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Antitumor activities of O-sulfonated derivatives of (1-->3)-alpha-D-glucan from different Lentinus edodes.

Four water-insoluble (1-->3)-alpha-D-glucans, coded L-II1, L-II2, L-II3 and L-II4, with different molecular weights were isolated from four kinds of fruiting bodies of Lentinus Edodes. The four alpha-D-glucans were O-sulfonated to obtain derivatives (SL-II) having degrees of substitution (DS) from 0.9 to 2.1 respectively. The structure of the samples was analyzed by infrared spectra, elemental analysis, and 13C NMR. The weight-average molecular weight (Mw), radii of gyration ( z1/2) and intrinsic viscosity ([eta]) of the native alpha-D-glucans and O-sulfonated derivatives were measured by size-exclusion chromatography combined with laser light scattering (SEC-LLS), LLS, and viscometry in 0.2 M aqueous NaCl and in dimethyl sulfoxide (DMSO) containing 0.25 M LiCl at 25 degrees C respectively. The Mw values of the O-sulfonated derivatives were much lower than those of the native alpha-D-glucans. The experimental results indicate that the O-sulfonated derivatives are water-soluble and exist as an expanded flexible chain in aqueous solution owing to intramolecular hydrogen bonding or interaction between charge groups. The in vivo and in vitro antitumor activities of the native alpha-D-glucans and their O-sulfonated derivatives against solid tumor Sarcoma 180 cells were evaluated and compared. Interestingly, all of the O-sulfonated derivatives exhibited higher antitumor activities than those of the native glucans. The results reveal that the effect of O-sulfonation of the alpha-D-glucan on the improvement of their antitumor activities was considerable.

Animals↗

[Antifungal activity of sulfonated shale oils].

Bituminous shale, developed from marine sediments during the Jura era, is the raw substance for the production of shale oil. The shale oil undergoes heating, distillation, fractionated refining and sulfonation (according to a patented method) resulting in water-soluble sulfonated shale oils (Ichthyol) for medical purposes. The antifungal effect of sulfonated shale oils have been described earlier. In this study an in vitro method is applied which is based upon the CO2 detection as a measure for the sensitivity of fungi to sulfonated shale oils. In addition to the minimal inhibitory concentration values (MIC values), sub-inhibitory concentrations are also determined. The actual efficacy of these antifungal agents is demonstrated via dose-effect curves. Our results show that the fractions of sulfonated shale oils refined at 150 to 210 degrees C (Ichthyol, dark) are fungicidal in concentrations between 0.2 and 16.8% for yeasts, dermatophytes and other hyphomycetes. The fractions of sulfonated shale oils refined at 85 to 150 degrees C (Ichthyol, light), on the other hand, showed a clearly higher antifungal activity (concentrations between 0.1 and 5.9%) for all fungi tested. An extended exposition (24 to 168 h) of Candida albicans to these fractions resulted in a further increase of fungicidal activity. Due to the complex nature of sulfonated shale oils the chemically defined antifungal substance(s) have not yet been identified.

Antifungal Agents↗

Effect of some sulfonate analogues of ursodeoxycholic acid on biliary lipid secretion in the rat.

The effect of the sulfonate analogues of ursodeoxycholic acid, namely sodium 3 alpha,7 beta-dihydroxy-24-nor-5 beta-cholane-23-sulfonate (norUDC-SO3Na) and sodium 3 alpha, 7 beta-dihydroxy-5 beta-cholane-24-sulfonate (UDC-SO3Na), on biliary lipid secretion was studied in bile fistula rats. During intravenous infusion of the two sulfonate analogues, bile flow and biliary lipid secretion were stimulated in a dose-dependent manner. This suggests that the analogues exert an effect on biliary lipid secretion comparable to that of the naturally occurring bile acid, ursodeoxycholyltaurine (UDC-tau). The effects of norUDC-SO3Na and UDC-SO3Na on bile flow were similar but slightly smaller than that of UDC-tau. The output of bile salts was similar with both sulfonates but greater than that with UDC-tau. The infusion of norUDC-SO3Na or UDC-SO3Na induced cholesterol secretion and phospholipid secretion more significantly than UDC-tau infusion. The increase in phospholipid secretion was particularly pronounced during high-dose administration of norUDC-SO3Na. Although norUDC-SO3Na stimulated cholesterol secretion more intensely than the other two bile salts, it also facilitated phospholipid output, perhaps as a compensatory mechanism, and the biliary cholesterol/phospholipid ratio was decreased to a greater extent by the sulfonates than by UDC-tau. Consequently, the administration of norUDC-SO3Na or UDC-SO3Na produces a more "stable" bile than UDC-tau, suggesting that these sulfonates possess potential cholelitholytic activity.

