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PubMed2005

Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, IV, V, and IX with anions isosteric and isoelectronic with sulfate, nitrate, and carbonate.

The inhibition of five human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes; the cytosolic hCA I and II, the membrane-bound hCA IV, the mitochondrial hCA V, and the tumor-associated, transmembrane hCA IX, with anions isosteric and isoelectronic with sulfate, nitrate, and carbonate; such as chlorate, perchlorate, bromate, iodate, periodate, silicate, bismuthate, vanadate, molybdate, and wolframate is reported. Apparently, the geometry of the inhibitor (tetrahedral or trigonal) does not influence its binding to the Zn(II) ion of the enzyme active site, but the nature of the central element is the most important factor influencing potency. Isozymes hCA I and II are best inhibited by chlorate, perchlorate, and silicate, together with the anions structurally related to sulfate, sulfamate, and sulfamidate, but sulfate itself is a weak inhibitor (inhibition constant of 74 mM against hCA I and 183 mM against hCA II). Molybdate is a very weak hCA I inhibitor (K(I) of 914 mM) but it interacts with hCA II (K(I) of 27.5mM). Isozyme IV is well inhibited by sulfate (K(I) of 9 mM), sulfamate, and sulfamidate (in the low micromolar range), but not by perchlorate (K(I) of 767 mM). The mitochondrial isozyme V has the lowest affinity for sulfate (K(I) of 680 mM) and carbonate (K(I) of 95 mM) among all the investigated isozymes, suggesting on one hand its possible participation in metabolon(s) with sulfate anion exchanger(s), and on the other hand an evolutionary adaptation to working at higher pH values (around 8.5 in mitochondria) where rather high amounts of carbonate in equilibrium with bicarbonate may be present. Metasilicate, isosteric to carbonate, is also about a 10 times weaker inhibitor of this isozyme as compared to other CAs investigated here (K(I) of 28.2 mM). Surprisingly, the tumor-associated isozyme IX is resistant to sulfate inhibition (K(I) of 154 mM) but has affinity in the low micromolar range for carbonate, sulfamate, and sulfamidate (K(I) in the range of 8.6-9.6 microM). This constitutes another proof that this isozyme best works at acidic pH values present in tumors, being inhibited substantially at higher pH values when more carbonate may be present. Bromate and chlorate are quite weak CA IX inhibitors (K(I) s of 147-274 mM).

Anions↗
PubMed2005

Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, IX, and XII with N-hydroxysulfamides--a new zinc-binding function in the design of inhibitors.

A small library of N-hydroxysulfamides was synthesized by an original approach in order to investigate whether this zinc-binding function is efficient for the design of inhibitors targeting the cytosolic (hCA I and II) and transmembrane, tumor-associated (hCA IX and XII) isozymes of carbonic anhydrase (CA, EC 4.2.1.1). The parent derivative, N-hydroxysulfamide was a more potent inhibitor as compared to sulfamide or sulfamic acid against all isozymes, with inhibition constants in the range of 473 nM-4.05 microM. Its substituted n-decyl-, n-dodecyl-, benzyl-, and biphenylmethyl-derivatives were less inhibitory against hCA I (K(I)s in the range of 5.8-8.2 microM) but more inhibitory against hCA II (K(I)s in the range of 50.5-473 nM). The same situation was true for the tumor-associated isozymes, with K(I)s in the range of 353-790 nM against hCA IX and 372-874 nM against hCA XII. Some sulfamides/sulfamates possessing similar substitution patterns have also been investigated for the inhibition of these isozymes, being shown that in some particular cases sulfamides are more efficient inhibitors as compared to the corresponding sulfamates. Potent CA inhibitors targeting the cytosolic or tumor-associated CA isozymes can thus be designed from various classes of sulfonamides, sulfamides, or sulfamates and their derivatives, considering the extensive interactions in which the inhibitor and the enzyme active site are engaged, based on recent X-ray crystallographic data.

Amides↗
PubMedDate not supplied

[Changes in the antibacterial activity of nitrofurantoin preparations induced by peptone and hydrolysates].

