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| 1 | S-Nitroso-N-acetyl-L-cysteine ethyl ester(SNACET) and N-acetyl-L-cysteine ethyl ester(NACET)–Cysteine-based drug candidates with unique pharmacological profiles for oral use as NO, H_2S and GSH suppliers and as antioxidants: Results and overview显示文摘S-Nitrosothiols or thionitrites with the general formula RSNO are formally composed of the nitrosyl cation(NOt) and a thiolate(RSà), the base of the corresponding acids RSH. The smallest S-nitrosothiol is HSNO and derives from hydrogen sulfide(HSH, H_2S). The most common physiological S-nitrosothiols are derived from the amino acid L-cysteine(Cys SH). Thus, the simplest S-nitrosothiol is S-nitroso-L-cysteine(Cys SNO). Cys SNO is a spontaneous potent donor of nitric oxide(NO) which activates soluble guanylyl cyclase to form cyclic guanosine monophosphate(c GMP). This activation is associated with multiple biological actions that include relaxation of smooth muscle cells and inhibition of platelet aggregation.Like NO, Cys SNO is a short-lived species and occurs physiologically at concentrations around 1 n M in human blood. Cys SNO can be formed from Cys SH and higher oxides of NO including nitrous acid(HONO)and its anhydride(N_2O_3). The most characteristic feature of RSNO is the S-transnitrosation reaction by which the NOtgroup is reversibly transferred to another thiolate. By this way numerous RSNO can be formed such as the low-molecular-mass S-nitroso-N-acetyl-L-cysteine(SNAC) and S-nitroso-glutathione(GSNO), and the high-molecular-mass S-nitrosol-L-cysteine hemoglobin(Hb Cys SNO) present in erythrocytes and S-nitrosol-L-cysteine albumin(Alb Cys SNO) present in plasma at concentrations of the order of 200 n M. All above mentioned RSNO exert NO-related biological activity, but they must be administered intravenously. This important drawback can be overcome by lipophilic charge-free RSNO.Thus, we prepared the ethyl ester of SNAC, the S-nitroso-N-acetyl-L-cysteine ethyl ester(SNACET), from synthetic N-acetyl-L-cysteine ethyl ester(NACET). Both NACET and SNACET have improved pharmacological features over N-acetyl-L-cysteine(NAC) and S-nitroso-N-acetyl-L-cysteine(SNAC), respectively,including higher oral bioavailability. SNACET exerts NO-related activities which can be utilized in the urogenital tract and in the cardiovascular system. NACET, with high oral bioavailability, is a strong antioxidant and abundant precursor of GSH, unlike its free acid N-acetyl-L-cysteine(NAC). Here, we review the chemical and pharmacological properties of SNACET and NACET as well as their analytical chemistry.We also report new results from the ingestion of S-[^(15) N]nitroso-N-acetyl-L-cysteine ethyl ester(S^(15) NACET) demonstrating the favorable pharmacological profile of SNACET. | Dimitrios Tsikas Kathrin S.Schwedhelm Andrzej Surdacki Daniela Giustarini Ranieri Rossi Lea Kukoc-Modun George Kedia Stefan ückert | 2018 | Journal of Pharmaceutical Analysis2018，8，1： | 3 |
| 2 | Relationship betwwen hyperinsulinemia and angio- graphically defined coronary atherosclerosis in non-diabetic men显示文摘 | Kruszelnicka-Kwiatkowska O Surdacki A Goldsztajn P | 2002 | Diabete Metab2002，28，41： | 1 |
| 3 | Reduced urinary excretion of nitric oxide metaboihes and increase plasma levels of asymmetric dimethylarginine in men with essential hypertension 显示文摘 | Surdacki A Nowicki M Sandmann J | 1999 | J Cardiovascular Pharmacology1999，33，4： | 1 |