Animals↗

Sulindac sulfone inhibits azoxymethane-induced colon carcinogenesis in rats without reducing prostaglandin levels.

Nonsteroidal anti-inflammatory drugs (NSAIDs), such as sulindac, have cancer chemopreventive properties by a mechanism that has been suggested to involve cyclooxygenase inhibition and reduction of prostaglandin (PGE2) levels in the target tissue. To test this hypothesis, we studied the effect of dietary sulindac sulfone (500-2000 ppm), a metabolite of sulindac reported to lack cyclooxygenase inhibitory activity, on tumor formation and PGE2 levels in the azoxymethane model of colon carcinogenesis. Rats treated with sulindac at 400 ppm and piroxicam at 150 ppm were used as positive controls. Rats received two s.c. injections of azoxymethane (15 mg/kg) for 2 weeks and were fed either experimental or control diets until necropsy. After 31 weeks of sulfone treatment, a dose-related increase in sulfone levels in both serum and cecal contents was measured; there was no evidence of metabolic conversion to sulindac or other metabolites. Rats treated with sulfone at 1000 and 2000 ppm, sulindac, and piroxicam had significantly fewer colonic adenomas and carcinomas compared with rats fed control diet as measured by tumor incidence, multiplicity, and tumor burden. Sulfone-treated rats also showed a dose-response relationship for inhibiting all tumor parameters. Colons from rats treated with sulindac or piroxicam contained PGE2 levels that ranged from approximately 16-49% of control levels. PGE2 levels in rats treated with sulfone up to 2000 ppm ranged from 78-118% of control levels. Moreover, the effects of sulindac sulfone on various enzymes responsible for regulating prostaglandin levels were evaluated. No significant inhibitory effects were observed for cyclooxygenase, lipoxygenase, or phospholipase A2. These results suggest that reduction of prostaglandin levels in the target tissue may not be necessary for the chemopreventive properties of sulindac.

Animals↗

Morphogenetic control of calcite crystal growth in sulfonic acid based hydrogels.

In this paper the mineralization of CaCO(3) in various hydrogel matrices is presented. Sulfonic acid based hydrogels were prepared by introduction of sulfonate-containing monomers into a polyacrylamide network. The sulfonate content of polyacrylamide-co-vinylsulfonate and polyacrylamide-co-allylsulfonate decreases during elution of the copolymers in demineralized water, indicating insufficient linking of the sulfonate-bearing monomers within the hydrogel. In contrast to this, acrylamidomethylpropanesulfonate (AMPS) effectively copolymerizes with acrylamide (AAm) monomers. To study the influence of spatial arrangement of ionic functional groups within hydrogel networks on the mineralization of CaCO(3), AMPS copolymers with different degrees of AMPS cross-linking were synthesized. For the mineralization experiments the copolymers were placed into a double-diffusion arrangement. Calcite as the thermodynamically stable modification of CaCO(3) was obtained with a particular morphology. The pseudocubic habitus resembles aggregates obtained by mineralization in pure polyacrylamide. However, closer examination of the aggregates by scanning electron microscopy (SEM) shows that the crystal growth in the AMPS copolymers is different from that observed in polyacrylamide. Whereas the morphology of the calcite aggregates could be fine-tuned by using copolymers with different sulfonate content, the spatial distribution of the ionic functional groups alters the course of crystallization. Calcium ions are locally accumulated due to the heterogeneous distribution of functional sulfonate groups within the copolymer network. Thereby the nucleation of calcite is triggered, resulting in enhanced mineralization.

Calcium Carbonate↗

Physical and blood-contacting properties of polyurethanes based on a sulfonic acid-containing diol chain extender.

