Cyclopentenylcytosine
Based on 1 publication(s) in Google Scholar
Cyclopentenylcytosine (CPEC), a carbocyclic nucleoside analog of cytosine, is a potent inhibitor of CTP synthetase and causes depletion of CTP and dCTP pools. Cyclopentenylcytosine shows broad-spectrum (both DNA and RNA viruses) antiviral activity. Cyclopentenyl cytosine increases Gemcitabine (HY-17026) radiosensitisation in human pancreatic cancer cells. Cyclopentenylcytosine shows effective antiviral activity in the Ad5/NZW rabbit ocular replication model and shows anti-tumor activity in various tumor xenografts model. Cyclopentenylcytosine can be used for the study of infection and cancer.
For research use only. We do not sell to patients.
- Purity: 99.76%
- CAS No.: 90597-22-1
- Formula: C10H13N3O4
- Molecular Weight:239.23
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Storage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
Publications Citing Use of MedChemExpress (MCE) Cyclopentenylcytosine
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Biological Activity
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| CCRF-CEM | IC50 |
0.08 μM
Compound: 55
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In vitro cytotoxicity in CEM cells.
In vitro cytotoxicity in CEM cells.
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[PMID: 11689085] |
| Vero | EC50 |
<0.05 μg/mL
Compound: 14
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Antiviral activity was measured against Monkeypox virus MPX in Vero 76 (ATCC CRL 1587) cell
Antiviral activity was measured against Monkeypox virus MPX in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
| Vero | EC50 |
<0.05 μg/mL
Compound: 14
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Antiviral activity was measured against Smallpox virus 7124 in Vero 76 (ATCC CRL 1587) cell
Antiviral activity was measured against Smallpox virus 7124 in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
| Vero | EC50 |
>100 μg/mL
Compound: 14
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Antiviral activity was measured against Smallpox virus BSH in Vero 76 (ATCC CRL 1587) cell
Antiviral activity was measured against Smallpox virus BSH in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
| Vero | EC50 |
0.04 μg/mL
Compound: 14
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Antiviral activity was measured against Vaccinia virus VAC in Vero 76 (ATCC CRL 1587) cell
Antiviral activity was measured against Vaccinia virus VAC in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
| Vero | EC50 |
0.05 μg/mL
Compound: 14
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Antiviral activity was measured against Cowpox virus CPX in Vero 76 (ATCC CRL 1587) cell
Antiviral activity was measured against Cowpox virus CPX in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
| Vero | IC50 |
>100 μg/mL
Compound: 14
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Cytotoxicity was measured against Smallpox virus 7124 in Vero 76 (ATCC CRL 1587) cell
Cytotoxicity was measured against Smallpox virus 7124 in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
| Vero | IC50 |
1 μg/mL
Compound: 14
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Cytotoxicity was measured against Cowpox virus CPX in Vero 76 (ATCC CRL 1587) cell
Cytotoxicity was measured against Cowpox virus CPX in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
| Vero | IC50 |
1.95 μM
Compound: 55
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In vitro cytotoxicity in vero cells.
In vitro cytotoxicity in vero cells.
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[PMID: 11689085] |
| Vero | IC50 |
30 μg/mL
Compound: 14
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Cytotoxicity was measured against Smallpox virus BSH in Vero 76 (ATCC CRL 1587) cell
Cytotoxicity was measured against Smallpox virus BSH in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
| Vero | IC50 |
4 μg/mL
Compound: 14
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Cytotoxicity was measured against Monkeypox virus MPX in Vero 76 (ATCC CRL 1587) cell
Cytotoxicity was measured against Monkeypox virus MPX in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
| Vero | IC50 |
40 μg/mL
Compound: 14
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Cytotoxicity was measured against Vaccinia virus VAC in Vero 76 (ATCC CRL 1587) cell
Cytotoxicity was measured against Vaccinia virus VAC in Vero 76 (ATCC CRL 1587) cell
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[PMID: 12467606] |
Cyclopentenylcytosine (0.001-100 µg/mL) exhibits potent antiviral activity against nine common ocular adenovirus types (HAdV8, HAdV19/64, HAdV37 (EKC), HAdV3, HAdV4, HAdV7a,HAdV1, HAdV2, HAdV5) in A549 cells using plaque reduction assays with EC50 values ranging from 0.03 to 0.059 µg/mL [1].
Cyclopentenylcytosine induces rapid and complete differentiation of HL-60 promyelocytic cells, with a concomitant reduction in c-myc RNA levels preceding the appearance of differentiated cells[2].
Cyclopentenylcytosine (0.1 µg/mL, 4 days) reduces the number of viable Vero cells[2].
