-1-8(2-4-9)17(26)29-5-10-12(24)13(25)16(30-10)23-7-22-11-14(19)20-6-21-15(11)23;/h1-4,6-7,10,12-13,16,24-25H,5H2,(H2,19,20,21);1H/t10-,12-,13-,16-;/m1./s1

InChI key

ZUHVYHQVJYIHPN-KHXPSBENSA-N

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Application

5′-(4-Fluorosulfonylbenzoyl)adenosine (FSBA) is an ATP analog used to study the mechanism of action of wortmannin. FSBA has been used to study vesicular transport in intestinal cells such as Caco-2, and to covalently modify residues in the nucleotide-binding domains (NBDs) of various ATPases, kinases, and other proteins.

5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride has been used to incubate with Ime2 (inducer of meiosis 2) to determine the sensitivity of Ime2 to the adenosine triphosphate (ATP) analog 5′-fluorosulfonylbenzoyladenosine (FSBA).

Biochem/physiol Actions

5′-(4-Fluorosulfonylbenzoyl)adenosine helps to recognize adenosine triphosphate (ATP)-binding sites in kinases due to its reaction with nucleophilic amino acids happening within these motifs.

Pictograms

GHS05

Signal Word

Danger

Hazard Statements

H314

Precautionary Statements

P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mitochondrial regulation of insect cell apoptosis: evidence for permeability transition pore-independent cytochrome-c release in the Lepidopteran Sf9 cells.

Regalla Kumarswamy et al.

The international journal of biochemistry & cell biology, 41(6), 1430-1440 (2009-01-17)

Role of cytochrome-c in insect cell apoptosis is highly controversial, with many earlier reports suggesting lack of involvement of mitochondrial factors in Drosophila while more recent studies have indicated otherwise, thus warranting more in-depth studies of insect cell apoptosis. In

Inactivation of isocitrate dehydrogenase kinase/phosphatase by 5'-[p-(fluorosulfonyl)benzoyl]adenosine is not due to the labeling of the invariant lysine residue found in the protein kinase family.

C Oudot et al.

European journal of biochemistry, 258(2), 579-585 (1999-01-05)

The ATPase activity of Escherichia coli isocitrate dehydrogenase kinase/phosphatase was rapidly lost after prior incubation with the ATP analogue 5'-[p-(fluorosulfonyl)benzoyl]adenosine (FSBA). This inactivation was prevented by the presence of either 5 mM ATP or 5 mM ADP plus Mg2+, while

Selective Ion Tracing and MS n Analysis of Peptide Digests from FSBA-Treated Kinases for the Analysis of Protein ATP-Binding Sites

Renzone G, et al.

Journal of Proteome Research, 5(8), 2019-2024 (2006)

Synthesis and characterization of 5'-p-fluorosulfonylbenzoyl-2' (or 3')-(biotinyl)adenosine as an activity-based probe for protein kinases.

Steven J Ratcliffe et al.

Journal of biomolecular screening, 12(1), 126-132 (2006-12-15)

Most of the kinase inhibitors that are approved for therapeutic uses or that are undergoing clinical trials are directed toward the adenosine triphosphate (ATP) binding site of protein kinases. 5'-Fluorosulfonylbenzoyl 5'-adenosine (FSBA) is an activitybased probe (ABP) that covalently modifies

Clopidogrel (Plavix) and cardiac surgical patients: implications for platelet function monitoring and postoperative bleeding.

Kenichi A Tanaka et al.

Platelets, 15(5), 325-332 (2004-09-17)

The use of clopidogrel (Plavix), an inhibitor of adenosine diphosphate (ADP)-induced platelet aggregation, has been proven to reduce ischemic events in cardiovascular patients, but little information is available for optimal monitoring of platelet function in patients receiving the drug preoperatively.

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