| 4 | Nontraditional atherosclerotic risk factors and extent of coronary atherosclerosis in patients with combined impaired fasting glucose and impaired glucose tolerance显示文摘 | Surdacki A Stochmal E Szurkowska M etal | 2007 | Metabolism2007，56，1： | 1 |
| 5 | Reduced urinary excretion of nitric oxide metaboiltes and increase plasma levels of asymmetric dimethylarginine in men with essential hypertension显示文摘 | Surdacki A Nowickim Sandmann J | | 0，，04： | 1 |
| 6 | Relationship between Hyperinsulinemia and Angiographically Defined Coronary Atherosclerosis in Non-diabetic Men显示文摘 | Kwiatkowska K Surdacki A Goldsztajn P | 2002 | Diabetes Metab2002，28，： | 1 |
| 7 | Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hyper-tension 显示文摘 | Surdacki A Nowicki M Sandmann J | 1999 | J Cardiovasc Pharmacol1999，33，4： | 1 |
| 8 | Oral L-arginine improves endothelial function in healthy individuals older than 70 years显示文摘 | Bode Boger SM Muke J Surdacki A | 2003 | Vasc Med2003，8，： | 1 |
| 9 | Nontraditional atherosclerotic risk factors and extent of coronary atherosclerosis in patients with combined impaired fasting glucose and impaired glucose tolerance 显示文摘 | Surdacki A Stochmal E Szurkowska M | 2007 | Metabolism2007，56，1： | 1 |
| 10 | Plasma ANP and cyclic GMP levels versus left ventricular performance at different AV delays in AV sequential pacing显示文摘 | Surdacki A Bednarek J Radziszewski W | 1994 | Pacing Clin Electrophysiol1994，17，41： | 1 |
| 11 | Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension显示文摘 | Surdacki A Nowicki M Sandmann J | 1999 | J Cardiovasc Pharmacol1999，33，4： | 1 |
| 12 | Nontraditional atherosclerotic risk factors and extent of coronary atherosclerosis in patients with combined impaired fasting glucose and impaired glucose tolerance显示文摘 | SURDACKI A STOCHMAL E SZURKOWSKA M | 2007 | Metabolism2007，56，1： | 1 |
| 13 | Effect of a hemodialysis session on plasma levels of endothelin- 1 in hypertensive and normotensive subjects with end-stage renal failure显示文摘 | Surdacki A Sulowicz W Wieczorek Surdacka E | 1999 | Nephron1999，81，1： | 1 |
| 14 | Nontraditional atherosclerotic risk factors and extent of coronary atherosclerosis in patients with combined impaired fasting glucose and impaired glucose tolerance显示文摘 | SURDACKI A STOCHMAL E SZURKOWSKA M | 2007 | Metabolism2007，56，1： | 1 |
| 15 | Lack of beneficial effects of L-arginine infusion in primary pulmonary hypertension 显示文摘 | Surdacki A Zmudka K Bieron K | 1994 | Wien Klin Wochenschr1994，106，16： | 1 |
| 16 | Reduced urinary excretion of nitric oxide metabolites and increase plasma levels of asymmetric dimethylarginine in men with essential hypertension显示文摘 | Surdacki A Nowicki M Sandmann J | 1999 | J Cardiovascular Pharmacol1999，33，： | 1 |
| 17 | Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension显示文摘 | Surdacki A Nowicki M Sandmann J | 1999 | J Cardiovasc Pharmacol1999，33，4： | 1 |
| 18 | Oral L-arginine Improves Endothelial Function in Healthy Individuals Older than 70 Years显示文摘 | Bode-boger S M Muke J Surdacki A | 2003 | Vasc Med2003，8，2： | 1 |
| 19 | Differential associations of angiographie extent and severity of coronary artery disease with asymmetric dimethylarginine but not insulin resistance in non-dia- betic men with stable angina: a cross-sectional study 显示文摘 | Kruszelnicka O Surdacki A Golay A | 2013 | Cardio- vasc Diabetol2013，12，： | 1 |
| 20 | Reduced urinary excretion of nitric oxide metabolisms and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension显示文摘 | Surdacki A Nowicki M Sandmann J | 1999 | Cardiovasc Pharmacol1999，33，8： | 1 |
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