1234064-11-9

Basic information

• Product Name: FFN102
• Synonyms: FFN102;FFN-102 (trifluoroacetate salt)
• CAS NO: 1234064-11-9
• Molecular Formula: C13H11ClF3NO5
• Molecular Weight: 353.6783496
• Mol File: 1234064-11-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: FFN102(CAS DataBase Reference)
• NIST Chemistry Reference: FFN102(1234064-11-9)
• EPA Substance Registry System: FFN102(1234064-11-9)

Safety Data

• Hazardous Substances Data: 1234064-11-9(Hazardous Substances Data)

Usage

Description

FFN-102 is a fluorescent false neurotransmitter (FFN) that is a substrate for the dopamine transporter (DAT) and vesicular monoamine transporter 2 (VMAT2). It is a pH-dependent fluorescent probe that labels dopamine cell bodies, axons, and presynaptic terminals. It can also be used to monitor dopamine exocytosis. It has a pKa of 6.2 and displays pH-dependent excitation spectra of 340 and 370 nm at pH 5 and 7.4, respectively, which correspond to vesicular and cytoplasmic pH values. The emission spectrum of FFN-102 is pH-independent at 453 nm, but the intensity of emission is pH-dependent with a higher intensity at a pH of 7.4. FFN-102 inhibits DAT (13.6% at a concentration of 10 μM) and the serotonin (5-HT) receptor subtype 5-HT2c (Ki = ~3 μM) but does not bind to 37 other central nervous system receptors and transporters, including dopamine receptors, up to a concentration of 10 μM.

Upstream product

• 95-88-5 4-Chlororesorcinol 
• 141734-32-9 5-((tert-butoxycarbonyl)amino)-3-oxopentanoic acid methyl ester 
• 76-05-1 trifluoroacetic acid 

Relevant articles and documents

pH-responsive fluorescent false neurotransmitters and their use

This invention relates to compounds having the following structure: wherein Y is O, X is O, bond α is absent and bond β is present, or Y is H, X is CH, bond α is present, and bond β is absent; atom Z is a carbon and bonds χ, δ and γ are present, or atom Z is a nitrogen and bonds χ, δ and γ are absent, or atom Z is a nitrogen and bonds χ and δ are present and γ is absent. R1, R2, R3, R4, R5, and R6 are various substituents as described in the specification.

Development of pH-responsive fluorescent false neurotransmitters

We introduce pH-responsive fluorescent false neurotransmitters (pH-responsive FFNs) as novel probes that act as vesicular monoamine transporter (VMAT) substrates and ratiometric fluorescent pH sensors. The development of these agents was achieved by systematic molecular design that integrated several structural elements, including the aminoethyl group (VMAT recognition), halogenated hydroxy-coumarin core (ratiometric optical pH sensing in the desired pH range), and N- or C-alkylation (modulation of lipophilicity). Of 14 compounds that were synthesized, the probe Mini202 was selected based on the highest uptake in VMAT2-transfected HEK cells and desirable optical properties. Using Mini202, we measured the pH of catecholamine secretory vesicles in PC-12 cells (pH -5.9) via two-photon fluorescence microscopy. Incubation with methamphetamine led to an increase in vesicular pH (pH - 6.4), consistent with a proposed mechanism of action of this psychostimulant, and eventually to redistribution of vesicular content (including Mini202) from vesicles to cytoplasm. Mini202 is sufficiently bright, photostable, and suitable for two-photon microscopy. This probe will enable fundamental neuroscience and neuroendocrine research as well as drug screening efforts.