Md. Travis et al., L-S-NITROSO-BETA,BETA-DIMETHYLCYSTEINE AND D-S-NITROSO-BETA,BETA-DIMETHYLCYSTEINE DIFFERENTIALLY INCREASE CGMP IN CULTURED VASCULAR SMOOTH-MUSCLE CELLS, European journal of pharmacology, 318(1), 1996, pp. 47-53
We examined the effects of the L- and D-isomers of S-nitroso-beta,beta
-dimethylcysteine (L- and D-S-nitrosopenicillamine, 10(-7)-10(-5) M) o
n the guanosine 3',5'-cyclic monophosphate (cGMP) content of cultured
porcine aortic smooth muscle cells and the decomposition of these ster
eoisomers to nitric oxide (NO). L-S-nitrosopenicillamine was a more po
tent generator of cGMP than D-S-nitrosopenicillamine although both ste
reoisomers equally decomposed to NO. The 10(-7) M concentration of L-
or D-S-nitrosopenicillamine did not generate detectable amounts of NO
although 10(-7) M L-S-nitrosopenicillamine but not D-S-nitrosopenicill
amine generated significant amounts of cGMP. This study shows that the
stereoisomeric configuration of S-nitrosopenicillamine is an importan
t factor in its biological potency. The data suggest that the extracel
lular or intracellular generation of NO is not the only mechanism by w
hich this S-nitrosothiol generates cGMP in vascular smooth muscle.