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PubMed2004

pi-Stacked hydrogen-bonded sheets in N,N'-bis(4-nitrobenzylidene)ethane-1,2-diamine and pi-stacked hydrogen-bonded chains in N,N'-bis(4-nitrobenzylidene)propane-1,3-diamine.

Molecules of N,N'-bis(4-nitrobenzylidene)ethane-1,2-diamine, C16H14N4O4, (I), lie across centres of inversion in space group P2(1)/n and are linked into (10-1) sheets by a single C-H...O hydrogen bond [H...O = 2.40 A, C...O = 3.2166 (13) A and C-H...O = 146 degrees ]; these sheets are linked into a three-dimensional array by a single aromatic pi-pi stacking interaction. Molecules of N,N'-bis(4-nitrobenzylidene)propane-1,3-diamine, C17H16N4O4, (II), lie across twofold rotation axes in space group C2/c and are linked into chains of spiro-fused rings by a single C-H...O hydrogen bond [H...O = 2.54 A, C...O = 3.267 (2) A and C-H...O = 130 degrees ]; these chains are linked into sheets by a single aromatic pi-pi stacking interaction.

Journal Article↗

PubMed2005

Three-dimensional supramolecular structures in (E,E)-N,N'-bis(4-nitrobenzylidene)butane-1,4-diamine and (E,E)-N,N'-bis(4-nitrobenzylidene)hexane-1,6-diamine.

In both (E,E)-N,N'-bis(4-nitrobenzylidene)butane-1,4-diamine, C18H18N4O4, (III), and (E,E)-N,N'-bis(4-nitrobenzylidene)hexane-1,6-diamine, C20H22N4O4, (IV), the molecules lie across centres of inversion in space groups P-1 and P2(1)/c, respectively. In (III), the three-dimensional supramolecular structure is built from pi-stacked chains of edge-fused R(2)(2)(30) rings, while in (IV), chains of edge-fused R(2)(2)(38) rings are linked by dipolar nitro-nitro interactions.

Journal Article↗

PubMed1988

Oxidation of some seleno-diamines by pig kidney diamine oxidase.

The enzymatic deamination of Se-lanthionamine (Se-L), Se-homolanthionamine (Se-HL) and Se-homocystamine (Se-HC) catalyzed by pig kidney diamine oxidase (PKAO) has been studied to collect information about the possible metabolic reactions of selenocompounds in comparison with the sulfur ones. The results indicate that: Se-L, Se-HL and Se-HC are substrates for PKAO. The first product of Se-L, Se-HL and Se-HC oxidative deamination, in analogy with other thio and seleno diamines, may be the cyclized aminoaldehyde. The final product of Se-L, Se-HL and Se-HC degradation are ammonia, elemental selenium and C2 or C3 compounds.

Amine Oxidase (Copper-Containing)↗

PubMed2004

Water-soluble platinum(II) complexes of diamine chelating ligands bearing amino-acid type substituents: the effect of the linked amino acid and the diamine chelate ring size on antitumor activity, and interactions with 5'-GMP and DNA.

Six new Pt(II) complexes are described having the general formula PtCl(2)(LL), in which LL is a chelating diamine ligand bearing an amino acid as substituent. The amino acids chosen are l-alanine and its methyl ester, and l-phenylalanine. The compounds have been characterized using analytical and spectroscopic methods. The influence on the biological properties of the size of the chelate ring and the structure of the amino acid substituent has been studied. The effect of the presence of a carboxylic or carboxylate group on the amino acid C-terminus has also been determined. It is demonstrated by circular dichroism (CD) that the effect on the secondary structure of DNA induced by the six complexes differ from each other. In all cases, the interaction takes place at the N7 position of the purine bases, as shown by NMR monitoring. The general behavior of these platinum complexes, with one exception, is to uncoil the DNA from the B form to the C form. The interactions with 5'-GMP and DNA have been compared with their expected antitumour activity. The complexes with l-alanine and l-phenylalanine exhibit cytotoxic activity in HeLa and HL-60 cell lines, in a dose- and time-dependent manner. No cytotoxic activity of the methyl ester derivatives have been determined because of their low solubility in aqueous solution.

