Hypolipidemic Activity of Trimethylamine-Carbomethoxyborane and Related Derivatives in Rodents

Hall, Iris H.; Spielvogel, Bernard F.; Sood, Anup; Ahmed, Fahim; Jafri, Samir

doi:10.1002/jps.2600760504

Cited by 30 publications

(18 citation statements)

References 28 publications

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“…Source of compounds All of the compounds were synthesized previously and chemically and physically charectezized [13] cyclohexylamine-cyanoborane _i, cyclohexylamine-carboxyborane 2, N-methylcyclohexylamine-carboxyborane 3_, N-ethylcyclohexylamine-carboxyborane 4, N,N-dimethylcyclohexylaminecarboxyboranes 5, 2-methylcyclohexylamine-carboxyborane 6, 3-methylcyclohexylamine-carboxyborane 7, 4-methylcyclohexylaminecarboxyborane 8, N-ethylcyclohexylamine-cyanoborane 9, N-Vol. 2, No.…”

Section: Methodsmentioning

confidence: 99%

“…2, No. 4,1995 Hypolipidemic Activity of Amine-Borane Aducts of Cyclohexylamine and Toluidine in Rodents methylcyclohexylamine-cyanoborane IO, N,N-dimethylcyclohexylaminecyanoborane ii, 2-methylcyclohexylamine-cyanoborane 12, 3-methylcyclohexylamii'e-cyanoborane 13, 4- …”

Section: Methodsmentioning

confidence: 99%

“…2, No. 4,1995 Hypolipidemic Activity of Amine-Borane Aducts of Cyciohexylamine and Toluidine in Rodents [ 35]. The mode of action of the derivatives on regulatory enzyme activities involved in lipid metabolism appeared to be at site which regulated cytoplasmic formation of acetyl-CoA for cholesterol and fatty acid synthesis.…”

Section: Normolipidemic Studiesmentioning

confidence: 99%

“…Previously we have examined a number of amine-cyanoboranes [l] aminecarboxyboranes and their amides and esters [2][3][4][5], di-and triopeptide boranes [6], heterocyclic-amine boranes [7], polyborate salts [8], choline and thiocholine boranes [9], phosphoacetate boranes[10] and deoxyribonucleoside cyanoboranes [ll]. These agents were effective in rodents at 8 mg/kg/day, significantly lowering both serum cholesterol and triglyceride levels after 14-16 days.…”

Section: Introductionmentioning

confidence: 99%

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Hypolipidemic Activity of Amine‐Borane Aducts of Cyclohexylamineand Toluidine in Rodents

Burnham

Chen

Sood³

et al. 1995

Metal-Based Drugs

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The amine-borane adducts of cyclohexylamine and toluidine were observed to be potent hypolipidemic agents in mice, I.P. and rats orally at 8 mg/kg/day lowering both serum cholesterol and triglyceride levels after 14-16 days. These compounds were able to lower tissue lipids including the cholesterol content of the aorta wall. The agents successfully lower VLDL-and LDLocholesterol content while elevating HDL-cholesterol content significantly. The agents also modulate lipid regulatory enzyme activities in a manner to reduce liver lipid levels. These studies demonstrate that the nitrogen atom does not have to be apart of the aromatic ring as in heterocyclic-amine borane to afford good hypolipidemic activity in rodents.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Normolipidemic Studiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Hypolipidemic Activity of Amine‐Borane Aducts of Cyclohexylamineand Toluidine in Rodents

Burnham

Chen

Sood³

et al. 1995

Metal-Based Drugs

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“…The amine-borane derivatives were synthesized as amine-, cyano-and carboxyboranes (1)(2)(3)(4); di-and tripeptides of boron analogues of amino acids (5); aminomethylphosphonate cyanoborane adducts (6,7); tricyclohexyl-and triphenylphosphineboranes (8); metal complexes and salts of substituted hydroborates (9); boron analogues of phosphonoacetates (10); heterocyclic amine-carboxyboranes (11); hydropolyborates (12), boron analogs of choline and thiocholine (13); and activities. This discussion will concentrate on the amine carboxyboranes and their esters as representative therapeutic agents of the entire boron group of chemicals.…”

