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N5751 Sigma

Nω-Nitro-L-arginine methyl ester hydrochloride

≥98% (TLC), powder

Synonym: L-NAME hydrochloride

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Description

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Biochem/physiol Actions

An analog of arginine that inhibits NO production. It has multiple effects on the vascular system. Inhibits relaxation induced by acetylcholine and induces an increase in arterial blood pressure. Abolishes lecithinized superoxide dismutase induced vasodilation when used to pretreat aortic ring preparations of mice. Induces leukocyte adhesion and increases microvascular fluid and protein fluxes and permeability. It has also been used in many studies of learning and memory.

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This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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<I>N</I><SUB>ω</SUB>-Nitro-<SC>L</SC>-arginine

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puriss. p.a., ACS reagent, reag. Ph. Eur., Reag. Ph. Eur., ≥99%

Safety & Documentation

Safety Information

WGK Germany 
3

Protocols & Articles

Peer-Reviewed Papers

References

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Nitric oxide modulates microvascular permeability. Kubes, P., and Granger, D.N. Am. J. Physiol. 262, H611-H615, (1992)

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Nitric oxide synthase inhibitors impair reference memory formation in a radial arm maze task in rats. Zou, L.B., et al. Neuropharmacology 37, 323-330, (1998)

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Lecithinized superoxide dismutase induces vasodilation; evidence of direct contribution of superoxide anions to modulating vascular tone. Nakamura, T., et al. Life Sci. 64, PL65-PL70, (1999)

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Characterization of three inhibitors of endothelial nitric oxide synthase in vitro and in vivo. Rees, D.D., et al. Br. J. Pharmacol. 101, 746-752, (1990)

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Nitric oxide: an endogenous modulator of leukocyte adhesion. Kubes, P., et al. Proc. Natl. Acad. Sci. U. S. A. 88, 4651-4655, (1991)

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Protective effects of brain-derived neurotrophic factor against neurotoxicity of 3-nitropropionic acid in rat cortical neurons. Wu, C.L., et al. Neurotoxicology 30, 718-26, (2009)

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Impairment of neocortical long-term potentiation in mice deficient of endothelial nitric oxide synthase. Haul, S., et al. J. Neurophysiol. 81, 494-497, (1999)

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Effects of nitric oxide synthase inhibitor NG-nitro-L-arginine methyl ester on spatial and cued learning. Knepper, B.R., and Kurylo, D.D. Neuroscience 83, 837-841, (1998)

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Nitric Oxide Mediates Feedback Inhibition In Angiotensin II-induced Upregulation Of Vasopressin MRNA. Zhang, L., et al. Peptides 30, 913-7, (2009)

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Effects Of Tumor Necrosis Factor-alpha And Nitric Oxide On Prostaglandins Secretion By The Bovine Oviduct Differ In The Isthmus And Ampulla And Depend On The Phase Of The Estrous Cycle. Siemieniuch, M.J., et al. Exp. Biol. Med. 234, 1056-66, (2009)

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Shear stress regulates endothelial microparticle release. Vion AC, Ramkhelawon B, Loyer X, et al. Circ. Res. 112(10), 1323-33, (2013)

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Iodixanol, constriction of medullary descending vasa recta, and risk for contrast medium-induced nephropathy. Sendeski M Radiology 251(3), 697-704, (2009)

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Plasminogen activator inhibitor-1 antagonist TM5441 attenuates Nω-nitro-L-arginine methyl ester-induced hypertension and vascular senescence. Boe AE, Eren M, Murphy SB, et al. Circulation 128(21), 2318-24, (2013)

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Tetrahydrobiopterin deficiency induces gastroparesis in newborn mice. Welsh C, Enomoto M, Pan J, et al. Am. J. Physiol. Gastrointest. Liver Physiol. 305(1), G47-57, (2013)

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Nitric oxide-angiotensin II interactions and renal hemodynamic function in patients with uncomplicated type 1 diabetes. Montanari A, Pelà G, Musiari L, et al. Am. J. Physiol. Renal Physiol. 305(1), F42-51, (2013)

