Indocarbazostatin B
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| Category | Others |
| Catalog number | BBF-01501 |
| CAS | |
| Molecular Weight | 526.50 |
| Molecular Formula | C28H22N4O7 |
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Description
Indocarbazostatin B is originally isolated from Streptomyces sp. TA-0403. In rat pheochromocytoma PC12 cells, the minimum effective concentration of indocarbazostatin B against Neurite outgrowth induced by NGF was 24nmol/L.
Specification
| IUPAC Name | ethyl (15S,16S,18R)-9-amino-10,16-dihydroxy-15-methyl-3,5-dioxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.115,18.02,6.07,27.08,13.019,26.020,25]octacosa-1,6,8(13),9,11,20,22,24,26-nonaene-16-carboxylate |
| Canonical SMILES | CCOC(=O)C1(CC2N3C4=CC=CC=C4C5=C6C(=C7C8=C(C=CC(=C8N)O)N(C7=C53)C1(O2)C)C(=O)NC6=O)O |
| InChI | InChI=1S/C28H22N4O7/c1-3-38-26(36)28(37)10-15-31-12-7-5-4-6-11(12)16-19-20(25(35)30-24(19)34)18-17-13(8-9-14(33)21(17)29)32(23(18)22(16)31)27(28,2)39-15/h4-9,15,33,37H,3,10,29H2,1-2H3,(H,30,34,35)/t15-,27+,28-/m1/s1 |
| InChI Key | VEXMHCAEEISMPG-ZXOINBKBSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 255°C |
Reference Reading
1. Indocarbazostatin and indocarbazostatin B, novel inhibitors of NGF-induced Neuronal differentiation in PC12 cells. II. Isolation, physicochemical properties and structural elucidation
Norimasa Tamehiro, Nobuyasu Matsuura, Yufei Feng, Noriyuki Nakajima, Makoto Ubukata J Antibiot (Tokyo). 2002 Apr;55(4):363-70. doi: 10.7164/antibiotics.55.363.
Two novel indolocarbazol-type bioactive molecules, indocarbazostatin (1) and indocarbazostatin B (2), were isolated as inhibitors of NGF-induced neuronal differentiation in rat pheochromocytoma PC12 cells from a culture broth of a Streptomyces sp. The structures of these compounds were determined by HR-FAB-MS, UV, 1H and 13C NMR, 1H-1H COSY, PFG HMBC, PFG HMQC and DIF NOE experiments. The relative and absolute configurations were deduced from MM2, MOPAC and CONFLEX calculations, and CD analyses. The imide/amide sector rule was proposed from the analyses of CD data of 1 and other indolocarbazole antibiotics. It was concluded that the minor compound 2 has a negative atropisomeric chirality in the aglycone.
2. Biosynthesis of indocarbazostatin B, incorporation of D-[U-13C] glucose and L-[2-13C] tryptophan
Yufei Feng, Shinya Mitsuhashi, Takao Kishimoto, Makoto Ubukata J Antibiot (Tokyo). 2005 Dec;58(12):759-65. doi: 10.1038/ja.2005.103.
High incorporation of D-[U-13C] glucose and L-[indole-2-13C] tryptophan into indocarbazostatin B (2) was observed in a biosynthetic study using a mutant strain, Streptomyces sp. MUV-7-8. The original strain, Streptomyces sp. TA-0403 produced a small amount of indocarbazostatin (1) and indocarbazostatin B (2), which displayed potent biological activities. To facilitate biosynthetic studies, we selected high indocarbazostatin producing mutant strains. The first mutants, Streptomyces sp. MUV-6-83 and MUV-6-17, produced indocarbazostatins C (3) and D (4) as well as 1 and 2. When the production medium was supplemented with D-tryptophan, the MUV-6-17 mutant produced K252c (5), whereas when L-tryptophan was added, it produced K252d (6). On further UV treatment of the mutant strain MUV-6-83, we finally obtained a new mutant producer, Streptomyces sp. MUV-7-8, that produced 2 as a major metabolite with higher productivity. This mutant producer enabled us to do a feeding experiment of the envisioned precursors, glucose and tryptophan.
3. Indocarbazostatins C and D, new inhibitors of NGF-induced neuronal differentiation in PC12 cells
Yufei Feng, Nobuyasu Matsuura, Makoto Ubukata J Antibiot (Tokyo). 2004 Oct;57(10):627-33. doi: 10.7164/antibiotics.57.627.
Indocarbazostatins C (3) and D (4), new inhibitors of NGF-induced neurite outgrowth were isolated from culture broth of a mutant strain, Streptomyces sp. MUV-6-83. The structural elucidation of 3 and 4 revealed that these inhibitors were methyl ester analogs of the corresponding ethyl ester compounds, indocarbazostatin (1) and indocarbazostatin B (2), respectively.
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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 ╳
