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At least 649 records · Page 36Linked to original sources
PubMed2005

The first carborane triflates: synthesis and reactivity of 1-trifluoromethanesulfonylmethyl- and 1,2-bis(trifluoromethanesulfonylmethyl)-o-carborane.

The first carborane triflates, namely, 1-trifluoromethanesulfonylmethyl-o-carborane (2) and 1,2-bis(trifluoromethanesulfonylmethyl)-o-carborane (7), were obtained in high yields in the reactions of 1-hydroxymethyl-o-carborane (1) or 1,2-bis(hydroxymethyl)-o-carborane (6) with triflic anhydride (Tf2O) in CH2Cl2 in the presence of pyridine. When an excess of pyridine is employed, 1-o-carboranylmethylpyridinium triflate (3), which retains a closo-icosahedral structure, or a pyridinium salt (4) with a zwitterionic nido-dicarbaundecaborate anion are obtained from 1, while the nido compound 8 is formed from 6. The reaction of compound 2 or 7 with excess pyridine also gave 3 or 8, respectively. Compound 2 proved to be a convenient carboranylmethylating agent which reacts with nucleophiles (e.g., potassium phthalimide, PPh3 or KCN) to give the corresponding substitution products N-[(o-carboranyl-1-yl)methyl]phthalimide (9), o-carboranylmethylphosphonium salt 10, and 1-cyanomethyl-o-carborane (11). All compounds were characterized by 1H and 11B NMR spectroscopy. The structures of compounds 4, 7 and 8 were established by X-ray analysis.

Boron Compounds↗
PubMed2004

Determination of the DNA methylation level in tumor cells by capillary electrophoresis and laser-induced fluorescence detection.

An analytical method to determine the genome-wide DNA methylation in only 100 ng DNA is presented. The analysis is based on DNA isolation and hydrolysis followed by derivatization of the 2'-desoxyribonucleoside-3'-monophosphates with a fluorescence dye (4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-propionyl ethylene diamine hydrochloride, Bodipy FL EDA). The separation of the derivatives was carried out by micellar electrokinetic chromatography, and laser-induced fluorescence was used for detection. To calculate the methylation level, the derivatization factor and the quantum yields of the Bodipy conjugates of 2'-desoxycytidine-3'-monophosphate (dCMP) and 2'-desoxy-5-methylcytidine-3'-monophosphate (5m-dCMP) were determined by measurement of methylated Lambda DNA. The assignment was made by cochromatography with the synthesized and characterized standard compound 5m-dCMP. After optimization of the method it was possible to determine the methylation level in 100-ng DNA samples with a standard deviation of less than 5%.

Bacteriophage lambda↗
PubMed2005

Monitoring the effects of antagonists on protein-protein interactions with NMR spectroscopy.

We describe an NMR method that directly monitors the influence of ligands on protein-protein interactions. For a two-protein interaction complex, the size of one component should be small enough (less than ca. 15 kDa) to provide a good quality (15)N((13)C) HSQC spectrum after (15)N((13)C) labeling. The size of the second unlabeled component should be large enough so that the molecular weight of the preformed complex is larger than ca. 40 kDa. When the smaller protein binds to a larger one, broadening of NMR resonances results in the disappearance of most of its cross-peaks in the HSQC spectrum. Addition of an antagonist that can dissociate the complex would restore the HSQC spectrum of the smaller component. The method directly shows whether an antagonist releases proteins in their wild-type folded states or whether it induces their denaturation, partial unfolding, or precipitation. We illustrate the method by studying lead compounds that have recently been reported to block the MDM2-p53 interaction. Activation of p53 in tumor cells by inhibiting its interaction with MDM2 offers new strategy for cancer therapy.

Boron Compounds↗
PubMed1999

Localization of carbonic anhydrase in living osteoclasts with bodipy 558/568-modified acetazolamide, a thiadiazole carbonic anhydrase inhibitor.

