Anti‐inflammatory Activity of Amine‐carboxyboranes in Rodents

Hall, Iris H.; Rajendran, K. G.; Chen, S. Y.; Wong, Oi T.; Sood, Anup; Spielvogel, Bernard F.

doi:10.1002/ardp.19953280108

Cited by 21 publications

(24 citation statements)

References 27 publications

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“…Tricyclohexylphosphine-borane (CyH 3 PBH 3 ) and triphenylphosphine-carboxyborane (Ph 3 PBH 2 COOH), the two most active compounds in this series, inhibited carrageenan-induced edema by 60 and 59%, respectively, in mice at a dose of 8 mg/kg x 2, I.P. In further studies [69], Ph 3 PBH 2 COOH demonstrated potent acute antiinflammatory activity in the rat Winter's and pleurisy tests reducing edema 39% and 72%, respectively. A 51% reduction in edema in the chronic arthritis test was also observed for this compound.…”

Section: Phosphine Boranesmentioning

confidence: 95%

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Synthesis and Pharmacological Activities of Amine-Boranes

Burnham¹

2005

CMC

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A number of amine-boranes and related derivatives possess a wide range of biological activities including antineoplastic, antiviral, hypolipidemic, anti-inflammatory activities, anti-osteoporotic and dopamine receptor antagonist activities. The compounds include borane complexes of alpha-amino acids, aromatic, aliphatic and heterocyclic amines, and nucleosides. The syntheses of amine-borane derivatives are generally carried out by first preparing a tertiary amine- or phosphine-cyano- or carboxyborane to serve as a borane donor for a subsequent Lewis acid exchange reaction. Borane adducts of simple aliphatic amines, heterocyclic amines and nucleic acids demonstrated potent cytotoxic activity in vitro and in vivo against murine and human tumor models. These boron-containing compounds were shown to inhibit DNA synthesis; such inhibition was caused primarily by reducing de novo purine biosynthesis via inhibition of PRPP amidotransferase, IMP dehydrogenase and dihydrofolate reductase activities. Aliphatic, heterocyclic and nucleoside amine-boranes have also been shown to possess hypolipidemic activity in mice and rats. Many boron derivatives from different chemical classes demonstrated both cytotoxic and hypolipidemic activities. They decreased low-density lipoprotein (LDL) cholesterol while increasing high-density lipoprotein (HDL) cholesterol levels. The mode of action of these compounds in the 50-100 microM concentration range appeared to be by increasing lipid excretion from the body and by inhibiting rate-limiting enzyme activities for the de novo synthesis of lipids and cholesterol (e.g., phosphatidylate phosphohydrolase, ATP-dependent citrate lyase, cytoplasmic acetyl coenzyme A [CoA] synthetase, HMG CoA reductase, and acetyl CoA carboxylase). Selected amine-boranes (e.g., trimethylamine-cyanoborane, N-methylmorpholine-cyanoborane, and the base-boronated 2'-deoxynucleosides) have anti-inflammatory, analgesic, anti-arthritic and anti-osteoporotic activities.

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Section: Phosphine Boranesmentioning

confidence: 95%

“…The phosphine borane affected cytokine levels to a lesser extent, reducing TNF-α, IL-1 and IL-2 levels approximately 35% for each. [69].…”

Section: Phosphine Boranesmentioning

confidence: 95%

Synthesis and Pharmacological Activities of Amine-Boranes

Burnham¹

2005

CMC

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“…Reaction with ( þ )-pinanediol then provided the boronic ester (111). The boropeptide (112) was obtained in 80% yield and it was transformed to (113) and (114). DuPont 714 (75) obtained from (114) The asymmetric synthesis of an unprotected a-aminoboronic acid analog of L-arginine (104) and its N-acetyl derivatives (115 and 116) provided alternative substrates or inhibitors of nitric oxide synthase (Scheme 4.23) [80].…”

Section: Synthesis Of Arginine A-aminoboronic Acidsmentioning

confidence: 99%

“…R see in Table 4 Today, many of these molecules are known to possess remarkable antitumor [110,111], antiosteoporotic ( [112] and references therein), anti-inflammatory ( [113] and references therein), and hypolipidemic activities [114], and their mode of action is under investigation [115].…”

Section: Synthesis and Activity Of Amine-carboxyboranes And Their Dermentioning

confidence: 99%

Chemistry of α‐Aminoboronic Acids and their Derivatives

Dembitsky

Srebnik

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…o-phenantroline , EDTA, and ferric chloride with drug concentrations at 25, 50, and 100 M measured at 510 n n~'~' ' .…”

Section: F W E Ktrdicul Assay\mentioning

confidence: 99%

The Anti‐inflammatory Activity of N‐Substituted Indazolones in Mice

Tse

Butner

Huang

et al. 1996

Archiv der Pharmazie

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N-Substituted indazolones were shown to be potent anti-inflammatory and analgesic agents in mice at 8 mg/kg. In addition, the agents were able to protect against death caused by endotoxins similar to those found in chronic infections. In part, the ability of these agents to suppress the inflammatory process is due to their blockage of cytokine release, e.g.TNF alpha and IL-1, as well as their inhibition of high affinity binding to receptors on target cells of inflammation. Suppressing these receptors can be linked to the inhibition by the agents of lysosomal hydrolytic enzymes, prostaglandin cyclooxygenase and 5'-lipoxygenase activities. Free radical generation involved in inflammation was also stabilized in the presence of most of these agents.

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Anti‐inflammatory Activity of Amine‐carboxyboranes in Rodents

Cited by 21 publications

References 27 publications

Synthesis and Pharmacological Activities of Amine-Boranes

Synthesis and Pharmacological Activities of Amine-Boranes

Chemistry of α‐Aminoboronic Acids and their Derivatives

The Anti‐inflammatory Activity of N‐Substituted Indazolones in Mice

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