Fluorescent ATP derivatives
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2'(3')-O-(5-Chloroanthraniloyl)adenosine-5'-O-triphosphate (sodium salt)

Item No. 38449

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2′(or 3′)-[N-(2-aminoethyl)carbamate]adenosine 5′-(tetrahydrogen triphosphate), tetrasodium salt
Synonyms
  • 2'(3')-chloro ANT-ATP
Molecular Formula
C17H16ClN6O14P3 • 4Na
Formula Weight
748.7
Purity
≥95% (mixture of isomers)
Formulation (Request formulation change)
A solution in water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O[C@@H]1[C@@H](COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O)O[C@@H](N2C3=NC=NC(N)=C3N=C2)[C@@H]1OC(C4=C(N)C=CC(Cl)=C4)=O.O[C@@H]5[C@H](OC(C6=C(N)C=CC(Cl)=C6)=O)[C@@H](COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O)O[C@H]5N7C8=NC=NC(N)=C8N=C7.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/2C17H20ClN6O14P3.8Na/c18-7-1-2-9(19)8(3-7)17(26)36-13-10(4-34-40(30,31)38-41(32,33)37-39(27,28)29)35-16(12(13)25)24-6-23-11-14(20)21-5-22-15(11)24;18-7-1-2-9(19)8(3-7)17(26)36-13-12(25)10(4-34-40(30,31)38-41(32,33)37-39(27,28)29)35-16(13)24-6-23-11-14(20)21-5-22-15(11)24;;;;;;;;/h2*1-3,5-6,10,12-13,16,25H,4,19H2,(H,30,31)(H,32,33)(H2,20,21,22)(H2,27,28,29);;;;;;;;/q;;8*+1/p-8/t2*10-,12-,13-,16-;;;;;;;;/m11......../s1
InChi Key
RPTRUPLZRAXXSY-HTDIHFSASA-F
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    3.3 mg

    $448

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    Product Description

    2'-O-(5-Chloroanthraniloyl)adenosine-5'-O-triphosphate (2'-chloro ANT-ATP) and 3'-chloro ANT-ATP are fluorescent ATP derivatives, which undergo spontaneous isomerization.1 2'(3')-chloro ANT-ATP is an inhibitor of mammalian adenylyl cyclase 1 (AC1), AC2, and AC5 (Kis = 80, 490, and 45 nM, respectively), B. anthracis edema factor AC toxin (Ki = 170 nM), and B. pertussis AC toxin CyaA (Ki = 350 nM).1,2 A related derivative, 2'(3')-ANT-ATP (Item No. 38546), displays an emission maximum of 428 nm upon excitation at 330 nm.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Geduhn, J., Dove, S., Shen, Y., et al. Bis-halogen-anthraniloyl-substituted nucleoside 5'-triphosphates as potent and selective inhibitors of Bordetella pertussis adenylyl cyclase toxin. J. Pharmacol. Exp. Ther. 336(1), 104-115 (2011).

    2. Taha, H., Dove, S., Geduhn, J., et al. Inhibition of the adenylyl cyclase toxin, edema factor, from Bacillus anthracis by a series of 18 mono- and bis-(M)ANT-substituted nucleoside 5'-triphosphates. Naunyn Schmiedebergs Arch. Pharmacol. 385(1), 57-68 (2012).

    3. Hiratsuka, T. New ribose-modified fluorescent analogs of adenine and guanine nucleotides available as substrates for various enzymes. Biochim. Biophys. Acta 742(3), 496-508 (1983).