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

Walder, Joseph A.; Zaugg, Robert H.; Iwaoka, Robert S; Watkin, William; Klotz, Irving M.

doi:10.1073/pnas.74.12.5499

Cited by 37 publications

(21 citation statements)

References 24 publications

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“…The acetyl-3,5-dibromosalicylic acid (dibromo aspirin), a derivative of aspirin, has been reported to exhibit the erythrocyte sickling [15]. Acetylation of hemoglobin by aspirin and other acetylating agents has been used to generate haemoglobin analogs with altered structural and functional properties, and may prove useful in the treatment of sickle cell disease [16].…”

Section: Mode Of Action Of Aspirin and Nsaidsmentioning

confidence: 99%

Structure Activity Relationship (SAR) of Some Benzoic Acid Derivatives from Plant Origin that Exhibit Anti-Sickling Properties in vitro - (Review)

Pierre¹,

Moses²,

Peter³

2015

Nat Prod Chem Res 2015

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Section: Mode Of Action Of Aspirin and Nsaidsmentioning

confidence: 99%

Structure Activity Relationship (SAR) of Some Benzoic Acid Derivatives from Plant Origin that Exhibit Anti-Sickling Properties in vitro - (Review)

Pierre¹,

Moses²,

Peter³

2015

Nat Prod Chem Res 2015

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“…Since "Br may become more available in the future (8), radiobromine labeled pharmaceuticals could play an increasing role in diagnostic studies.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and biodistribution of acetyl‐3,5‐br‐82‐dibromosalicylic acid

Wong

Spencer

1981

Labelled Comp Radiopharmac

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l a t i o n o f t h i s i n t e rmediate. B i o d i s t r i b u t i o n s t u d i e s i n mice w i t h and w i t h o u t a neuroblastoma showed t h a t t h e tumor/blood r a d i o a c t i v i t y r a t i o was low (0.3 a t one hour). d i c a t e d t h a t o n l y 20 t o 30% o f t h e r a d i o a c t i v i t y corresponded t o dibromoaspirin.Studies o f r a b b i t s w i t h inflammatory l e s i o n s showed t h a t t h e inflammatory/normal t i s s u e uptake r a t i o was 1.0 t o 1.9. Low uptake of r a d i o a c t i v i t y was l i k e l y due t o r a p i d dehalogenation i n v i v o .T h i n l a y e r chromatography o f u r i n e i nThe RBC/plasma r a t i o was l e s s than 0.5.

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“…Moreover, some halo-aspirin derivatives may have unique pharmacological actions of their own (see Refs. [25,26]) so that making non-ulcerogenic pre-drugs of these may be considered an added therapeutic benefit.…”

Section: Drugsmentioning

confidence: 97%

Anti-inflammatory/anti-pyretic salicylic acid esters with low gastric ulcerogenic activity

Rainsford

Whitehouse

1980

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The methyl and some other esters of acetylsalicylic and salicylic acids and their derivatives were found to have much lower gastric ulcerogenic activity (when assayed in the stress-sensitized rat) compared with their corresponding acids. There was little or no loss in therapeutic potencies of these salicylate esters as determined by assessment of anti-inflammatory activity (against the carrageenan-induced oedema) and antipyretic activity (against yeast-induced fever in rats. The methyl ester of acetylsalicylic acid (=AME) was almost devoid of gastric irritancy/ulcerogenicity (as observed with acetylsalicylic acid) when given orally to pigs for 10 days. AME had appreciable anti-inflammatory activity in the adjuvant-arthritis model and at high doses (200 mg/kg t.i.d.) was without the lethal effects seen with acetylsalicylic acid. Moreover, no toxic effects were seen after long-term administration of 100-1000 mg/kg/day AME for 3-4 months. The results provide further evidence for the hypothesis that the carboxylic acid moiety of salicylates is a major factor in the gastric ulcerogenic activity of these drugs. The methyl esters of these salicylates may be considered as models for the development of pro-drugs and in some cases may be therapeutic alternatives to acetylsalicylic acid or salicylate.

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

Cited by 37 publications

References 24 publications

Structure Activity Relationship (SAR) of Some Benzoic Acid Derivatives from Plant Origin that Exhibit Anti-Sickling Properties in vitro - (Review)

Structure Activity Relationship (SAR) of Some Benzoic Acid Derivatives from Plant Origin that Exhibit Anti-Sickling Properties in vitro - (Review)

Synthesis and biodistribution of acetyl‐3,5‐br‐82‐dibromosalicylic acid

Anti-inflammatory/anti-pyretic salicylic acid esters with low gastric ulcerogenic activity

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