Compounds that inhibit chymotrypsin and cell replication

Goz, Barry; Ganguli, Chandana; Troconis, Marysabel; Wyrick, Steven D.; Ishaq, Khalid S.; Katzenellenbogen, John A.

doi:10.1016/0006-2952(86)90630-1

Cited by 15 publications

(3 citation statements)

References 13 publications

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“…Subtilisin Carlsberg (27) and cholesterol esterase (28,29) also are inhibited by a range of aliphatic and aromatic boronic acids. Work on inhibiting a-CHT and cell replication with a variety of boronic acids concluded that the a-CHT activity was associated with chromatin in normal and tumorous tissue of mice (30). It has been demonstrated that certain boronic acids inhibit protease activity in rat liver chro-matin (31).…”

Section: Chemistrymentioning

confidence: 99%

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An Introduction to Boron: History, Sources, Uses, and Chemistry

Woods¹

1994

Environmental Health Perspectives

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Following a brief overview of the terrestrial distribution of boron in rocks, soil, and water, the history of the discovery, early utilization, and geologic origin of borate minerals is summarized. Modern uses of borate-mineral concentrates, borax, boric acid, and other refined products include glass, fiberglass, washing products, alloys and metals, fertilizers, wood treatments, insecticides, and microbiocides. The chemistry of boron is reviewed from the point of view of its possible health effects. It is concluded that boron probably is complexed with hydroxylated species in biologic systems, and that inhibition and stimulation of enzyme and coenzymes are pivotal in its mode of action.

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Section: Chemistrymentioning

confidence: 99%

“…It has been demonstrated that certain boronic acids inhibit protease activity in rat liver chro-matin (31). It was concluded that good boronate inhibitors of CHT, like PEBA, inhibit cell replication and that this effect is expected to be higher in rapidly proliferating cancer cells than in normal tissue (30).…”

Section: Chemistrymentioning

confidence: 99%

An Introduction to Boron: History, Sources, Uses, and Chemistry

Woods¹

1994

Environmental Health Perspectives

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“…For example, compounds having inhibitory activity against serine proteases (Philip and Bender 1971), chromatin bound protease (Carter et al, 1977), and dihydroorotase (Kinder et al, 1990) have been prepared. In addition, boronic acid derivatives have inhibited cell replication (Goz et al, 1986). Other investigators (Schinazi and Prusoff 1985) have introduced the boronic acid functionality into the 5-and 6-positions of pyrimidine as potential antiviral and antitumour agents.…”

Section: Introductionmentioning

confidence: 99%

Boronic Acid Derivatives Targeting HIV-1

Chen

Bastow

Goz

et al. 1996

Antivir Chem Chemother

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SummaryA series of novel boronic acid derivatives containing either a pyrimidine or purine base was synthesized. The preparation involved the condensation of 4-bromobutyl boronic acid with the appropriate base. These acyclic nucleosides were designed as potential antiviral agents especially targeting the human immunodeficiency virus. Two analogues, 6-chloro-9-(4-dihydroxyborylbutyl)purine and 2,6-dichloro-9-(4-dihydroxyborylbutyl)purine, exhibited EC so values of 7.7l!M and O.99l!M, respectively, in an HIV-1 syncytial plaque reduction assay.

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Molecular simulation of alkyl boronic acids: Molecular mechanics and solvation free energy calculations

et al. 1994

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The alkyl boronic acid moiety is incorporated into many biologically interesting structures. To provide parameters for molecular mechanics and dynamics studies of compounds containing this group, we performed ab initio calculations at the 6-31G* level to obtain bond stretching, bending, and torsion constants. The hydrodynamic formulation of the time-dependent density functional theory was used to calculate the attractive part of van der Waals (VDW) 6-12 potential. The geometry of boronic acid moiety of the 6-31G* optimized methyl boronic acid was similar to that of the X-ray crystal structure of phenyl boronic acid. To test the reliability of nonbonded parameters, Monte Carlo free energy perturbation simulations and the thermodynamic cycle approach were used to estimate the differences in solvation free energy between alkyl alcohol and alkyl boronic acid, both in water and in chloroform. These free energy differences were also obtained experimentally by measuring the vapor-water and water-chloroform partition coefficients. The close agreement between experimental values and the results of our simulations suggests the reliability of new molecular mechanics forcefield parameters for alkyl boronic acids. 0 1994 by John Wiley & Sons, Inc.tease,3 and dihydro~rotase~ and of cell replicat i~n .~ Several side-chain derivatives of natural aamino acids such as leucine and phenylalanine, containing boronic acid moiety, were shown to be inhibitors of amino peptidases.6 ne c5 and c6 rofic acid derivatives of fie pyrimidine &splayed

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Compounds that inhibit chymotrypsin and cell replication

Cited by 15 publications

References 13 publications

An Introduction to Boron: History, Sources, Uses, and Chemistry

An Introduction to Boron: History, Sources, Uses, and Chemistry

Boronic Acid Derivatives Targeting HIV-1

Molecular simulation of alkyl boronic acids: Molecular mechanics and solvation free energy calculations

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