Physicochemical Properties
| Molecular Formula | C10H12N5O11P2-3 |
| Molecular Weight | 440.17678 |
| Exact Mass | 443.024 |
| CAS # | 146-91-8 |
| Related CAS # | Guanosine 5'-diphosphate disodium salt;7415-69-2;Guanosine 5'-diphosphate sodium;43139-22-6 |
| PubChem CID | 135398619 |
| Appearance | Typically exists as solid at room temperature |
| Density | 2.63 g/cm3 |
| Boiling Point | 961ºC at 760 mmHg |
| Flash Point | 535ºC |
| Vapour Pressure | 0mmHg at 25°C |
| Index of Refraction | 1.94 |
| LogP | -4.6 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 13 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 28 |
| Complexity | 760 |
| Defined Atom Stereocenter Count | 4 |
| SMILES | O[C@@H]([C@H]([C@H](N1C=NC2=C1N=C(N)NC2=O)O3)O)[C@H]3COP(O)(OP(O)(O)=O)=O |
| InChi Key | QGWNDRXFNXRZMB-UUOKFMHZSA-N |
| InChi Code | InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1 |
| Chemical Name | [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono hydrogen phosphate |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro |
In inside-out patch membrane configurations from rabbit portal vein smooth muscle cells, bath application of GDP (≥ 100 µM) re-activated the pinacidil-sensitive 15 pS ATP-sensitive K⁺ channel that had undergone “run-down” after membrane excision. This effect required the presence of pinacidil (100 µM) either in the pipette or bath. GDP (1 mM) increased the mean open time and open probability (channel activity) of the 15 pS K⁺ channel more potently than GTP (1 mM). The channel activity induced by 1 mM-GDP was about three times greater than that induced by 1 mM-GTP. The activation by GDP was concentration-dependent (effective concentrations ≥ 30 µM). It increased the mean open time of the channel (e.g., from 369 ms at 100 µM to 1171 ms at 1 mM) without changing the number of channel openings. Other guanine nucleotides (GMP, GTPγS, GDPβS at 1 mM) failed to activate the channel. However, GDPβS (1 mM) inhibited the channel when it was pre-activated by 1 mM-GDP. The activation by GDP did not require the simultaneous presence of Mg²⁺. GDP (1 mM) had no effect on the large-conductance Ca²⁺-dependent K⁺ channel (150 pS) present in the same cells.[1] |
| Cell Assay |
Single-channel recordings were performed on enzymatically dispersed smooth muscle cells from rabbit portal vein. The patch-clamp technique (cell-attached, inside-out, and outside-out configurations) was used. Cells were placed in a recording chamber on an inverted microscope stage. Patch electrodes (5-10 MΩ resistance) were used to form high-resistance seals (>10 GΩ) on the cell membrane. The bath was perfused with a high-K⁺ solution (140 mM KCl, 0.3 mM EGTA, 5 mM HEPES, pH 7.25) to set the membrane potential and provide a K⁺ gradient. The pipette solution was physiological salt solution (PSS: 134 mM NaCl, 6 mM KCl, 2.5 mM CaCl₂, 12 mM glucose, 5 mM HEPES, pH 7.25) containing pinacidil (100 µM) and charybdotoxin (100 nM) to inhibit the large-conductance K⁺ channel. After obtaining a cell-attached patch, the membrane was excised to form an inside-out configuration. Test compounds, including GDP (dissolved in cold deionized water), were applied to the bath (cytosolic side). Single-channel currents were recorded using a patch-clamp amplifier, filtered at 300 Hz or 1 kHz, digitized, and analyzed using specialized software. Channel activity (NP₀) was calculated from all-point amplitude histograms.[1] |
| References |
[1]. Guanosine diphosphate activates an adenosine 5'-triphosphate-sensitive K+ channel in the rabbit portal vein. J Physiol. 1991 Dec;444:397-418. [2]. Identification of Guanosine 5'-diphosphate as Potential Iron Mobilizer: Preventing the Hepcidin-Ferroportin Interaction and Modulating the Interleukin-6/Stat-3 Pathway. Sci Rep. 2017 Jan 5;7:40097. |
| Additional Infomation |
GDP is a purine ribonucleoside 5'-diphosphate resulting from the formal condensation of the hydroxy group at the 5' position of guanosine with pyrophosphoric acid. It has a role as an Escherichia coli metabolite, a mouse metabolite and an uncoupling protein inhibitor. It is a guanosine 5'-phosphate and a purine ribonucleoside 5'-diphosphate. It is a conjugate acid of a GDP(2-). Guanosine diphosphate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Guanosine-5'-diphosphate has been reported in Arabidopsis thaliana, Homo sapiens, and other organisms with data available. Guanosine Diphosphate is a purine nucleotide diphosphate comprised of a guanine and a pyrophosphate moiety bound to a ribose moiety at its 1' and 5' sites, respectively. Guanosine diphosphate (GDP) is an inactive metabolite and intermediate in the synthesis of guanosine triphosphate (GTP). Guanosine diphosphate is a metabolite found in or produced by Saccharomyces cerevisiae. A guanine nucleotide containing two phosphate groups esterified to the sugar moiety. See also: ... View More ... Guanosine 5'-diphosphate (GDP) is identified as an indispensable endogenous factor for regulating the ATP-sensitive K⁺ channel in rabbit portal vein smooth muscle. This channel (15 pS) is activated by K⁺ channel openers like pinacidil and blocked by glibenclamide but is insensitive to cytosolic Ca²⁺. The channel activity rapidly disappears (“runs down”) after membrane excision or cell permeabilization with saponin. GDP, but not ATP, can re-activate this run-down channel in the presence of pinacidil. Its diphosphate structure is crucial for activity, as GMP and GTPγS are ineffective. ATP inhibits this GDP-activated channel with an IC₅₀ of 29 µM, and this inhibition is reduced by Mg²⁺.[1] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2718 mL | 11.3590 mL | 22.7180 mL | |
| 5 mM | 0.4544 mL | 2.2718 mL | 4.5436 mL | |
| 10 mM | 0.2272 mL | 1.1359 mL | 2.2718 mL |