Nucleocidin
(Synonyms: 次氮基三乙酸-6-异硫氰酸荧光素,4'-Fluoro-5'-O-sulfamoyladenosine; NSC 521007) 目录号 : GC33985
Nucleocidin 是一种抗锥虫抗生素，可抑制标记的氨基酸从 S-RNA 转移到蛋白质。
Cas No.:24751-69-7
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Nucleocidin is an antitrypanosomal antibiotic, inhibiting the transfer of labeled amino acid from S-RNA to protein.
Although appreciable inhibition occurrs at low concentrations of nucleocidin, it is not possible to obtain complete inhibition even at 10-3 M. An appreciable lag occurrs before any inhibition by nucleocidin is detectable, and the length of this lag period varies inversely with the concentration of nucleocidin. Similar results are obtained when nucleocidin is added to the cell-free system from reticulocytes. By contrast, essentially complete inhibition is obtained at 10-3 M puromycin, and only at the lowest concentrations is any lag detectable. It seems that nucleocidin exhibits the pattern typical of many antibiotics, i.e. it inhibits incorporation at a stage subsequent to the formation of aminoacyl-S-RNA[1].
[1]. Florini JR, et al. Inhibition of protein synthesis in vitro and in vivo by nucleocidin, an antitrypanosomal antibiotic. J Biol Chem. 1966 Mar 10;241(5):1091-8.
| Cas No. | 24751-69-7 | SDF | |
| 别名 | 次氮基三乙酸-6-异硫氰酸荧光素,4'-Fluoro-5'-O-sulfamoyladenosine; NSC 521007 | ||
| Canonical SMILES | O[C@@H]([C@H]([C@H](N1C=NC2=C1N=CN=C2N)O3)O)[C@@]3(F)COS(=O)(N)=O | ||
| 分子式 | C10H13FN6O6S | 分子量 | 364.31 |
| 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.7449 mL | 13.7246 mL | 27.4492 mL |
| 5 mM | 0.549 mL | 2.7449 mL | 5.4898 mL |
| 10 mM | 0.2745 mL | 1.3725 mL | 2.7449 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。
4'-Fluoro-nucleosides and nucleotides: from Nucleocidin to an emerging class of therapeutics
Chem Soc Rev 2023 Jan 3;52(1):248-276.PMID:36472161DOI:10.1039/d2cs00762b.
The history and development of 4'-fluoro-nucleosides is discussed in this review. This is a class of nucleosides which have their origin in the discovery of the rare fluorine containing natural product Nucleocidin. Nucleocidin contains a fluorine atom located at the 4'-position of its ribose ring. From its early isolation as an unexpected natural product, to its total synthesis and bioactivity assessment, Nucleocidin has played a role in inspiring the exploration of 4'-fluoro-nucleosides as a privileged motif for nucleoside-based therapeutics.
Identification of Genes Essential for Sulfamate and Fluorine Incorporation During Nucleocidin Biosynthesis
Chembiochem 2022 Aug 3;23(15):e202200140.PMID:35544615DOI:10.1002/cbic.202200140.
Nucleocidin is an adenosine derivative containing 4'-fluoro and 5'-O-sulfamoyl substituents. In this study, Nucleocidin biosynthesis is examined in two newly discovered producers, Streptomyces virens B-24331 and Streptomyces aureorectus B-24301, which produce Nucleocidin and related derivatives at titers 30-fold greater than S. calvus. This enabled the identification of two new O-acetylated Nucleocidin derivatives, and a potential glycosyl-O-acetyltransferase. Disruption of nucJ, nucG, and nucI, within S. virens B-24331, specifying a radical SAM/Fe-S dependent enzyme, sulfatase, and arylsulfatase, respectively, led to loss of 5'-O-sulfamoyl biosynthesis, but not fluoronucleoside production. Disruption of nucN, nucK, and nucO specifying an amidinotransferase, and two sulfotransferases respectively, led to loss of fluoronucleoside production. Identification of S. virens B-24331 as a genetically tractable and high producing strain sets the stage for understanding Nucleocidin biosynthesis and highlights the utility of using 16S-RNA sequences to identify alternative producers of valuable compounds in the absence of genome sequence data.
Two 3'- O-β-glucosylated nucleoside fluorometabolites related to Nucleocidin in Streptomyces calvus
Chem Sci 2019 Aug 20;10(41):9501-9505.PMID:32110306DOI:10.1039/c9sc03374b.
The antibiotic Nucleocidin is a product of the soil bacterium Streptomyces calvus T-3018. It is among the very rare fluorine containing natural products but is distinct from the other fluorometabolites in that it is not biosynthesised from 5'-fluorodeoxyadenosine via the fluorinase. It seems to have a unique enzymatic fluorination process. We disclose here the structures of two 4'-fluoro-3'-O-β-glucosylated metabolites (F-Mets I and II) which appear and then disappear before Nucleocidin production in batch cultures of S. calvus. Full genome sequencing of S. calvus T-3018 and an analysis of the putative biosynthetic gene cluster for Nucleocidin identified UDP-glucose dependent glucosyl transferase (nucGT) and glucosidase (nucGS) genes within the cluster. We demonstrate that these genes express enzymes that have the capacity to attach and remove glucose from the 3'-O-position of adenosine analogues. In the case of F-Met II, deglucosylation with the NucGS glucosidase generates Nucleocidin suggesting a role in its biosynthesis. Gene knockouts of nucGT abolished nucelocidin production.
Isolation of 5'- O-sulfamyladenosine and related 3'- O-β-glucosylated adenosines from the Nucleocidin producer Streptomyces calvus
RSC Adv 2021 Jan 28;11(10):5291-5294.PMID:35423098DOI:10.1039/d1ra00235j.
The isolation of three adenosine based metabolites 6-8 from Streptomyces calvus is reported. The metabolites are structurally related to the fluorine containing antibiotic Nucleocidin 1 and two recently identified glycosylated fluoroadenosines 2 and 3, however in this case the three metabolites do not contain a fluorine, suggesting that the biosynthetic enzymes to the fluorometabolites also process their non-fluorinated counterparts.
Biosynthesis of the Fluorinated Natural Product Nucleocidin in Streptomyces calvus Is Dependent on the bldA-Specified Leu-tRNA(UUA) Molecule
Chembiochem 2015 Nov;16(17):2498-506.PMID:26374477DOI:10.1002/cbic.201500402.
Nucleocidin is one of the very few natural products known to contain fluorine. Mysteriously, the Nucleocidin producer Streptomyces calvus ATCC 13382 has not been observed to synthesize the compound since its discovery in 1956. Here, we report that complementation of S. calvus ATCC 13382 with a functional bldA-encoded Leu-tRNA(UUA) molecule restores the production of Nucleocidin. Nucleocidin was detected in culture extracts by (19) F NMR spectroscopy, HPLC-ESI-MS, and HPLC-continuum source molecular absorption spectroscopy for fluorine-specific detection. The molecule was purified from a large-scale culture and definitively characterized by NMR spectroscopy and high-resolution MS. The Nucleocidin biosynthetic gene cluster was identified by the presence of genes encoding the 5'-O-sulfamate moiety and confirmed by gene disruption. Two of the genes within the Nucleocidin biosynthetic gene cluster contain TTA codons, thus explaining the dependence on bldA and resolving a 60-year-old mystery.