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PubMed1985

Mutagenicity of some monoaromatic hydroxamic acids.

The mutagenicity of some monoaromatic hydroxamic acids was tested in the presence and absence of rat liver S-9 with Salmonella typhimurium tester strains TA98 and TA100. Of the five N-(chlorophenyl)-substituted hydroxamic acids and seven N-arylformohydroxamic acids tested, 2 of the first and 4 of the latter series were mutagenic to both strains upon metabolic activation. None of the four N-acetyl-type hydroxamic acids was mutagenic to either strain, even upon activation. Because some of the N-acetyl-derived hydroxamic acids were inactive, whereas the same aromatic nucleus possessing a formyl group displayed significant activity, a consideration of the nature of the aryl group in hydroxamic acid mutagenicity is important.

Animals↗
PubMed1989

Hydroxamic Acid glucosyltransferases from maize seedlings.

Hydroxamic acids occur in several forms in maize (Zea mays L.) with 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) being the predominant form and others including 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) being found at lower concentrations. Two enzymes capable of glucosylating hydroxamic acids were identified in maize protein extracts and partially purified and characterized. The total enzyme activity per seedling increased during the first 4 days of germination and was concurrent with the accumulation of DIMBOA. Purification of the enzymes by ammonium sulfate precipitation followed by Sephadex G-200 and Q-Sepharose gel chromatography resulted in a 13-fold increase in specific activity. The enzymes are initially separated into two peaks (peak 1 and peak 2) of activity by Q-Sepharose gel chromatography. The peak 1 glucosyltransferase had 3.6% of the DIMBOA glucosylating activity when DIBOA was used as substrate, whereas this percentage increased to 57% for the peak 2 enzyme. The enzyme in peak 2 has a K(m) of 174 micromolar for DIMBOA and a K(m) of 638 micromolar for DIBOA; the enzyme in peak 1 has a K(m) of 217 micromolar for DIMBOA and its activity on DIBOA was too low to determine a K(m). The identification of two glucosyltransferases capable of glucosylating hydroxamic acids in vitro serves as an initial step in the characterization of the enzymes involved in production of hydroxamic acids in maize.

Journal Article↗
PubMed1977

Mutagenicity of hydroxamic acids for Salmonella typhimurium.

P-Butoxyphenylacethydroxamic acid, benzohydroxamic acid, salicylhydroxamic acid, 2-naphthohydroxamic acid, indole-2-carbohydroxamic acid and benzoylaminoacethydroxamic acid were synthesized, and their mutagenicity for Salmonella typhimurium strains TA98 and TA100 were determined. Except for p-butoxyphenylacethydroxamic acid, all the hydroxamic acids were mutagenic for both strains. The mutagenicity progressed in the following order: 2-naphthohydroxamic acid greater than benzohydroxamic acid and salicylhydroxamic acid greater than benzoylaminoacethydroxamic acid and indole-2-carbohydroxamic acid. The starting materials for the synthesis of these acids including hydroxylamine were not in themselves mutagenic for TA98 and TA100. Thus, while the mutagenicity may require the hydroxamic acid as a whole, the acyl group may determine the mutagenic potency.

Genetic Techniques↗
PubMed2004

[Research advance in cyclic hydroxamic acids, main allelochemicals of Zea mays].

The research advance in cyclic hydroxamic acids was reviewed in this paper. Cyclic hydroxamic acids are the important natural products of cereal crops. They and their respective derivatives are the constitutive compounds of a wide variety of gramineous plants and few dicot plants. They have structural diversity and different natural occurrences. Because of their phytotoxic properties, cyclic hydroxamic acids show a great variety of biological activities. They are the defensive agents against plant diseases, pests, nematodes and other plants. The distribution of cyclic hydroxamic acids in Zea mays and their variation in relation to the age were focused on in the paper. In Zea mays, there are structural diversity of cyclic hydroxamic acids and related benzoxazolinones. DIMBOA (1,4-benzoxazin-3(4H)-ones) is the most abundant derivative in Zea mays. The content of cyclic hydroxamic acids is strongly cultivar-dependent in Zea mays. Hydroxamic acids are not present in seeds. After germination, the level of DIMBOA increases, and the maximum level occurs in young seedlings a few days after germination. DIMBOA exists in all parts of plants, and its concentration is generally higher in shoots than in roots. In all stages, the young leaves of Zea mays have relatively high content of DIMBOA. The concentrations of these hydroxamic acids are highly dependent on environmental growth conditions. Under UV-light and water deficiencies, the levels of hydroxamic acids in plant increase rapidly. Cyclic hydroxamic acids exuded by Zea mays root can be quantitatively analyzed by HPLC. Supplying iron can significantly increase the exudation of DIMBOA from Zea mays root.

