A Smart Molecule for Selective Sensing of Nitric Oxide: Conversion of NO to HSNO; Relevance of Biological HSNO Formation

Abstract

A smart molecule, QT490, containing thiosemicarbazide moiety acts as a highly selective turn-on in vitro NO sensor through the unprecedented NO-induced transformation of thiosemicarbazide moiety to 1,3,4-oxadiazole heterocycle with the concomitant release of HSNO, thereby eliminating any interference from various endogenous biomolecules including dehydroascorbic acid, ascorbic acid, etc. The kinetic studies of the reactions between QT490 and NO provide a mechanistic insight into formation of HSNO/RSNO from the reaction between H2S/RSH and NO in the biological system. This novel probe is non-cytotoxic, cell permeable, water-soluble, and appropriate for intracellular cytoplasmic NO sensing with the possibilities of in vivo applications.

Design of a Pyrene Scaffold Multifunctional Material: Real-Time Turn-On Chemosensor for Nitric Oxide, AIEE Behavior, and Detection of TNP Explosive

“…The PyDA-NP probe reacts with NO in the presence of O 2 through the formation of intermediate N 2 O 3 , which acts as a source of NO + (N 2 O 3 → NO + + NO 2 – ) to give N -nitroso amine. 43 On the other hand, NO + (NO + BF 4 – ) in CH 3 CN also directly reacts with PyDA-NP to give deep yellow N -nitrosamine. The pure product thus obtained was analyzed by the 1 H NMR (Figure S7), HRMS (Figure S8), and FT-IR studies (Figure S9).…”

Fundamental chemistry of binary S,N and ternary S,N,O anions: analogues of sulfur oxides and N,O anions

“…Indeed, very recently, the formation of HSNO in aqueous solution under physiological conditions from the treatment of a molecule containing a thiosemicarbazide moiety has been established by high-resolution mass spectrometry. 50 In the absence of stabilising counter-cations, the conjugate acids of these anions are labile species that have been identified either by the formation of either main-group element or transition-metal complexes, e.g. HNSO (Section 2.2, Scheme 2), or by a combination of matrix isolation and IR spectroscopy, e.g.…”

Chemical Biology of H2S Signaling through Persulfidation

“…Reaction of thiosemicarbazide with NO • results in HSNO formation under physiological conditions; thiosemicarbazides are therefore proposed to serve as a tool capable of transforming intracellular NO • into HSNO. 478…”