The effect of some oligo-amines and -guanidines on membrane permeability in higher plants

Srivastava, Santosh K.; Smith, Terence A.

doi:10.1016/s0031-9422(00)82404-8

Cited by 42 publications

(19 citation statements)

References 34 publications

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“…The guanidines were donated, or synthesized as described in ref. [15]. The ratio of hordatine A and B to M was ca 1 to 1.7 in this preparation.…”

Section: Enzymes and Substratesmentioning

confidence: 67%

The inhibition and activation of polyamine oxidase from oat seedlings

Smith

1985

Plant Growth Regul

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In a homologous series of di-guanidines (NH2C(= NH)NH(CH2)xNHC(= NH) NH2) where x = 2-12, greatest inhibition of polyamine oxidase was found with x : 8. The synthetic fungicide guazatine NH2C(= NH)NH --(CH ~)s,....~ N H NH2C(= NH)NH --(CH2)8 /was particularly effective as an inhibitor of polyamine oxidase, with Ki of ca 10-~ M. Inhibition due to the tri-amine derived from guazatine by hydrolysis was less effective by a factor of ca 200. Comparison of various inorganic salts at I Mshowed that polyamine oxidase activity was enhanced in the order RbC1 > KCI > KBr > NH,CI > NaNO 3 > LiCI = NaC1 > control (no salt) > CaC12 = MgCI~. Activity in RbC1 was about 4 to 5 times greater than in the salt-free control. Enzyme activity is rapidly lost during assay. This loss of activity could not be attributed to inhibition by aminopropylpyrroline or diaminopropane. Moreover the superoxide scavenger copper salicylate had no protective effect on enzyme activity.

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“…The guanidines were donated, or synthesized as described in ref. [15]. The ratio of hordatine A and B to M was ca 1 to 1.7 in this preparation.…”

Section: Enzymes and Substratesmentioning

confidence: 67%

The inhibition and activation of polyamine oxidase from oat seedlings

Smith

1985

Plant Growth Regul

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“…In the above cited work, Srivastava and Smith (26) reported that exogenously applied putrescine, spermidine, and spermine decreased betacyanin efflux in temperature stressed beet root discs, while total ion efflux was shown to increase. To explain this discrepancy, they speculated that polyamines may disrupt the plasmalemma but stabilize the tonoplast.…”

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confidence: 97%

“…They reported that exogenously applied spermidine and spermine decreased betacyanin efflux from the discs of beet (Beta vulgaris L.) roots treated with ethanol. Polyamines were also effective in reducing betacyanin efflux in beet root tissues wounded with ethylene, ammonium sulfate (15), RNAase, or high temperature (1,26).…”

mentioning

confidence: 99%

Putrescine-Induced Wounding and Its Effects on Membrane Integrity and Ion Transport Processes in Roots of Intact Corn Seedlings

DiTomaso

Shaff²,

Kochian³

1989

Plant Physiol.

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Interactions between putrescine and membrane function were examined with the use of a recently developed microelectrode system that enables us simultaneously to quantify membrane potentials and net K+ fluxes associated with individual cells at the root surface of an intact corn (Zea mays L.) seedling. In contrast to the results of others, our analyses indicate that exogenous putrescine (0.5 millimolar), in the absence of calcium, does not maintain membrane stability. In addition, putrescine caused a wound response characterized by a gradual depolarization of the membrane potential and a considerable net efflux of K+ from the root. In the presence of calcium, both short term (20 minutes) and long term (24 hours) exposure to a high concentration of exogenous putrescine (5 millimolar) also caused a reduction in the resting membrane potential and a significant K+ efflux. However, preincubating corn roots in a solution containing the antioxidant ascorbate ameliorated the wounding effects of putrescine and slightly increased potassium uptake. A similar preincubation in the absence of calcium did not protect membranes against putrescine-induced damage. The ameliorating effect of ascorbate on putrescine-induced membrane damage suggests that the wounding response of high putrescine levels in corn roots involves the catabolism of the polyamine by a cell wall diamine oxidase, with the concomitant production of hydrogen peroxide and free radicals resulting in peroxidative damage of the plasmalemma.

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“…1 The mode of action is not known, but the closely related dodecylguanidinium acetate ( 4 , dodine) has been in widespread use since 1956 as a fungicide and may act by membrane disruption. 3 As part of an ongoing program in the synthesis of structurally novel guanidine-containing natural products, 4 we planned to prepare phidianidines A ( 1a ) and B ( 1b ) by coupling of the appropriate ethyl indole-3-acetate ( 2a or 2b ) with hydroxyguanidine 3 containing a suitably protected nitrogen on the other end of the five carbon side chain. There is limited precedent for the synthesis of 3-amino-1,2,4-oxadiazoles by coupling of esters with hydroxyguanidines 5 and nature may use a related route for the biosynthesis of the phidianidines.…”

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confidence: 99%

Synthesis of Phidianidines A and B

Lin

Snider

2012

J. Org. Chem.

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Reaction of a substituted indole-3-acetyl chloride with N-5-azidopentyl-N′-hydroxyguanidine generated a substituted 3-(5-azidopentylamino)-5-((indol-3-yl)-methyl)-1,2,4-oxadiazole. Reduction of the azide with zinc and ammonium formate afforded the amine, which was elaborated to the guanidine, completing short and efficient syntheses of the cytotoxic natural products phidianidines A and B in 19% overall yield by a convergent route that will make analogues readily available for biological evaluation. Initial screening in the NCI 60 cell line at 10−5 M indicated that the bromine on the indole is necessary for activity and that the amine precursor to phidianidine A is more potent than phidianidine A.

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The effect of some oligo-amines and -guanidines on membrane permeability in higher plants

Cited by 42 publications

References 34 publications

The inhibition and activation of polyamine oxidase from oat seedlings

The inhibition and activation of polyamine oxidase from oat seedlings

Putrescine-Induced Wounding and Its Effects on Membrane Integrity and Ion Transport Processes in Roots of Intact Corn Seedlings

Synthesis of Phidianidines A and B

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