Amino-naphthalene sulfonates

EFFECT OF AMINO NAPHTHALENE SULFONIC ACID NATURE ON THE STRUCTURE AND PHYSICAL PROPERTIES OF THEIR COPOLYMERS WITH ANILINE... 

Effect of Amino Naphthalene Sulfonic Acid Nature... 

SCHEME 1 Chemical stmcture of amino naphthalene sulfonic acids... 

TABLE 2 Physical properties of copolymers of aniline with amino naphthalene sulfonic... 

Z. Wei and M. Wan, Synthesis and characterization of self-doped poly(aniline-co-amino-naphthalene sulfonic acid) nanotubes, J. Appl. Polym. Set, 87, 1297-1301 (2003). 

Anti-HIV agents N-acyl amino-naphthalene sulfonic acid derivatives... 

Amino-3-hydroxy-7-nitro-l-naphthalene-sulfonic acid [6259-63-8]... 

Abbreviations EPR, electron paramagnetic resonance FITC, fluorescein-5 -isothiocyanate lAEDANS, iV-iodoacetyl-N -(5-sulfo-l-naphthyl)ethylenediamine NCD, fluorescent yV-cyclohexyl-N -(4-dimethyl-amino-a-naphthyl)carbodiimide RITC, rhodamine-5 -isothiocyanate DPPE, dipalmitoylphosphatidyl-ethanolamine PE, egg phosphatidyl-ethanolamine ANS, 8-anilino-l-naphthalene sulfonate DPH, diphenylhexatriene e-ADP, l,iV -ethanoadenosine-5 -diphosphate TNP-ADP, 2 [3 ]-0-(2,4,6-trinitrophe-nyl)adenosine-5 -diphosphate. 

Proteases are enzymes that break peptide bonds in proteins. As such they lend themselves to a variety of homogeneous assay techniques. Most employ labeling both ends of the substrate with a different tag, and looking for the appearance (disappearance) of the signal generated in the intact substrate (product). As an example, for a fluorescence quench assay, the N-terminal of a peptide is labeled with DNP and the C-terminal with MCA. As such, the peptide is fluorescently silent since the fluorescence from DNP is quenched by absorption by the MCA. Another very popular donor/acceptor pair is EDANS 5-[(2-aminoethyl)amino] naphthalene-1-sulfonic acid and DABCYL 4-(4-dimethylaminophenylazo)benzoic acid) (a sulfonyl derivative (DABSYL) [27], Upon peptide cleavage, the two products diffuse, and due to a lack of proximity, the fluorescence increases. 

The amine-reactive 5-(dimethylamino)naphthalene-l-sulfonyl (dansyl) chloride 28 [80] and related fluorophores [81, 82], as well as the 5-((2 aminoethyl)amino) naphthalene-1-sulfonic acid (EDANS) 29, are included in the naphthalene fluorophore family. Derivatives of the latter, such as compound 30, exhibit a Lm.ix/ Lem 336/520 nm, molar absorptivity (e) of 6.1 x 103 M-1 cm-1, and a fluorescent quantum yield of 0.27 in water [83], The use of EDANS is particularly interesting in FRET experiments [84, 85]. Furthermore, 4-amino-3,6-disulfonylnaphthalimides (e.g., Lucifer yellow 31), associated to a longer absorption (Lmax 428 nm) [86] are suitable polar tracers [87]. 

Fig. 4 Optical reflectivity measurement (intensity vs temperature recorded at 1 K min-1) for [Fe(4-amino-1,2,4-triazole)3] (2-naphthalene sulfonate)2.xH20 (x=0, 2) ([31] (reproduced with permission of the Royal Society of Chemistry)...

V-octadecyl)amino-naphthalene-6-sulfonic acid, sodium salt. 7 3-palmitoyl-2-(l-pyrenedecanoyl)-L-a-phosphatidylcholine. 

