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6-Amino-5-azacytidine, an aminated derivative of Azacytidine, is able to inhibit the growth of bacteria E. coli. Azacytidine has been used as an antineoplastic agent. A pyrimidine nucleoside analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA
| Targets |
Anti-bacteria (E. coli)
|
|---|---|
| ln Vitro |
6-Amino-5-azacytidine has an ID50 of 33.9 μM against CCRF-CEM cells and inhibits the growth of WI-L2 cells by 39% at 100 μM[1].
- 6-Amino-5-azacytidine inhibited the growth of E. coli B by 46% at a concentration of 100 μg/ml. In contrast, the 6‑oxo derivative (VI) and 6‑methoxy‑5‑azacytidine (VIII) were completely inactive at the same concentration. [1] - The antibacterial activity of 6-Amino-5-azacytidine could be reversed by low levels of natural purine bases and/or nucleosides, whereas natural pyrimidine bases and thymidine did not reverse the inhibition at all. Only a partial reversion was achieved by high doses of uridine and cytidine. [1] - Against tumor cell lines in vitro: 6-Amino-5-azacytidine had an ID50 of 33‑9 μM against CCRF‑CEM (T‑lymphoblastic leukemia) cells. It inhibited WI‑L2 (human B‑lymphoblastic leukemia) cells by 39% at 100 μM concentration. It did not inhibit the growth of L1210 murine lymphocytic leukemia or LoVo/L human colon carcinoma cells at concentrations ≤100 μM. [1] - 6-Amino-5-azacytidine exhibited no in vitro antiviral activity against herpes simplex, adeno, rhino, influenza and parainfluenza viruses at concentrations ≤1 μM. [1] |
| Cell Assay |
- For antibacterial testing: Escherichia coli B was grown statically at 37 °C in a mineral medium containing glucose. Test compounds were added before inoculation, and bacterial growth was measured after 16 hours. [1]
- For tumor cell growth inhibition: Four cell lines were used – L1210 murine lymphocytic leukemia, WI‑L2 human B‑lymphoblastic leukemia, CCRF‑CEM T‑lymphoblastic leukemia, and LoVo/L human colon carcinoma. The compound’s ability to inhibit cell growth was tested in vitro, but no detailed protocol (e.g., cell seeding density, incubation time, viability assay method) is provided. The ID50 (33‑9 μM for CCRF‑CEM) and percent inhibition (39% at 100 μM for WI‑L2) are reported, while no inhibition was observed for L1210 and LoVo/L at ≤100 μM. [1] |
| References | |
| Additional Infomation |
- Molecular conformation of 6-Amino-5-azacytidine was determined by 1H NMR: the ribose ring conformation (Keq = 2.12) resembles that of adenosine (Keq = 1.78) rather than cytidine (Keq = 0.69), indicating a conformational similarity to purine nucleosides. The population of the g+ rotamer around the C(5′)‑C(4′) bond is 80%. The anti conformation around the C‑N glycosyl bond is preferred. [1]
- The amino group at position 6 of the triazine ring may allow 6-Amino-5-azacytidine to bind guanine via three hydrogen bonds, similar to cytosine, or to bind complementary pyrimidines (uracil or thymine) in analogy to adenine, also with three hydrogen bonds. This could enable the compound to act as a “universal” base when incorporated into oligonucleotides. [1] - Biochemical investigations (referenced but not detailed in this paper) suggest that 6-Amino-5-azacytidine interferes with purine metabolism rather than pyrimidine metabolism, and it is therefore considered a purine antimetabolite. [1] |
| Molecular Formula |
C8H13N5O5
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|---|---|
| Molecular Weight |
259.219321012497
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| Exact Mass |
259.091
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| CAS # |
105331-00-8
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| PubChem CID |
13630026
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
-2.8
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| Hydrogen Bond Donor Count |
5
|
| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
|
| Heavy Atom Count |
18
|
| Complexity |
424
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
C([C@@H]1[C@H]([C@H]([C@@H](O1)N2C(=NC(=NC2=O)N)N)O)O)O
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| InChi Key |
HHBIDXKTBPRKSK-TXICZTDVSA-N
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| InChi Code |
InChI=1S/C8H13N5O5/c9-6-11-7(10)13(8(17)12-6)5-4(16)3(15)2(1-14)18-5/h2-5,14-16H,1H2,(H4,9,10,11,12,17)/t2-,3-,4-,5-/m1/s1
|
| Chemical Name |
4,6-diamino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
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| Synonyms |
QS4CCV9ZS5
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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 : ~14.71 mg/mL (~56.75 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 8.33 mg/mL (32.13 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.8577 mL | 19.2886 mL | 38.5773 mL | |
| 5 mM | 0.7715 mL | 3.8577 mL | 7.7155 mL | |
| 10 mM | 0.3858 mL | 1.9289 mL | 3.8577 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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