Steffimycin B
(Synonyms: 司替霉素B) 目录号 : GC40859
An anthracycline bacterial metabolite
Cas No.:54526-94-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Steffimycin B is an anthracycline bacterial metabolite originally isolated from Streptomyces. It binds to DNA, preferentially intercalating at sites containing cytosine and guanine. Steffimycin B is cytotoxic to MCF-7, KB, NCI-H187, and Vero cells (IC50s = 3.5, 6.75, 3.28, and 10.5 μM, respectively). It is active against M. tuberculosis (MIC = 5.2 nM), B. cereus (MIC = 1.56 μg/ml), and P. falciparum (IC50 = 2.19 μM).
| Cas No. | 54526-94-2 | SDF | |
| 别名 | 司替霉素B | ||
| Canonical SMILES | OC1=CC(OC)=CC2=C1C(C(C(O)=C([C@@H](O[C@]3([H])O[C@@H](C)[C@H](OC)[C@@H](O)[C@H]3OC)[C@H](OC)[C@](C)(O)C4=O)C4=C5)=C5C2=O)=O | ||
| 分子式 | C29H32O13 | 分子量 | 588.6 |
| 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 | 1.6989 mL | 8.4947 mL | 16.9895 mL |
| 5 mM | 0.3398 mL | 1.6989 mL | 3.3979 mL |
| 10 mM | 0.1699 mL | 0.8495 mL | 1.6989 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。
Microbial conversion of steffimycin and Steffimycin B to 10-dihydrosteffimycin and 10-dihydrosteffimycin B
J Antibiot (Tokyo) 1980 Aug;33(8):819-23.PMID:7429984DOI:10.7164/antibiotics.33.819.
It has been shown that steffimycin (1) and steffmycin B (2) are reduced at the C-10 carbonyl by Actinoplanes utahensis, UC-5885 and Chaetomium sp., UC-4634, respectively. Using cell-free extracts of the latter organism, the optimum conversion time, pH, and enzyme concentration have been determined for the conversion of 2 to 4. The biochemical conversion of 2 has been found to be TPNH linked.
Steffimycin B, a DNA binding agent
Biochim Biophys Acta 1975 Mar 21;383(3):266-73.PMID:1090304DOI:10.1016/0005-2787(75)90055-6.
The antibiotic Steffimycin B binds to double-stranded DNA as evidenced by difference spectroscopy and an increase of the thermal stability of DNA in the presence of the antibiotic. Salmon sperm DNA-steffimycin B complexes show a drastic decrease in template activity for Escherichia coli DNA polymerase I but not for DNA-idrected RNA polymerase. The differences in template properties of poly[d(A-T)] and poly (dG) - poly(dC)-antibiotic complexes,respectively, for DNA polymerase I and RNA polymerase suggest that the antibiotic interacts primarily with adenine or thymine bases or both in double-stranded DNA.
Steffimycin C, a new member of the steffimycin anthracyclines. Isolation and structural characterization
J Antibiot (Tokyo) 1985 Jul;38(7):849-55.PMID:3839781DOI:10.7164/antibiotics.38.849.
Mother liquors from Steffimycin B crystallizations have been processed to yield steffimycin C, a new member of the steffimycin family of anthracyclines. It has been identified, using spectroscopic methods, as 10-deoxysteffimycin B. Steffimycin C has antibacterial activity only against Streptococcus pneumoniae. Whether steffimycin C is a precursor of Steffimycin B or a metabolic reduction product is unknown at this time.
Bioinformatic comparison of three Embleya species and description of steffimycins production by Embleya sp. NF3
Appl Microbiol Biotechnol 2022 Apr;106(8):3173-3190.PMID:35403858DOI:10.1007/s00253-022-11915-0.
The Embleya genus is a new member of the Streptomycetaceae family formed by only two species isolated from soil (Embleya scabrispora and Embleya hyalina). Strain NF3 is an endophytic actinobacterium obtained from the medicinal tree Amphipterygium adstringens. By 16S rRNA gene analysis, NF3 strain was identified as Embleya sp., closely related to E. hyalina. In our interest to deep into the NF3 strain features, a bioinformatic study was performed on the Embleya genus based on their genome information to produce secondary metabolites. A comparative analysis of the biosynthetic gene clusters (BGCs) of NF3 with the two released Embleya genomes revealed that NF3 has 49 BGCs, E. scabrispora DSM41855 has 50 BGCs, and E. hyalina NBRC13850 has 46 BGCs. Although bearing similar cluster numbers, the three strains shared only 25% of the BGCs information. NF3 encoded the nybomycin cluster detected in E. hyalina NBRC13850 and lacked the hitachimycin cluster present in E. scabrispora DSM41855. On the contrary, strain NF3 contained a cluster for the anthracycline steffimycin, neither encoded by E. hyalina NBRC13850 nor by E. scabrispora DSM41855. Our results and previous characterization studies supported strain NF3 as a new member of the genus Embleya. The chemical analysis of the steffimycins produced by strain NF3 showed the production of eight compounds of the steffimycins and steffimycinone families. Four of these molecules have already been described: Steffimycin B, steffimycin C, 8-demethoxy-10-deoxysteffimycinone, and 7-deoxiesteffimycinone, and four are new natural products: 8-demethoxysteffimycin B, 8-demethoxy-10-deoxysteffimycin B, 7-deoxy-8-demethoxysteffimycinone, and 7-deoxy-10-deoxysteffimycinone. With this information, we proposed an alternative pathway to produce StefB. Among steffimycins, StefB was the main compound produced by this strain (29.8%) and showed the best cytotoxic activity. KEY POINTS: • The Embleya genus and its biosynthetic potential • An alternative biosynthetic pathway for steffimycins biosynthesis • Four new natural products of the steffimycin family.
Chemical modification of Steffimycin B
J Antibiot (Tokyo) 1988 Mar;41(3):343-51.PMID:3366692DOI:10.7164/antibiotics.41.343.
Fifteen 3-substituted analogues of Steffimycin B (1) have been synthesized and their activity against P388 murine leukemia has been determined. Three of these were substantially more active than the parent compound.