Benzoxazines↗
PubMed2002

Formation and structure of 1:1 complexes between aryl hydroxamic acids and vanadate at neutral pH.

Although aryl hydroxamic acids are well-known to form coordination complexes with vanadate (V(V)), the nature of these complexes at neutral pH and submillimolar concentrations, the conditions under which such complexes inhibit various serine amidohydrolases, is not well established. A series of qualitative and quantitative experiments, involving UV/vis, (1)H NMR, and (51)V NMR spectroscopies, established that both 1:1 and 1:2 vanadate/hydroxamate complexes form at pH 7.5, with the former dominating at submillimolar concentrations. Formation constants for the complexes of several aryl and alkyl hydroxamic acids were determined; for example, for benzohydroxamic acid, the stepwise formation constants of the 1:1 and 1:2 complexes were 3000 and 400 M(-1), respectively. The (51)V chemical shift of the 1:1 4-nitrobenzohydroxamic acid complex was -497 ppm, and that of its unsubstituted analogue was -498 ppm. A (1)H-(15)N HSQC spectrum of the 4-nitrobenzo-(15)N-hydroxamic acid/vanadate complex indicated the presence of an N-H group with (15)N and (1)H chemical shifts of 115 and 5.83 ppm, respectively. A (13)C NMR spectrum of the complex of 4-nitrobenzo-(13)C-hydroxamic acid with vanadate displayed a resonance at 170.1 ppm and thus a coordination-induced shift (CIS) of +3.8 ppm. In contrast, the CIS value of an established 1:2 complex, thought to contain chelated hydroxamic acid ligands, was +11.9 ppm. These spectral data led to the following structural picture of 1:1 complexes of vanadate and aryl hydroxamic acids. They contain penta- or hexa-coordinated vanadium. The ligand is in the hydroxamate rather than hydroximate form. The ligand is presumably bound to vanadium through the hydroxamic hydroxyl oxygen, but the hydroxamic acid carbonyl oxygen interacts weakly with vanadium. These species are the most likely candidates for the inhibitors of serine amidohydrolases found in vanadate/hydroxamic acid mixtures.

Hydrogen-Ion Concentration↗
PubMed1985

A colorimetric method for the determination of hydroxamic acid by iodine oxidation.

A new colorimetric method for the determination of hydroxamic acid is described. Hydroxamic acid was oxidized quantitatively by iodine to produce nitrous acid, which was thereafter determined according to the diazocoupling reaction. This method is sensitive to as little as 5 nmol of hydroxamic acid, and the calibration curve is linear up to 50 nmol. Using this method, acyl-CoAs were determined after conversion to hydroxamic acid by the addition of hydroxylamine. The present method is applicable to the determination of free fatty acids which are activated by acyl-CoA synthetase.

Chemical Phenomena↗
PubMed1987

Hydroxamic acid inhibitors of 5-lipoxygenase.

The hydroxamic acid functionality can be incorporated in a variety of simple molecules to produce potent inhibitors of 5-lipoxygenase. As an example of this, the structure-activity relationships in a series of omega-phenylalkyl and omega-naphthylalkyl hydroxamic acids are presented. Among the features described are the influence of hydrophobicity, aryl substitution, and modifications of the hydroxamate group on enzyme inhibitory potency. To assist in the selection of more potent hydroxamic acid inhibitors, a simple hypothesis about the nature of enzyme-inhibitor binding was devised. In this hypothesis, the structures of compounds were matched to a proposed geometry of arachidonic acid when bound to the enzyme. Compounds that match best without extending into disfavored regions were predicted to be the best inhibitors. Three series of hydroxamates selected according to this approach are described. Within these series are some of the most potent inhibitors of 5-lipoxygenase reported to date.