Polyurethanes chain extended with N,N-bis (2-hydroxyethyl)-2-aminoethane-sulfonic acid (BES) were synthesized. The effect of the sulfonic acid group on the polymers' bulk, surface, and blood-contacting properties was evaluated by comparing the BES-based polymers with polyurethanes based on N-ethyldiethanolamine (EDEA). In addition, the effect of soft-segment polarity was addressed by comparing polyurethanes based on polytetramethylene oxide (PTMO) (MW = 1000) with polymers based on polyethylene oxide (PEO) (MW = 1000). The EDEA control samples had physical properties similar to a viscous fluid. The presence of the sulfonic acid group dramatically enhanced the degree of microphase separation and the mechanical strength of all the polymers. The more polar PEO soft segment resulted in polymers which were more phase mixed than the PTMO-based polyurethanes. Surface characterization studies revealed that in vacuum, all the surfaces were enriched in the polyether soft-segment phase. After 24-h equilibration in water, all the surfaces had similar surface polarities independent of the SO3H content. The canine ex vivo blood-contacting results showed that the sulfonic acid group in the PTMO-based polymers significantly reduced the number and activation of the adherent platelets. Fibrinogen deposition, however, increased with increasing sulfonic acid content. In contrast, platelet and fibrinogen deposition on the sulfonic acid-containing PEO-based polymers was greatly enhanced.

Adsorption↗

Tandem mass spectra of divalent metal ion adducts of glycosyl sulfides, sulfoxides and sulfones; distinction among stereoisomers.

The tandem mass spectra of the divalent metal ion (Mg2+, Ca2+, Sr2+, Ba2+, Mn2+, Ni2+, Co2+ and Zn2+) adducts of acetylated 1,2-trans-glycosyl sulfides, sulfoxides and sulfones were examined using low energy collision-induced dissociation on a Quattro II quadrupole tandem mass spectrometer. Abundant doubly charged ions, such as [3M + Met]2+ and [2M + Met]2+, were observed with alkaline earth metal chlorides. The other ions observed were [M + MetCl]+, [M + MetOAc]+, [M + MetO2SPh]+ and [2M + MetCl]+. The deprotonated metal adducts [M + Met-H]+ were seen only in the sulfones. The divalent metal ion adducts showed characteristic fragmentation pathways for the glycosyl sulfides, sulfoxides and sulfones, depending on the site of metal attachment. The doubly charged metal ion adducts dissociate to two singly charged ions, [M + MetOAc]+ and [M - OAc]+, in the sulfides and sulfoxides. In the sulfones, the adducts dissociate to [M + MetO2SPh]+ and [M - O2SPh]+. In contrast to the alkaline earth metals, which attach to the acetoxy functions, the transition metals attach to the sulfide and sulfoxide functions. The metal chloride adducts display characteristic fragmentation for the sulfides, sulfoxides and sulfones. The glucosyl, mannosyl and galactosyl sulfides, sulfoxides and sulfones could be differentiated on the basis of the stereochemically controlled MS/MS fragmentations of the metal chloride adducts.

Chlorides↗

Recombinant human insulin. VIII. Isolation of fusion protein--S-sulfonate, biotechnological precursor of human insulin, from the biomass of transformed Escherichia coli cells.

Various methods have been investigated for the isolation and purification of fusion proteins of precursors of human insulin in the form of S-sulfonates, from the biomass of transformed Escherichia coli cells. Fusion proteins were prepared with different sizes and structures of the leader peptide and the poly-His position (inserted for purification by metal chelate affinity chromatography). The fusion proteins contained an IgG-binding B domain of protein A from Staphylococcus aureus at the N-terminus and an Arg residue between the leader peptide of the molecule and the proinsulin sequence, for trypsin cleavage of the leader peptide. Six residues of Cys in proinsulin allow the chemical modification of the protein as a (Cys-S-SO(-)(3))(6) derivative (S-sulfonate), which increases its polyelectrolytic properties and improves the efficiency of its isolation. Various methods of oxidative sulfitolysis were compared with catalysis by sodium tetrathionate or cystine and Cu2+ or Ni2+ ions. An optimum scheme for the isolation and purification of S-sulfonated fusion proteins was developed by the combination of metal-chelating affinity and ion-exchange chromatography. Highly purified (95%) S-sulfonated fusion protein was recovered which was 85% of the fusion protein contained in the biomass of E. coli cells. Folding of fusion protein S-sulfonate occurred with high yield (up to 90-95%). We found that the fusion protein-S-sulfonate has proinsulin-like secondary structure. This structure causes highly efficient fusion protein folding.

