CXCR4 antagonist 7 (Compound PARA-B) is a novel CXCR4 antagonist with anti-inflammatory, anticancer, anti-WHIM syndrom and anti-HIV activity. It inhibits CXCR4 with an IC50 of 9.3 nM.
Physicochemical Properties
| Molecular Formula | C15H17N5O3 |
| Molecular Weight | 315.327 |
| Exact Mass | 315.133 |
| CAS # | 1185451-72-2 |
| PubChem CID | 44482059 |
| Appearance | Typically exists as solid at room temperature |
| LogP | 0 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 23 |
| Complexity | 543 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1=CC(=CC=C1/C=C/N2C(=O)/C(=C/CCN=C(N)N)/NC2=O)O |
| InChi Key | BRHUBARRWPTWNX-MMYPVXKMSA-N |
| InChi Code | InChI=1S/C15H17N5O3/c16-14(17)18-8-1-2-12-13(22)20(15(23)19-12)9-7-10-3-5-11(21)6-4-10/h2-7,9,21H,1,8H2,(H,19,23)(H4,16,17,18)/b9-7+,12-2- |
| Chemical Name | 2-[(3Z)-3-[1-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,5-dioxoimidazolidin-4-ylidene]propyl]guanidine |
| 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 | CXCR4 antagonist 7 (PARA-B, 10 nM-1 μM, 20 hours) suppresses the proliferation of GH4C1 cells triggered by CXCL12 with an IC50 value of 9.3 nM [1]. GH4C1 cell migration that is dependent on CXCL12 is 50% inhibited by CXCR4 antagonist 7 (1 μM, 12 h) [1]. Reduces CXCL12-induced ERK1/2 phosphorylation with CXCR4 antagonist 7 (50 nM, 30 minutes) [1]. GH4C1-induced proliferation and migration are restored by CXCR4 Antagonist 7 (50 nM-1 μM, 30 minutes) by means of CXCR4 antagonist [1]. |
| Cell Assay |
Cell viability assay [1] Cell Types: GH4C1 cells (48 hrs (hours) without serum) Tested Concentrations: 1 μM Incubation Duration: 24 hrs (hours) Experimental Results: No effect on the cell viability of GH4C1 cells. Cell proliferation assay[1] Cell Types: GH4C1 cells (FBS-starved GH4C1 cells treated with CXCL12 (25 nM) for 12 hrs (hours)) Tested Concentrations: 10 nM-1 μM Incubation Duration: 20 hrs (hours), 24 hrs (hours) Experimental Results: Inhibition of proliferation of multiple cancers The IC50 values of the cell lines ranged from 1.08 to 3.45 μM and had no effect on cell viability of GH4C1 cells. Cell migration assay[1] Cell Types: GH4C1 and GH4A11 cells (FBS starved cells treated with CXCL12 (25 nM) for 48 hrs (hours)) Tested Concentrations: 50 nM-1 μM Incubation Duration: 12 hrs (hours) for GH4C1, 30 minutes for GH4A11 Experimental Results: Significant reduction The number of migrating GH4C1 cells had no effect on the migration of GH4A11 cells (CRISPR-CAS9, CXCR4 mRNA reduction). Western Blot Analysis[1] Cell Types: GH4C1 cells (FBS-starved cells treated with CXCL12 (25 nM) for 15 minutes) Concen |
| References |
[1]. Identification of the hydantoin alkaloids parazoanthines as novel CXCR4 antagonists by computational and in vitro functional characterization. Bioorg Chem. 2020 Dec;105:104337. |
| Additional Infomation | parazoanthine B has been reported in Parazoanthus axinellae with data available. |
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 | 3.1713 mL | 15.8564 mL | 31.7128 mL | |
| 5 mM | 0.6343 mL | 3.1713 mL | 6.3426 mL | |
| 10 mM | 0.3171 mL | 1.5856 mL | 3.1713 mL |