Fluorescent GTP derivatives
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2'(3')-O-Anthraniloylguanosine-5'-O-triphosphate (sodium salt)

Item No. 38812

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2' or 3′-(2-aminobenzoate)guanosine 5′-(tetrahydrogen triphosphate), tetrasodium salt
Synonyms
  • 2'(3')-ANT-GTP
Molecular Formula
C17H17N6O15P3 • 4Na
Formula Weight
730.2
Purity
≥95% (mixture of isomers)
Emission
428 nm
Excitation
330 nm
Formulation (Request formulation change)
A solution in water
Solubility(Learn about Variance in Solubility)
Water: Soluble
SMILES
O[C@@H]1[C@H](OC(C2=C(N)C=CC=C2)=O)[C@@H](COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O)O[C@H]1N3C(NC(N)=NC4=O)=C4N=C3.O[C@@H]5[C@@H](COP(OP(OP([O-])([O-])=O)([O-])=O)([O-])=O)O[C@@H](N6C(NC(N)=NC7=O)=C7N=C6)[C@@H]5OC(C8=C(N)C=CC=C8)=O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/2C17H21N6O15P3.8Na/c18-8-4-2-1-3-7(8)16(26)36-12-9(5-34-40(30,31)38-41(32,33)37-39(27,28)29)35-15(11(12)24)23-6-20-10-13(23)21-17(19)22-14(10)25;18-8-4-2-1-3-7(8)16(26)36-12-11(24)9(5-34-40(30,31)38-41(32,33)37-39(27,28)29)35-15(12)23-6-20-10-13(23)21-17(19)22-14(10)25;;;;;;;;/h2*1-4,6,9,11-12,15,24H,5,18H2,(H,30,31)(H,32,33)(H2,27,28,29)(H3,19,21,22,25);;;;;;;;/q;;8*+1/p-8/t2*9-,11-,12-,15-;;;;;;;;/m11......../s1
InChi Key
QPOHPZRXQPNOLA-RZIDVFHFSA-F
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    3.2 mg

    $369

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    Product Description

    2'(3')-O-Anthraniloylguanosine-5'-O-triphosphate (2'-ANT-GTP) and 3'-ANT-GTP are fluorescent GTP derivatives, which undergo spontaneous isomerization.1 2'(3')-ANT-GTP displays an emission maximum of 428 nm upon excitation at 330 nm in water.2 It inhibits mammalian adenylyl cyclase 1 (AC1; Ki = 10 nM in the presence of manganese), B. anthracis AC toxin edema factor (Kis = 4.1 and 13 µM in the presence of manganese and magnesium, respectively), and B. pertussis AC toxin CyaA (Ki = 29 µM in the presence of manganese).1,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pinto, C., Lushington, G.H., Richter, M., et al. Structure-activity relationships for the interactions of 2'- and 3'-(O)-(N-methyl)anthraniloyl-substituted purine and pyrimidine nucleotides with mammalian adenylyl cyclases. Biochem. Pharmacol. 82(4), 358-370 (2011).

    2. 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).

    3. Taha, H.M., Schmidt, J., Göttle, M., et al. Molecular analysis of the interaction of anthrax adenylyl cyclase toxin, edema factor, with 2'(3')-O-(N-(methyl)anthraniloyl)-substituted purine and pyrimidine nucleotides. Mol. Pharmacol. 75(3), 693-703 (2009).

    4. Göttle, M., Dove, S., Steindel, P., et al. Molecular analysis of the interaction of Bordetella pertussis adenylyl cyclase with fluorescent nucleotides. Mol. Pharmacol. 72(3), 526-535 (2007).