Tom 17, Nr 4 (2020)
Artykuł przeglądowy
Opublikowany online: 2021-02-28
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Siarkowodór — od kłopotliwego zapachu do podręcznika farmakologii
Choroby Serca i Naczyń 2020;17(4):225-235.
Streszczenie
Historia siarkowodoru (H2S) — bezbarwnego, toksycznego gazu o charakterystycznej, odrażającej woni zepsutych jajek — jest długa. Odegrał on istotną rolę nie tylko w ewolucji wszechświata, ale również w ewolucji ustrojów żywych. Poza swoim udziałem w historii ewolucji gaz ten jest jednym z ważnych gazoprzekaźników i odgrywa kluczową rolę w wielu procesach biologicznych. W pracy omówiono drogi syntezy endogennego siarkowodoru, a także dokonano przeglądu najistotniejszych działań biologicznych istotnych dla czynności układu krążenia. W dalszej części wskazano niektóre substancje pochodzenia naturalnego oraz uzyskane drogą syntezy chemicznej i zarejestrowane jako leki, które drogą różnych działań przyczyniają się do zwiększenia biodostępności siarkowodoru. Jednym z leków stosowanych w terapii jest zofenopril. Lek ten należy do klasy inhibitorów konwertazy angiotensyny (ACEI) zawierających w swojej chemicznej strukturze grupę sulfhydrylową. Metabolit zofenoprilu zwiększa ekspresję enzymu tworzącego siarkowodór oraz podwyższa jego stężenie we krwi i w mięśniu sercowym. Działań takich nie wykazano w odniesieniu do innych ACEI. Ta szczególna, wybiegająca poza hamowanie układu renina–angiotensyna, właściwość może stanowić jedno z wyjaśnień faktu, że w prospektywnym, randomizowanym badaniu klinicznym zofenopril skuteczniej niż inne ACEI ograniczał chorobowość i śmiertelność u pacjentów obciążonych wysokim ryzykiem sercowo-naczyniowym.
Słowa kluczowe: siarkowodórpochodzenieefekty sercowo-naczyniowegrupy sulfhydryloweleki modyfikujące
Referencje
- Olson KR, Straub KD. The role of hydrogen sulfide in evolution and the evolution of hydrogen sulfide in metabolism and signaling. Physiology (Bethesda). 2016; 31(1): 60–72.
- Smith R. A short history of hydrogen sulfide. American Scientist. 2010; 98(1): 6.
- Gorini F, Bustaffa E, Chatzianagnostou K, et al. Hydrogen sulfide and cardiovascular disease: doubts, clues, and interpretation difficulties from studies in geothermal areas. Sci Total Environ. 2020; 743: 140818.
- Kump LR, Pavlov A, Arthur M. Massive release of hydrogen sulfide to the surface ocean and atmosphere during intervals of oceanic anoxia. Geology. 2005; 33(5): 397.
- Goodwin LR, Francom D, Dieken FP, et al. Determination of sulfide in brain tissue by gas dialysis/ion chromatography: postmortem studies and two case reports. J Anal Toxicol. 1989; 13(2): 105–109.
- Abe K, Kimura H. The possible role of hydrogen sulfide as an endogenous neuromodulator. J Neurosci. 1996; 16(3): 1066–1071.
- Cao Xu, Ding L, Xie ZZ, et al. A review of hydrogen sulfide synthesis, metabolism, and measurement: is modulation of hydrogen sulfide a novel therapeutic for cancer? Antioxid Redox Signal. 2019; 31(1): 1–38.
- Rose P, Moore P, Zhu Y. H2S biosynthesis and catabolism: new insights from molecular studies. Cell Mol Life Sci. 2016; 74(8): 1391–1412.
- Huang CW, Moore PK. H2S synthesizing enzymes: biochemistry and molecular aspects. Handb Exp Pharmacol. 2015; 230: 3–25.
- Shen X, Carlström M, Borniquel S, et al. Microbial regulation of host hydrogen sulfide bioavailability and metabolism. Free Radic Biol Med. 2013; 60: 195–200.
- Yang J, Minkler P, Grove D, et al. Non-enzymatic hydrogen sulfide production from cysteine in blood is catalyzed by iron and vitamin B. Commun Biol. 2019; 2: 194.
- Lv B, Chen S, Tang C, et al. Hydrogen sulfide and vascular regulation — an update. J Adv Res. 2021; 27: 85–97.
