Carbodine
目录号 : GC35606
Carbodine (Carbocyclic cytidine) 是一种广谱抗病毒药物，对 DNA 病毒、(+)RNA 病毒、(-)RNA 病毒、paramyxo, rhabdo 和 (+/-)RNA 病毒均有活性，靶向将 UTP 转换为 CTP 的 CTP 合成酶。Carbodine (Carbocyclic cytidine) 在体外具有显著的抗流感病毒 A0/PR-8/34 和 A2/Aichi/2/68 活性。
Cas No.:71184-20-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Carbodine (Carbocyclic cytidine) is a broad-spectrum antiviral agent active against DNA viruses, (+)RNA viruses, (-)RNA viruses, paramyxo, rhabdo and (+/-)RNA viruses, targets CTP synthetase that converts UTP to CTP. Carbodine (Carbocyclic cytidine) possesses significant antiviral activity against influenza virus types A0/PR-8/34 and A2/Aichi/2/68 in vitro[1][2].
[1]. De Clercq E, et al. Broad-spectrum antiviral activity of carbodine, the carbocyclic analogue of cytidine. Biochem Pharmacol. 1990 Jan 15;39(2):319-25. [2]. Shannon WM, et al. Evaluation of carbodine, the carbocyclic analog of cytidine, and related carbocyclic analogs of pyrimidine nucleosides for antiviral activity against human influenza Type A viruses. Antimicrob Agents Chemother. 1981 Dec;20(6):769-76.
| Cas No. | 71184-20-8 | SDF | |
| Canonical SMILES | O=C1N=C(N)C=CN1[C@H]2[C@H](O)[C@H](O)[C@@H](CO)C2 | ||
| 分子式 | C10H15N3O4 | 分子量 | 241.24 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.1452 mL | 20.7262 mL | 41.4525 mL |
| 5 mM | 0.829 mL | 4.1452 mL | 8.2905 mL |
| 10 mM | 0.4145 mL | 2.0726 mL | 4.1452 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Evaluation of Carbodine, the carbocyclic analog of cytidine, and related carbocyclic analogs of pyrimidine nucleosides for antiviral activity against human influenza Type A viruses
Antimicrob Agents Chemother 1981 Dec;20(6):769-76.PMID:7325642DOI:10.1128/AAC.20.6.769.
Carbodine, the carbocyclic analog of cytidine, was found to possess significant antiviral activity against influenza virus types A0/PR-8/34 and A2/Aichi/2/68 (Hong Kong) in vitro. The compound selectively inhibited PR-8 influenza virus-induced cytopathogenic effects in Madin-Darby canine kidney and inhibited Hong Kong influenza virus replication in primary rhesus monkey kidney cell cultures. The 50% minimum inhibitory concentration for inhibition of human influenza type A viruses by Carbodine was approximately 2.6 microgram/ml (i.e., in the range of antiviral potency of ribavirin, but less potent than amantadine hydrochloride in concomitant assays). The fact that Carbodine is metabolized to Carbodine triphosphate in mammalian cells makes interference with the viral ribonucleic acid-dependent ribonucleic acid polymerase reaction a likely possibility for its principal mode of action. The carbocyclic analogs of uridine (the deamination product of Carbodine), 2'-deoxycytidine, 3'-deoxycytidine, N,N-dimethylcytidine, N-methylcytidine, and some related carbocyclic analogs of pyrimidine nucleosides were inactive against PR-8 influenza virus in vitro. The combination of Carbodine plus tetrahydrouridine was no more effective in vitro than Carbodine alone, thus indirectly indicating that deamination of Carbodine probably did not occur to a significant degree during the cell culture experiments. Although reproducibly active in vitro, Carbodine did not exhibit any efficacy against lethal influenza virus infections in mice when administered by either the intraperitoneal or intranasal routes up to dose-limiting toxic levels.
Treatment of Venezuelan equine encephalitis virus infection with (-)-carbodine
Antiviral Res 2008 Dec;80(3):309-15.PMID:18675850DOI:10.1016/j.antiviral.2008.07.002.
