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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-04-23 20:52:13 UTC |
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HMDB ID | HMDB0001314 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cyclic GMP |
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Description | Cyclic GMP, also known as CGMP or 3',5'-cyclic GMP, belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. For example, PKG (protein kinase G) is a dimer consisting of one catalytic and one regulatory unit, with the regulatory units blocking the active sites of the catalytic units.cGMP binds to sites on the regulatory units of PKG and activates the catalytic units, enabling them to phosphorylate their substrates. cGMP in the olfactory is synthesized by both membrane guanylyl cylcase (mGC) as well as soluble guanylyl cyclase (sGC). Cyclic GMP is a drug. Cyclic GMP is a moderately basic compound (based on its pKa). Cyclic GMP exists in all living species, ranging from bacteria to humans. In humans, cyclic GMP is involved in ion channels and their functional role in vascular endothelium. Outside of the human body, cyclic GMP has been detected, but not quantified in, several different foods, such as corns, peppermints, broccoli, chinese cabbages, and redcurrants. This could make cyclic GMP a potential biomarker for the consumption of these foods. The sodium ion channels in photoreceptors are cGMP-gated, so degradation of cGMP causes sodium channels to close, which leads to the hyperpolarization of the photoreceptor's plasma membrane and ultimately to visual information being sent to the brain.cGMP is also seen to mediate the switching on of the attraction of apical dendrites of pyramidal cells in cortical layer V towards semaphorin-3A (Sema3a). This enzyme converts GTP to cGMP. |
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Structure | |
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Synonyms | Value | Source |
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CGMP | ChEBI | Guanosine 3',5'-cyclic monophosphate | ChEBI | Guanosine 3',5'-cyclic phosphate | ChEBI | Guanosine cyclic monophosphate | ChEBI | Guanosine 3',5'-cyclic monophosphoric acid | Generator | Guanosine 3',5'-cyclic phosphoric acid | Generator | Guanosine cyclic monophosphoric acid | Generator | 3',5'-Cyclic GMP | HMDB | 3',5'-Guanosine | HMDB | 3',5'-Guanosine monophosphate | HMDB | Cyclic 3',5'-guanosine monophosphate | HMDB | Cyclic guanosine 3',5'-monophosphate | HMDB | Cyclic-GMP | HMDB | Guanosine 3',5'-cyclic-monophosphate | HMDB | Guanosine 3',5'-monophosphate | HMDB | Guanosine cyclic-monophosphate | HMDB | Guanosine-cyclic-phosphoric-acid | HMDB | Cyclic 3',5'-monophosphate, guanosine | HMDB | GMP, Cyclic | HMDB | Guanosine cyclic-3',5'-monophosphate | HMDB | monoPhosphate, guanosine cyclic | HMDB | 3',5'-monoPhosphate, guanosine cyclic | HMDB | Cyclic-3',5'-monophosphate, guanosine | HMDB | Guanosine cyclic 3',5'-monophosphate | HMDB | Guanosine cyclic 3,5 monophosphate | HMDB | Cyclic monophosphate, guanosine | HMDB | Guanosine cyclic 3',5' monophosphate | HMDB |
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Chemical Formula | C10H12N5O7P |
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Average Molecular Weight | 345.2053 |
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Monoisotopic Molecular Weight | 345.047434275 |
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IUPAC Name | 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one |
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Traditional Name | cyclic-GMP |
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CAS Registry Number | 7665-99-8 |
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SMILES | NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1 |
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InChI Identifier | InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 |
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InChI Key | ZOOGRGPOEVQQDX-UUOKFMHZSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleotides |
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Sub Class | Cyclic purine nucleotides |
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Direct Parent | 3',5'-cyclic purine nucleotides |
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Alternative Parents | |
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Substituents | - 3',5'-cyclic purine ribonucleotide
- Pentose phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-oxopurine
- Hypoxanthine
- Monosaccharide phosphate
- Purinone
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Pyrimidone
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Pyrimidine
- Vinylogous amide
- Azole