Amino Acids↗

PubMed1986

[Experimental teratological studies on facial anomalies induced in mice by bis (dichloroacetyl) diamine. I. Establishment of an animal model of the median cleft face syndrome by the administration of bis (dichloroacetyl) diamine to mice].

Bis (dichloroacetyl) diamine (abbreviated as bisdiamine hereafter) was administered by oral intubation to pregnant Jcl: ICR and A/J mice at a dosage of 3,200 mg/kg/day at days 7.5 and 8.5, 8.5 and 9.5, 9.5 and 10.5 or 10.5 and 11.5 of gestation (VP = day 0). Fetuses were recovered at day 17.5 of gestation following maternal sacrifice. The numbers of resorptions, live fetuses and malformed fetuses were counted in the two strains of mice and the induced craniofacial anomalies were examined macroscopically and histopathologically. In both strains, median facial cleft, cleft palate, exencephalocele and open eyelids were commonly induced craniofacial anomalies. Bisdiamine-induced median facial cleft ranging in severity from minor midfacial disorganization to completely divided nose with a median cleft lip in Jcl: ICR and A/J was strikingly similar to a spectrum of midline defects of the median cleft face syndrome in humans. Histopathological examinations of severe median facial cleft in the two strains revealed that the bifurcated nasal septal cartilage showed irregular hypoplasia and that it was partly disorganized into several nodules of various shapes and sizes. These results indicate that bisdiamine treatment in mice provides a useful animal model of the median cleft face syndrome. Furthermore, higher frequency of median facial cleft and lower mortality in bisdiamine-treated Jcl: ICR indicate that bisdiamine treatment in Jcl: ICR is more effective than that in A/J to make an animal model of this syndrome.

Abnormalities, Drug-Induced↗

PubMed1986

[Experimental teratological studies on facial anomalies induced in mice by bis(dichloroacetyl)diamine. II. Pathogenesis of bis(dichloroacetyl)diamine-induced median cleft face syndrome in mice].

The present study was performed to clarify the pathogenesis of bis(dichloroacetyl)diamine (abbreviated as bisdiamine hereafter)-induced median cleft face syndrome in mice. Bisdiamine was administered by oral intubation to pregnant Jcl: ICR mice at a dosage of 3,200 mg/kg/day at days 7.5 and 8.5 of gestation (VP = day 0). Embryos were recovered at 4, 12, 24, 48, 72 and 96 hr after bisdiamine treatment at day 8.5 of gestation and morphological differences between the bisdiamine-treated and control embryos at the specific time intervals were quantitatively examined by the light and scanning electron microscopy. First, bisdiamine caused extensive death of cranial, mainly prosencephalic and mesencephalic, neural crest cells and neuroepithelial cells. Second, the former damage resulted in reduced numbers of mesenchymal cells in the frontonasal prominences and the latter resulted in dorsolateral deviation of the nasal placodes. Consequently, the medial nasal prominences were abnormally widely spaced and then, the median cleft face syndrome was induced. In addition, the findings suggesting that bisdiamine might cause aberrant movement of neural crest cells and/or mesenchymal cells were observed.

Abnormalities, Drug-Induced↗

PubMed1988

Induction and quail liver diamine oxidase (histaminase). Part I: Interference of spermidine synthase on the diamine oxidase activity assay using putrescine as substrate.

Treatment with Aroclor 1254 produces a decrease of diamine oxidase (DAO) activity in quail liver microsomes evaluated on deamination of 14C-putrescine and of histamine. The inhibition observed with the 14C-putrescine assay has peculiar behavior; it increase with the increase of 14C-putrescine concentrations until it produces values of extracted radioactivity which are less than the blanks which do not contain proteins. This effect is reserved by dicyclohexylammonium, an inhibitor of spermidine synthase (SPDS). This paper shows that SPDS rapidly decreases the putrescine concentration during the assay of DAO in tissues, particularly when SPDS is increased by induction with Arocolor.

Amine Oxidase (Copper-Containing)↗

PubMedDate not supplied

Electrophilic substitution of (diamine)tetrahydroxoplatinum(IV) with carboxylic anhydrides. Synthesis and characterization of (diamine)platinum(IV) complexes of mixed carboxylates.

