Page last updated: 2024-10-15

8-bromocyclic gmp

Description

8-bromo-3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP bearing an additional bromo substituent at position 8 on the guanine ring. A membrane permeable cGMP analogue that activates protein kinase G (PKG). It is 4.3-fold more potent than cGMP in activating PKG1alpha and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID135419186
CHEMBL ID1741141
CHEBI ID64108
SCHEMBL ID3991263
MeSH IDM0066188

Synonyms (27)

Synonym
8-bromo-cyclic gmp
8-bromoguanosine 3',5'-monophosphate
8-bromoguanosine, cyclic 3',5'-(hydrogen phosphate)
8-bromo cgmp
8-bromocyclic guanosine monophosphate
8-br-cyclic gmp
br cgmp
8-bromoguanosine 3',5'-cyclic monophosphate
8-bromo-cgmp
8-bromocyclic gmp
31356-94-2
8-bromoguanosine-3',5'-cyclic-monophosphoric acid
SCHEMBL3991263
4-methyl-2-phenyl-1,3-thiazole-5-sulfonylchloride
guanosine, 8-bromo-, cyclic 3',5'-(hydrogen phosphate)
8-bromoguanosine 3',5'-(hydrogen phosphate)
8-bromo-3',5'-cyclic gmp
CHEBI:64108 ,
CHEMBL1741141
2-amino-8-bromo-9-[(2r,4ar,6r,7r,7as)-2,7-dihydroxy-2-oxotetrahydro-2h,4h-2lambda~5~-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-1,9-dihydro-6h-purin-6-one
6j7 ,
8-bromoguanosine 3', 5' -cyclic monophosphoric acid
J-018395
Q4644268
YUFCOOWNNHGGOD-UMMCILCDSA-N
9-[(4ar,6r,7r,7as)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-8-bromo-1h-purin-6-one
DTXSID50953395

Toxicity

ExcerptReference
"The results presented in this study indicate that the toxic response brought about by increasing concentrations of tert-butylhydroperoxide in CHP100 cells was mitigated significantly by exogenously added nitric oxide donors via a cyclic GMP-independent mechanism."( Different signalling pathways mediate the opposite effects of endogenous versus exogenous nitric oxide on hydroperoxide toxicity in CHP100 neuroblastoma cells.
Cantoni, O; Clementi, E; Guidarelli, A; Sciorati, C, 1999
)
" Furthermore, while the toxic effect of NOR3 was attenuated by replacing the medium at 20 min, 1 or 2 h after drug addition, it was continued by replacing the medium at 3 h or later after drug addition."( Kinetic characterization of the nitric oxide toxicity for PC12 cells: effect of half-life time of NO release.
Kato, T; Nakamura, K; Yamamoto, H; Yamamoto, T; Yuyama, K, 2000
)

Pharmacokinetics

ExcerptReference
" The mechanism by which caffeine increases the antinociceptive action of NSAIDs does not appear to include a pharmacokinetic interaction."( A review of the pharmacokinetic and pharmacodynamic factors in the potentiation of the antinociceptive effect of nonsteroidal anti-inflammatory drugs by caffeine.
Castañeda-Hernández, G; Granados-Soto, V, 1999
)

Bioavailability

ExcerptReference
"05), mimicking the effect of an apparent decrease in bioavailability of endogenous NO."( Chronic nicotine alters NO signaling of Ca(2+) channels in cerebral arterioles.
Gerzanich, V; Simard, JM; West, GA; Zhang, F, 2001
)
"Reduced endothelium-dependent vasorelaxation partly due to loss of nitric oxide (NO) bioavailability occurs in most cases of chronic hypertension."( Altered vascular function in fetal programming of hypertension.
Beauchamp, M; Bernier, S; Chemtob, S; Gobeil, F; Hou, X; Lahaie, I; Lamireau, D; Nuyt, AM; Varma, DR, 2002
)
" Nonetheless, DM may cause uncoupling of nitric oxide synthases (NOSs) with reduction in the bioavailability of nitric oxide (NO), which is critical to maintain oocyte viability and prevent aging."( Activation of the cGMP signaling pathway is essential in delaying oocyte aging in diabetes mellitus.
Abu-Soud, HM; Diamond, MP; Gonik, B; Goud, AP; Goud, PT, 2006
)
" reduced bioavailability of nitric oxide (NO)."( Endothelial dysfunction enhances the pulmonary and systemic vasodilator effects of phosphodiesterase-5 inhibition in awake swine at rest and during treadmill exercise.
Beier, N; Duncker, DJ; Houweling, B; Merkus, D; Quispel, J; Verdouw, PD, 2012
)
": ED in middle-aged rats is associated with decreased NO bioavailability in erectile tissue due to upregulation of NADPH oxidase subunit gp91(phox) and downregulation of nNOS/p-eNOS."( Superoxide anion production by NADPH oxidase plays a major role in erectile dysfunction in middle-aged rats: prevention by antioxidant therapy.
Antunes, E; Báu, FR; Brugnerotto, AF; Mónica, FZ; Priviero, FB; Silva, FH; Toque, HA, 2013
)
"There is increasing evidence that the permeability of the glomerular filtration barrier (GFB) is partly regulated by a balance between the bioavailability of nitric oxide (NO) and that of reactive oxygen species (ROS)."( Nitric oxide synthase inhibition causes acute increases in glomerular permeability in vivo, dependent upon reactive oxygen species.
Dolinina, J; Öberg, CM; Rippe, A; Rippe, B; Sverrisson, K, 2016
)

