Hypolipidemic Activity of Tetrakis-μ-(trimethylamine-boranecarboxylato)-bis(trimethylamine-carboxyborane)-dicopper(II) in Rodents and Its Effect on Lipid Metabolism

Hall, I. H.; Williams, W.L.; Gilbert, Colleen; McPhail, Andrew T.; Spielvogel, Bernard F.

doi:10.1002/jps.2600730728

Cited by 26 publications

(13 citation statements)

References 21 publications

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“…One particular derivative tetrakis-u-(trimethylamine-boranecarboxylato)-bis(trimethylaminecarboxyborane)-dicopper (II), compound 1, demonstrated excellent activity at 2.5 mg/kg/day [5]. Preliminary studies suggested that this derivative increase lipid excretion in the bile of rats [5]. Thus, the present study extends the investigation of metal complexes of amine-carboxyboranes as hypolipidemic agents and their role on biliary lipid excretion in rodents.…”

Section: Introductionsupporting

confidence: 55%

“…One of the modes of action of the derivatives was the suppression of rate limiting enzyme activities of de novo synthesis of lipids. One particular derivative tetrakis-u-(trimethylamine-boranecarboxylato)-bis(trimethylaminecarboxyborane)-dicopper (II), compound 1, demonstrated excellent activity at 2.5 mg/kg/day [5]. Preliminary studies suggested that this derivative increase lipid excretion in the bile of rats [5].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The Hypolipidemic Activity of Metal Complexes of AmineCarboxyboranes in Rodents

Hall

Spielvogel²,

Sood³

et al. 1993

Metal-Based Drugs

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The metal complexes of amine-carboxyborane including copper, chromium, zinc, calcium amd cobalt were effective hypolipidemic agents lowering both serum cholesterol and triglyceride levels significantly in mice at 8 mg/kg/day, I.P. after 16 days. The agents reduced acetyl CoA synthetase, ATP-dependent citrate lyase, acyl CoA cholesterol acyl transferase, sn-glycerol-3-phosphate acyl transferase activities of rat liver and small intestinal mucosa after 14 days treatment. The neutral cholesterol ester hydrolase activity was elevated by the agents in both tissues. The metal complexes altered lipid levels in the bile of rats after treatment as well as the bile acid composition after 14 days administration, orally. The agents blocked enterohepatic absorption of cholesterol from rat isolated intestinal loops.

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Section: Introductionsupporting

confidence: 55%

Section: Introductionmentioning

confidence: 99%

The Hypolipidemic Activity of Metal Complexes of AmineCarboxyboranes in Rodents

Hall

Spielvogel²,

Sood³

et al. 1993

Metal-Based Drugs

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“…2Me 3 NBH 2 CO 2 H, also was active as a hypolipidemic agent in mice at 2.5 mg/kg/day, I.P. for 16 days [53,55]. It lowered serum cholesterol and triglyceride levels to 62 and 50%, respectively.…”

Section: Trimethyl-amine-carboxyborane)-dicopper(ii)mentioning

confidence: 92%

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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“…Amine and phosphine cyanoboranes are an intriguing group of compounds that have inspired extensive biological screening. The promising early results led to the synthesis of a large number derivatives, some of which have been shown in model studies to have potent antitumor [10][11][12][13][14][15], anti-inflammatory [16][17][18], hypolipidemic [11,19], anti-hyperlipidemic [20], anti-ostoeoporotic [21], anti-neoplastic [22][23][24], BNCT [25], and other promising biological activities [26,27]. In the present study, the diborane (4) derivatives of the corresponding amine cyanoborane were synthesized as their 2LiBr complexes from of the monobromo derivative of the corresponding amine cyanoborane, followed by B-B coupling using elemental sodium or n-BuLi.…”

Section: Introductionmentioning

confidence: 99%