Section: Introductionmentioning

confidence: 99%

Hypolipidemic, Anti-Obesity, Anti-Inflammatory, Anti-Osteoporotic, and Anti-Neoplastic Properties of Amine Carboxyboranes

Hall¹,

Chen²,

Rajendran³

et al. 1994

Environmental Health Perspectives

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The amine-carboxyborane derivatives were shown to be effective antineoplastic/cytotoxic agents with selective activity against single-cell and solid tumors derived from murine and human leukemias, lymphomas, sarcomas, and carcinomas. The agents inhibited DNA and RNA synthesis in preference to protein synthesis in L1210 lymphoid leukemia cells. Inosine-monophospate dehydrogenase apparently is a target site of the compounds; similar effects on phosphoribosyl-pyrophosphate amido transferase, orotidine-monophosphate decarboxylase, and both nucleoside and nucleotide kinases were observed. Deoxyribonucleotide pool levels were reduced in the cells; DNA strand scission was observed with the agents. In rodents, the amine carboxyboranes were potent hypolipidemic agents, lowering both serum cholesterol and triglyceride concentrations, in addition to lowering cholesterol content of very low-density lipoprotein and low-density lipoprotein (LDL) and elevating high-density lipoprotein (HDL) cholesterol concentrations. De novo regulatory enzymes involved in lipid synthesis were also inhibited (e.g., hypocholesterolemic 3-hydroxy-3-methyl-Coenzyme A reductase, acyl-Coenzyme A cholesterol acyltransferase, and sn-glycerol-3-phosphate acyltransferase). Concurrently, the agents modulated LDL and HDL receptor binding, internalization, and degradation, so that less cholesterol was delivered to the plaques and more broken down from esters and conducted to the liver for biliary excretion. Tissue lipids in the aorta wall of the rat were reduced and fewer atherosclerotic morphologic lesions were present in quail aortas after treatment with the agents. Cholesterol resorption from the rat intestine was reduced in the presence of drug. Genetic hyperlipidemic mice demonstrated the same types of reduction after treatment with the agents. The agents would effectively lower lipids in tissue based on the inhibition of regulatory enzymes in pigs. These findings should help improve domestic meat supplies from fowl and pigs. The amine-carboxyboranes were effective anti-inflammatory agents against septic shock, induced edema, pleurisy, and chronic arthritis at 2.5 to 8 mg/kg. Lysosomal and proteolytic enzyme activities were also inhibited. More significantly, the agents were dual inhibitors of prostaglandin cyclooxygenase and 5-lipoxygenase activities. These compounds also affected cytokine release and white cell migration. Subsequent studies showed that the aminecarboxyboranes were potent anti-osteoporotic agents reducing calcium resorption as well as increasing calcium and proline incorporation into mouse pup calvaria and rat UMR-106 collagen. -Environ Health Perspect 102(Suppl 3): 21-30 (1994)

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Synthesis of Trimethylamine-[14C]carboxyborane and Trimethylamine-[14C]carboxymethoxyborane and L1210 Leukemia Cell Uptake

Chen

Burnham

Spielvogel³

et al. 1996

Appl. Organometal. Chem.

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Hypolipidemic Activity of Trimethylamine-Carbomethoxyborane and Related Derivatives in Rodents

Cited by 30 publications

References 28 publications

Hypolipidemic Activity of Amine‐Borane Aducts of Cyclohexylamineand Toluidine in Rodents

Hypolipidemic Activity of Amine‐Borane Aducts of Cyclohexylamineand Toluidine in Rodents

Hypolipidemic, Anti-Obesity, Anti-Inflammatory, Anti-Osteoporotic, and Anti-Neoplastic Properties of Amine Carboxyboranes

Synthesis of Trimethylamine-[14C]carboxyborane and Trimethylamine-[14C]carboxymethoxyborane and L1210 Leukemia Cell Uptake

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