A novel series of (diamine)platinum(IV) complexes of mixed carboxylates have been synthesized by electrophilic substitution of the tetrahydroxoplatinum(IV) complex (dach)Pt(OH)4 (dach = trans-(+/-)-1,2-diaminocyclohexane) with three different carboxylic anhydrides, pivalic, acetic, and trifluoroacetic anhydrides. Consecutive two-step acylations with two different carboxylic anhydrides in acetone or dichloromethane gave the mixed carboxylate complexes (dach)Pt(O2CR)x(O2CR')4 - x (R = C(CH3)3 or CF3, R' = CH3, x = 1-4) including all the possible stereoisomers, which could be separated and identified by means of HPLC, column chromatography, 1H NMR, and X-ray crystallography. From analysis of the reaction products we have found that the positions of electrophilic substitution of (dach)Pt(OH)4 were influenced by the kinds of carboxylic anhydrides exhibiting different electrophilicity or steric effects. The initial substitution by the first reactant occurs more favorably on axial OH, but in the case of pivalic anhydride, equatorial substitution is favored probably because of the bulkiness of the pivalate group. Such a result seems to be related to their stereochemical factors rather than to differences in electrophilicity. The lipophilicity of the title complexes was affected not only by the carbon numbers of substituents but also by the conformation of the resulting compound.

Journal Article↗

PubMed2001

Chiral diamines 4: a computational study of the enantioselective deprotonation of Boc-pyrrolidine with an alkyllithium in the presence of a chiral diamine.

The enantioselective deprotonation of N-Boc-pyrrolidine (1) with i-PrLi-(-)-sparteine has been studied at theoretical levels up through B3P86/6-31G. Four low-energy intermediate complexes involving i-PrLi-(-)-sparteine and 1 were located via geometry optimizations; two of these complexes would lead to abstraction of the pro-S hydrogen from 1, and the other two complexes would lead to loss of the pro-R hydrogen. The lowest-energy intermediate complex was found to lead to loss of the pro-S hydrogen as observed experimentally. Transition states for the deprotonations were located using the synchronous transit-guided quasi-Newton method. The calculated activation enthalpy for transfer of the pro-S hydrogen within the lowest-energy intermediate complex, 10.8 kcal/mol, is reasonable for a reaction that occurs at a relatively low temperature, and the calculated kinetic hydrogen isotope effect is in agreement with experimental data. The lower enantioselectivity observed experimentally for deprotonation of 1 using t-BuLi-(-)-sparteine is attributed to a transition-state effect due to increased steric interaction engendered by the bulky t-BuLi. Replacement of the tert-butoxycarbonyl group in 1 by a methoxycarbonyl is predicted to result in a slower deprotonation with somewhat decreased enantioselectivity. Asymmetric deprotonation of 1 using i-PrLi in combination with the C(2)-symmetric diamine, (S,S)-1,2-bis(N,N-dimethylamino)cyclohexane, was calculated to be much less selective than is the deprotonation mediated by (-)-sparteine as observed experimentally. The relative energies of the intermediate complexes were fairly well-reproduced by ONIUM calculations in which the sparteine ligand less its nitrogen atoms was treated by molecular mechanics and the remainder of the complex was treated by quantum mechanics.

Formic Acid Esters↗

PubMed1988

The glycoprotein nature of pig kidney diamine oxidase. Role of disulphide groups and arginine residues in the concanavalin A-diamine oxidase interaction.

Pig kidney diamine oxidase (DAO) was found to contain 5% (w/w) natural hexose, 3.25% glucosamine, 2.61% N-acetylglucosamine and 0.25% N-acetylneuraminic acid. The enzyme exhibited strong affinity towards concanavalin A (Con A) with a stoichiometry of 1:4.6. The kinetics of interaction approached an apparent first-order rate, with a rate constant (Kapp.) value of 1.5 x 10(-2) min-1. The enzyme reduced with dithiothreitol followed by alkylation with iodoacetamide showed an increase in the stoichiometry of the Con A-DAO interaction. Similarly arginine modification by phenylglyoxal caused decreased affinity, with an altered Kapp. value of 9.09 x 10(-3) min-1. The results suggest that, besides the carbohydrate content, the protein moiety of the enzyme also plays a significant role in the Con A-DAO interaction.

Amine Oxidase (Copper-Containing)↗

PubMed1956