The determination of the activity of the product nitrofurantoin (10 and 100 mcg) versus 324 strains of Gram-negative bacteria showed that the diameter of the inhibition zones and the MIC values on a medium with a definite composition (7SG) are considerably larger than on the Mueller-Hinton (MH) medium, in the bacto-tryptose (BT) medium. An increase with 8-12 mm phi or with 2-4 binary dilutions changes the interpretation from resistant, on the MH and BT media into sensitive on the 7SG medium. The low results recorded on the conventional media reveal the existence of an antagonism between peptone and nitrofurantoin, similar to that known for sulfamides. The authors believe that the peptone antagonism has hindered the knowledge of the activity of the nitrofurfural derivatives and the correct assessment of the bacteria sensitivity. They also consider questionable the elimination tendency of the small dosage of microtablets of nitrofurantoin (10 mcg) and sulfamide (30 mcg), since their apparent insufficiency might be due less to the inadequate contraction of substances and more to the inadequate testing media. The results plead for the use of the media with definite chemical composition sulfamide and nitrofuran antagonists free and for reconsideration of several methodologic problems: use of the media with definite chemical composition; introduction of an intermediary dosage of maximum 100 mcg/microtablet; reassessment of the sensitivity categories for sulphafurazole and nitrofurantoin.

Culture Media↗
PubMed1992

Heavy metal binding to heparin disaccharides. I. Iduronic acid is the main binding site.

As model compounds for Ni(II)-binding heparin-like compounds isolated from human kidneys (Templeton, D.M. & Sarkar, B. (1985) Biochem. J. 230 35-42.), we investigated two disaccharides--4-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-2,5-anhydro- D-mannitol, disodium salt (1a), and 4-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-6-O- sulfo-2,5-anhydro-D-mannitol, trisodium salt (1b)--that were isolated from heparin after nitrous acid hydrolysis and reduction. The monosulfate (1a) was active whereas the disulfate (1b) was inactive in a high-performance liquid chromatography (HPLC) binding assay with the tracer ions 63Ni(II) 54Mn(II), 65Zn(II), and 109Cd(II). This result is in accord with the isolation of two 67Cu(II) and 63Ni(II) binding fractions from a complete pool of nitrous-acid-derived heparin disaccharides using sulfate gradients and a MonoQ anion exchange column on an FPLC system. One was identified as compound (1a) and the other as a tetrasulfated trisaccharide by high resolution FAB-MS, NMR and HPLC-PAD. Similarly, two synthetic disaccharides-methyl, 2-O-sulfo-4-O-(alpha-L-idopyranosyluronic acid)-2-deoxy-2-sulfamide-alpha-D-glucosamine, trisodium salt [IdopA2S(alpha 1,4)GlcNS alpha Me, 2a], and 2-O-sulfo-4-O-(alpha-L-idopyranosyluronic acid)-2-deoxy-2-sulfamide-6-O-sulfo- alpha-D-glucosamine, tetrasodium salt [IdopA2S (alpha 1,4)GlcNS6S alpha Me, 2b]--were shown to bind tracer amounts of 63Ni and 67Cu using chromatographic assays. Subsequently, 1H NMR titrations of 1a, 1b, 2a, and 2b with Zn (OAc)2 were analyzed to yield 1:1 Zn(II)-binding constants of 472 +/- 59, 698 +/- 120, 8,758 +/- 2,237 and 20,100 +/- 5,598 M-1, respectively. The values for 2a and 2b suggest chelation. It is suggested that the idopyranosiduronic acid residue is the major metal binding site. NMR evidence for this hypothesis comes from marked 1H and 13C chemical shift changes to the iduronic acid resonances after addition of diamagnetic Zn(II) ions.

Binding Sites↗
PubMed2004

Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions.

