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Searching for new NO-donor aspirin-like molecules: a new class of nitrooxy-acyl derivatives of salicylic acid.

Journal of medicinal chemistry (2008-02-26)
Loretta Lazzarato, Monica Donnola, Barbara Rolando, Elisabetta Marini, Clara Cena, Gabriella Coruzzi, Elena Guaita, Giuseppina Morini, Roberta Fruttero, Alberto Gasco, Stefano Biondi, Ennio Ongini
ABSTRACT

A new class of products in which the phenol group of salicylic acid is linked to alkanoyl moieties bearing nitrooxy functions has been synthesized and studied for their polyvalent actions. The products were stable in acid and neutral media, while they were hydrolyzed in human serum. Their half-lives were dependent upon the structure of alkanoyl moieties. The products showed anti-inflammatory activities similar to aspirin when tested in the carrageenan-induced paw edema assay in the rat. Interestingly, unlike aspirin, they showed reduced or no gastrotoxicity in a lesion model in rats at equimolar doses. A number of them were able to inhibit platelet aggregation induced by collagen in human platelet-rich plasma. All of the products were capable of relaxing rat aortic strips precontracted with phenylephrine in a concentration-dependent manner. Selected members of this new class of nonsteroidal anti-inflammatory drugs might represent possible safer alternatives to aspirin in different clinical settings.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Salicylic acid, ACS reagent, ≥99.0%
Sigma-Aldrich
Acetylsalicylic acid, ≥99.0%
Sigma-Aldrich
Aspirin, meets USP testing specifications
Sigma-Aldrich
Salicylic acid, suitable for plant cell culture
Sigma-Aldrich
Salicylic acid, puriss. p.a., ≥99.0% (T)
Sigma-Aldrich
Salicylic acid, ≥99%, FG
Sigma-Aldrich
Salicylic acid, BioXtra, ≥99.0%
Sigma-Aldrich
Acetylsalicylic acid, analytical standard
Sigma-Aldrich
Salicylic acid, meets analytical specification of Ph. Eur., BP, USP, 99.5-100.5% (calc. to the dried substance)
Sigma-Aldrich
Salicylic acid, ReagentPlus®, ≥99%
Supelco
Salicylic acid, certified reference material, TraceCERT®