Boiling point	239 ºC
Flash point	51 ºC
Density	1.169
Refractive index	1.583-1.585

Symbol(GHS)	Xn
Hazard Codes	R10;R20/21/22;R36/37/38
SDS/MSDS	S16;S26;S36/37/39

Source	SDS/MSDS Samples
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Switch in signaling control of mTORC1 activity after oncoprotein expression in thyroid cancer cell lines.Roberta Malaguarnera et al.The Journal of clinical endocrinology and metabolism, 99(10), E1976-E1987 (2014-07-17) Sinapic acid induces the expression of thermogenic signature genes and lipolysis through activation of PKA/CREB signaling in brown adipocytes.Monir Hossain et al.BMB reports, 53(3), 142-147 (2019-08-14) High-density lipoprotein cholesterol efflux capacity as a relevant predictor of atherosclerotic coronary disease.Tetsuya Ishikawa et al.Atherosclerosis, 242(1), 318-322 (2015-08-08) Mapping Atheroprotective Functions and Related Proteins/Lipoproteins in Size Fractionated Human Plasma.Debi K Swertfeger et al.Molecular & cellular proteomics : MCP, 16(4), 680-693 (2017-02-23) Vasodilatory effect of 14,15-epoxyeicosatrienoic acid on mesenteric arteries in hypertensive and aged rats.Cui Yang et al.Prostaglandins & other lipid mediators, 112, 1-8 (2014-06-01) The proliferative phase endometrium in IVF/ICSI: an in-cycle molecular analysis predictive of the outcome following fresh embryo transfer.S Mackens et al.Human reproduction (Oxford, England), 35(1), 130-144 (2020-01-10) Structure-function analyses of the Pth11 receptor reveal an important role for CFEM motif and redox regulation in rice blast.Yanjun Kou et al.The New phytologist, 214(1), 330-342 (2016-11-30) A Cyclic Nucleotide-Gated Channel, HvCNGC2-3, Is Activated by the Co-Presence of Na⁺ and K⁺ and Permeable to Na⁺ and K⁺ Non-Selectively.Izumi C Mori et al.Plants (Basel, Switzerland), 7(3) (2018-07-28) Photochemical crosslinking in oligonucleotide-protein complexes between a bromine-substituted 2-5A analog and 2-5A-dependent RNase by ultraviolet lamp or laser.N L Nolan-Sorden et al.Analytical biochemistry, 184(2), 298-304 (1990-02-01) Onset and Heterogeneity of Responsiveness to FSH in Mouse Preantral Follicles in Culture.Kate Hardy et al.Endocrinology, 158(1), 134-147 (2016-11-08) Evidence on the existence of a purine ligand induced conformational change in the active site of bovine pancreatic ribonuclease A studied by proton nuclear magnetic resonance spectroscopy.C Arús et al.Biochemistry, 21(18), 4290-4297 (1982-08-31) Molecular modeling studies of a parallel stranded quadruplexes containing a 8-bromoadenosine.Veronica Esposito et al.Nucleosides, nucleotides & nucleic acids, 24(5-7), 789-794 (2005-10-27) Steroid biosynthesis by zona glomerulosa-fasciculata cells in primary culture of guinea-pig adrenals.P Provencher et al.Journal of steroid biochemistry, 36(6), 589-596 (1990-08-28) In vitro effects of single and binary mixtures of regulated mycotoxins and persistent organochloride pesticides on steroid hormone production in MA-10 Leydig cell line.Ukpai A Eze et al.Toxicology in vitro : an international journal published in association with BIBRA, 60, 272-280 (2019-06-14) Effects of caffeine on circadian phase, amplitude and period evaluated in cells in vitro and peripheral organs in vivo in PER2::LUCIFERASE mice.Seira Narishige et al.British journal of pharmacology, 171(24), 5858-5869 (2014-08-28) Expressions of Sox9, Sox5, and Sox13 transcription factors in mice testis during postnatal development.Mikella Daigle et al.Molecular and cellular biochemistry, 407(1-2), 209-221 (2015-06-06) βTiina Keränen et al.Cytokine, 94, 1-7 (2017-02-07) The relationship between pulsatile GnRH secretion and cAMP production in immortalized GnRH neurons.John L Frattarelli et al.American journal of physiology. Endocrinology and metabolism, 300(6), E1022-E1030 (2011-03-31) Modulation of signaling through GPCR-cAMP-PKA pathways by PDE4 depends on stimulus intensity: Possible implications for the pathogenesis of acrodysostosis without hormone resistance.Emmanuelle Motte et al.Molecular and cellular endocrinology, 442, 1-11 (2016-12-03) Organoids of Human Endometrium: A Powerful In Vitro Model for the Endometrium-Embryo