SnitrosoNacetylpenicillamine

S-nitroso-N-acetylpenicillamine, commonly abbreviated SNAP, is an organic S-nitrosothiol used as a nitric oxide (NO) donor in biological and chemical research. It is derived from N-acetylpenicillamine and features a nitroso group attached to the sulfur atom of a thiol. SNAP serves as a controllable source of NO for experiments investigating nitrosative signaling, vasodilation, and related processes.

As an NO donor, SNAP releases nitric oxide under certain conditions. NO release can occur spontaneously at physiological temperatures or be accelerated by light, heating, or interactions with thiols and metal ions through established nitrosothiol chemistry. Compared with some other S-nitrosothiols, SNAP is valued for its relative stability in aqueous solutions and its suitability for use in cell culture and biochemical assays, where a gradual and measurable NO flux is desirable.

Applications of SNAP span multiple fields. In vascular biology, it is used to study NO-mediated vasodilation and endothelial signaling. In cell biology and biochemistry, SNAP facilitates examination of S-nitrosylation, nitrosative stress, and NO-dependent signaling pathways. It also serves as a standard NO source for calibrating detectors and validating assay systems.

Storage and safety are important considerations. SNAP is typically stored at low temperature, away from light, and in appropriate solvent systems to preserve stability. It should be handled using standard laboratory safety practices with precautions to avoid inhalation, ingestion, or skin and eye contact. As with other reactive nitrogen species, improper handling can lead to unintended NO release and reactive byproducts.

Synthesis, at a conceptual level, involves nitrosation of the thiol group in N-acetylpenicillamine, yielding the S-nitrosothiol SNAP.