Cyclopentenylcytosine shows potent activity against HSV-1 (TK+ and TK-) with ID50 values of 0.3 μg/mL and 0.6 μg/mL respectively, against HSV-2 (ID50 = 2.7 μg/mL), vaccinia virus (ID50 = 0.1 μg/mL), Japanese encephalitis virus (ID50 = 0.10 μg/mL), vesicular stomatitis virus (ID50 = 0.25-0.57 μg/mL), yellow fever (ID50 = 5.05 μg/mL), Punta Toro virus (ID50 = 1.01 μg/mL), and Hong Kong influenza virus (ID50 = 18.2 μg/mL) in vitro[2].
Cyclopentenylcytosine (100 nM, 0-4 days) causes accumulation of cells in the S phase and inhibits DNA synthesis in SK-N-BE(2)c cells[3].
Cyclopentenylcytosine (100 nM, 1-4 days) increases caspase-3 activity in SK-N-BE(2)c cells, indicating induction of apoptosis[3].
Cyclopentenylcytosine (30-1000 nM, 4-72 h) specifically reduces CTP levels and increases gemcitabine (dFdC) incorporation into DNA in a dose-dependent manner in human pancreatic cancer cells (Panc-1, Miapaca-2, BxPC-3) and NSCLC cells (SWp)[4].
Cyclopentenylcytosine (100 nM, 48 h) enhances the cytotoxicity of dFdC (300 nM, 4 h) in dFdC-sensitive cells (Panc-1, Miapaca-2, BxPC-3, SWp), increasing growth inhibition, reducing clonogenic capacity, and promoting apoptosis[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:SK-N-BE(2)c cells
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Concentration:100 nM
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Incubation Time:0, 1, 2, 3, 4 days
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Result:Caused accumulation of cells in the S phase in SK-N-BE(2)c cells.
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Cell Line:SK-N-BE(2)c cells
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Concentration:100 nM
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Incubation Time:0, 1, 2, 3, 4 days
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Result:Induced apoptosis and increased caspase-3 activity in SK-N-BE(2)c cells.
Cyclopentenylcytosine (0.5-4 mg/kg, intraperitoneal injection, daily on days 1-9or every 4 times day on days 1, 5, 9 or every 3 hours for 8 times on days 1, 5, 9) exhibits an increase in life span (ILS) with a log cell kill (LCK) in CD2F1 mice bearing L1210 leukemia[2].
Cyclopentenylcytosine (1.0-2.25 mg/kg, subrenal capsule injection, daily on days 1-9) inhibits the growth of tumor in mice bearing A549 lung tumor xenografts, LOX melanoma xenografts and MX-1 mammary xenografts[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:HAdV5 (1.5 × 106 PFU in 50 µL) was topically inoculated into both eyes of 2-3-pound female New Zealand white rabbits after corneal epithelial scarification with 12 cross-hatched strokes[1]
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Dosage:3% ointment
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Administration:Topical application 2 or 4 times daily for 7 days
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Result:Achieved a 15% rate of HAdV5-positive eye cultures overall (Days 1-14) (4 times daily).
Resulted in a 19% rate of HAdV5-positive eye cultures overall (2 times daily).
Reduced mean combined HAdV5 ocular titers to 16 Log10 PFU/mL (4 times daily) and 35 Log10 PFU/mL (2 times daily) overall.
Shortened the duration of HAdV5 shedding to 1.3 days (4 times daily) and 2.5 days (2 times daily).
Chemical Information
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CAS No. 90597-22-1
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Appearance Solid
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Molecular Weight 239.23
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Formula C10H13N3O4
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Color White to off-white
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SMILES
O[C@H]1[C@H](N2C(N=C(N)C=C2)=O)C=C(CO)[C@H]1O
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Synonyms
CPEC; NSC 375575
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Publications (1)
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Journal Impact Factor
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Most Recent
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Antiviral Res
Inhibitors of pyrimidine synthesis synergize with N4-hydroxycytidine to diminish influenza virus replication. [Abstract]2025 Dec:244:106286. PMID: 41047107
Solvent & Solubility
DMSO : 1 mg/mL (4.18 mM; Need ultrasonic and warming; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (280 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[1]. Romanowski EG, Yates KA, Gordon YJ. Cyclopentenylcytosine (CPE-C): In Vitro and In Vivo Evaluation as an Antiviral against Adenoviral Ocular Infections. Molecules. 2023 Jun 29;28(13):5078. [Content Brief]
[2]. Marquez VE, et al. Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties. J Med Chem. 1988 Sep;31(9):1687-94. [Content Brief]
[3]. Bierau J, Van Gennip AH, Leen R, Helleman J, Caron HN, Van Kuilenburg AB. Cyclopentenyl cytosine primes SK-N-BE(2)c neuroblastoma cells for cytarabine toxicity. Int J Cancer. 2003 Jan 20;103(3):387-92. [Content Brief]
[4]. van Bree C, et al. Cyclopentenyl cytosine increases gemcitabine radiosensitisation in human pancreatic cancer cells. Br J Cancer. 2008 Apr 8;98(7):1226-33. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 4.1801 mL | 20.9004 mL | 41.8008 mL | 104.5019 mL |
Cyclopentenylcytosine Related Classifications
HY-106777 Related Classifications
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