Cross-Talk at the Implantation Site.Alice Luddi et al.Cells, 9(5) (2020-05-06) Expression of the facilitated glucose transporters (GLUT1 and GLUT3) by a choriocarcinoma cell line (JAr) and cytotrophoblast cells in culture.L H Clarson et al.Placenta, 18(4), 333-339 (1997-05-01) ADAM12-directed ectodomain shedding of E-cadherin potentiates trophoblast fusion.M Aghababaei et al.Cell death and differentiation, 22(12), 1970-1984 (2015-04-25) Regulation of the human NBC3 Na+/HCO3- cotransporter by carbonic anhydrase II and PKA.Frederick B Loiselle et al.American journal of physiology. Cell physiology, 286(6), C1423-C1433 (2004-01-23) Characterization of the interaction between 8-bromoadenosine with human serum albumin and its analytical application.Fengling Cui et al.Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 74(4), 964-971 (2009-09-25) Cyclic AMP-dependent protein kinase A and EPAC mediate VIP and secretin stimulation of PAK4 and activation of Na+,K+-ATPase in pancreatic acinar cells.Irene Ramos-Alvarez et al.American journal of physiology. Gastrointestinal and liver physiology, 316(2), G263-G277 (2018-12-07) Bromo-adenosine stimulates choriogonadotropin production in JAr and cytotrophoblast cells: evidence for effects on two stages of differentiation.C P Sibley et al.Molecular endocrinology (Baltimore, Md.), 5(4), 582-586 (1991-04-01) Transcription factors SF1 and cJUN cooperate to activate the Fdx1 promoter in MA-10 Leydig cells.Pauline Roumaud et al.The Journal of steroid biochemistry and molecular biology, 171, 121-132 (2017-03-10) Lithium and GADL1 regulate glycogen synthase kinase-3 activity to modulate KCTD12 expression.Tai-Na Wu et al.Scientific reports, 9(1), 10255-10255 (2019-07-18) Channelrhodopsin-1 Phosphorylation Changes with Phototactic Behavior and Responds to Physiological Stimuli in Chlamydomonas.Michaela Böhm et al.The Plant cell, 31(4), 886-910 (2019-03-14) Synthesis of the 2'-deoxy-2'-fluoro and 3'-deoxy-3'-fluoro analogues of 8-bromoadenosine.T Maruyama et al.Nucleic acids symposium series, (37)(37), 17-18 (1997-01-01) Prostaglandin E2--mediated relaxation of the ductus arteriosus: effects of gestational age on g protein-coupled receptor expression, signaling, and vasomotor control.Nahid Waleh et al.Circulation, 110(16), 2326-2332 (2004-10-13) Arginine reprogramming in ADPKD results in arginine-dependent cystogenesis.Josephine F Trott et al.American journal of physiology. Renal physiology, 315(6), F1855-F1868 (2018-10-04) Prostaglandin E2 suppresses hCAP18/LL-37 expression in human macrophages via EP2/EP4: implications for treatment of Mycobacterium tuberculosis infection.Min Wan et al.FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 32(5), 2827-2840 (2018-02-07) Selective generation and reactivity of 5'-adenosinyl and 2'-adenosinyl radicals.Chryssostomos Chatgilialoglu et al.Chemistry (Weinheim an der Bergstrasse, Germany), 10(5), 1249-1255 (2004-03-10) Inhibition of progesterone biosynthesis induced by deca-brominated diphenyl ether (BDE-209) in mouse Leydig tumor cell (MLTC-1).Xiumei Han et al.Toxicology in vitro : an international journal published in association with BIBRA, 60, 383-388 (2019-05-28) Androgens regulate follicle stage-dependent pro- and anti-apoptosis in teleost ovaries through ZIP9 activation of different G proteins†.Aubrey Converse et al.Biology of reproduction, 101(2), 377-391 (2019-05-11) Enhanced neurite outgrowth of human model (NT2) neurons by small-molecule inhibitors of Rho/ROCK signaling.Frank Roloff et al.PloS one, 10(2), e0118536-e0118536 (2015-02-26) CNGC2 Is a Ca2+ Influx Channel That Prevents Accumulation of Apoplastic Ca2+ in the Leaf.Yan Wang et al.Plant physiology, 173(2), 1342-1354 (2016-12-22) The mammalian decidual cell evolved from a cellular stress response.Eric M Erkenbrack et al.PLoS biology, 16(8), e2005594-e2005594 (2018-08-25) Synergistic effect of phosphodiesterase 4 inhibitor and serum on migration of endotoxin-stimulated macrophages.Jing-Xing Yang et al.Innate immunity, 24(8), 501-512 (2018-11-10) Prostaglandin E2 Inhibits NLRP3 Inflammasome Activation through EP4 Receptor and Intracellular Cyclic AMP in