Figure 15 Representative RP-HPLC Separation of the Tryptic/Chymotryptic Peptides of Bovine Thyrotropin p-Subunit bTSHfS Labeled In Situ with the Fluorescent Reagent 5-[(Iodoacetamidoethyl)amino]naphthalene-l-sulfonic acid (5-l-AEDANS) MI a b...

Heterocycles are known to have O—S, S—N, and O—N bonds. The cyclization of peri-hydroxy and peri-amino-substituted naphthalene sulfonic acids gives rise to 1,8-naphthosultone 246 and 1,8-naphthosultam 247, respectively (33MI2 63MI1). On gas phase photolysis of naphtho[/>c]-... 

Reaction of a similar triazine component with I acid (1-hydroxy-6-amino-naphthalene-3-sulfonic acid), followed by coupling with diazotized 4-aminoazo-benzene gives the cationic substantive azo dye 4 [71032-95-6], which colors paper in red hues. 

Abz was combined with a broad variety of non-fluorescent acceptors such as p-nitrobenzyl for leucine aminopeptidase (Carmel et al., 1977), pNA for trypsin (Bratanova and Petkov, 1987), 4-ni-trophenylalanine [Phe(NC>2)] for HIV protease (Toth and Marshall, 1990), and V-(2,4-di n itrophenyl) ethylenediamine (EDDnp) for thermolysin and trypsin (Nishino et al., 1992). Lecaille et al. (2003) described a FRET quench assay based on a specific substrate for cathepsin K labeled with Abz and EDDnp. This substrate is not cleaved by the other Cl cysteine cathepsins and serine proteases in contrast to methoxycoumarin (Mca)-based substrates described earlier (Aibe et al., 1996 Xia et al., 1999) and merely covered the non-primed site of the scissile bond. The 5-[(2-aminoethyl)amino] naphthalene-l-sulfonic acid (EDANS) compound is a second example of a fluorescence donor historically used for many FRET quench-based protease assays, e.g., in combination with tryptophan as a quencher in an ECE activity assay (Von Geldren et al., 1991). The FRET-1 example in Table 2.2 shows the typical dynamic range that can be achieved with an EDANS/DABCYL-based assay. 

Threading such an oriented ring onto a dumbbell end capped with two different stoppers will give rise to two diastereoisomers, as shown schematically in Figure 2.12c. Such rotaxanes were actually described by Isnin and Kaifer, and were characterized as CDX-positional isomers (Figure 2.17).41 Thus reaction of ferrocenyl derivative 40 (1 equiv) with 2 equiv of a-CDX, and potassium 5-amino-2-naphthalene sulfonate 41 in water, in the presence of EDC (EDC = l-(3-[dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride) as a catalyst, afforded a mixture of diastereoisomeric [2]-rotaxanes 42a and 42b in 15% yield and 6 4 ratio. 

When given orally, 8% of the amaranth is absorbed from the intestinal tract. Intestinal flora have a reducing effect on amaranth, and azo reduction is also mediated by the hepatic monooxygenase system. Aromatic amine metabolites, including 1-amino-4-naphthalene sulfonic acid and l-amino-2-hydro-xy-3,6-naphthalene disulfonic acid, are excreted in the urine and bile. 

Naphthalene Sulfonic Acid as a Reagent for Amino Acids. J. biol. 

An example of this technology is the HIV protease assay shown in Fig. 9, which was published by Wang and co-workers [67]. The peptide substrate is labeled at the amino terminus with EDANS (5-((2 -aminoethyl)amino)naphthalene-l-sulfonic acid) as a donor fluorophore and at the carboxyl terminus with DABCYL (4-((4 -(di-methylamino)phenyl)azo)benzoic acid) as the acceptor chromophore. In the intact peptide, fluorescence resonance energy transfer (FRET) from EDANS to DABCYL results in quenching of the EDANS fluorescence. On cleavage of the peptide by HIV protease, the fluorescence of EDANS is restored. 

EDANS 5-((2 -aminoethyl)amino)naphthalene-l-sulfonic acid... 

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