77840-23-4

Usage

InChI:InChI=1/C20H31N3O2S/c1-23(2)19-13-9-12-18-17(19)11-10-14-20(18)26(24,25)22-16-8-6-4-3-5-7-15-21/h9-14,22H,3-8,15-16,21H2,1-2H3

Upstream product

• 373-44-4 1,8-diaminooctan 
• 605-65-2 5-(dimethylamino)naphth-1-ylsulfonyl chloride 
• 1431-39-6 dansylamide 
• 17702-83-9 N-8-bromooctylphthalimide 
• 219981-97-2 5-Dimethylamino-naphthalene-1-sulfonic acid [8-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-octyl]-amide 

Relevant academic research and scientific papers

Fluorescent probes for cytochrome P450 structural characterization and inhibitor screening

We have synthesized two luminescent probes (D-4-Ad and D-8-Ad) that target cytochrome P450cam. D-4-Ad luminescence is quenched by Foerster energy transfer upon binding (Kd = 0.83 μM) but is restored when the probe is displaced from the active site by camphor. In contrast, D-8-Ad (Kd ≈ 0.02 μM) is not displaced from the enzyme, even in the presence of a large excess of camphor. The 2.2 A resolution crystal structure of the D-8-Ad:P450cam complex reveals extensive hydrophobic contacts between the probe and the enzyme, which result from the conformational flexibility of the B-, F, and G helices. Probes with properties similar to those of D-4-Ad potentially could be useful for screening P450 inhibitors. Copyright

Solvatochromic characteristics of dansyl molecular probes bearing alkyl diamine chains

A series of dansyl-based fluorescent probes bearing linear alkyl-1,n-diamine chains of different length (DA1.n, n = 2–8, 10, 12) was characterized in terms of the absorptive and emissive features in solvents of different polarity and hydrogen bond donor/hydrogen bond acceptor character. The probes show solvent-dependent absorption, a feature that is uncommon among dansyl derivatives. The dual emission of DA1.n probes is strong in non-aqueous solvents and is influenced by the chain length and interactions with the solvent. Solvent effects on the spectral parameters were rationalized on the basis of the Kamlet-Taft and Catalán solvatochromic models, in order to quantify the degree of polarity-driven and hydrogen bonding interactions. A comparative discussion of the results predicted by the two models was made. In ground state, the DA1.n probes act as hydrogen bond acceptors. In excited state, hydrogen bonding is less favoured, the solute-solvent interactions being governed by the increasing polarity of the solvent that results in a large bathochromic shift of the emission. A comparison was made with the spectral features previously reported for the corresponding series of bis-dansyl fluorescent probes (2DA1.n).

Fluorescence anisotropy and mobility of dansyl fluorophore in labelled homologous alkanes

Using the steady-state and time-resolved fluorescence anisotropy, the mobility of 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl) fluorophore in homologous 1-[2-acetamido-3-(1H-indol-3-yl)propanamido[-n-]5-(dimethylamino)naphthalene-1-s ulfonamido]alkanes 1 was studied in binary solvents glycerol-water. Steady-state fluorescence data were evaluated by the generalized Perrin equation and the micro-Brownian motion of dansyl fluorophore was described by means of average characteristics (rotational relaxation times) of the rotational relaxation spectrum. The rotational relaxation time of "fast" motions caused by torsional vibrations of single bonds within the rotational-isomeric states decreases with increasing number of methylene groups in homologous compounds. The rotational relaxation time of "slow" motions due to conformational changes of the chain between the tryptophane and dansyl fluorophore remains at first approximately constant with increasing number of methylene groups but increases considerably for long aliphatic chains. The observed decrease in the rate of conformational changes of a long aliphatic chain is probably due to intramolecular interaction of parts of the methylene chain in a medium with high water content. The values of activation enthalpy ΔH+ and activation entropy ΔS≠ calculated from experimental data corroborate such interpretation. Time-resolved anisotropy of dansyl fluorophore at a particular binary solvent composition confirmed the shape of rotational relaxation spectrum and the measured rotational correlation times have been discussed. The time-dependent decays of anisotropy supported our previous interpretation in terms of intramolecular association of the long aliphatic chain in polar medium.

Fluorescent probes for adenosine receptors: Synthesis and biology of N6-dansylaminoalkyl-substituted NECA derivatives

New fluorescent ligands for adenosine receptors are described; these compounds were obtained by the insertion, in the N6 position of NECA (a potent adenosine agonist), of dansylaminoalkyl moieties with alkyl spacers of increasing carbon chain length (from 3 to 12). Among them, the compound with a C6 alkyl spacer proved to be the most interesting one, showing a marked selectivity for the A1 receptor subtype; furthermore, in fluorescence microscopy assays it proved to be able to visualize and localize this receptor subtype at the level of the molecular layer of the rat cerebellar cortex.