The inhibition of the newly discovered cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isozyme XIII of murine origin (mCA XIII) has been investigated with a series of anions, such as the physiological ones (bicarbonate, chloride), or the metal complexing anions (cyanate, cyanide, azide, hydrogen sulfide, etc), nitrate, nitrite, sulfate, sulfamate, sulfamide as well as with phenylboronic and phenylarsonic acids. The best mCA XIII inhibitors were cyanate, thiocyanate, cyanide and sulfamide, with K(I)-s in the range of 0.25microM-0.74 mM, whereas fluoride, iodide, azide, carbonate and hydrogen sulfide were less effective (K(I)-s in the range of 3.0-5.5mM). The least effective inhibitors were sulfate, chloride and bicarbonate (K(I)-s in the range of 138-267 mM). The affinity of mCA XIII for anions is very different from that of the other cytosolic isozymes (hCA I and II) or the mitochondrial isozyme hCA V. This resistance to inhibition by the physiological anions bicarbonate and chloride suggests an evolutionary adaptation of CA XIII to the presence of high concentrations of such anions (e.g., in the reproductive tract of both female and male), and the possible participation of this isozyme (similarly to CA II, CA IV and CA V) in metabolons with proteins involved in the anion exchange and transport, such as the anion exchangers (AE1-3) or the sodium bicarbonate co-transporter (NBC1 and NBC3) proteins, which remain to be identified.

Animals↗
PubMed2005

Identification of nonpeptidic small-molecule inhibitors of interleukin-2.

The identification, design, and synthesis of a series of novel sulfamide- and urea-based small-molecule antagonists of the protein-protein interaction IL-2/IL-2Ralpha are described. Installation of a furan carboxylic acid fragment onto a low-micromolar sulfamide resulted in a 23-fold improvement in activity, providing a sub-micromolar, nonpeptidic IL-2 inhibitor (IC(50)=0.60 microM).

Humans↗
PubMed2002

Selective surface adhesion of the toxic microalga Alexandrium minutum induced by contact with substituted polystyrene derivatives.

On the basis of observations that biospecific random copolymers (RACS) could induce phenotypic changes on contact with selected eukaryotic or prokaryotic cell lines, polystyrene derivatives of known compositions and obtained by random substitutions of sodium sulfonate and of sulfamides of aspartic acid dimethyl ester, phenylalanine and leucine, were placed in contact with swimming dinophytes of the PSP toxin producing species Alexandrium minutum and of the non-toxic species Heterocapsa triquetra. A. minutum cells exhibited higher adhesion for the random copolymer made up of polystyrene (29%), polystyrene aspartic acid dimethyl ester sulfamide (47%) and polystyrene sodium sulfonate (24%), than for samples of this series with different compositions. In contrast to this, A. minutum adhesion remained very low throughout the phenylalanine and leucine copolymer series. These results indicate that the cell-substrate adhesion phenomenon is dependent upon the final composition of the copolymer, i.e. that it is composition-specific. Taxonomic specificity was then demonstrated by presenting the PSAspOMe copolymer series with cells of the non toxic species H. triquetra (Peridinialia) related to A. minutum (Gonyaulacacea), and by observing no specific association, i.e. no signal above background levels at any composition. Specific ligand-cell adhesion is evidenced for the first time between biospecific RACS and phytoplankton, which may inspire a new generation of structures to be used in aquaculture as protective nets over shellfish clusters, or as selective filtering devices to assist in shellfish depuration from toxic microalgae.

Animals↗
PubMed2004

[Maternal pancytopenia during antenatal treatment of congenital toxoplasmosis].

INTRODUCTION: The treatment of reference of congenital toxoplasmosis combines two folate synthesis inhibitors, pyrimethamine and an antibacterial sulfamide (sulfadiazine or sulfadoxine). Despite the efficacy of this combination, the possibility of eventually severe side effects must also be taken into account. OBSERVATION: A pancytopenia occurred at 37 weeks of amenorrhea during antenatal treatment for congenital toxoplasmosis in a tripara. The outcome was positive following administration of strong doses of parenteral folinic acid combined with platelet transfusion and broad-spectrum antibiotics. DISCUSSION: Each of the molecules (pyrimethamine and antibacterial sulfamide) used for the treatment of congenital toxoplasmosis can lead to acute haematological problems. The occurrence of maternal pancytopenia however remains exceptional. It is principally related to pyrimethamine and is usually observed in the presence of factors enhancing folate deficiency.

