5-Hydroxymethyldeoxyuridine is a nucleoside analog with potent anticancer and antiviral activities. It inhibits the replication of murine S180 lung carcinoma cells and Ehrlich ascites mammary carcinoma cells (ED50s = 8.5 and 4 μM, respectively) and multiple human leukemia cell lines (IC50s = 1.7-5.8 μM).
Physicochemical Properties
| Molecular Formula | C10H14N2O6 |
| Molecular Weight | 258.22796 |
| Exact Mass | 258.085 |
| Elemental Analysis | C, 46.51; H, 5.46; N, 10.85; O, 37.17 |
| CAS # | 5116-24-5 |
| PubChem CID | 91541 |
| Appearance | White to off-white solid powder |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 401.48°C (rough estimate) |
| Melting Point | 176-179 °C |
| Index of Refraction | 1.610 |
| LogP | -1.49 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 18 |
| Complexity | 396 |
| Defined Atom Stereocenter Count | 3 |
| SMILES | OC[C@@H]1[C@H](O)C[C@H](N2C=C(C(NC2=O)=O)CO)O1 |
| InChi Key | IPAVKOYJGUMINP-XLPZGREQSA-N |
| InChi Code | InChI=1S/C10H14N2O6/c13-3-5-2-12(10(17)11-9(5)16)8-1-6(15)7(4-14)18-8/h2,6-8,13-15H,1,3-4H2,(H,11,16,17)/t6-,7+,8+/m0/s1 |
| Chemical Name | Uridine, 2'-deoxy-5-(hydroxymethyl) |
| Synonyms | 5-Hydroxymethyldeoxyuridine; α-Hydroxythymidine; 2'-Deoxy-5-(hydroxymethyl)uridine; 5-Hydroxymethyl-2'-deoxyuridine |
| 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 5-Hydroxymethyl-2'-deoxyuridine (0-10 μM) has an ED50 value of 8.5 μM for Ehrlich ascites cancer cells and 4 μM for sarcoma 180 cells, which both impede the multiplication of these cells [1]. Herpes simplex virus type 1 (HSV-1) pyrimidine 2'-deoxyribonucleoside kinase is inhibited by 5-hydroxymethyl-2'-deoxyuridine, with a Ki value of 3.5 μM [1]. 5-Hydroxymethyl-2'-deoxyuridine, with IC50 values ranging from 1.7 to 5.8 μM, inhibits the reproduction of several human leukemia cell lines[2]. Human acute promyelocytic leukemia cell lines are toxic to 5-hydroxymethyl-2'-deoxyuridine (10-100 μM) in a dose-dependent manner [2]. |
| ln Vivo | The survival of DBA/2 mice harboring L1210 leukemia is increased by 5-hydroxymethyl-2'-deoxyuridine (0, 5 and 50 mg/kg; intraperitoneal injection; once) [3]. |
| References |
[1]. Synthesis and biological activities of 5-(hydroxymethyl, azidomethyl, or aminomethyl)-2'-deoxyuridine and related 5'-substituted analogues. J Med Chem. 1980 Feb;23(2):127-33. [2]. 5-Hydroxymethyl-2'-deoxyuridine. Cytotoxicity and DNA incorporation studied by using a novel [2-14C]-derivative with normal and leukemic human hematopoietic cells. Acta Chem Scand B. 1985;39(6):477-84. [3]. 5-Hydroxymethyl-2′-Deoxyuridine: Studies of Antileukemic Properties in Vitro and in Vivo. Nucleosides and Nucleotides . 1987. |
| Additional Infomation | 5-hydroxymethyl-2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside composed of 2'-deoxyuridine having a 5-hydroxymethyl substituent. It is functionally related to a 5-hydroxymethyluracil. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~ 125 mg/mL (~484.06 mM) |
| 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 | 3.8725 mL | 19.3626 mL | 38.7252 mL | |
| 5 mM | 0.7745 mL | 3.8725 mL | 7.7450 mL | |
| 10 mM | 0.3873 mL | 1.9363 mL | 3.8725 mL |