8-[Fluo]-cAMP

• CAS: 293296-57-8
• Catalog Number: ACM293296578
• Category: Main Products
• Molecular Weight: 815.7
• Molecular Formula: C33H2NO11PS2·Na
• Synonyms: 8- (2- [Fluoresceinyl]aminoethylthio)adenosine- 3', 5'- cyclic monophosphate sodium salt
• Appearance: White powder

Case Study

8-[Fluo]-cAMP: a Fluorescent Probe for Oat3/Mrp4 Efflux Activity at the Inner Blood-Retinal Barrier

Tajima, Kosuke, et al. Journal of Controlled Release 343 (2022): 434-442.

This study described the use of 8-[Fluo]-cAMP, a fluorescent adenosine-3',5'-cyclic monophosphate derivative, as a functional probe to evaluate organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4) activity at the inner blood-retinal barrier (BRB).
Fresh retinal capillaries were prepared from rat retinae using serial filtration and density-gradient centrifugation without enzymatic digestion or freezing, preserving native capillary structure. Marker expression (for example, facilitative glucose transporter-1 and claudin-5) was confirmed by RT-PCR and immunostaining to verify endothelial and barrier identity. Functional assays employed fluorescent transporter substrates (including 8-[Fluo]-cAMP) to measure luminal accumulation within the intact capillary lumen; changes in accumulation in the presence of known transporter substrates or inhibitors were used to attribute activity to specific transporters.
8-[Fluo]-cAMP was used as a fluorescent probe whose luminal accumulation in freshly isolated retinal capillaries responds to modulation of Oat3 and Mrp4. The study reported that luminal accumulation of 8-[Fluo]-cAMP decreased when Oat3 and Mrp4 substrates/inhibitors were applied, indicating that its translocation across capillary endothelium is mediated, at least in part, by these transporters. In this experimental context, 8-[Fluo]-cAMP functioned as a practical readout of SLC (Oat) and ABC (Mrp) transporter activities at the inner BRB.

Application of 8-[Fluo]-cAMP in a Sensitive FRET-Based Assay for Characterizing Cyclic Nucleotide-Binding Domains

Romero, Francisco, et al. FEBS letters 591.18 (2017): 2869-2878.

Characterizing the molecular interactions between cyclic nucleotide-binding domains (CNBDs) and their ligands is fundamental to understanding cellular signaling pathways. This study examined the development and advantages of a fluorescence resonance energy transfer (FRET)-based binding assay utilizing 8-(2-[Fluoresceinyl]aminoethylthio) adenosine-3', 5'-cyclic monophosphate (8-[Fluo]-cAMP) as a key fluorescent probe.
Assay Design: The assay pairs CFP fused to a CNBD (serving as the FRET donor) with 8-[Fluo]-cAMP (the acceptor). Upon ligand binding, close proximity between CFP and the fluorescein label produces efficient FRET that can be measured ratiometrically on standard fluorescence readers.
Performance: The CFP-CNBD / 8-[Fluo]-cAMP FRET pair resulted in ~80% energy transfer, which enabled high detection power for binding events. The high brightness of 8-[Fluo]-cAMP enabled measurements of binding at low (nanoM) concentrations of both ligand and protein with conventional laboratory fluorescence instruments. The CFP fusion allowed specific binding measurements even without full purification of the CNBD, simplifying workflows and lowering material needs.

Custom Q&A

What is the molecular formula of 8-[Fluo]-cAMP?

The molecular formula of 8-[Fluo]-cAMP is C33H27N7O11PS2-.

What is the molecular weight of 8-[Fluo]-cAMP?

The molecular weight of 8-[Fluo]-cAMP is 792.7 g/mol.

What is the parent compound of 8-[Fluo]-cAMP?

The parent compound of 8-[Fluo]-cAMP is not mentioned in the reference.

When was 8-[Fluo]-cAMP created?

8-[Fluo]-cAMP was created on March 25, 2017.

When was 8-[Fluo]-cAMP last modified?

8-[Fluo]-cAMP was last modified on October 21, 2023.

What is the IUPAC name of 8-[Fluo]-cAMP?

The IUPAC name of 8-[Fluo]-cAMP is 5-[2-[6-amino-9-(7-hydroxy-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)purin-8-yl]sulfanylethylcarbamothioylamino]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid.

What is the InChI of 8-[Fluo]-cAMP?

The InChI of 8-[Fluo]-cAMP is InChI=1S/C33H28N7O11PS2/c34-28-25-29(37-13-36-28)40(30-26(43)27-23(50-30)12-48-52(46,47)51-27)33(39-25)54-8-7-35-32(53)38-14-1-4-17(20(9-14)31(44)45)24-18-5-2-15(41)10-21(18)49-22-11-16(42)3-6-19(22)24/h1-6,9-11,13,23,26-27,30,41,43H,7-8,12H2,(H,44,45)(H,46,47)(H2,34,36,37)(H2,35,38,53)/p-1.

What is the InChIKey of 8-[Fluo]-cAMP?

The InChIKey of 8-[Fluo]-cAMP is CQCCASCBDPGSNI-UHFFFAOYSA-M.

What is the canonical SMILES of 8-[Fluo]-cAMP?

The canonical SMILES of 8-[Fluo]-cAMP is C1C2C(C(C(O2)N3C4=NC=NC(=C4N=C3SCCNC(=S)NC5=CC(=C(C=C5)C6=C7C=CC(=O)C=C7OC8=C6C=CC(=C8)O)C(=O)O)N)O)OP(=O)(O1)[O-].

How many hydrogen bond donor count does 8-[Fluo]-cAMP have?

8-[Fluo]-cAMP has 6 hydrogen bond donor counts.