Amino Acid Sequence↗

S-sulfonate contents in raw and cooked meat products.

S-Sulfonates (R-S-SO3-) are compounds formed by the reaction between the sulfites added to foodstuffs and the disulfide bonds of cystine, peptides, and proteins. The content of S-sulfonates has been determined in raw sausages and burgers (n = 62). The range of variation in the contents of the determined S-sulfonates is very wide and varies between 47 and 267 microg of SO2/g. The degree of formation of S-sulfonates with regard to the determined sulfite (total SO2 + S-sulfonates) is similar in all of the samples and does not seem to be conditioned by the meat compound (chicken or beef) or by the process of elaboration or type of product (burgers or sausages). In grilled burgers (n = 20) significant losses are produced in the levels of the additive in any of its forms. The value for the S-sulfonates is 31 +/- 9.8%, 29 +/- 6.6% corresponding to the free sulfite and a very similar percentage to the total sulfite (free + reversibly bound) 28 +/- 6.7%. It is possible that during the cooking process cleavages of some bound compounds occur, releasing SO2 and reacting to form new adducts.

Animals↗

Controlling {beta}-amyloid oligomerization by the use of naphthalene sulfonates: trapping low molecular weight oligomeric species.

Aggregation of proteins and peptides has been shown to be responsible for several diseases known as amyloidoses, which include Alzheimer disease (AD), prion diseases, among several others. AD is a neurodegenerative disorder caused primarily by the aggregation of beta-amyloid peptide (Abeta). Here we describe the stabilization of small oligomers of Abeta by the use of sulfonated hydrophobic molecules such as AMNS (1-amino-5-naphthalene sulfonate); 1,8-ANS (1-anilinonaphthalene-8-sulfonate) and bis-ANS (4,4'-dianilino-1,1'-binaphthyl-5,5'-disulfonate). The experiments were performed with either Abeta-1-42 or with Abeta-13-23, a shorter version of Abeta that is still able to form amyloid fibrils in vitro and contains amino acid residues 16-20, previously shown to be essential to peptide-peptide interaction and fibril formation. All sulfonated molecules tested were able to prevent Abeta aggregation in a concentration dependent fashion in the following order of efficacy: 1,8-ANS < AMNS < bis-ANS. Size exclusion chromatography revealed that in the presence of bis-ANS, Abeta forms a heterogeneous population of low molecular weight species that proved to be toxic to cell cultures. Since the ANS compounds all have apolar rings and negative charges (sulfonate groups), both hydrophobic and electrostatic interactions may contribute to interpeptide contacts that lead to aggregation. We also performed NMR experiments to investigate the structure of Abeta-13-23 in SDS micelles and found features of an alpha-helix from Lys(16) to Phe(20). 1H TOCSY spectra of Abeta-13-23 in the presence of AMNS displayed a chemical-shift dispersion quite similar to that observed in SDS, which suggests that in the presence of AMNS this peptide might adopt a conformation similar to that reported in the presence of SDS. Taken together, our studies provide evidence for the crucial role of small oligomers and their stabilization by sulfonate hydrophobic compounds.

Amyloid↗

Utilisation of aminomethane sulfonate by Chromohalobacter marismortui VH1.

Chromohalobacter marismortui VH1 was screened for its ability to utilise organosulfonate compounds at a range of NaCl concentrations. Only aminomethane sulfonate, of seven sulfonates tested, was utilised. Length of lag phase during growth on aminomethane sulfonate, as either nitrogen and/or sulfur source, increased with increasing NaCl concentration. Cell yields increased linearly with increasing aminomethane sulfonate concentration up to 5 mM. Resting cells pregrown on aminomethane sulfonate as sole nitrogen source exhibited carbon-sulfur bond cleaving [0.123 nmol sulfate accumulated h(-1) (mg cells)(-1)] and sulfite-oxidising [0.185 nmol sulfate accumulated h(-1) (mg cells)(-1)] activities. C. marismortui VH1 is capable of sulfur-starvation deregulated metabolism of aminomethane sulfonate under high salt conditions.

Biodegradation, Environmental↗

Sulfone metabolite of fipronil blocks gamma-aminobutyric acid- and glutamate-activated chloride channels in mammalian and insect neurons.