- Huang CW, Moore PK. H2S synthesizing enzymes: biochemistry and molecular aspects. Handb Exp Pharmacol. 2015; 230: 3–25.
- Filipovic MR. Persulfidation (S-sulfhydration) and H2S. Handb Exp Pharmacol. 2015; 230: 29–59.
- Meng QH, Yang G, Yang W, et al. Protective effect of hydrogen sulfide on balloon injury-induced neointima hyperplasia in rat carotid arteries. Am J Pathol. 2007; 170(4): 1406–1414.
- Kamoun P, Belardinelli MC, Chabli A, et al. Endogenous hydrogen sulfide overproduction in Down syndrome. Am J Med Genet A. 2003; 116A(3): 310–311.
- Yang G, Wu L, Jiang Bo, et al. H2S as a physiologic vasorelaxant: hypertension in mice with deletion of cystathionine gamma-lyase. Science. 2008; 322(5901): 587–590.
- Sun Nl, Xi Y, Yang Sn, et al. [Plasma hydrogen sulfide and homocysteine levels in hypertensive patients with different blood pressure levels and complications]. Zhonghua Xin Xue Guan Bing Za Zhi. 2007; 35(12): 1145–1148.
- Whiteman M, Gooding KM, Whatmore JL, et al. Adiposity is a major determinant of plasma levels of the novel vasodilator hydrogen sulphide. Diabetologia. 2010; 53(8): 1722–1726.
- Ali MY, Ping CY, Mok YY, et al. Regulation of vascular nitric oxide in vitro and in vivo; a new role for endogenous hydrogen sulphide? Br J Pharmacol. 2006; 149(6): 625–634.
- Zhao W, Zhang J, Lu Y, et al. The vasorelaxant effect of H2S as a novel endogenous gaseous KATP channel opener. EMBO J. 2001; 20(21): 6008–6016.
- Papapetropoulos A, Pyriochou A, Altaany Z, et al. Hydrogen sulfide is an endogenous stimulator of angiogenesis. Proc Natl Acad Sci USA. 2009; 106(51): 21972–21977.
- Chen PH, Fu YS, Wang YM, et al. Hydrogen sulfide increases nitric oxide production and subsequent S-nitrosylation in endothelial cells. ScientificWorldJournal. 2014; 2014: 480387.
- Cao Xu, Wu Z, Xiong S, et al. The role of hydrogen sulfide in cyclic nucleotide signaling. Biochem Pharmacol. 2018; 149: 20–28.
- Ng HH, Yildiz GS, Ku JM, et al. Chronic NaHS treatment decreases oxidative stress and improves endothelial function in diabetic mice. Diab Vasc Dis Res. 2017; 14(3): 246–253.
- Cheung SHa, Lau JY. Hydrogen sulfide mediates athero-protection against oxidative stress via S-sulfhydration. PLoS One. 2018; 13(3): e0194176.
- Wang Y, Zhao X, Jin H, et al. Role of hydrogen sulfide in the development of atherosclerotic lesions in apolipoprotein E knockout mice. Arterioscler Thromb Vasc Biol. 2009; 29(2): 173–179.
- Krüger-Genge A, Blocki A, Franke RP, et al. Vascular endothelial cell biology: an update. Int J Mol Sci. 2019; 20(18).
- Charbonier FW, Zamani M, Huang NF. Endothelial cell mechanotransduction in the dynamic vascular environment. Adv Biosyst. 2019; 3(2): e1800252.
- Deanfield JE, Halcox JP, Rabelink TJ. Endothelial function and dysfunction: testing and clinical relevance. Circulation. 2007; 115(10): 1285–1295.
- Muellner MK, Schreier SM, Laggner H, et al. Hydrogen sulfide destroys lipid hydroperoxides in oxidized LDL. Biochem J. 2009; 420(2): 277–281.
- Du C, Lin X, Xu W, et al. Sulfhydrated sirtuin-1 increasing its deacetylation irtuin-1 increasing its deacetylation activity is an essential epigenetics mechanism of anti-atherogenesis by hydrogen sulfide. Antioxid Redox Signal. 2019; 30(2): 184–197.
- Xiong Q, Wang Z, Yu Y, et al. Hydrogen sulfide stabilizes atherosclerotic plaques in apolipoprotein E knockout mice. Pharmacol Res. 2019; 144: 90–98.
- Vacek TP, Rehman S, Neamtu D, et al. Matrix metalloproteinases in atherosclerosis: role of nitric oxide, hydrogen sulfide, homocysteine, and polymorphisms. Vasc Health Risk Manag. 2015; 11: 173–183.