We describe the synthesis of Bodipy 558/568-modified acetazolamide, a fluorescent inhibitor of carbonic anhydrase and its use to localize the enzyme in living cells. The modified acetazolamide, with its specific sulfonamide group intact, labeled cells at concentrations as low as 10(-9) M, with a minimal loading time of 5 min. The staining was decreased by 57.4% by preincubating cells with unaltered acetazolamide (1:100) or with trifluoromethane sulfonamide, 6-ethoxyzolamide, and 5-(3-hydroxybenzoyl)-thiophene-2-sulfonamide. The efficacy of the inhibitor was unchanged by the fluorescent label, as determined by an acridine orange assay that detects acidification of osteoclasts, the cell model used in this study. This compound should prove to be useful for studying carbonic anhydrase in many organisms because of the high degree of conservation of the active site of this enzyme. (J Histochem Cytochem 47:545-550, 1999)

Acetazolamide↗
PubMed2006

Lipid peroxidation inhibition capacity assay for antioxidants based on liposomal membranes.

An in vitro antioxidant assay has been developed to better reflect the in vivo conditions of antioxidants interacting with membrane and lipid surfaces. The lipid peroxidation inhibition capacity (LPIC) method measures the ability of both lipophilic and hydrophilic antioxidants to protect a lipophilic fluorescent probe 4, 4-difluoro-5-(4-phenyl-1,3-butadienyl)-4-bora-3a,4a-diaza-s-indacene-3-undecanoic acid, incorporated in the membrane, from 2,2'-azobis(2-amidinopropane)hydrochloride generated radicals in the surrounding aqueous solution. Antioxidant activities of test compounds were measured either after they were mixed with preformed liposomes (LPIC(Mixed)) or after they were incorporated into liposomes (LPIC(Inco)) as they were made. The results were analysed to determine how the method of mixing and the structures of the antioxidants influenced their protection of the membrane from free radical attack. The LPIC(Mixed) values were larger than the LPIC(Inco) values for a range of 12 structurally diverse antioxidant compounds. However, there was no linear correlation between the lipophilicities, as measured by their partition coefficient, log P and either LPIC(Inco) or LPIC(Mixed) values. A strong correlation was found between LPIC(Inco) and LPIC(Mixed) values.

Antioxidants↗
PubMed1998

Rational design of boropeptide thrombin inhibitors: beta, beta-dialkyl-phenethylglycine P2 analogs of DuP 714 with greater selectivity over complement factor I and an improved safety profile.

The potent boropeptide thrombin inhibitor DuP 714 caused side effects in laboratory animals that appear to be related to its ability to inhibit complement factor I, thereby activating the complement cascade. Using X-ray crystal structure information, we have designed compounds that have greater selectivity for thrombin over factor I and that have reduced tendency to produce these side effects.

Animals↗
PubMed1993

Synthesis and biological activity of 125I/127I-phenylboronic acid derivatives.

Three iodinated phenylboronic acids have been synthesized: 4-iodophenylboronic acid (2a), 3-(4-iodobenzenesulfonamido)phenylboronic acid (5a) and 3-(5-dimethylamino-6-iodo-1-naphthalenesulfonamido)phenylboronic acid (6a). The corresponding no-carrier-added 125I derivatives 2b, 5b and 6b have been prepared in good yield by selective displacement of the tributylstannyl group. Compound 6b was concentrated in vitro preferentially in HT-29 human colon carcinoma cells compared to V79 Chinese hamster lung fibroblasts and showed selective retention in PaCa-2 human pancreatic cancer cells grown as solid tumor xenografts in the nude mouse.

Animals↗
PubMedDate not supplied

Thermal neutron capture therapy of malignant melanoma using 10B-monoclonal antibodies: in vitro and in vivo analysis.