Adult↗
PubMed2001

Tetraaza analogues of lithium and sodium alums: synthesis and X-ray structures of the single strand polymer [Li(THF)2(Al[SO2(NtBu)2]2)] infinity and the contact ion pairs [Na(15-crown-5)][Al(SO2(NtBu)2)2] and ([Na(15-crown-5)][O2S(mu-NBn)2Al(mu-NBnSO2NBn)])2.

The reaction of an alkali metal aluminohydride MAlH4 (M = Li, Na) with N,N'-bis-(tert-butyl)sulfamide or N,N'-bis-(benzyl)sulfamide in THF produces the complex ions (Al[SO2(NR)2]2)- (R = tBu, Bn). The X-ray structures of [Li(THF)2(Al[SO2(NtBu)2]2)] infinity (1), [Na(15-crown-5)][Al(SO2(NtBu)2)2], (2) and ([Na(15-crown-5)][O2S(mu-NBn)2Al(mu-NBnSO2NBn)])2 (3.3THF) are reported. The two diazasulfate ligands [SO2(NtBu)2]2- are N,N' chelated to Al3+ in both 1 and 2. In the lithium derivative 1 the spirocyclic (Al[SO2(NtBu)2]2)- anions are bridged by the bis-solvated cations Li(THF)2+ to give a polymeric strand. In the sodium salt 2 the complex anion is O,O' chelated to Na+, which is further encapsulated by a 15-crown-5 ligand to give a monomeric ion-pair complex. By contrast, the benzyl derivative 3 forms a dimer in which the terminal [SO2(NBn)2]2- ligands are (N,N'),(O,O') bis-chelated to Al3+ and Na+, respectively, and the bridging ligands adopt a novel N,O-chelate, N'-monodentate bonding mode. The central core of 3 consists of two four-membered AlOSN rings bridged by two NtBu groups. Crystal data: 1, orthorhombic, Pna2(1), a = 20.159(5) degrees, b = 10.354(3) degrees, c = 15.833(4) degrees, alpha = beta = gamma = 90 degrees, V = 3304.7(15) A3, Z = 4; 2, monoclinic, P2(1)/n, a = 16.031(2) A, b = 9.907(2) A, c = 23.963(4) A, beta = 103.326(2) degrees, Z = 4; 3, triclinic, P1, a = 12.7237(11) A, b = 14.0108(13) A, c = 16.2050(14) A, alpha = 110.351(2) degrees, beta = 111.538(2) degrees, gamma = 97.350(2) degrees, Z = 1.

Journal Article↗
PubMed1999

Grafting of aliphatic and aromatic probes on rapeseed 2S and 12S proteins: influence on their structural and physicochemical properties.

Lysyl residues of rapeseed napin (2S) and cruciferin (12S) were acylated and sulfamidated by means of anhydrides and sulfonyl chlorides, respectively. The secondary and tertiary structures as well as the surface hydrophobicity of the modified proteins were studied using circular dichroism, intrinsic fluorescence, and binding of anilinonaphthalenesulfonic acid. The results showed clearly that grafting of hydrophobic chains induced different structural modifications and surface hydrophobicities on the monomeric (2S) and on the hexameric (12S) proteins. Thus, the original structure of the 2S modified protein seemed to be preserved. Therefore, the surface hydrophobicity increased proportionally with the number of groups grafted. Conversely, after modification, 12S was shown to be expanded. As a result, hydrophobic regions were exposed, leading to a much greater hydrophobization of the protein surface. Acylation and sulfamidation appeared, therefore, to be good methods to hydrophobize efficiently the surface of the two proteins and thus might probably induce new functional properties.

2S Albumins, Plant↗
PubMed2003

Discovery of a long-chain carbamoyl aminocarnitine derivative, a reversible carnitine palmitoyltransferase inhibitor with antiketotic and antidiabetic activity.