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P2X7 receptor activation contributes to an initial upstream mechanism of lipopolysaccharide-induced vascular dysfunction. Chiao CW, da Silva-Santos JE, Giachini FR, et al. Clin. Sci. (Lond.) 125(3), 131-41, (2013)

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Rats with adenine-induced chronic renal failure develop low-renin, salt-sensitive hypertension and increased aortic stiffness. Nguy L, Johansson ME, Grimberg E, et al. Am. J. Physiol. Regul. Integr. Comp. Physiol. 304(9), R744-52, (2013)

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Nitric oxide enhances extracellular ATP induced Ca²⁺ oscillation in HeLa cells. Tang Y, Yin Y, Miao L, et al. Arch. Biochem. Biophys. 565, 68-75, (2015)

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CRLI induces vascular smooth muscle relaxation and suggests a dual mechanism of eNOS activation by legume lectins via muscarinic receptors and shear stress. Rocha BA, Barroso-Neto IL, Teixeira CS, et al. Arch. Biochem. Biophys. 565, 32-9, (2015)

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Acute ketamine impairs mitochondrial function and promotes superoxide dismutase activity in the rat brain. Venâncio C, Félix L, Almeida V, et al. Anesth. Analg. 120(2), 320-8, (2015)

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The influence of L-NAME on iNOS expression and markers of oxidative stress in allergen-induced airway hyperreactivity. Antošová M, Strapková A, Mikolka P, et al. Adv. Exp. Med. Biol. 838, 1-10, (2015)

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Renal angiotensin-converting enzyme is essential for the hypertension induced by nitric oxide synthesis inhibition. Giani JF, Janjulia T, Kamat N, et al. J. Am. Soc. Nephrol. 25(12), 2752-63, (2014)

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Akt1-mediated fast/glycolytic skeletal muscle growth attenuates renal damage in experimental kidney disease. Hanatani S, Izumiya Y, Araki S, et al. J. Am. Soc. Nephrol. 25(12), 2800-11, (2014)

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Possible nitric oxide modulation in the protective effects of rutin against experimental head trauma-induced cognitive deficits: behavioral, biochemical, and molecular correlates. Kumar A, Rinwa P, and Dhar H J. Surg. Res. 188(1), 268-79, (2014)

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[Effect of L-arginine on the oxygen balance of the liver and its bile secretion function]. Ianchuk PI, Bondzyk OV, Reshetnik IeM, et al. Fiziol. Zh. 59(2), 31-8, (2013)

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[Role of NO/cGMP signaling cascade in the development of opium dependency]. Peregud DI, Iakovleva AA, Stepanichev MIu, et al. Eksp. Klin. Farmakol. 76(3), 3-6, (2013)

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[Electron paramagnetic resonance study of nitric oxide production in rat heart during hypokinesia]. Gaĭnutdinov KhL, Andrianov VV, Iiudin VS, et al. Biofizika 58(2), 276-80, (2013)

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Mechanisms of vasorelaxation to gamma-mangostin in the rat aorta. Tep-Areenan P and Suksamrarn S J. Med. Assoc. Thai. 95 Suppl 12, S63-8, (2012)

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Effects of Phikud Navakot extract on vascular reactivity in the isolated rat aorta. Nusuetrong P, Sotanaphun U, and Tep-Areenan P J. Med. Assoc. Thai. 95 Suppl 12, S1-7, (2012)

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The role of NO in the posterior hypothalamus in amygdala-generated pressor responses in conscious rats. Özyurt Bayraktar H, Yananlı H, Terzioğlu B, et al. Auton. Autacoid Pharmacol. 33(1-2), 7-16, (2013)

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Detecting physiological systems with laser speckle perfusion imaging of the renal cortex. Scully CG, Mitrou N, Braam B, et al. Am. J. Physiol. Regul. Integr. Comp. Physiol. 304(11), R929-39, (2013)

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The absence of intrarenal ACE protects against hypertension. Gonzalez-Villalobos RA, Janjoulia T, Fletcher NK, et al. J. Clin. Invest. 123(5), 2011-23, (2013)