We have established methods of targeting a sufficient number of 10B atoms on human melanoma cells to allow selective destruction of the cancer cells by thermal neutron irradiation. Thermal neutron capture therapy (NCT)1-3 requires the presence of at least 10(9) 10B atoms on each target cell for specific killing of that cell without injuring normal tissues. In order to accumulate an adequate number of 10B atoms on target cells, we first created an effective compound containing 12 atoms of 10B per molecule (10B12-chlorpromazine) and 10B-dopa analogue (10B1-paraboronophenylalanine). In the present study, about three molecules of our newly synthesized 10B12-compound were conjugated to an avidin molecule. The resulting 10B38.5-avidin compound can be specifically directed to human melanoma cells by biotinated monoclonal antibodies (MAbs) specific for the cells. We were able to accumulate 2.6 x 10(8) 10B atoms on a melanoma cell using this method. Cultured human melanoma cells treated with 10B-avidin-biotin-MAb (10B-AB-MAb) were selectively damaged by thermal neutron irradiation in vitro. This is the first study to indicate that thermal neutrons selectively damage target cells boronated by MAbs.

Animals↗
PubMed2003

Feasibility study on epithermal neutron field for cyclotron-based boron neutron capture therapy.

To realize the accelerator-based boron neutron capture therapy (BNCT) at the Cyclotron and Radioisotope Center of Tohoku University, the feasibility of a cyclotron-based BNCT was evaluated. This study focuses on optimizing the epithermal neutron field with an energy spectrum and intensity suitable for BNCT for various combinations of neutron-producing reactions and moderator materials. Neutrons emitted at 90 degrees from a thick (stopping-length) Ta target, bombarded by 50 MeV protons of 300 microA beam current, were selected as a neutron source, based on the measurement of angular distributions and neutron energy spectra. As assembly composed of iron, AlF3/Al/6LiF, and lead was chosen as moderators, based on the simulation trials using the MCNPX code. The depth dose distributions in a cylindrical phantom, calculated with the MCNPX code, showed that, within 1 h of therapeutic time, the best moderator assembly, which is 30-cm-thick iron, 39-cm-thick AlF3/Al/6LiF, and 1-cm-thick lead, provides an epithermal neutron flux of 0.7 x 10(9) [n cm(-2) s(-1)]. This results in a tumor dose of 20.9 Gy-eq at a depth of 8 cm in the phantom, which is 6.4 Gy-eq higher than that of the Brookhaven Medical Research Reactor at the equivalent condition of maximum normal tissue tolerance. The beam power of the cyclotron is 15 kW, which is much lower than other accelerator-based BNCT proposals.

Aluminum Compounds↗
PubMed2005

A chloro-bridged dimanganese complex and an oxo-bridged dititanium complex of a ditopic bis(pyrazol-1-yl)borate ligand.

The synthesis and crystal structure analysis of the ditopic p-phenylene-bridged bis(pyrazol-1-yl)borate [[p-C6H4(Bpz2tBu)2]Li2] (LLi2; pz=pyrazol-1-yl) is described. A salt metathesis reaction between LLi2 and MnCl2 in THF leads to the dinuclear complex [L[Mn(THF)]2(mu-Cl)2] featuring a central diamond MnII-(mu-Cl)2-MnII core (X-ray crystal structure analysis). Treatment of LLi2 with 2 equiv of [Ti(NMe2)3Cl] gives the dinuclear titanium compound [L[Ti(NMe2)3]2]. Upon reaction of LLi2 with [Ti(NMe2)2Cl2] and water, the mu-oxo-bridged dititanium species [L[Ti(NMe2)Cl]2(mu-O)] is obtained in excellent yield (X-ray crystal structure analysis).

Boron Compounds↗
PubMed2006

An in vitro fluorescence screen to identify antivirals that disrupt hepatitis B virus capsid assembly.

