Quinaldopeptin
(Synonyms: 喹哪朵肽) 目录号 : GC44798
A quinomycin antibiotic
Cas No.:130743-07-6
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: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Quinaldopeptin is a quinomycin antibiotic. It is active against a variety of bacteria, including S. pyogenes, S. aureus, C. perfringens, S. faecalis, E. coli, and K. pneumoniae (MICs = 0.2, 0.4, 0.8, 1.6, 3.1 and 6.3 µg/ml, respectively). It is cytotoxic to B16/F10 and Moser cells (IC50s = 0.0008 and 0.04 µg/ml, respectively) and increases survival in a P388 leukemia mouse model. Quinaldopeptin is a bis-intercalator depsipeptide (NPBID) that binds to and intercalates into DNA (Kd = 32 nM).
| Cas No. | 130743-07-6 | SDF | |
| 别名 | 喹哪朵肽 | ||
| Canonical SMILES | O=C(CN(C)C(CNC([C@@]1([H])N(C([C@@](NC(C2=NC(C=CC=C3)=C3C=C2O)=O)([H])[C@H](C)NC([C@@]4([H])N5CCCC4)=O)=O)CCCC1)=O)=O)N(CCCC6)[C@]6([H])C(N[C@@H](C)[C@](NC(C7=NC(C=CC=C8)=C8C=C7O)=O)([H])C(N9CCCC[C@@]9([H])C(NCC(N(C)CC5=O)=O)=O)=O)=O | ||
| 分子式 | C62H78N14O14 | 分子量 | 1243.4 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: slightly soluble,Methanol: slightly soluble | 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 | 0.8042 mL | 4.0212 mL | 8.0425 mL |
| 5 mM | 0.1608 mL | 0.8042 mL | 1.6085 mL |
| 10 mM | 0.0804 mL | 0.4021 mL | 0.8042 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。
Total synthesis of Quinaldopeptin and its analogues
J Org Chem 2013 Dec 20;78(24):12662-70.PMID:24236405DOI:10.1021/jo402267r.
The first total synthesis of Quinaldopeptin (1) was accomplished. Our approach to the synthesis of 1 includes the solid-phase peptide synthesis of the linear decapeptide 4 followed by macrocyclization and introduction of the quinoline chromophores 2 at a late stage of the synthesis. As for the preparation of 4, a fragment coupling approach was applied considering the C2 symmetrical structure of 1. Chromophore analogues 22 and 23 and desmethyl analogue 27 were also prepared in a manner similar to the synthesis of 1. Synthetic 1 exhibits a strong cytotoxicity with the IC50 value of 3.2 nM. On the other hand, the activity of 23 and 27 was largely reduced.
Quinaldopeptin, a novel antibiotic of the quinomycin family
J Antibiot (Tokyo) 1990 Jul;43(7):796-808.PMID:2387774DOI:10.7164/antibiotics.43.796.
Quinaldopeptin, a new type of quinomycin antibiotic, was isolated from the culture of Streptoverticillium album strain Q132-6. The antibiotic exhibited strong in vitro antimicrobial and cytotoxic activity and significantly prolonged the survival time of mice inoculated with a murine tumor. Quinaldopeptin is a symmetric cyclic peptide linked only by peptide bonds and differs from known antibiotics of the quinomycin family by the lack of ester linkage.
Synthesis and biological evaluation of Quinaldopeptin
J Org Chem 2014 Mar 21;79(6):2580-90.PMID:24555872DOI:10.1021/jo500039d.
The second-generation total synthesis of Quinaldopeptin (1) was established via a Staudinger/aza-Wittig/diastereoselective Ugi three-component reaction sequence and a racemization-free [5 + 5] coupling and macrolactamization. A single-crystal X-ray structure of the chromophore analogue 26 confirmed the structural and stereochemical assignments of the macrocycle. Synthetic 1 successfully unwound supercoiled DNA to form a relaxed DNA in a dose-dependent manner, the binding affinity of 1 to four dsODNs was within a similar range (K(b) = 1.45-2.53 × 10(7) M(-1)), and the sequence selectivity was subtle. It was suggested that 1 possesses biological behaviors similar to those of sandramycin (2) in terms of cytotoxic activity against human cancer cell lines (IC50 = 3.2-12 nM) and HIF-1 inhibitory activity.
Structure of actinotetraose hexatiglate, a unique glucotetraose from an actinomycete bacterium
J Antibiot (Tokyo) 1998 Dec;51(12):1093-8.PMID:10048568DOI:10.7164/antibiotics.51.1093.
An Actinomycete strain A499 belonging to the genera Amycolatopsis or Amycolata isolated from a Western Australian soil sample produced the cyclic decapeptide antibiotic Quinaldopeptin (1), together with the actinotetraose hexatiglate (2), the hexa-ester of a novel non-reducing glucotetraose.
Introduction of novel drug targets against Staphylococcus aureus and proposing putative inhibitors against adenine N1 (m1A22)-tRNA methyltransferase (TrmK) using computer-aided drug discovery
Curr Pharm Des 2023 Apr 28.PMID:37132149DOI:10.2174/1381612829666230428105643.
Background: Nowadays, the emergence of methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA) strains has dramatically restricted the treatment options against this microorganism. Therefore, in this study, we aimed to discover new drug targets and inhibitors against S. aureus. Methods: This study consists of two major sections. In the upstream evaluation, after a comprehensive core-proteome analysis, essential cytoplasmic proteins with no similarity to the human proteome were selected. Then the S. aureus metabolome-specific proteins were selected, and novel drug targets were identified using the DrugBank database. In the downstream analysis, a structure-based virtual screening approach was performed to reveal potential hit compounds against adenine N1 (m1A22)-tRNA methyltransferase (TrmK) using the StreptomeDB library and AutoDock Vina software. The compounds with a binding affinity > -9 kcal/mol were analyzed based on ADMET properties. Finally, the hit compounds were selected based on Lipinski's rule of five (RO5). Results: Three proteins, including glycine glycosyltransferase (FemA), TrmK, and heptaprenyl pyrophosphate synthase subunit A (HepS1), were selected as feasible and promising drug targets based on PDB file availability and their essential role in the survival of the S. aureus. Finally, seven hit compounds, including Nocardioazine_A, Geninthiocin_D, Citreamicin_delta, Quinaldopeptin, Rachelmycin, Di-AFN_A1 and Naphthomycin_K were introduced against the binding cavity of TrmK, as a feasible drug target. Conclusion: The results of this study provided three feasible drug targets against S. aureus. In the following, seven hit compounds were introduced as potential inhibitors of TrmK, and Geninthiocin_D was identified as the most desirable agent. However, in vivo and in vitro investigations are needed to confirm the inhibitory effect of these agents on S. areus.