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Nitric oxide reduces Cl⁻ absorption in the mouse cortical collecting duct through an ENaC-dependent mechanism. Pech V, Thumova M, Dikalov SI, et al. Am. J. Physiol. Renal Physiol. 304(11), F1390-7, (2013)

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Quantification of cardiomyocyte hypertrophy by cardiac magnetic resonance: implications for early cardiac remodeling. Coelho-Filho OR, Shah RV, Mitchell R, et al. Circulation 128(11), 1225-33, (2013)

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Calcium entry and α-synuclein inclusions elevate dendritic mitochondrial oxidant stress in dopaminergic neurons. Dryanovski DI, Guzman JN, Xie Z, et al. J. Neurosci. 33(24), 10154-64, (2013)

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Perturbed neural activity disrupts cerebral angiogenesis during a postnatal critical period. Whiteus C, Freitas C, and Grutzendler J Nature 505(7483), 407-11, (2014)

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Nitric oxide directly promotes vascular endothelial insulin transport. Wang H, Wang AX, Aylor K, et al. Diabetes 62(12), 4030-42, (2013)

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Nitric oxide regulates vascular adaptive mitochondrial dynamics. Miller MW, Knaub LA, Olivera-Fragoso LF, et al. Am. J. Physiol. Heart Circ. Physiol. 304(12), H1624-33, (2013)

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Chemerin reduces vascular nitric oxide/cGMP signalling in rat aorta: a link to vascular dysfunction in obesity? Neves KB, Lobato NS, Lopes RA, et al. Clin. Sci. 127(2), 111-22, (2014)

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The sGC activator BAY 60-2770 has potent erectile activity in the rat. Lasker GF, Pankey EA, Frink TJ, et al. Am. J. Physiol. Heart Circ. Physiol. 304(12), H1670-9, (2013)

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AT₂ receptor activation induces natriuresis and lowers blood pressure. Kemp BA, Howell NL, Gildea JJ, et al. Circ. Res. 115(3), 388-99, (2014)

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Sphingosine-1-phosphate receptor 2 protects against anaphylactic shock through suppression of endothelial nitric oxide synthase in mice. Cui H, Okamoto Y, Yoshioka K, et al. J. Allergy Clin. Immunol. 132(5), 1205-1214.e9, (2013)

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Neuroprotective effect of tadalafil, a PDE-5 inhibitor, and its modulation by L-NAME in mouse model of ischemia-reperfusion injury. Gulati P and Singh N J. Surg. Res. 186(1), 475-83, (2014)

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A nitric oxide-dependent cross-talk between class I and III histone deacetylases accelerates skin repair. Spallotta F, Cencioni C, Straino S, et al. J. Biol. Chem. 288(16), 11004-12, (2013)

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Hyperglycemic Myocardial Damage Is Mediated By Proinflammatory Cytokine: Macrophage Migration Inhibitory Factor. Yu, X.Y., et al. PLoS ONE 6, e16239, (2011)

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Impaired L-arginine uptake but not arginase contributes to endothelial dysfunction in rats with chronic kidney disease. Martens CR, Kuczmarski JM, Lennon-Edwards S, et al. J. Cardiovasc. Pharmacol. 63(1), 40-8, (2014)

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Female SHR have greater blood pressure sensitivity and renal T cell infiltration following chronic NOS inhibition than males. Brinson KN, Elmarakby AA, Tipton AJ, et al. Am. J. Physiol. Regul. Integr. Comp. Physiol. 305(7), R701-10, (2013)

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Local NOS inhibition impairs vascular and metabolic actions of insulin in rat hindleg muscle in vivo. Bradley EA, Richards SM, Keske MA, et al. Am. J. Physiol. Endocrinol. Metab. 305(6), E745-50, (2013)

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Analysis of responses to the TRPV4 agonist GSK1016790A in the pulmonary vascular bed of the intact-chest rat. Pankey EA, Zsombok A, Lasker GF, et al. Am. J. Physiol. Heart Circ. Physiol. 306(1), H33-40, (2014)