The synthesis and pharmacological activity of reversible CPT I inhibitors as potential antiketotic and antidiabetic drugs are reported. Such inhibitors constitute a series of enantiomerically pure aminocarnitine derivatives having the general formula (CH3)3N+CH2CH(ZR)CH2COO- (with Z = ureido, carbamate, sulfonamide, and sulfamide moieties; R = C7-C14 linear alkyl chains). A primary pharmacological screening based on the evaluation of CPT I activity in intact rat liver (L-CPT I) mitochondria revealed the best activity for the (R) forms of ureidic derivative 17 (ZR = NHCONHR, R = C14), sulfonamidic derivative 7 (ZR = NHSO2R, R = C12), and sulfamidic derivative 9 (ZR = NHSO2NHR, R = C11). The IC50 values are 1.1, 0.7, and 0.8 microM, respectively. For the carbamic derivative 11 (ZR = NHCOOR, R = C8), an IC50 of 9.5 microM was observed. In addition, an extraordinarily high selectivity toward the liver isoform with respect to the heart isoform (muscle-CPT I identical with M-CPT I) was found for the ureidic compound 17 (IC50(M-CPT I) vs IC50(L-CPTI) = 39.4), as well as for other ureidic or carbamic compounds. Diabetic db/db mice treated orally with 17 and 7 for 45 days at a dose of 50 mg/kg twice a day showed a good reduction of serum glucose levels with respect to the untreated db/db mice (p < 0.01). In addition, 17 showed antiketotic activity in normal fasted rats. 17 has been selected for development as a potential antiketotic and antidiabetic drug.

3-Hydroxybutyric Acid↗
PubMed1989

New perspectives in the chemoprophylaxis of toxoplasmosis.

The usual chemoprophylaxis of toxoplasmosis consists of spiramycin or the combination of pyremethamine-sulfamide. This chemoprophylaxis can be used: 1 - In the pregnant woman: spiramycin avoids or has low fetal damage. In case of maternal contamination after 33 weeks of pregnancy, pyrimethamine-sulfadiazine combination should be used in spite of its potential toxicity. 2 - In the newborn infant, chemoprophylaxis prevents the emergence of retinochoroiditis. 3 - In congenital toxoplasmic retinochoroiditis, systematic repetitive cures of pyrimethamine-sulfamide reduce frequency of recurrences. 4 - In immunocompromised patients, the systematic use of pyrimethamine and sulfadoxine prevents neurotoxoplasmosis, in case of kidney, heart, and allogeneic bone marrow transplantations, and also in case of patients with malignant hemopathy or AIDS.

Chorioretinitis↗
PubMed2000

[Description of type 2 diabetes mellitus in residents of Ile-de-France aged at most 70 years].

Our study of patients with type 2 diabetes mellitus residing in the Paris area (Ile-de-France) aged 70 years or younger included 1 591 patients examined by national health insurance expert physicians who also filled out a self-administrated questionnaire. Their primary care physicians also answered a questionnaire (79% participation, indicating their personal implication). We found that diabetes was most often discovered during regular check-ups. Single-drug regimens were the most widely used. Sulfamides were prescribed for 77% of the patients. Among the 912 patients who were overweight (BMI > 28 Kg/m2), 34.3% were taking sulfamides alone despite the fact that metformin is recommended as the first intention drug for these patients. Blood pressure control was not satisfactory in 30% of the patients who were treated or not for high blood pressure. This proportion rose to about 50% among treated patients alone. The patients appeared to be knowledgeable about the risk of complications, particularly ocular complications. They were aware of a certain number of messages but the results would suggest difficulty in application.

Adult↗
PubMedDate not supplied

[Medical mangement of Crohn's disease (author's transl)].

Medical management of Crohn's disease is above all symptomatic. According to the severeness of the case, treatment varies and may be simple (regimen, antidiarrheic agents and sulfamid drugs) or more sophisticated (continous parenteral alimentation). Sulfamids and antibiotics have a definite although temporary action. Pathogenic medication includes: 1) steroid therapy who is active, but its effects are not long stand; 2) immunosuppressors who allow for the reduction of steroid therapy dosages; 3) immunostimulants as proposed by Geffroy. Among those presently studied are Calmette-Guérin vaccine, either given orally or by scarification, and two anti-parasitic drugs, metronidazole and levamisole. Short term results are good but they worsen with time. The main problem is to know when to discuss surgery. As need be, resection although mutilating, should be timely indicated.

