Biological activity in steroids possessing nitrogen atoms: recent advances

Martin‐Smith, M.; Sugrue, Michael F.

doi:10.1111/j.2042-7158.1964.tb07517.x

Cited by 32 publications

(9 citation statements)

References 167 publications

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“…It is important, therefore, that certain hypocliolesteremic drugs inhibit the multiplication of microorganisms which represent both cellular groups. The growth inhibition by hypocholesteremic drugs of certain bacteria, algae, fungi, and ascomycetes has previously been reported (34)(35)(36)(37)(38). The precedence for showing the inhibition of growth of microorganisms by both nonsteroidal (14 and references therein) and azasteroid hypocholesteremic drugs (13,38,39) has been established.…”

Section: Discussionmentioning

confidence: 92%

Structure‐function activity of azasterols and nitrogen‐containing steroids

Kabara¹,

Holzschu²,

Catsoulacos³

1976

Lipids

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Thirty-nine nitrogen-containing steroids were tested against two gram-negative, five gram-positive, and two yeast organisms. Many of these steroids have been previously reported to inhibit various metabolic processes involving sterol metabolism. While low minimal inhibitory concentration (MIC) values were recorded for sterol producing yeast, growth of bacteria which contain no sterols was also inhibited. Structure-function studies provided no relationship between biological activity and hypocholesteremic effects of these azasteroids. A hypothesis put forward is that amino and azasteroids are effectors of membrane which, in the case of mitochondria, lead to changes in adenosine triphosphate levels and/or dehydrogenase activity. Their effects on sterol metabolism, therefore, may be of secondary consideration.

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Section: Discussionmentioning

confidence: 92%

Structure‐function activity of azasterols and nitrogen‐containing steroids

Kabara¹,

Holzschu²,

Catsoulacos³

1976

Lipids

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“…The sensitivity of bacteria to a disc soaked in as little as I mM of the compound and to a variety of hypocholesteremic compounds, i.e. azasteroids (Martin-Smith & Sugrue, 1964;Smith et al 1963), triparanol and benzmalecene (Aaronson, 1965) and SKF 525-A, SKF ~~o I -A , and SKF 16467-A, implies that these compounds may offer leads to compounds which inhibit pathogenic bacteria, especially the Gram-positive ones, as well as other pathogens.…”

Section: Discussionmentioning

confidence: 99%

“…Gram-positive bacteria are more inhibited by hypocholesteremic compounds than are Gram-negative bacteria (Aaronson, 1965 ;Martin-Smith & Sugrue, 1964;Smith et al 1963). The results here with the SKF compounds (Table I) bear this out.…”

Section: Discussionmentioning

confidence: 99%

Effect of Hypocholesteremic Compounds on Bacterial Multiplication

Aaronson

Fulco

1968

Journal of General Microbiology

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S U M M A R YHypocholesteremic compounds, triparanol, SKF 525-A, SKF 330 I -A, SKF I 6467-A, inhibited the multiplication of some bacteria and ascomycetes ; phycomycetes were not inhibited. Gram-positive bacteria were most sensitive to these compounds. Dimethyl or diethyl aminoethanol and SKF 2314, compounds resembling the major moieties of the SKF compounds, were not inhibitory alone or together; the whole molecule was necessary for inhibition. Inhibition by triparanol of the multiplication of several Gram-positive bacteria was annulled by albumin and ergosterol; oleic acid and squalene were mostly inactive. I N T R O D U C T I O NCompounds which inhibit steroid metabolism in mammals (' hypocholesteremics ') inhibit the multiplication of a wide variety of micro-organisms, especially Grampositive bacteria (Aaronson, 1965; Martin-Smith & Sugrue, 1964; Smith, Shay & Doorenbas, 1963). We have examined the effect on bacterial multiplication of several related hypocholesteremic compounds to determine (a) whether the Gram-positive bacteria are most sensitive; (b) the active moiety of the inhibitory compounds; (c) compounds which annul the inhibition; ( d ) the potential of these compounds as antibacterial compounds ; (e) whether the hypocholesteremic compounds can be used to study bacterial metabolism, especially the role of steroids in bacterial metabolism. M E T H O D SMicro-organisms from the collection of the Biology Department, Queens College, New York, were used. For disc assay, Whatman no. 50 filter-pad discs (0.6 cm. diam.) were soaked in solutions of the test compound at the concentration indicated, dried, and autoclaved. Bacteria were grown on nutrient agar; fungi on Sabouraud's glucose agar. Cultures in triplicate were incubated at 25' for 2 days or until they showed good growth over the surface of the Petri dish. Triparanol (I -[p-(4-diethylaminoethoxy)phenyl]-1-(p-tolyl)-2-p-chlorophenylethanol) was supplied by Dr F. J. Murray (W. S. Merrell, Cincinanti, Ohio); the SKF compounds by Dr W. L. Holmes (Smith Kline and French Laboratories, Philadelphia, Pa.). All other chemicals were bought from commercial sources. Triparanol, SKF-23 14, oleic acid, squalene, and ergosterol were dissolved in 95 % ethanol in water. Other compounds were dissolved in water.

