Inhibition of sickling by methyl acetimidate

Chao, Tessa L.; Berenfeld, Marion R.; Gabuzda, Thomas G.

doi:10.1016/0014-5793(76)80015-4

Cited by 18 publications

(2 citation statements)

References 14 publications

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“…at the pH range we employed for these studies, monofunctional reagents may form transient intermediates that have crosslinking capabilities [28] . That monofunctional reagent are, indeed, capable of crosslinking reactions in red cells and other tissues has been confirmed by several investigators [29,301 . The relatively small amount of such transient intermediates available for crosslinking would then explain the much larger concentration requirement for monofunctional reagents noted in the present study.…”

Section: Jss:287mentioning

confidence: 76%

Membrane effects of imidoesters in hereditary stomatocytosis

et al. 1978

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The marked increase in cation (Na+, K+) permeability that results in swollen, cup-shaped red cells in the hereditary stomatocytosis syndrome can be corrected in vitro with a bifunctional crosslinking reagent, dimethyl adipimidate (DMA). 45Ca influx in intact RBC, 45Ca efflux in red ghosts, and 45Ca retention in red ghosts are normal and not influenced by DMA. Endocytosis in resealed red ghosts is strikingly impaired but becomes normal if cells are first treated with 2 mM DMA. Protein kinase mediated phosphorylation of membrane proteins by AT32P--only 20--40% of normal control values in both shortterm (5 min) and more extended (60 min) incubations--is not improved by DMA. After reaction of 14C-DMA with stomatocytes, radiolabel is found associated with phosphatidyl serine and phosphatidyl ethanolamine and is also widely distributed among membrane proteins. Cation permeability of stomatocytes in corrected at DMA concentrations (1 mM) that result in barely detectable crosslinking of aminophospholipids or proteins, suggesting that either crosslinking of a minor component present in only small quantities or intramolecular (rather than intermolecular) crosslinking is responsible for the permeability effects. DMA, whose maximal crosslinking dimension is 7.3--9 A, is the most effective bifunctional imidoester of those tested. Shorter (dimethyl malonimidate) or longer (dimethylsuberimidate) reagents are either less effective than DMA or totally without effect.

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Section: Jss:287mentioning

confidence: 76%

Membrane effects of imidoesters in hereditary stomatocytosis

et al. 1978

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“…It has occurred to a number of investigators that the aggregation of deoxy Hb S might be inhibited by chemical modification of the protein (6)(7)(8)(9)(10)(11). Of the different functional groups in the side chains of this protein, the amino group seems particularly attractive because it can be modified with relatively mild reagents that might be pharmacologically acceptable.…”

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confidence: 99%

Alternative aspirins as antisickling agents: acetyl-3,5-dibromosalicylic acid.

Walder¹,

Zaugg²,

Iwaoka³

et al. 1977

Proc. Natl. Acad. Sci. U.S.A.

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Acetyl-3,5-dibromosalicylic acid (dibromoas irin) is shown to be a potent acylating agent of intracellular hemoglobin in vitro. Transfer of the actyl group of dibromoaspirin to amino groups of hemoglobins A and S seems to occur predominantly at just two or three sites on these proteins. This acetylation produces moderate increases in the oxygen affinities of normal and sickle erythrocytes. Furthermore, treatment of intracellular hemoglobin S with dibromoaspirin directly inhibits erythrocyte sickling. This antisickling effect is paralleled by an increase in the minimum gelling concentration of deoxy hemoglobin S extracted from sickle erthrocytes that had been exposed to low concentrations of dibromoaspirin. These observations suggest that dibromoaspirin might be an effective antisickling agent in vivo.

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Covalent Inhibitors of the Gelation of Sickle Cell Hemoglobin and Their Effects on Function

Manning

1991

Advances in Enzymology - And Related Areas of Molecular Biology

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Inhibition of sickling by methyl acetimidate

Cited by 18 publications

References 14 publications

Membrane effects of imidoesters in hereditary stomatocytosis

Membrane effects of imidoesters in hereditary stomatocytosis

Alternative aspirins as antisickling agents: acetyl-3,5-dibromosalicylic acid.

Covalent Inhibitors of the Gelation of Sickle Cell Hemoglobin and Their Effects on Function

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