Walker, Jeffery W.; Martin, Hunter; Schmitt, Frederick R.; Barsotti, Robert J. published the artcile< Rapid release of an α-adrenergic receptor ligand from photolabile analogs>, Formula: C9H9NO4, the main research area is alpha adrenergic receptor agonist photorelease; phenylephrine analog photorelease adrenergic receptor.
A series of 2-nitrobenzyl derivatives of the α1-selective adrenergic agonist, L-phenylephrine [(R)-N-[2-(3-hydroxyphenyl)-2-hydroxyethyl]-N-methylammonium chloride], were synthesized and characterized for the purpose of developing biol. inert compounds that can be rapidly converted to L-phenylephrine by near-UV irradiation The compounds, derivatized on the phenolic oxygen, were O-(1-(2-nitrophenyl)ethyl)phenylephrine (I), O-(2-nitrobenzyl)phenylephrine (II), O-(4,5-dimethoxy-2-nitrobenzyl)phenylephrine (III), and O-(α-carboxyl-2-nitrobenzyl)phenylephrine (IV). All 4 compounds photolyzed to free phenylephrine following a brief exposure to 300-350-nm light or 347-nm laser light with steady-state quantum yields ranging from 0.05 to 0.28. The rates of phenylephrine formation on photolysis were estimated from the decay rates of aci-nitro intermediates detected by absorbance between 380 and 500 nm. IV displayed the highest quantum yield (0.28) and most rapid photolysis rate (1980 s-1) measured under near physiol. conditions, pH 8.0, 22°. Biol. properties of the compounds were examined in smooth muscle from rat caudal artery. Laser pulse photolysis of IV at 347 nm initiated a maximal contraction in Krebs buffer, pH 7.1, 25°, that mimicked the response to 50 μM phenylephrine but was faster in onset. Photoinitiated contractions were characterized by a delay of 0.93 s followed by a rising phase with a 10-90% rise time of 3.56 s. Responses were fully blocked by the α1-selective antagonist prazosin. Similar results were obtained using I-III, but a slowly developing sustained phase of smooth muscle contraction was altered in the presence of I-III. IV represents a useful new biol. inactive caged phenylephrine that should facilitate temporally and spatially resolved studies of α1-adrenergic receptor mechanisms in cells and tissues.
Biochemistry published new progress about Caudal artery. 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Formula: C9H9NO4.
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