Arachidonate Lipoxygenases↗
PubMed2002

Solution equilibrium studies on metal complexes of 2,3-dihydroxy-phenylalanine-hydroxamic acid (Dopaha) and models: catecholate versus hydroxamate coordination in iron(III)-, aluminium(III)- and molybdenum(VI)-Dopaha complexes.

Equilibrium results based on pH potentiometric, spectrophotometric and (1)H NMR measurements for the complexes of Fe(III), Al(III) and Mo(VI) with 2,3-dihydroxy-phenylalanine-hydroxamic acid (Dopaha) as well as for binary model systems Fe(III)-, Al(III)-, Mo(VI)-acetohydroxamic acid (Aha), -alpha-alaninehydroxamic acid (alpha-Alaha) and -1,2-dihydroxy-3,5-benzene-disulphonate (Tiron) and ternary model systems Fe(III)-, Al(III)-, Mo(VI)-Tiron-Aha, are summarized in this paper. The amine-type coordination mode is not detectable with these metal ions at all. Precipitation occurs at pH <5.5 with Fe(III) and Al(III) even at a Dopaha-to-metal ion ratio of 10:1. Hydroxamate-type coordination was demonstrated with both metals below the pH range of precipitation but, after dissolution, catecholate-type coordination was exclusively found. The hydroxamate-type coordination mode occurs only in the very acidic pH range for Mo(VI) complexes and the crossover from hydroxamate to catecholate binding occurs at pH >3. A ligand-bridged dinuclear species, [(MoO(2))(2)(Dopaha)(2)](2+), involving mixed-type (catecholate and hydroxamate) coordination modes is formed in the pH range 2.5-5.5. [MoO(2)A(2)H(2)], with catecholate-type coordination, forms above pH 3. On increasing the pH further, deprotonation of the coordinated Dopaha and hydrolytic processes result in the formation of catecholate-coordinated [MoO(3)AH] and [MoO(3)A]. MoO(4)(2-) and free Dopaha exist above pH 10.

Journal Article↗
PubMed2004

Chemical basis for the antifeedant activity of natural hydroxamic acids and related compounds.

Natural hydroxamic acids and related compounds derived from the 1,4-benzoxazin-3-one structure show antifeedant activity against the aphid Rhopalosiphum padi. This antifeeding activity is based on the electrophilic character of the hydroxamic acid function, the opening of the hemiacetal function and the lipophilic character of the molecule. In addition, the antifeedant activity of the aqueous extracts of different tissues of Acanthus mollis (Acanthaceae) was determined. The activity observed is attributed to the presence of 2,4-dihydroxy-1,4-benzoxazin-3-one in the extracts.

Acanthaceae↗
PubMed1985

Inhibition of proliferation and differentiation of mouse erythroleukemia cells by hydroxamic acids.

The effect of several hydroxamic acids on cell growth and differentiation was studied in vitro in cultures of Friend erythroleukemia cells, line F4-6. Terminal differentiation in F4-6 cells can be induced by exposure to a variety of structurally unrelated compounds or to conditions which inhibit cell growth. Hydroxamic acids do not induce erythroid differentiation but interfere with both cell growth of F4-6 cells and the induction of differentiation by DMSO in these cells. DMSO-induced terminal differentiation is inhibited even when F4-6 cells are pretreated for 24 h with hydroxamates followed by removal of the hydroxamates and transfer to fresh medium containing 1% DMSO. Reduction of cell growth by hydroxamates is completely and immediately reversible upon removal. In contrast, the inhibition of DMSO inducibility is not reversible within 24 h. Cell pretreated with hydroxamates for 24 h prior to a 96 h-exposure to DMSO show the same reduction in synthesis of hemoglobin as cells simultaneously exposed to DMSO and hydroxamates.

Animals↗
PubMed1992

Inhibition of urease activity by dipeptidyl hydroxamic acids.