Virus assembly has not been routinely targeted in the development of antiviral drugs, in part because of the lack of tractable methods for screening in vitro. We have developed an in vitro assay of hepatitis B virus (HBV) capsid assembly, based on fluorescence quenching of dye-labeled capsid protein, for testing potential inhibitors. This assay is adaptable to high-throughput screening and can identify small-molecule inhibitors of virus assembly that prevent, inappropriately accelerate and/or misdirect capsid formation to yield aberrant particles. An in vitro primary screen has the advantage of identifying promising lead compounds affecting assembly without the requirement that they be taken up by cells in culture and be nontoxic. Our approach may facilitate the identification of antivirals targeting viruses other than HBV, such as avian influenza and HIV.

Antiviral Agents↗
PubMed2000

New estrogenic antagonists bearing dicarba-closo-dodecaborane as a hydrophobic pharmacophore.

We have designed and synthesized estrogen antagonists bearing dicarba-closo-dodecaborane (carborane) as a hydrophobic pharmacophore based on the structure of 1-(4-hydroxyphenyl)-1,12-dicarba-closo-dodecaborane, a potent estrogen agonist that we reported previously. Compounds with a long alkyl chain bearing an amide moiety on the carborane skeleton (6, 7) showed estrogen antagonistic activity in a luciferase reporter gene assay using COS-1 cells transfected with a rat ER alpha-expression plasmid and as an appropriate reporter plasmid.

Animals↗
PubMed2004

Indirect nuclear spin-spin coupling constants in 1,2-diboretane-3-ylidene, a homoaromatic system with pi and sigma 3c/2e bonds. Comparison of experimental data with calculations using density functional theory (DFT).

The non-classical 1,2-diboretane-3-ylidene 1a was studied by 13C and 29Si NMR spectroscopy in order to obtain coupling constants 1J(13C,11B) and 1J(29Si,13C). The magnitudes of 1J(13C,11B) were deduced from linewidth measurements in low-temperature 13C and 11B NMR spectra. Calculation of the coupling constants for model compounds related to 1a, using DFT methods based on optimized geometries [B3LYP/6-311+G(d,p)], gave data in agreement with the experiments. Furthermore, the calculations predict for the first time a negative sign of 1J(13C,11B) which mirrors the bonding situation in 1 as described by theory.

Algorithms↗
PubMed2004

Crystal structure of transglutaminase 3 in complex with GMP: structural basis for nucleotide specificity.

Epidermal-type Transglutaminase 3 (TGase 3) is a Ca(2+)-dependent enzyme involved in the cross-linking of structural proteins required in the assembly of the cell envelope. We have recently shown that calcium-activated TGase 3, like TGase 2, can bind, hydrolyze, and is inhibited by GTP despite lacking structural homology with other GTP-binding proteins. Here we report the crystal structure determined at 2.0 A resolution of TGase 3 in complex with GMP to elucidate the structural features required for nucleotide recognition. Binding affinities for various nucleotides were found by fluorescence displacement to be as follows: guanosine 5'-3-O-(thio)triphosphate (GTPgammaS) (0.4 microm), GTP (0.6 microm), GDP (1.0 microm), GMP (0.4 microm), and ATP (28.0 microm). Furthermore, we found that GMP binds as a reversible, noncompetitive inhibitor of TGase 3 transamidation activity, similar to GTPgammaS and GDP. A genetic algorithm similarity program (GASP) approach (virtual ligand screening) identified three compounds from the Lead Quest trade mark data base (Tripos Inc.) based on superimposition of GTPgammaS, GDP, and GMP guanine nucleotides from our crystal structures to generate the minimum align flexible fragment. These three were nucleotide analogs without a phosphate group containing the minimal binding motif for TGase 3 that includes a nucleoside recognition groove. Binding affinities were measured as follows: TP349915 (K(d) = 4.1 microm), TP395289 (K(d) = 38.5 microm), TP394305 (K(d) = 1.0 mm). Remarkably, these compounds do not inhibit but instead activate TGase 3 transamidation by about 10-fold. These results suggest that the nucleotide binding pocket in TGase 3 may be exploited to either enhance or inhibit the enzymatic activity as required for different therapeutic approaches.