Venezuelan equine encephalitis virus (VEEV) may cause encephalitis in humans, for which no FDA-approved antiviral treatment is available. Carbocyclic cytosine (Carbodine) has broad-spectrum activity but toxicity has limited its utility. It was anticipated that one of the enantiomers of Carbodine would show enhanced activity and reduced toxicity. The activity of the d-(-) enantiomer of Carbodine [(-)-carbodine] was evaluated by infectious cell culture assay and was found to have a 50% effective concentration (EC50) of 0.2 microg/ml against the TC-83 vaccine strain of VEEV in Vero cells, while the l-(+) enantiomer had no activity. Virus titer inhibition correlated with intracellular cytidine triphosphate reduction after treatment with (-)-carbodine, as determined by HPLC analysis. Pre-treatment with 200 mg/(kgd) resulted in significant improvement in survival, virus load in the brain, weight change, and mean day-to-death in a mouse model of TC-83 VEEV disease. A single dose of (-)-carbodine resulted in a slight extension of mean time to death in mice infected with wild-type VEEV. Post-virus exposure treatment with (-)-carbodine was effective in significantly improving disease parameters in mice infected with TC-83 VEEV when treatment was initiated as late as 4 days post-virus installation (dpi). It is remarkable that (-)-carbodine is effective when initiated after the establishment of brain infection.
Synthesis of novel 4'α-trifluoromethyl-2'β-C-methyl-carbodine analogs as anti-hepatitis C virus agents
Nucleosides Nucleotides Nucleic Acids 2015;34(2):79-91.PMID:25621702DOI:10.1080/15257770.2014.960977.
Novel 4 'α-trifluoromethyl-2 'β-methyl carbocyclic nucleoside analogs have been prepared and evaluated for inhibition of hepatitis C virus (HCV) RNA replication in cell cultures. Construction of cyclopentene intermediate 10a was achieved via sequential Johnson-Claisen orthoester rearrangement and ring-closing metathesis starting from the α-trifluoromethyl-α,β-unsaturated ester 5. Stereoselective dihydroxylation and desilylation yielded the target Carbodine analogs. The synthesized nucleoside analogs mentioned above (18 and 19) were assayed for their ability to inhibit HCV RNA replication in a subgenomic replicon Huh7 cell line (LucNeo#2). However, the synthesized nucleosides showed neither significant antiviral activity nor toxicity up to 50 μM.
Broad-spectrum antiviral activity of Carbodine, the carbocyclic analogue of cytidine
Biochem Pharmacol 1990 Jan 15;39(2):319-25.PMID:1689159DOI:10.1016/0006-2952(90)90031-f.
Carbocyclic cytidine (C-Cyd) is a broad-spectrum antiviral agent active against DNA viruses [pox (vaccinia)], (+)RNA viruses [toga (Sindbis, Semliki forest), corona], (-)RNA viruses [orthomyxo (influenza), paramyxo (parainfluenza, measles), rhabdo (vesicular stomatitis)] and (+/-)RNA viruses (reo). The target enzyme of C-Cyd is supposed to be CTP synthetase that converts UTP to CTP. In keeping with this assumption are the observations that (i) C-Cyd effects a dose-dependent inhibition of RNA synthesis in both virus-infected and uninfected cells, and (ii) exogenous addition of either Urd or Cyd reverses both the antiviral and cytocidal activity of C-Cyd, whereas addition of dThd or dCyd fails to do so. The selectivity of C-Cyd against Sindbis, vesicular stomatitis and reo virus is markedly increased when C-Cyd is combined with Cyd (10 micrograms/mL). This combination may therefore be worth pursuing as a chemotherapeutic modality for the treatment of virus infections.
Synthesis and anti-HCV evaluation of 4'(alpha)-ethyl and 2'(beta)-methyl-carbodine analogues
Nucleosides Nucleotides Nucleic Acids 2009 Sep;28(9):809-20.PMID:20183620DOI:10.1080/15257770903170294.
Novel 4'(alpha)-ethyl-2'(beta)-methyl carbocyclic nucleoside analogues have been prepared and evaluated for inhibition of hepatitis C virus (HCV) RNA replication in cell culture. The construction of cyclopentene intermediate 12 beta was successfully made via sequential Johnson-Claisen orthoester rearrangement and ring-closing metathesis (RCM) starting from Weinreb amide 5. Selective dihydroxylation and desilylation gave the target Carbodine analogues. The synthesized nucleoside analogues mentioned above 18 and 19 were assayed for their ability to inhibit HCV RNA replication in a subgenomic replicon Huh7 cell line (LucNeo#2). However, the synthesized nucleosides neither showed any significant antiviral activity nor toxicity up to 50 microM.