A series of dipeptidyl hydroxamic acids (H-X-Gly-NHOH: X = amino acid residues) was synthesized, and the inhibitory activity against Jack bean and Proteus mirabilis ureases [EC 3.5.1.5] was examined. A number of H-X-Gly-NHOH inhibited Jack bean urease with an I50 of the order of 10(-6) M and inhibited Proteus mirabilis urease with an I50 of the order of 10(-5) M. The inhibition against Jack bean urease was more potent than that with the corresponding aminoacyl hydroxamic acids (H-X-NHOH).

Dipeptides↗
PubMedDate not supplied

Occurrence and characterization of a UDP-glucose:hydroxamic acid glucosyltransferase isolated from wheat (Triticum aestivum) seedlings.

Cyclic hydroxamic acid glucosides are present at high concentrations immediately after germination in wheat (Triticum aestivum L.). Changes in the activity of UDP-Glucose:cyclic hydroxamic acid glucosyltransferase (EC 2.4.1.-) in wheat were investigated using the cyclic hydroxamic acids 2.4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) and its 7-methoxy derivative (DIMBOA) as sugar acceptors. Glucosyltransferase activity on both substrates was detected in dry seeds, with activity increasing after imbibition, peaking in shoots and roots 36-48 hours after imbibition and decreasing thereafter. The transience of glucosyltransferase activity was concurrent with the transient occurrence of the hydroxamic acid glucosides [Nakagawa E., Amano T., Hirai N., and Iwamura H. (1995) Phytochemistry 38, 1349-1354], suggesting that glucosyltransferases regulate the accumulation of hydroxamic acid glucosides in wheat seedlings. Two peaks in activity of UDP-Glucose:DIMBOA glucosyltransferase were detected using a Mono Q column, indicating the presence of at least two isozymes of this glucosyltransferase. The enzyme in the major peak was purified about 1500-fold and shown to be in a monomeric form with a molecular mass of 47 or 49 kDa. The enzyme reacted strongly with DIMBOA, less so with DIBOA. The enzyme of the minor peak on the Mono Q chromatogram, which was also a monomeric enzyme with a molecular mass of 47 kDa, showed similar substrate specificity to that of the major peak enzyme.

Chromatography, Affinity↗
PubMed2002

[Synthesis of hydroxamic acids and study of their complexes with iron (II) and (III) ions].

Hydroxamic acids are widespread in the tissues of plants, in metabolites of bacteria and fungi, including complex compounds with metal ions. These acids have wide spectrum of biological activity and therefore are perspective reagents for analysis of chemical elements. Fourteen aliphatic and aromatic derivatives of hydroxamic acids have been synthesized from esters of carboxylic acids. Photometric reactions of hydroxamic acids with iron (II) and (III) were investigated. Complex formation of iron (II) and (III) depending on pH was studied with series of synthesized hydroxamic acids: octanohydroxamic, maleic hydroxamic, 2-hydroxybenzoxydroxamic, benzoxydroxamic, phthalmonoxydroxamic and 3-metoxybenzohydroxamic acids. Composition of iron (III) complexes with 2-hydroxybenzohydroxamic, octanoxydroxamic, 3-metoxybenzohydroxamic acids and iron (II) with 2-hydroxybenzohydroxamic acid was studied by methods of mole ratio and isomolar solutions. Sensitivity of reagents was evaluated by values of absorption coefficients (epsilon). Stability of complexes in water and organic solvents was investigated. Interaction between iron (III) and hydroxamic acids (octanoxydroxamic, 2-hydroxybenzohydroxamic, 3-metoxybenzohydroxamic) have been applied for quantitative photometric analysis of iron (III) salts. Color reaction of iron (II) with 2-hydroxybenzohydroxamic acid was applied for quantitative photometric determination of iron (II) salts. 3-Metoxybenzohydroxamic acid was proposed as a new indicator for complexonometric analysis of iron (III). Chelatometric titration of iron (III) using this indicator is not influenced by copper, cobalt, zinc, manganese, so this methods is recommended for iron quantity detection in antianemic drugs, which are composed of latter microelements. Synthesis procedure of 2-benzoylamino-3-arylacrylhydroxamic acids from saturated azlactones was created. Color and precipitate reactions of iron (II) and (III), copper (II), nickel (II) and cobalt (II) ions with four newly synthesized acids (with and without substitutes in aromatic ring) were studied. Sensitivities of reactions between 2-benzoylamino-3-arylacrylhydroxamic acids and iron (II) and (III) were evaluated and compared with 2-hydroxybenzohydroxamic acid.