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Role of macrophage PPARγ in experimental hypertension. Kriska T, Cepura C, Gauthier KM, et al. Am. J. Physiol. Heart Circ. Physiol. 306(1), H26-32, (2014)

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Breast meat quality of broiler chickens can be affected by managing the level of nitric oxide. Zhang W, Marwan AH, Samaraweera H, et al. Poult. Sci. 92(11), 3044-9, (2013)

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Differential effects of synaptic and extrasynaptic NMDA receptors on Aβ-induced nitric oxide production in cerebrocortical neurons. Molokanova E, Akhtar MW, Sanz-Blasco S, et al. J. Neurosci. 34(14), 5023-8, (2014)

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Role of glutamate receptors and nitric oxide on the effects of glufosinate ammonium, an organophosphate pesticide, on in vivo dopamine release in rat striatum. Faro LR, Ferreira Nunes BV, Alfonso M, et al. Toxicology 311(3), 154-61, (2013)

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Antiretroviral agents increase NO production in gp120/IFNγ-stimulated cultures of rat microglia via an arginase-dependent mechanism. Lisi L, Tramutola A, Navarra P, et al. J. Neuroimmunol. 266(1-2), 24-32, (2014)

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An anatomically unbiased approach for analysis of renal BOLD magnetic resonance images. Menzies RI, Zammit-Mangion A, Hollis LM, et al. Am. J. Physiol. Renal Physiol. 305(6), F845-52, (2013)

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Protein phosphatase-dependent circadian regulation of intermediate-term associative memory. Michel M, Gardner JS, Green CL, et al. J. Neurosci. 33(10), 4605-13, (2013)

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Involvement of H1 and H2 receptors and soluble guanylate cyclase in histamine-induced relaxation of rat mesenteric collecting lymphatics. Kurtz KH, Moor AN, Souza-Smith FM, et al. Microcirculation 21(7), 593-605, (2014)

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Partial role of multiple pathways in infarct size limiting effect of quercetin and rutin against cerebral ischemia-reperfusion injury in rats. Annapurna A, Ansari MA, and Manjunath PM Eur. Rev. Med. Pharmacol. Sci. 17(4), 491-500, (2013)

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Influence of parafascicular thalamic input on neuronal activity within the nucleus accumbens is mediated by nitric oxide - an in vivo study. Kraus MM, Prast H, and Philippu A Life Sci. 102(1), 49-54, (2014)

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Inhibition of human platelet aggregation by eosinophils. Maziero AM, Lorenzetti R, Donato JL, et al. Life Sci. 93(9-11), 416-22, (2013)

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Vasoactive effects of prostaglandins from the perivascular fat of mesenteric resistance arteries in WKY and SHROB rats. Mendizábal Y, Llorens S, and Nava E Life Sci. 93(25-26), 1023-32, (2013)

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Analysis of the mechanisms underlying the antinociceptive effect of epicatechin in diabetic rats. Quiñonez-Bastidas GN, Cervantes-Durán C, Rocha-González HI, et al. Life Sci. 93(17), 637-45, (2013)

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Angiotensin II Type 1 receptor blockade protects endothelium-derived hyperpolarising factor-mediated relaxation in a rat model of monoarthritis. Mackenzie A, Dunning L, Ferrell WR, et al. Life Sci. 92(23), 1131-7, (2013)

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Involvement of proteinase activated receptor-2 in the vascular response to sphingosine 1-phosphate. Roviezzo F, De Angelis A, De Gruttola L, et al. Clin. Sci. 126(8), 545-56, (2014)

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The hemodynamically-regulated vascular microenvironment promotes migration of the steroidogenic tissue during its interaction with chromaffin cells in the zebrafish embryo. Chou CW, Zhuo YL, Jiang ZY, et al. PLoS ONE 9(9), e107997, (2014)

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Brain BDNF levels elevation induced by physical training is reduced after unilateral common carotid artery occlusion in rats. Banoujaafar H, Van Hoecke J, Mossiat CM, et al. J. Cereb. Blood Flow Metab. 34(10), 1681-7, (2014)