Fipronil sulfone, a major metabolite of fipronil in both insects and mammals, binds strongly to GABA receptors and is thought to play a significant role in poisoning by fipronil. To better understand the mechanism of selective insecticidal action of fipronil, we examined the effects of its sulfone metabolite on GABA- and glutamate-activated chloride channels (GluCls) in cockroach thoracic ganglion neurons and on GABA(A) receptors in rat dorsal root ganglion neurons using the whole-cell patch-clamp technique. Fipronil sulfone blocked both desensitizing and nondesensitizing GluCls in the cockroach. Activation was required for block and unblock of desensitizing GluCls. In contrast, activation was not prerequisite for block and unblock of nondesensitizing channels. After repetitive activation of the receptors, the IC50 of fipronil sulfone to block the desensitizing GluCls was reduced from 350 to 25 nM and that for blocking nondesensitizing GluCls was reduced from 31.2 to 8.8 nM. This use-dependent block may be explained by its slow unbinding rate. In cockroach and rat neurons, fipronil sulfone blocked GABA receptors in both activated and resting states, with IC50 values ranging from 20 to 70 nM. In conclusion, although fipronil sulfone is a potent inhibitor of cockroach GABA receptors, desensitizing and nondesensitizing GluCls, and rat GABA(A) receptors, its selective toxicity in insects over mammals appears to be associated with its potent blocking action on both desensitizing and nondesensitizing GluCls, which are lacking in mammals.

Animals↗

Comparative effects of sulfones and rifampin on growth of Mycobacterium lepraemurium in macrophage diffusion chamber cultures.

A cell-impermeable diffusion chamber technique has been developed that lends itself to growth studies of Mycobacterium lepraemurium. This technique, in which the organism grows within macrophage cultures inside the chambers that are maintained on monolayer cultures of macrophages, provides a method for a strict in vitro evaluation of antileprosy drugs without the influence of a multiplicity of host factors. This system was used to compare the effect of three sulfone derivatives and rifampin on the growth of M. lepraemurium within these diffusion chamber cultures. Two sulfones, 4,4'-diaminodiphenyl sulfone and 4,4'-diacetamidodiphenyl sulfone, as well as rifampin, suppressed the growth of M. lepraemurium, but monoacetyl sulfone 4-amino-4'acetamidodiphenyl sulfone had no effect. The results indicate that the diffusion chamber technique can be used to evaluate the inhibitory effect of antileprosy drugs on the growth of M. lepraemurium. Also, the method provides for the first time a relatively rapid in vitro method for directly comparing the effects of drugs or their analogs when outside the metabolic influence of an animal host. This technique may be a useful tool for chemotherapy studies with other antileprosy compounds.

Animals↗

Structure-activity relationships for inhibition of cysteine protease activity and development of Plasmodium falciparum by peptidyl vinyl sulfones.

The Plasmodium falciparum cysteine proteases falcipain-2 and falcipain-3 appear to be required for hemoglobin hydrolysis by intraerythrocytic malaria parasites. Previous studies showed that peptidyl vinyl sulfone inhibitors of falcipain-2 blocked the development of P. falciparum in culture and exerted antimalarial effects in vivo. We now report the structure-activity relationships for inhibition of falcipain-2, falcipain-3, and parasite development by 39 new vinyl sulfone, vinyl sulfonate ester, and vinyl sulfonamide cysteine protease inhibitors. Levels of inhibition of falcipain-2 and falcipain-3 were generally similar, and many potent compounds were identified. Optimal antimalarial compounds, which inhibited P. falciparum development at low nanomolar concentrations, were phenyl vinyl sulfones, vinyl sulfonate esters, and vinyl sulfonamides with P(2) leucine moieties. Our results identify independent structural correlates of falcipain inhibition and antiparasitic activity and suggest that peptidyl vinyl sulfones have promise as antimalarial agents.

Animals↗

Surface characterization and platelet compatibility evaluation of surface-sulfonated chitosan membrane.

