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| 1mg |
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Cyclic-di-GMP is a novel and potent STING agonist with anticancer and antiviral effects. It is a ubiquitous and bacterial second messenger that regulates biofilm formation, motility, and virulence in diverse bacterial species.
| ln Vitro |
Human colon cancer cells are inhibited from proliferating when exposed to cyclic-di-GMP (0.5-50 µM; 5 days) [1]. In Jurkat cells, cyclic-di-GMP (0.5-50 µM; 5 days) selectively upregulates CD4 expression [2]. In the S phase of Jurkat cells, cyclic-di-GMP (0.5-50 µM; 5 days) causes cell cycle arrest [2].
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| ln Vivo |
In mice, cyclic-di-GMP (100 µg/per; intravenous injection; two doses separated by nine days) can boost the immunological response TriVax elicits against melanoma and significantly amplify the vaccine's anti-tumor impact [3].
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| Cell Assay |
Cell proliferation assay [1]
Cell Types: H508 Cell Tested Concentrations: 0.5-50 µM Incubation Duration: 5 days Experimental Results: H508 cell basal proliferation was diminished by approximately 15%, and even inhibited cell proliferation induced by acetylcholine and EGF. Cell viability assay [2] Cell Types: Jurkat cells Tested Concentrations: 50 µM Incubation Duration: 24 hrs (hours) Experimental Results: Specific induction of CD4 (no effect on the expression of CD8), up-regulated 6.3 times compared to the control, in a dose-dependent manner. Cell cycle analysis [2] Cell Types: Jurkat cell Tested Concentrations: 50 µM Incubation Duration: 24 hrs (hours) Experimental Results: The percentage of cells in S phase increased by 79%, and the cells in G2/M phase almost completely disappeared, reducing by 93%. |
| Animal Protocol |
Animal/Disease Models: C57BL/6 (B6) mice (8 to 10 weeks old) [3].
Doses: 100 mcg/Route of Administration: intravenous (iv) (iv)injection; two consecutive vaccinations, 9 days apart; combined with TriVax. Experimental Results: The number of antigen-specific CD8 T cells increased Dramatically when combined with TriVax. (TriVax consists of a mixture of 120 μg Pam-hgp100, 100 μg hgp100 or 100 μg Ova, 50 or 25 μg anti-CD40 antibody, and 25 μg Poly-IC). Enhances the anti-tumor activity of TriVax. |
| References | |
| Additional Infomation |
C-di-GMP is a cyclic purine dinucleotide that is the 3',5'-cyclic dimer of MP. It has a role as an immunomodulator and a signalling molecule. It is a guanyl ribonucleotide and a cyclic purine dinucleotide. It is a conjugate acid of a c-di-GMP(2-).
Cyclic di-3',5'-guanylate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). |
| Molecular Formula |
C20H24N10O14P2
|
|---|---|
| Molecular Weight |
690.4107
|
| Exact Mass |
690.095
|
| CAS # |
61093-23-0
|
| Related CAS # |
Cyclic-di-GMP diammonium;609343-82-0;Cyclic-di-GMP disodium;2222132-40-1;Cyclic-di-GMP sodium
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| PubChem CID |
135440063
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| Appearance |
White to off-white solid powder
|
| LogP |
-6.8
|
| Hydrogen Bond Donor Count |
8
|
| Hydrogen Bond Acceptor Count |
18
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
46
|
| Complexity |
1340
|
| Defined Atom Stereocenter Count |
8
|
| SMILES |
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(OC[C@@H]5[C@H]([C@H]([C@@H](O5)N6C=NC7=C6N=C(NC7=O)N)O)OP(=O)(O1)O)O
|
| InChi Key |
PKFDLKSEZWEFGL-MHARETSRSA-N
|
| InChi Code |
InChI=1S/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1
|
| Chemical Name |
2-amino-9-[(1S,6R,8R,9R,10S,15R,17R,18R)-17-(2-amino-6-oxo-1H-purin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]-1H-purin-6-one
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
H2O : ≥ 25 mg/mL (~36.21 mM)
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|---|---|
| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4484 mL | 7.2421 mL | 14.4841 mL | |
| 5 mM | 0.2897 mL | 1.4484 mL | 2.8968 mL | |
| 10 mM | 0.1448 mL | 0.7242 mL | 1.4484 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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