7665-99-8

Basic information

• Product Name: GUANOSINE 3':5'-CYCLIC MONOPHOSPHATE
• Synonyms: Cyclic 3',5'-guanylic acid;Cyclic guanosine phosphate;Guanosine 3',5'-phosphoric acid;Guanosine cyclic 3',5'-monophosphate;Guanosine 3′,5′-cyclic monophosphate,cGMP, cyclic GMP;Guanosine 3',5'-Monophosphate;3',5'-Cyclic guanosine Monophosphate;3',5'-cGMPH
• CAS NO: 7665-99-8
• Molecular Formula: C₁₀H₁₂N₅O₇P
• Molecular Weight: 345.21
• EINECS: 231-641-6
• Product Categories: Alphabetic;Analytical Standards;Food&Beverage Standards;GChromatography;Nucleotides&Nucleosides
• Mol File: 7665-99-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 792.7 °C at 760 mmHg
• Flash Point: 433.2 °C
• Appearance: white/powder
• Density: 2.64 g/cm³
• Vapor Pressure: 1.71E-26mmHg at 25°C
• Refractive Index: 2.064
• Storage Temp.: −20°C
• Solubility: 1% sodium bicarbonate: 50 mg/mL
• PKA: 1.03±0.60(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: GUANOSINE 3':5'-CYCLIC MONOPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: GUANOSINE 3':5'-CYCLIC MONOPHOSPHATE(7665-99-8)
• EPA Substance Registry System: GUANOSINE 3':5'-CYCLIC MONOPHOSPHATE(7665-99-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-26-36
• WGK Germany: 3
• Hazardous Substances Data: 7665-99-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Guanosine 3'',5''-Cyclic Monophosphate is an intracellular second messenger which are involved in the transduction of a diverse array of stimuli, mediating metabolic and growth regulation.

Definition

ChEBI: A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP.

InChI:InChI=1/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

Upstream product

• 86-01-1 Guanosine 5'-triphosphate 
• 118-00-3 G 
• 339291-46-2 cyclic guanosine-3',5'-monophosphate [6,7-bis(carboxymethoxy)coumarin-4-yl]methyl ester 
• 339291-52-0 cyclic guanosine-3',5'-monophosphate [6,7-bis(carboxymethoxy)coumarin-4-yl]methyl ester 
• 339291-45-1 [7-(carboxymethoxy)coumarin-4-yl]methyl ester of cGMP 
• 339291-50-8 [7-(carboxymethoxy)coumarin-4-yl]methyl ester of cGMP 

Downstream Products

• 85-32-5 Guanosine 5'-monophosphate 
• 31356-94-2 8-bromo-cyclic guanosine 3':5'-monophosphate 
• 117-68-0 guanosine 3'-monophosphate 
• 118-00-3 G 
• 32266-35-6 dibutyryl guanosine 3',5'-cyclic monophosphate 

Relevant articles and documents

Photolabile Coumarinylmethyl Esters of Cyclic Nucleotides, Methods for their Preparation and Their Use

The invention relates to new photolabile coumarinylmethyl esters of cyclic nucleotides of general formula I wherein R1 represents hydrogen, bromine or p-chlorophenylthio R4 represents 7-carboxymethoxy, 6,7-, 5,7- or 7,8-bis-(carboxymethoxy), 7-C1-C3-alkoxycarbonylmethoxy, 6,7-bis(C1-C3-alkoxycarbonylmethoxy), 5,7-bis(C1-C3-alkoxy-carbonylmethoxy), or 7,8-bis(C1-C3-alkoxycarbonylmethoxy), R2 represents —NH2 and R3 is hydrogen (adenine residue), or R2 represents —OH and R3 represents NH2 (guanine residue) The inventive compounds are biologically inactive and exhibit high solubility in aqueous buffer solutions, high efficiency in photocleavage and rapid kinetics of liberation, together with high resistance to solvolysis.

Highly efficient and ultrafast phototriggers for cAMP and cGMP by using long-wavelength uv/vis-activation

Caged cyclic nucleotides exhibiting remarkable advantageous properties have been developed through the use of novel photolabile coumarinylmethyl protecting groups (see scheme). They serve as excellent intracellular sources of cAMP and cGMP and allow the study of spatial- and time-dependent aspects of cyclic nucleotide signaling.

Secretion of cyclic GMP by cultured epithelial and fibroblast cell lines in response to nitric oxide

LLC-PK1 epithelial cells and RFL-6 fibroblasts secreted both cyclic AMP (cAMP) and cyclic GMP (cGMP) when costimulated with forskolin and 3- morpholinosydnonimine (a chemical nitric oxide generator). Intracellular cAMP levels as high as 1100 and 12,000 pmol/106 cells were achieved for the two cell types, respectively. These levels were high enough to reach approximately 50% saturation of the cAMP transporter and inhibited transport of cGMP to an equal extent, suggesting that the two cyclic nucleotides compete for a common transport system. The rates of secretion of cGMP and cAMP from LLC-PK1 cells increased in proportion to their rates of synthesis as concentrations of stimulant were varied, but increased only 25% relative to intracellular concentrations in response to inhibition of phosphodiesterases by 3-isobutylmethylxanthine. It is proposed that secretion of cyclic nucleotides is not simply proportional to the total intracellular pool in these cells, but rather is coupled to synthesis. In support of this model, oxyhemoglobin was used to trap nitric oxide and block activity of guanylate cyclase in cells treated with 3-morpholinosydnonimine. As a result, secretion of cGMP ceased within 1 min, whereas intracellular levels decreased slowly over 60 min. Probenecid [p(dipropylsulfamoyl)benzoic acid] is a nonselective antagonist of anion transport that inhibited secretion of cAMP in both cell types but, unexpectedly, blocked synthesis of cGMP, and this was reflected in direct inhibition of soluble guanylate cyclase in cell lysates. Two heat-stable, high molecular weight factors that confer sensitivity to probenecid were identified, and these factors increased the sensitivity of guanylate cyclase to nitric acid by an order of magnitude.