- Wójcicka G, Jamroz-Wiśniewska A, Atanasova P, et al. Differential effects of statins on endogenous H2S formation in perivascular adipose tissue. Pharmacol Res. 2011; 63(1): 68–76.
- Xu Y, Du HP, Li J, et al. Statins upregulate cystathionine γ-lyase transcription and H2S generation via activating Akt signaling in macrophage. Pharmacol Res. 2014; 87: 18–25.
- Wu Sy, Pan Cs, Geng B, et al. Hydrogen sulfide ameliorates vascular calcification induced by vitamin D3 plus nicotine in rats. Acta Pharmacol Sin. 2006; 27(3): 299–306.
- Sikura KÉ, Potor L, Szerafin T, et al. Hydrogen sulfide inhibits calcification of heart valves; implications for calcific aortic valve disease. Br J Pharmacol. 2020; 177(4): 793–809.
- Sikura KÉ, Combi Z, Potor L, et al. Hydrogen sulfide inhibits aortic valve calcification in heart via regulating RUNX2 by NF-κB, a link between inflammation and mineralization. J Adv Res. 2021; 27: 165–176.
- Zagli G, Patacchini R, Trevisani M, et al. Hydrogen sulfide inhibits human platelet aggregation. Eur J Pharmacol. 2007; 559(1): 65–68.
- Grambow E, Mueller-Graf F, Delyagina E, et al. Effect of the hydrogen sulfide donor GYY4137 on platelet activation and microvascular thrombus formation in mice. Platelets. 2014; 25(3): 166–174.
- Grambow E, Leppin C, Leppin K, et al. The effects of hydrogen sulfide on platelet-leukocyte aggregation and microvascular thrombolysis. Platelets. 2017; 28(5): 509–517.
- Wallace JL, Wang R. Hydrogen sulfide-based therapeutics: exploiting a unique but ubiquitous gasotransmitter. Nat Rev Drug Discov. 2015; 14(5): 329–345.
- Benavides GA, Squadrito GL, Mills RW, et al. Hydrogen sulfide mediates the vasoactivity of garlic. Proc Natl Acad Sci USA. 2007; 104(46): 17977–17982.
- Martelli A, Testai L, Citi V, et al. Arylthioamides as H2S donors: l-cysteine-activated releasing properties and vascular effects in vitro and in vivo. ACS Med Chem Lett. 2013; 4(10): 904–908.
- Martelli A, Piragine E, Citi V, et al. Erucin exhibits vasorelaxing effects and antihypertensive activity by H2S-releasing properties. Br J Pharmacol. 2020; 177(4): 824–835.
- Wallace JL, Vaughan D, Dicay M, et al. Hydrogen sulfide-releasing therapeutics: translation to the clinic. Antioxid Redox Signal. 2018; 28(16): 1533–1540.
- Daniell HB, Carson RR, Ballard KD, et al. Effects of captopril on limiting infarct size in conscious dogs. J Cardiovasc Pharmacol. 1984; 6(6): 1043–1047.
- Westlin W, Mullane K. Does captopril attenuate reperfusion-induced myocardial dysfunction by scavenging free radicals? Circulation. 1988; 77(6 Pt 2): I30–I39.
- Bucci M, Vellecco V, Cantalupo A, et al. Hydrogen sulfide accounts for the peripheral vascular effects of zofenopril independently of ACE inhibition. Cardiovasc Res. 2014; 102(1): 138–147.
- Monti M, Terzuoli E, Ziche M, et al. HS dependent and independent anti-inflammatory activity of zofenoprilat in cells of the vascular wall. Pharmacol Res. 2016; 113(Pt A): 426–437.
- Donnarumma E, Ali MJ, Rushing AM, et al. Zofenopril protects against myocardial ischemia-reperfusion injury by increasing nitric oxide and hydrogen sulfide bioavailability. J Am Heart Assoc. 2016; 5(7).
- Liu X, Xu X, Chu Yi, et al. Zofenopril versus ramipril in the early phase of acute myocardial infarction with systolic dysfunction: A retrospective study. J Renin Angiotensin Aldosterone Syst. 2020; 21(3): 1470320320946530.
- Borghi C, Omboni S. Angiotensin-converting enzyme inhibition: beyond blood pressure control-the role of zofenopril. Adv Ther. 2020; 37(10): 4068–4085.