Adrenal Cortex Hormones↗
PubMedDate not supplied

[Glycogen content in the placenta of rats in experimental diabetes].

Glycogen was determined histochemically and biochemically in the placenta of female rats with alloxan diabetes induced in sexually immature animals, including the placenta of rats treated with sulfamides before the occurrence of pregnancy. Histochemical studies were carried out on 18, and biochemical on 38 Wistar rats. Glycogen content in the mature placenta before labour was greater in animals with manifest alloxan diabetes than in healthy rats. This increase of glycogen granules took place on account of their increase both in the glycogen cells, and, extracellularly, in the spongious zone. A significant increase of glycogen content in the placenta in manifest and latent diabetes was also demonstrated by biochemical methods; as to "prediabetic" rats--elevation of glycogen content in their placenta was insignificant in comparison with control. In diabetes compensated with sulfamides glycogen content in glycogen cells changed differently: there was a disappearance of extracellular glycogen from the spongious zone, and numerous glycogen granules (determined in healthy rats and in those with alloxan diabetes in insignificant amount) appeared in the labyrinth.

Alloxan↗
PubMed1994

[Rhinopharyngeal carriage of Neisseria meningitidis serogroup C in the collectivity around the patients of Mali. Apropos of 1,033 subjects sampled].

This study showed that the carriage rate is nul or low in collectivity not in close contact, but high in collectivity in close contact (schools, particularly coranic schools). In this later case, the duration of the carriage may reach several weeks (2 to 6 in our study) at variable rates (3.7 to 9.6%; 12.5 to 62.5%; 14.3 to 42.9% according to the coranic school visited). For the strains of N. meningitidis serogroup C isolated, the rate of resistance to sulfamides and cotrimoxazole is 86.8%. These results explain why during epidemics, it is necessary to close schools and avoid to use for the chemoprophylaxis, sulfamids and their associations because of resistance.

Carrier State↗
PubMed1993

[Hypertension and hyperinsulinism in non-insulin-dependent diabetes. A study of 230 patients].

This study was designed to analyse the relationship between hypertension and hyperinsulinemia in type 2 diabetes (NIDDM). Two hundred and thirty male type 2 diabetic patients consecutively hospitalized from January to June 1991 were included in the study. The following parameters wer recorded: age, known duration of diabetes, BMI (kg/m2), waist to hip ratio (WHR), HbAlc, triglycerides, total and HDL cholesterol, fasting plasma insulin level (RIA determination), insulin-resistance assessment (fasting insulinemia/fasting glycemia), hypertension (BP > or = 160 and/or 95 mmHg or presence of antihypertensive treatment), parental history and hypertension, modalities of treatment of diabetes. The distribution of fasting insulin concentrations resulted in a skewed curve: mean +/- SD: 16.5 +/- 10.9, median (ranges): 13.0 (9.5-19). Hyperinsulinemia was defined as fasting insulin level > 22 mUI/ml (value corresponding to the last quintile of distribution of insulinemia in this population and to the extreme value of insulinemia in a cohort of 100 control subjects). Sixty five patients were on diet alone, 45 had biguanide alone, 39 had sulfamide alone and 81 had both biguanide and sulfamide medications. The prevalence of hypertension was 44% (n = 102). Patients with hypertension, compared to those without, had significant (p < 0.05) higher values for age, duration of diabetes, BMI, WHR, prevalence of hyperinsulinemia and plasma insulin levels. These two groups were similar as regards HbAlc, insulin resistance assessment, treatment of diabetes and parental history of hypertension. Patients with hyperinsulinemia were younger (p < 0.03), had higher prevalence of hypertension (p < 0.04), higher values for triglycerides (p 0.01) and lower values for HDL cholesterol (p < 0.003) than those without hyperinsulinemia.(ABSTRACT TRUNCATED AT 250 WORDS)

Aged↗