Human Macrophages.Milena Sokolowska et al.Journal of immunology (Baltimore, Md. : 1950), 194(11), 5472-5487 (2015-04-29) Shockwaves Suppress Adipocyte Differentiation via Decrease in PPARγ.Wonkyoung Cho et al.Cells, 9(1) (2020-01-16) MEF2 Cooperates With Forskolin/cAMP and GATA4 to Regulate Star Gene Expression in Mouse MA-10 Leydig Cells.Caroline Daems et al.Endocrinology, 156(7), 2693-2703 (2015-04-11) Chlamydia trachomatis infection of human endometrial stromal cells induces defective decidualisation and chemokine release.Sevi Giakoumelou et al.Scientific reports, 7(1), 2001-2001 (2017-05-19) Decidualization induces a secretome switch in perivascular niche cells of the human endometrium.Keisuke Murakami et al.Endocrinology, 155(11), 4542-4553 (2014-08-15) The effect of adenosine on cochlear potentials in the guinea pig.K Nario et al.European archives of oto-rhino-laryngology : official journal of the European Federation of Oto-Rhino-Laryngological Societies (EUFOS) : affiliated with the German Society for Oto-Rhino-Laryngology - Head and Neck Surgery, 251(7), 428-433 (1994-01-01) Bronchioalveolar stem cells derived from mouse-induced pluripotent stem cells promote airway epithelium regeneration.Naoya Kawakita et al.Stem cell research & therapy, 11(1), 430-430 (2020-10-04) Synthesis and properties of a modified 2'-5'-adenylate trimer containing 2'-terminal 8-bromoadenosine.S Yoshida et al.Nucleic acids symposium series, (16)(16), 133-136 (1985-01-01) Long-term, hormone-responsive organoid cultures of human endometrium in a chemically defined medium.Margherita Y Turco et al.Nature cell biology, 19(5), 568-577 (2017-04-11) High-quality human preimplantation embryos stimulate endometrial stromal cell migration via secretion of microRNA hsa-miR-320a.Robbert P Berkhout et al.Human reproduction (Oxford, England), 35(8), 1797-1807 (2020-07-10) Transcriptomic responses to hypoxia in endometrial and decidual stromal cells.Kalle T Rytkönen et al.Reproduction (Cambridge, England), 160(1), 39-51 (2020-04-10) Bronchoalveolar sublineage specification of pluripotent stem cells: effect of dexamethasone plus cAMP-elevating agents and keratinocyte growth factor.Katherina Katsirntaki et al.Tissue engineering. Part A, 21(3-4), 669-682 (2014-10-16) Internalized TSH receptors en route to the TGN induce local GAmod Godbole et al.Nature communications, 8(1), 443-443 (2017-09-07) PKA signaling drives mammary tumorigenesis through Src.A G Beristain et al.Oncogene, 34(9), 1160-1173 (2014-03-26) Glycolytic Switch Is Required for Transdifferentiation to Endothelial Lineage.Li Lai et al.Circulation, 139(1), 119-133 (2018-12-28) Regulation of Neuronal Na+/K+-ATPase by Specific Protein Kinases and Protein Phosphatases.Sandesh Mohan et al.The Journal of neuroscience : the official journal of the Society for Neuroscience, 39(28), 5440-5451 (2019-05-16) The diabetes drug liraglutide reverses cognitive impairment in mice and attenuates insulin receptor and synaptic pathology in a non-human primate model of Alzheimer's disease.Andre F Batista et al.The Journal of pathology, 245(1), 85-100 (2018-02-13) Purine 8-bromination modulates the ribonuclease L binding and activation abilities of 2',5'-oligoadenylates. Possible influence of glycosyl torsion angle.K Lesiak et al.The Journal of biological chemistry, 262(5), 1961-1965 (1987-02-15) Conformational analysis of brominated pA2'-5'A2'-5'A analogs. An NMR and model-building study.Y T van den Hoogen et al.European journal of biochemistry, 182(3), 629-637 (1989-07-01) Regulation of stanniocalcin-1 secretion by BeWo cells and first trimester human placental tissue from normal pregnancies and those at increased risk of developing preeclampsia.Naila Abid et al.FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(5), 6086-6098 (2020-03-13) Regulation of epithelial Na+ transport by soluble adenylyl cyclase in kidney collecting duct cells.Kenneth R Hallows et al.The Journal of biological chemistry, 284(9), 5774-5783 (2009-01-08) Ganoderic acid A is the effective ingredient of Ganoderma triterpenes in retarding renal cyst development in polycystic kidney disease.Jia Meng et al.Acta pharmacologica