Madindoline B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02290 |
| CAS | 184877-65-4 |
| Molecular Weight | 369.45 |
| Molecular Formula | C22H27NO4 |
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Description
It is produced by the strain of Str. sp. K93-0711. It is an interleukin-6 inhibitor. It inhibits IL-6-dependent MH-60 cells and has no inhibitory effect on IL-6-independent MH-60 cells. In the presence of 0.1 U/mL IL-6, it inhibits IL-6-dependent MH-60 cells with IC50 of 30 μmol/L. It has no antimicrobial effect.
Specification
| Synonyms | Antibiotic K93-0711 I2; (S)-4-butyl-2-(((3aR,8aS)-3a-hydroxy-2,3,3a,8a-tetrahydro-8H-furo[2,3-b]indol-8-yl)methyl)-2,5-dimethylcyclopent-4-ene-1,3-dione; (+)-Madindoline B |
| IUPAC Name | (2S)-2-[[(3aS,8bR)-8b-hydroxy-2,3a-dihydro-1H-furo[2,3-b]indol-4-yl]methyl]-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione |
| Canonical SMILES | CCCCC1=C(C(=O)C(C1=O)(C)CN2C3C(CCO3)(C4=CC=CC=C42)O)C |
| InChI | InChI=1S/C22H27NO4/c1-4-5-8-15-14(2)18(24)21(3,19(15)25)13-23-17-10-7-6-9-16(17)22(26)11-12-27-20(22)23/h6-7,9-10,20,26H,4-5,8,11-13H2,1-3H3/t20-,21-,22+/m0/s1 |
| InChI Key | XPVQXXLKOCZMGG-FDFHNCONSA-N |
Properties
| Appearance | Pale Yellow Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Melting Point | 105-107°C |
| Solubility | Soluble in Methanol, Ethanol, Chloroform, Ethyl Acetate, Acetone, Water |
Reference Reading
1. IL-6/STAT3 Is a Promising Therapeutic Target for Hepatocellular Carcinoma
Junnv Xu, Haifeng Lin, Gang Wu, Mingyue Zhu, Mengsen Li Front Oncol. 2021 Dec 15;11:760971. doi: 10.3389/fonc.2021.760971. eCollection 2021.
Hepatocellular carcinoma (HCC) is a common malignant tumor of which the occurrence and development, the tumorigenicity of HCC is involving in multistep and multifactor interactions. Interleukin-6 (IL-6), a multifunctional inflammatory cytokine, has increased expression in HCC patients and is closely related to the occurrence of HCC and prognosis. IL-6 plays a role by binding to the IL-6 receptor (IL-6R) and then triggering the Janus kinase (JAK) associated with the receptor, stimulating phosphorylation and activating signal transducer and activator of transcription 3 (STAT3) to initiate downstream signals, participating in the processes of anti-apoptosis, angiogenesis, proliferation, invasion, metastasis, and drug resistance of cancer cells. IL-6/STAT3 signal axes elicit an immunosuppressive in tumor microenvironment, it is important to therapy HCC by blocking the IL-6/STAT3 signaling pathway. Recent, some inhibitors of IL-6/STAT3 have been development, such as S31-201 or IL-6 neutralizing monoclonal antibody (IL-6 mAb), Madindoline A (Inhibits the dimerization of IL-6/IL-6R/gpl30 trimeric complexes), C188-9 and Curcumin (Inhibits STAT3 phosphorylation), etc. for treatment of cancers. Overall, consideration of the IL-6/STAT3 signaling pathway, and its role in the carcinogenesis and progression of HCC will contribute to the development of potential drugs for targeting treatment of liver cancer.
2. Formal synthesis of (+)-madindoline A, a potent IL-6 inhibitor, utilizing enzymatic discrimination of quaternary carbon
Ken-ichi Shimizu, Mina Tomita, Ken-ichi Fuhshuku, Takeshi Sugai, Mitsuru Shoji Nat Prod Commun. 2013 Jul;8(7):897-901.
A formal synthesis of (+)-madindoline A was achieved. The Sunazuka's key intermediate, (4R,5S)-(-)-3-butyl-4-(tert-butyldimethylsiloxy)-5-methoxycarbonyl-2,5-dimethyl-2-cyclopentenone, was synthesized from easily available (2S,3S)-3-acetoxy-2-ethenyl-2-methylcyclopentanone. The starting material was reliably supplied by a chemo-enzymatic procedure in enantiomerically pure form. The synthesis was performed by straightforward transformations involving enone formation and regioselective introduction of the two alkyl side chains.
3. Diversity-Oriented Synthetic Approaches for Furoindoline: A Review
Ramandeep Kaur, Yagyesh Kapoor, Sundeep K Manjal, Ravindra K Rawal, Kapil Kumar Curr Org Synth. 2019;16(3):342-368. doi: 10.2174/1570179416666190328211509.
The furo [2,3-b] indoline ring system is one of the most important structural units in various natural products. It has been known to have inherent biological activities and is utilized as a synthetic target for a number of natural compounds; therefore, this has contributed to a great demand for the growth of synthetic methods for this ring system. Most important compounds with furoindoline ring system are physovenine, madindoline A and B and makomotindoline etc. These compounds are well known to exhibit biological activity against different diseases such as glaucoma, cancer, cachexia, Castleman's disease, rheumatoid arthritis, etc. The current article focuses on various synthetic approaches for furoindoline containing compounds and essential furoindoline moiety, such as oxindole-5-O-tetrahydropyranyl ether route etc., and various other diastereoand enantio- controlled approach in a very concise way.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