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Modulation of stretch-induced myocyte remodeling and gene expression by nitric oxide: a novel role for lipoma preferred partner in myofibrillogenesis. Hooper CL, Paudyal A, Dash PR, et al. Am. J. Physiol. Heart Circ. Physiol. 304(10), H1302-13, (2013)

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Role of nitric oxide synthase isoforms for ophthalmic artery reactivity in mice. Laspas P, Goloborodko E, Sniatecki JJ, et al. Exp. Eye Res. 127, 1-8, (2014)

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A newly synthesized compound, 4'-geranyloxyferulic acid-N(omega)-nitro-L-arginine methyl ester suppresses inflammation-associated colorectal carcinogenesis in male mice. Shimizu M, Kochi T, Shirakami Y, et al. Int. J. Cancer 135(4), 774-84, (2014)

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Assessment of impaired vascular reactivity in a rat model of diabetic nephropathy: effect of nitric oxide synthesis inhibition on intrarenal diffusion and oxygenation measured by magnetic resonance imaging. Hueper K, Hartung D, Gutberlet M, et al. Am. J. Physiol. Renal Physiol. 305(10), F1428-35, (2013)

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Arginine affects appetite via nitric oxide in ducks. Wang C, Hou SS, Huang W, et al. Poult. Sci. 93(8), 2048-53, (2014)

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Imatinib mesylate (Gleevec) induces human corpus cavernosum relaxation by inhibiting receptor tyrosine kinases (RTKs): identification of new RTK targets. Gur S, Sikka SC, Abdel-Mageed AB, et al. Urology 82(3), 745.e11-6, (2013)

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Cessation of cyclic stretch induces atrophy of C2C12 myotubes. Soltow QA, Zeanah EH, Lira VA, et al. Biochem. Biophys. Res. Commun. 434(2), 316-21, (2013)

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Echinocystic acid, isolated from Gleditsia sinensis fruit, protects endothelial progenitor cells from damage caused by oxLDL via the Akt/eNOS pathway. Lai P and Liu Y Life Sci. 114(2), 62-9, (2014)

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Regulation of MMP/TIMP by HUVEC transplantation attenuates ventricular remodeling in response to myocardial infarction. Kwon JS, Kim YS, Cho AS, et al. Life Sci. 101(1-2), 15-26, (2014)

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Citronellal, a monoterpene present in Java citronella oil, attenuates mechanical nociception response in mice. de Santana MT, de Oliveira MG, Santana MF, et al. Pharm. Biol. 51(9), 1144-9, (2013)

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The effects of cyclooxygenase and nitric oxide synthase inhibition on oxidative stress in isolated rat heart. Barudzic N, Turjacanin-Pantelic D, Zivkovic V, et al. Mol. Cell Biochem. 381(1-2), 301-11, (2013)

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Acute nitric oxide synthase inhibition and cardiac conduction in persons with spinal cord injury: a short report. La Fountaine MF, Wecht JM, and Bauman WA Pharmazie 68(4), 245-50, (2013)

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Synergistic effects between catalase inhibitors and modulators of nitric oxide metabolism on tumor cell apoptosis. Scheit K and Bauer G Anticancer Res. 34(10), 5337-50, (2014)

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Effects of propolis on blood biochemical and hematological parameters in nitric oxide synthase inhibited rats by Nω-Nitro-L-arginine methyl ester. Talas ZS, Gogebakan A, and Orun I Pak. J. Pharm. Sci. 26(5), 915-9, (2013)

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GABA-induced vasorelaxation mediated by nitric oxide and GABAA receptor in non diabetic and streptozotocin-induced diabetic rat vessels. Kamran M, Bahrami A, Soltani N, et al. Gen. Physiol. Biophys. 32(1), 101-6, (2013)

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Effect of age on the contractile response of the rat carotid artery in the presence of sympathetic drugs and L-NAME. Omar NM, Abbas AM, Abdel-Malek H, et al. Acta Physiol. Hung. 100(3), 266-79, (2013)

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Plasminogen activator inhibitor-1: a novel therapeutic target for hypertension? Simon DI and Simon NM Circulation 128(21), 2286-8, (2013)

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