The effect of various sulfonated derivatives of chitosan on platelet activation and blood coagulation was examined. The surface properties of artificial biomaterials have been thought as the key factors which mediate the interactions between the biological environment and biomaterial itself. In this study, the sulfonation was directly performed on the chitosan membrane surface. The chitosan membrane was surface-sulfonated by reactions with sulfur-pyridine trioxide complex (SO3/pyridine) in H2O solution and N,N-sulfur-dimethylformamide trioxide complex (SO3/DMF) in DMF. Blood compatibility was evaluated by an in vitro platelet adhesion assay. The surface reaction of SO3/pyridine in aqueous acid medium yields N,O-sulfated chitosan with cationic NH3+ groups. After neutralization, this surface has been shown to induce a low degree of platelet adhesion and activation. When the surface-sulfonation is performed in an aqueous alkaline medium, although the degree of sulfonation is lower than the samples above, the N-sulfated chitosan significantly reduced the adhesion and activation of platelets. For the acidic SO3/DMF reaction system, N,O-sulfated chitosan was obtained with a high extent of sulfonation and cationic NH3+ groups. On this surface fully spread platelets and some platelet aggregates were found instead. This may be attributed to the ionic interactions between the platelets membrane surface and the cationic groups on the modified chitosan membrane.

Biocompatible Materials↗

Conversion of cloxacillin into a progressive inhibitor of beta-lactamases by sulfonation and its activity against various types of these enzymes.

On the assumption of the theory that the sulfone of a penam derivative should effectively act as a suicide substrate against beta-lactamases to which the parent compound is a poor substrate, the action of cloxacillin sulfone on four different types of beta-lactamases was studied. As we expected, cloxacillin sulfone showed strong mechanism-based irreversible inactivation against type Ib penicillinase and Proteus vulgaris cephalosporinase whereas it showed no progressive inactivation against cloxacillin-hydrolyzing type II penicillinase. However, an unexpected result was that cloxacillin sulfone could not inactivate Citrobacter freundii cephalosporinase which itself could hardly hydrolyze the parent cloxacillin. The number of hydrolytic events which occurred before inactivation of type Ib penicillinase, and P. vulgaris cephalosporinase, by the inactivator was 190 and 13, respectively. These values indicate that cloxacillin sulfone is far more effective as a suicide substrate against the two types of beta-lactamases than penam sulfones so far reported. The inactivation proceeded via the formation of an irreversible enzyme-inhibitor complex which could be detected by isoelectric focusing.

Cloxacillin↗

Biostability and blood-contacting properties of sulfonate grafted polyurethane and Biomer.

Sulfonate-containing polyurethanes were evaluated for in vivo biodegradation using subcutaneously implanted tensile bars. In addition, these anionically charged polyurethanes were evaluated for in vivo activation of human complement C3a and ex vivo platelet deposition in arteriovenously-shunted canines. The sulfonate derivatized polymers included laboratory synthesized polyurethane and Biomer. Other polymers used for references included Intramedic polyethylene, Silastic and a poly(ethylene oxide) based polyurethane. The biodegradation results indicated that Biomer and the laboratory sulfonated Biomer (both manufactured with stabilizers), remained mechanically stable, retaining both tensile strength and elasticity after 4 weeks of subcutaneous implantation. The unstabilized polyurethanes (with or without sulfonation), however, showed marked cracking and a loss of mechanical properties after the same period of subcutaneous implantation. Sulfonated polyurethanes depressed human complement C3a activation in plasma, as indicated by decreased levels of anaphylatoxin production. The results of canine ex vivo blood contacting experiments were conducted in both an acute and chronic model and demonstrated decreased platelet deposition and activation for the sulfonated polyurethanes.

Absorption↗

[Spectral evidences for aggregation of sulfonated naphthalocyanine zinc (II) and cobalt (II)].

When the naphthalocyanines were sulfonated to give sulfonated naphthalocyanine cobalt (II) and sulfonated naphthalocyanine zinc (II), enhanced aggregation tendency was observed. The Q band of the fluorescence emission spectra and electronic absorption spectra for sulfonated naphthalocyanine zinc (II) and sulfonated naphthalocyanine cobalt (II) in the solutions of DMF and ethanol showed that the excimer or the aggregation form coexists with the monomer, that the aggregation form dissociates into its monomer when the excimer releases a photon or the ground aggregation form absorbs a photon, and that mirror symmetry exists between the fluorescence emission spectrum of the excimer and the electronic absorption spectrum of the corresponding ground aggregation form. There is a red shift for the excimer in the fluorescence emission spectrum and a blue shift for the aggregation form in the electronic absorption spectrum of the Q band. The quenching effect in fluorescence emission spectrum is large when the concentration of sulfonated naphthalocyanine cobalt (II) is high.

Cobalt↗