Chelating Agents↗
PubMed1997

Pharmacokinetics and antiepileptic activity of valproyl hydroxamic acid derivatives.

PURPOSE: To explore the utilization of seven novel hydroxamic acid derivatives of valproic acid (VPA) as new antiepileptics. METHODS: The study was carried out by investigating the pharmacokinetics of two active compounds in dogs and pharmacodynamics (anticonvulsant activity and neurotoxicity) of valproyl hydroxamic acid and six of its derivatives. RESULTS: Three valproyl hydroxamic acid derivatives: valproyl hydroxamic acid-VPA-HA, N-(1-hydroxyethyl)-valpromide-HEV and N-methoxy valpromide, showed better anticonvulsant activity than VPA at the maximal electroshock (MES) test. The remaining four compounds, O-valproyl-VPA-HA, N-valproyl-O-valproyl-VPA-HA, N-(1-methoxyethyl) valpromide and N-(1,2-dihydroxylpropyl)-valpromide were found to be inactive. Therefore, only the pharmacokinetics of the active compounds VPA-HA and HEV was studied. CONCLUSIONS: In contrast to valpromide (VPD) which is biotransformed to VPA, VPA-HA and HEV were found to be stable in vivo to the biotransformation of the amide to its corresponding acid. VPA-HA and HEV showed improved anticonvulsant activity over VPA because of their greater intrinsic activity and not due to better pharmacokinetic characteristics. This paper discusses the structural requirements for active anticonvulsant valproyl hydroxamic acid derivatives.

Animals↗
PubMed1998

[Rapid determination of essential fatty acids of edible oils by conversion to their hydroxamic acids].

A simple and rapid HPLC method for the determination of essential fatty acids of edible oils was established. Oil samples were converted to their hydroxamic acids in a single step and analyzed without prior separation and purification. The chromatographic conditions were: Shim-pack CLC ODS, 5 microns, 150 mm x 6.0 mm i.d. column, 40 degrees C; MeOH: 0.02 mol/L NaH2PO4(pH 3.0) (81:19, V/V) as eluent and UV-213 nm detector. The linear range was 0.05-0.6 g/L, recovery was 96.93% and RSD was 1.80%(n = 4). The relative standard deviations for intra-day and inter-day assays were 1.24% and 1.62% respectively (n = 6). For 18:3, 18:2, 18:1, the difference between the derivatization yields from triglycerides and their methyl esters was almost one fold. That was confirmed by our recovery and determination results. The calibration curves for the oil samples should not be obtained from the derivatization of their methyl ester standards.

Chromatography, High Pressure Liquid↗
PubMed2006

Self-assembly and cytotoxicity study of waterwheel-like dinuclear metal complexes: the first metal complexes appended with multiple free hydroxamic acid groups.

Two waterwheel-like dinuclear complexes [M(2)(PHA)(4)(H(2)O)(2)] (M = Cu(II) (1), Zn(II) (2); HPHA = phthal-hydroxamic acid) appended with four free hydroxamic acid groups, namely, free hydroxamic acid metal complexes (FHAMCs) have been synthesized and characterized. The crystal structure of complex 1 was determined by single crystal X-ray diffraction, which adopts the paddlewheel motif with four bidentate carboxylate ligands joining two Cu(II) ions. The relative cytotoxicities of compounds 1 and 2 against SMMC-7721 and HO-8910 cell lines are similar and more predominant than HPHA (IC(50): Cu(II)>Zn(II)>>HPHA). The synergic effect of the bound water molecules, multiple free hydroxamic acid groups and dimetal active sites with bridging carboxylate may have significant impacts on their pharmacological activity. As the prototype for a new class of hydroxamic acid derivatives, the self-assembly of FHAMCs presents a promising new strategy in designing multiple hydroxamic acids with remarkable bioactivities.

Antineoplastic Agents↗