- Tetrahydrofuran
- Heteroaromatic compound
- Imidazole
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Alcohol
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Organic oxide
- Primary amine
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-001i-2972000000-80320c485cef8d6d91ad | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-001i-2972000000-80320c485cef8d6d91ad | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f76-3901000000-c970aad6713a547b2d8f | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-4590100000-edbc82f84eca5a64f5a5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0uec-2904000000-85af5865e64af24e7691 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udi-0904000000-e34bb3204af3b18ddf11 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udj-0908000000-35925bce602ee60e24ee | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udj-0904000000-93fabfb961527e02671e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udj-0907000000-60b56b2fcc437a04a7b8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udj-0908000000-16c413e42a41fa5e7262 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0udl-3904000000-051a745d5db4f607a935 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0901000000-a2a6721a5a98c3d3e945 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udj-0907000000-ae3d3b4dfb6aefdd34c3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udj-0904000000-fd635f17953dbbff039b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udi-0902000000-36d8b1a240f9f6471886 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0002-0009000000-4c75be42ba8dbd671bbf | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0002-0009000000-06ee1dc93418cde4fe39 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udi-0900000000-db6612a4a4b92db51507 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udi-0900000000-8455683aa1bc0141dd38 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udi-0900000000-196c267f58b468d3a8f5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0002-0009000000-7637808812023bf3fb33 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0002-0009000000-34c09019debbbd2ef2a6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0002-0009000000-db049b28da12291887ce | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0904000000-65ab088e129c01a9b140 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-fc45e23a1d622d9a6848 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udr-0900000000-d7d3bc38b1c32086753e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f6x-1709000000-881760c573673e832db8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-2900000000-f74b8ec55fbea3fdf8cd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-003u-9600000000-d7f00c8f8cec474c7304 | Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Nucleus
- Golgi apparatus
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
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Tissue Locations | - Kidney
- Platelet
- Smooth Muscle
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.0055 +/- 0.0003 uM | Adult (>18 years old) | Male | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.0024 +/- 0.0005 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.0035 +/- 0.0003 uM | Adult (>18 years old) | Both | Sildenafil-induced headache | | details |
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Associated Disorders and Diseases |
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Disease References | Headache |
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- Kruuse C, Frandsen E, Schifter S, Thomsen LL, Birk S, Olesen J: Plasma levels of cAMP, cGMP and CGRP in sildenafil-induced headache. Cephalalgia. 2004 Jul;24(7):547-53. [PubMed:15196297 ]
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB02315 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022549 |
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KNApSAcK ID | C00019673 |
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Chemspider ID | 22734 |
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KEGG Compound ID | C00942 |
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BioCyc ID | Not Available |
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BiGG ID | 1485267 |
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Wikipedia Link | Cyclic guanosine monophosphate |
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METLIN ID | 6152 |
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PubChem Compound | 24316 |
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PDB ID | Not Available |