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“…Suzuki (1964) has shown anti-andro¬ genic activity in four alkylamine derivatives of testosterone and nortestosterone. This subject has recently been reviewed by Alauddin & Martin-Smith (1962) and Martin-Smith & Sugrue (1964). In view of this interest, the aza-analogue 7,8,9,lO-tetrahydro-7-oxo-benzo (c) phenanthridine was tested for androgenic, anti-androgenic and anabolic activity on immature, castrated, male rats and adult, male rats.…”

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confidence: 99%

Anti-Androgenic Activity of 7,8,9,10-Tetrahydro-7-Oxo-Benzo (C) Phenanthridine (A11-Iv) on Immature, Castrated, Male Rats

Saksena¹,

Chaudhury²

1970

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One of the aza-analogues, 7,8,9,10-tetrahydro-7-oxo-benzo (c) phenanthridine exhibited an anti-androgenic activity on immature, castrated, male rats. The compound had an interesting anti-androgenic activity as the effect of testosterone-induced gain in weight of the ventral prostate was significantly inhibited by the compound. This compound did not, however, inhibit the androgen-induced weight increase of the seminal vesicle.Azasteroids, in which the nitrogen replaces the carbon atom of a perhydro-1,2-cyclopentanophenanthrene system, have been found to exhibit some androgenic, oestrogenic and progestational activity. Suzuki (1964) has shown anti-andro¬ genic activity in four alkylamine derivatives of testosterone and nortestosterone. This subject has recently been reviewed by Alauddin & Martin-Smith (1962) and Martin-Smith & Sugrue (1964). In view of this interest, the aza-analogue 7,8,9,lO-tetrahydro-7-oxo-benzo (c) phenanthridine was tested for androgenic, anti-androgenic and anabolic activity on immature, castrated, male rats and adult, male rats.The anti-androgenicity of the test compound was assessed by the method described by Hershberger, Shipley & Meyer (1953) as modified by Potts, Beyler & Burnham (1960) on castrated, immature, male rats. The castrated male rats were divided into four groups of ten rats each 1 week after the operation and treated as follows: Group-1 control animals were given 6% ethanol orally for 7 days. (Ethanol was the solvent used.) Group-2 animals were given the test compound at a dose of 10-0 mg/kg orally. Group-3 animals were given testosterone propionate, 10-0 mg/kg intra¬ muscularly. Group-4 animals were given the test compound, 10-0 mg/kg orally together with testosterone propionate 10-0 mg/kg intramuscularly. The test compound and testosterone propionate were given for 7 days. Twentyfour hours after the last medication, the animals were killed and the ventral 559

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Biological activity in steroids possessing nitrogen atoms: recent advances

Cited by 32 publications

References 167 publications

Structure‐function activity of azasterols and nitrogen‐containing steroids

Structure‐function activity of azasterols and nitrogen‐containing steroids

Effect of Hypocholesteremic Compounds on Bacterial Multiplication

Anti-Androgenic Activity of 7,8,9,10-Tetrahydro-7-Oxo-Benzo (C) Phenanthridine (A11-Iv) on Immature, Castrated, Male Rats

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