Adenosine Triphosphate↗
PubMed1994

The use of low-energy collisionally activated dissociation negative-ion tandem mass spectrometry for the characterization of dog and human urinary metabolites of the drug BW 1370U87.

Liquid chromatography (LC) combined with atmospheric pressure chemical ionization mass spectrometry was used to identify phase I and II metabolites of the drug BW 1370U87 in dog and human urine. Additional analysis of individual high-performance liquid chromatograph fractions collected from dog urine by combined gas chromatography/mass spectrometry identified one metabolite which was not detected by LC/MS methods. Using negative-ion LC/MS, the majority of BW 1370U87 metabolites in human urine were identified as glucuronic acid conjugates of phase I oxidative metabolites. The negative-ion fragmentation produced by low-energy collisionally activated decomposition (CAD), studied by tandem mass spectrometry experiments, confirmed that these compounds were drug-related and allowed metabolite structures to be assigned. Product-ion spectra of the metabolites were dominated by the loss of neutral molecules from even-electron deprotonated [M-H]- ions.

Animals↗
PubMed2003

Addition reactions at the 16(17) double bond of 3-methoxy-13alpha-estra-1,3,5(10),16-tetraene.

The epoxidation, the addition of hypobromous acid, and the hydroboration of 3-methoxy-13alpha-estra-1,3,5(10),16-tetraene 1 with diborane, catecholborane, and 9-BBN were investigated in order to determine the stereochemical outcome and to synthesize new 13alpha-estra-1,3,5(10)-trienes for biological and conformational investigations. It was shown that the sterically demanding reagent 9-BBN participated in a preferred beta attack (53% 16betaOH 10, 34% 17betaOH 8, 13% 16alphaOH 11). This stereochemical result is in agreement with that from another cis addition reaction, the recently described OsO4 dihydroxylation of 1 [Steroids 68 (2003) 113]. With smaller reagents such as B2H6, catecholborane, or magnesium monoperoxyphthalate, a diminished stereoselectivity was observed with only a slight excess of beta attack. The ionic trans addition of hypobromous acid gave two 17-bromo-16-alcohols with 16beta,17alpha (4, 76%) and 16alpha,17beta configuration (5, 24%) formed by trans cleavage of the 16,17alpha- and beta-bromonium ion at position 16. The same regioselective and stereoselective course was found for the cleavage of the 16alpha,17alpha- and 16beta,17beta-epoxides (3 and 2) with hydrazoic acid (3-->16betaN3,17alphaOH 7, 2-->16alphaN3,17betaOH 6). The stereochemistry of the addition reactions to 1 can be explained in terms of a twist-boat conformation involving the C ring of compound 1. From a synthetic viewpoint the synthesis of the beta-epoxide 2 from the bromohydrin 4, the cleavage of this epoxide to 16alpha-substituted-17beta-hydroxy compounds, such as 6, and hydroboration/oxidation with 9-BBN to the hitherto unknown 16beta-hydroxy compound 10 are useful procedures. The bromohydrin 5 is the first 13alpha-steroid with a 17beta-bromo substituent. X-ray analysis revealed twist-boat and 16beta-envelope conformations for rings C and D, respectively.

Borohydrides↗
PubMed1977

Cyclic alkylboronates as derivatives for the characterization of cannabinolic acids by combined gas chromatography and mass spectrometry.

Stable cyclic methyl- and n-butylboronates were prepared from the cannabinolic acids and used as derivatives for the characterization of these compounds by combined gas chromatography mass spectrometry. Retention times of the methylboronates were comparable with those of the trimethylsilyl derivatives. The mass spectra of these derivatives were more characteristic of the cannabinoid skeleton than were the spectra of the trimethylsilyl derivatives where fragmentation was associated with the trimethylsilyl groups. Molecular weights were lower and abundant molecular ions were obtained. These derivatives also offered the possibility of distinguishing between isomeric cannabinolic acids where only isomers possessing adjacent phenolic and carboxylic functions form cyclic boronates.

Boron Compounds↗