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ChEBI ID | 16356 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Sekhar, Konjeti R.; Grondin, Pascal; Francis, Sharron H.; Corbin, Jackie D. Design and synthesis of xanthines and cyclic GMP analogs as potent inhibitors of PDE5. Phosphodiesterase Inhibitors (1996), 135-146. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Young DV, Cochran ED, Dhawan V, Earl RA, Ellis JL, Garvey DS, Janero DR, Khanapure SP, Letts LG, Melim TL, Murty MG, Shumway MJ, Wey SJ, Zemtseva IS, Selig WM: A comparison of the cyclooxygenase inhibitor-NO donors (CINOD), NMI-1182 and AZD3582, using in vitro biochemical and pharmacological methods. Biochem Pharmacol. 2005 Nov 1;70(9):1343-51. [PubMed:16168964 ]
- Mashayekhi F, Aghahoseini F, Rezaie A, Zamani MJ, Khorasani R, Abdollahi M: Alteration of cyclic nucleotides levels and oxidative stress in saliva of human subjects with periodontitis. J Contemp Dent Pract. 2005 Nov 15;6(4):46-53. [PubMed:16299606 ]
- Dobrzynski E, Montanari D, Agata J, Zhu J, Chao J, Chao L: Adrenomedullin improves cardiac function and prevents renal damage in streptozotocin-induced diabetic rats. Am J Physiol Endocrinol Metab. 2002 Dec;283(6):E1291-8. [PubMed:12424108 ]
- Willoughby SR, Stewart S, Chirkov YY, Kennedy JA, Holmes AS, Horowitz JD: Beneficial clinical effects of perhexiline in patients with stable angina pectoris and acute coronary syndromes are associated with potentiation of platelet responsiveness to nitric oxide. Eur Heart J. 2002 Dec;23(24):1946-54. [PubMed:12473257 ]
- Barani J, Gottsater A, Mattiasson I, Lindblad B: Platelet and leukocyte activation during aortoiliac angiography and angioplasty. Eur J Vasc Endovasc Surg. 2002 Mar;23(3):220-5. [PubMed:11914008 ]
- Schiessl B, Strasburger CJ, Bidlingmaier M, Spannagl M, Ugele B, Kainer F: Decreasing resistance in the maternal uterine and peripheral arterial system is apparently unrelated to plasma and urinary levels of nitrite/nitrate and cyclic-guanosinmonophosohate during the course of normal pregnancies. J Perinat Med. 2003;31(4):281-6. [PubMed:12951882 ]
- Bai X, Wang H, Li Z, Liu K: Correlation between blood cAMP, cGMP levels and traumatic severity in the patients with acute trauma and its clinical significance. J Huazhong Univ Sci Technolog Med Sci. 2004;24(1):68-70. [PubMed:15165120 ]
- Beltowski J, Jamroz A, Borkowska E: [Heme oxygenase and carbon monoxide in the physiology and pathology of the cardiovascular system]. Postepy Hig Med Dosw (Online). 2004 Mar 3;58:83-99. [PubMed:15069378 ]
- Rudman D, O'Brien MS, McKinney AS, Hoffman JC Jr, Patterson JH: Observations on the cyclic nucleotide concentrations in human cerebrospinal fluid. J Clin Endocrinol Metab. 1976 Jun;42(6):1088-97. [PubMed:180045 ]
- Peracchi M, Lombardi L, Maiolo AT, Bamonti-Catena F, Toschi V, Chiorboli O, Mozzana R, Polli EE: Plasma and urine cyclic nucleotide levels in patients with acute and chronic leukemia. Blood. 1983 Mar;61(3):429-34. [PubMed:6297636 ]
- Ilecka J: Decreased cerebrospinal fluid cGMP levels in patients with amyotrophic lateral sclerosis. J Neural Transm (Vienna). 2004 Feb;111(2):167-72. Epub 2003 Dec 12. [PubMed:14767719 ]
- Kotikoski H, Moilanen E, Vapaatalo H, Aine E: Biochemical markers of the L-arginine-nitric oxide pathway in the aqueous humour in glaucoma patients. Acta Ophthalmol Scand. 2002 Apr;80(2):191-5. [PubMed:11952488 ]
- Hunter KA, Singh GJ, Simpkins CO: Cyclic gmp is a measure of physiologic stress. J Natl Med Assoc. 2001 Jul-Aug;93(7-8):256-62. [PubMed:11491275 ]
- Zhang H, Zheng RL, Xu CY: [Relationships between lipid peroxidation or cyclic nucleotides and motility in human asthenozoosperm and normosperm]. Shi Yan Sheng Wu Xue Bao. 1998 Dec;31(4):341-6. [PubMed:12016956 ]
- Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4. [PubMed:16487434 ]
- Engelhardt T, Galley HF, MacLennan FM, Webster NR: Saliva cyclic GMP increases during anaesthesia. Br J Anaesth. 2002 Oct;89(4):635-7. [PubMed:12393367 ]
- Galassi F, Renieri G, Sodi A, Ucci F, Vannozzi L, Masini E: Nitric oxide proxies and ocular perfusion pressure in primary open angle glaucoma. Br J Ophthalmol. 2004 Jun;88(6):757-60. [PubMed:15148207 ]
- Zhao L, Gray L, Leonardi-Bee J, Weaver CS, Heptinstall S, Bath PM: Effect of aspirin, clopidogrel and dipyridamole on soluble markers of vascular function in normal volunteers and patients with prior ischaemic stroke. Platelets. 2006 Mar;17(2):100-4. [PubMed:16421011 ]
- Martina V, Origlia C, Bruno GA, Messina M, Ferri M, Pescarmona GP: Serum DHEAS levels correlate with platelet cGMP in normal women. J Endocrinol Invest. 2001 Nov;24(10):RC28-30. [PubMed:11765058 ]
- St Pierre MV, Schlenker T, Dufour JF, Jefferson DM, Fitz JG, Arias IM: Stimulation of cyclic guanosine monophosphate production by natriuretic peptide in human biliary cells. Gastroenterology. 1998 Apr;114(4):782-90. [PubMed:9516399 ]
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