Sinica, 41(6), 782-790 (2020-01-09) Maintenance of hindgut reabsorption during cold exposure is a key adaptation for Drosophila cold tolerance.Mads Kuhlmann Andersen et al.The Journal of experimental biology, 223(Pt 4) (2020-01-19) Anticystogenic activity of a small molecule PAK4 inhibitor may be a novel treatment for autosomal dominant polycystic kidney disease.Vicki J Hwang et al.Kidney international, 92(4), 922-933 (2017-05-27) Emodin augments calcium activated chloride channel in colonic smooth muscle cells by Gi/Go protein.Long Xu et al.European journal of pharmacology, 615(1-3), 171-176 (2009-05-05) Bisphenol compounds regulate decidualized stromal cells in modulating trophoblastic spheroid outgrowth and invasion in vitro†.Hongjie Fan et al.Biology of reproduction, 102(3), 693-704 (2019-11-20) Adenosine 3':5'-cyclic monophosphate induces regulated secretion of tissue-type plasminogen activator and von Willebrand factor from cultured human endothelial cells.R J Hegeman et al.Thrombosis and haemostasis, 79(4), 853-858 (1998-05-06) CaFabio Fusi et al.Biochemical pharmacology, 140, 53-63 (2017-06-07) Crosstalk from cAMP to ERK1/2 emerges during postnatal maturation of nociceptive neurons and is maintained during aging.Joerg Isensee et al.Journal of cell science, 130(13), 2134-2146 (2017-05-19) Inferring biallelism of two FSH receptor mutations associated with spontaneous ovarian hyperstimulation syndrome by evaluating FSH, LH and HCG cross-activity.Clara Lazzaretti et al.Reproductive biomedicine online, 38(5), 816-824 (2019-03-27) The role of inhibition of pyruvate kinase in the stimulation of gluconeogenesis by glucagon: a reevaluation.R C Haynes et al.Archives of biochemistry and biophysics, 283(1), 51-59 (1990-11-15) Functional polarization of human hepatoma HepaRG cells in response to forskolin.Abdullah Mayati et al.Scientific reports, 8(1), 16115-16115 (2018-11-02) Patterns of human chorionic gonadotropin expression in untreated and 8-bromoadenosine-treated JAR choriocarcinoma cells.R E Martell et al.Endocrinology, 126(5), 2757-2764 (1990-05-01) The Effect of Copper on Endometrial Receptivity and Induction of Apoptosis on Decidualized Human Endometrial Stromal Cells.Jose P Carrascosa et al.Reproductive sciences (Thousand Oaks, Calif.), 25(7), 985-999 (2017-10-07) Fibroblast Growth Factor 7 Regulates Proliferation and Decidualization of Human Endometrial Stromal Cells via ERK and JNK Pathway in an Autocrine Manner.Wen-Jie Zhou et al.Reproductive sciences (Thousand Oaks, Calif.), 24(12), 1607-1619 (2017-03-09) Two-step synthesis of novel, bioactive derivatives of the ubiquitous cofactor nicotinamide adenine dinucleotide (NAD).Thomas Pesnot et al.Journal of medicinal chemistry, 54(10), 3492-3499 (2011-05-03) Relation of High-Density Lipoprotein Charge Heterogeneity, Cholesterol Efflux Capacity, and the Expression of High-Density Lipoprotein-Related Genes in Mononuclear Cells to the HDL-Cholesterol Level.Alexander D Dergunov et al.Lipids, 53(10), 979-991 (2018-11-16) Organoids Model Transcriptional Hallmarks of Oncogenic KRAS Activation in Lung Epithelial Progenitor Cells.Antonella F M Dost et al.Cell stem cell, 27(4), 663-678 (2020-09-07) Restoration of the cAMP second messenger pathway enhances cardiac preservation for transplantation in a heterotopic rat model.D Pinsky et al.The Journal of clinical investigation, 92(6), 2994-3002 (1993-12-01) T-2 toxin downregulates LHCGR expression, steroidogenesis, and cAMP level in human cumulus granulosa cells.Kristina Pogrmic-Majkic et al.Environmental toxicology, 34(7), 844-852 (2019-04-06) Deregulation of the endometrial stromal cell secretome precedes embryo implantation failure.Ruban Rex Peter Durairaj et al.Molecular human reproduction, 23(7), 478-487 (2017-04-13) EGF domain of coagulation factor IX is conducive to exposure of phosphatidylserine.Chiaki Hidai et al.Cell biology international, 41(4), 374-383 (2017-02-06) Functional characterization of the human facilitative glucose transporter 12 (GLUT12) by electrophysiological methods.Jonai Pujol-Giménez et al.American journal of physiology. 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