Dosage Studied

ExcerptReference
" Dose-response studies reveal that 10(-6) to 10(-4) M concentrations of 8-bromo-cAMP (8-Br-cAMP) elicit a maximal response."( Progesterone receptor regulation in uterine cells: stimulation by estrogen, cyclic adenosine 3',5'-monophosphate, and insulin-like growth factor I and suppression by antiestrogens and protein kinase inhibitors.
Aronica, SM; Katzenellenbogen, BS, 1991
)
" The ACTH dose-response curves for steroidogenic activity and for polyamine uptake were similar."( Hormonal control of polyamine levels in bovine adrenocortical cells.
Chambaz, EM; Feige, JJ; Madani, C, 1986
)
" The dose-response relationship for a cholinergic agonist, carbamylcholine, or an adrenergic agonist, norepinephrine, was unaffected by the presence of either 8-Br-cGMP or Bt2cGMP in the medium."( Evidence against a role for guanosine 3',5'-cyclic monophosphate in rat submandibular salivary gland potassium release.
Barzen, KA; Lafferty, JL; Quissell, DO, 1983
)
" It also produced a decrease in 8-Br-cGMP mediated inhibition which was more pronounced when the dosage of LH was increased to 10 microgram/ml."( Inhibitory action of cyclic guanosine 5'-phosphoric acid (GMP) on oocyte maturation: dependence on an intact cumulus.
Hubbard, CJ; Terranova, PF, 1982
)
" Calmodulin shifted to the right the dose-response relation for activation of the channels by 8-Br-cGMP, but did not change the maximum current or the form of the relation."( Modulation of the cGMP-gated ion channel in frog rods by calmodulin and an endogenous inhibitory factor.
Downing-Park, J; Gordon, SE; Zimmerman, AL, 1995
)
" Nitroprusside, atriopeptin II and 8-Br-cGMP all increased renin release but the dose-response relationships were biphasic."( Cyclic GMP-linked pathway for renin secretion.
Abu-Kishk, RA; D'Aloia, MA; Lush, DJ; Noble, AR; Williams, BC, 1994
)
" Dose-response curves for net fluid secretion (stimulated-basal (30 min)-1) activated by 5,50 and 500 ng ml-1 STa were obtained for jejuna and ilea from fed, starved and chronically undernourished rats."( Fluid hypersecretion induced by enterotoxin STa in nutritionally deprived rats: jejunal and ileal dynamics in vivo.
Levin, RJ; Nzegwu, HC, 1994
)
" The dose-response relations were much shallower than predicted by single-site activation models, but were well described by models in which there are two populations of sites, in roughly equal proportion, that bind cGMP with apparent affinities that differ by a factor of 25."( Covalent activation of retinal rod cGMP-gated channels reveals a functional heterogeneity in the ligand binding sites.
Brown, RL; Karpen, JW, 1996
)
" In permeabilized hepatocytes, the dose-response curve for InsP3-induced Ca2+ release was shifted to the left in the presence of 8-Br-cGMP."( 3':5'-cyclic guanosine monophosphate (cGMP) potentiates the inositol 1,4,5-trisphosphate-evoked Ca2+ release in guinea-pig hepatocytes.
Capiod, T; Combettes, L; Guihard, G, 1996
)
" However, the inhibition of the combined CPA and CCh response was reduced and the dose-response curve of SIN-1 shifted to the right."( Involvement of intracellular Ca2+ stores in inhibitory effects of NO donor SIN-1 and cGMP.
Allescher, HD; Franck, H; Puschmann, A; Schusdziarra, V; Storr, M, 1998
)
" Using an ex vivo model of coronary perfusion in rabbits, we found a dose-response relationship between VEGF and the efficiency of adenoviral gene transfer."( Phosphodiesterase inhibitor-mediated potentiation of adenovirus delivery to myocardium.
Donahue, JK; Lawrence, JH; Marbán, E; Nagata, K, 2001
)
" Dose-response curves for carbachol revealed a lower peak response in new-born bladders compared with adults."( Developmental regulation of nerve and receptor mediated contractions of mammalian urinary bladder smooth muscle.
Andersson, KE; Arner, A; Ekman, M, 2006
)
" The cell-permeable cGMP analog 8-bromo-cGMP produced a dose-dependent relaxation of the uterine artery and shifted norepinephrine (NE) dose-response curve to the right with a decreased maximal contraction."( Effect of cGMP on pharmacomechanical coupling in the uterine artery of near-term pregnant sheep.
Hu, X; Xiao, D; Zhang, L, 2008
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
muscle relaxantA drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
protein kinase G agonistAn agonist that selectively binds to and activates a protein kinase G receptor.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
3',5'-cyclic purine nucleotide
organobromine compoundA compound containing at least one carbon-bromine bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (1,489)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990205 (13.77)18.7374
1990's671 (45.06)18.2507
2000's501 (33.65)29.6817
2010's107 (7.19)24.3611
2020's5 (0.34)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.13%)5.53%
Reviews8 (0.53%)6.00%
Case Studies1 (0.07%)4.05%
Observational0 (0.00%)0.25%
Other1,505 (99.27%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]