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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 | Protein carbonylgroups as biomarkers of oxidative stress显示文摘 | Dalle-donne I Rossi R Giustarini D | 2003 | Clinica Chimica Acta2003，329，12： | 1 |
| 3 | Protein carbonylation in human diseases显示文摘 | Dalle-Donne I Giustarini D Colombo R | 2003 | Trends Mol Med2003，9，4： | 1 |
| 4 | Functional Roles of Protein Nitration in Acute and Chronic Liver Diseases显示文摘 | Mohamed A. Abdelmegeed Byoung-Joon Song Daniela Giustarini | 2014 | Oxidative Medicine and Cellular Longevity2014，，： | 1 |
| 5 | Protein carbonyl groups as biomarkersof oxidative stress显示文摘 | Dalle-Donne I Rossi R Giustarini D | 2003 | Clinica Chimica Acta2003，329，12： | 1 |
| 6 | Oxidative stress and human diseases:Origin,link,measurement,mechanisms,and biomarkers显示文摘 | Giustarini D Dalle-Donne I Tsikas D | 2009 | Crit Rev Clin Lab Sci2009，46，56： | 1 |
| 7 | Protein carbonyl groups as biomarkers of oxidative stress显示文摘 | Dalle-Donne I Rossi R Giustarini D | 2003 | Clinica Chimica Acta2003，29，12： | 1 |
| 8 | Nitric oxide and S-ni- trosothiols in human blood显示文摘 | Giustarini D Milzani A Colombo R | 2003 | Clin Chim Acta2003，330，12： | 1 |
| 9 | Thyroid autoimmunity in patients with malignant and benign breast diseases before surgery 显示文摘 | Giustarini E Pinchera A Fierabracci P | 2006 | Eur J Endocrinol2006，154，5： | 1 |
| 10 | Effects of hydrogen sulfidereleasing L-DOPA derivatives on glial activation:potential for treating Parkinson disease显示文摘 | Lee M Tazzari V Giustarini D | 2010 | J Biol Chem2010，285，17： | 1 |
| 11 | Protein carbonyl groups as biomarkers of oxidative stress显示文摘 | DaRe-Donne I Rossi R Giustarini D | 2003 | Clin Chim Acta2003，329，12： | 1 |
| 12 | A Change Detec- tion Approach to Flood Mapping in Urban Areas Using TerraSAR-X 显示文摘 | GIUSTARINI L HOSTACHE R | 2013 | IEEE Trans on Geoseience and Remote Sensing2013，51，4： | 1 |
| 13 | Is the risk of primary hyperparathyroidism increased in patients with untreated breast cancer显示文摘 | Belardi V Fiore E Giustarini E | 2013 | J Endocrinol Invest2013，36，5： | 1 |
| 14 | Protein carbonyl groups as biomarkers of oxidative stress显示文摘 | Rossi R Giustarini D | 2003 | Clin Chim Acta2003，329，： | 1 |
| 15 | Protein carbonyl groups as biomarkers of oxidative stress显示文摘 | Rossi R Giustarini D | 2003 | Clin Chim Acta2003，329，： | 1 |
| 16 | Protein carbonyl groups as biomarkers of oxidative stress 显示文摘 | Dalle-Donne I Rossi R Giustarini D | 2003 | Clin Chim Acta2003，329，： | 1 |
| 17 | Thyroid autoim- munity in patients with malignant and benign breast diseases be- fore surgery显示文摘 | Giustarini E Pinchera A Fierabracei P | 2006 | Eur J Endocrinol2006，154，5： | 1 |
| 18 | Protein carbonylation in human diseases显示文摘 | le-Donne I Giustarini D Colombo R | 2003 | Trends Mol Med2003，9，： | 1 |
| 19 | Protein carbonyl groups as biomarkers of oxidative stress 显示文摘 | Dalle-Donne I Rossi R Giustarini D | 2003 | Clin Chimicu Acta2003，29，： | 1 |
| 20 | Protein carbonylation in human diseases显示文摘 | Dalle-Donne I Giustarini D Colombo R | | 0，，04： | 1 |
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