TAN-1030A
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| Category | Bioactive by-products |
| Catalog number | BBF-02494 |
| CAS | 126221-76-9 |
| Molecular Weight | 466.5 |
| Molecular Formula | C27H22N4O4 |
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Description
TAN-1030A is an indolocarbazole derivative produced by Streptomyces sp. C-71799. It can activate macrophage in mice.
Specification
| Synonyms | TAN 1030A |
| IUPAC Name | (2S,3R,4Z)-4-hydroxyimino-3-methoxy-2-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one |
| Canonical SMILES | CC12C(C(=NO)CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)OC |
| InChI | InChI=1S/C27H22N4O4/c1-27-25(34-2)16(29-33)11-19(35-27)30-17-9-5-3-7-13(17)21-22-15(12-28-26(22)32)20-14-8-4-6-10-18(14)31(27)24(20)23(21)30/h3-10,19,25,33H,11-12H2,1-2H3,(H,28,32)/b29-16-/t19?,25-,27+/m1/s1 |
| InChI Key | XZPCNXORIOQSOG-FQZWZXDGSA-N |
Reference Reading
1. TAN-999 and TAN-1030A, new indolocarbazole alkaloids with macrophage-activating properties
S Tanida, M Takizawa, T Takahashi, S Tsubotani, S Harada J Antibiot (Tokyo). 1989 Nov;42(11):1619-30. doi: 10.7164/antibiotics.42.1619.
Two new indolocarbazole alkaloids, TAN-999 and TAN-1030A, were isolated from culture broths of Nocardiopsis dassonvillei C-71425 and Streptomyces sp. C-71799, respectively. Their structures were elucidated on the basis of their reactions, spectroscopic analyses and in particular, comparison of spectral data with that of staurosporine. These metabolites induced spreading of a murine macrophage cell line, Mm 1. They also augmented the phagocytic activity, Fc gamma receptor expression and beta-glucuronidase activity of murine macrophage cell lines, Mm 1 and J774A.1. When proteose-peptone elicited peritoneal macrophages from mice were incubated with these metabolites for 2 days, the phagocytosis-dependent respiratory burst of these cells was enhanced. Similar enhancement was also observed when the peritoneal macrophages in mice were modulated by intraperitoneal administration of these metabolites. These results reveal that TAN-999 and TAN-1030A can activate macrophage functions in mice.
2. A nitro analogue of staurosporine and other minor metabolites produced by a Streptomyces longisporoflavus strain
Y Cai, A Fredenhagen, P Hug, H H Peter J Antibiot (Tokyo). 1995 Feb;48(2):143-8. doi: 10.7164/antibiotics.48.143.
From the staurosporine-producing strain Streptomyces longisporoflavus R-19 various minor metabolites were isolated: They include a new compound with a nitro function in C-4' and other metabolites related to staurosporine. The new structures were elucidated by spectroscopic methods, mainly 1H NMR and 13C NMR and by comparison with TAN-1030A. The new compounds inhibited protein kinase C with IC50 values in the nanomolar range.
3. Further minor metabolites of staurosporine produced by a Streptomyces longisporoflavus strain
Y Cai, A Fredenhagen, P Hug, T Meyer, H H Peter J Antibiot (Tokyo). 1996 Jun;49(6):519-26. doi: 10.7164/antibiotics.49.519.
From the staurosporine producing strain R-19 Streptomyces longisporoflavus various minor metabolites were isolated: They include new compounds with a keto function at carbon 4' of staurosporine and several metabolites related to TAN-1030A. The new structures were elucidated by spectroscopic methods, mainly 1H NMR and 13C NMR and by comparison with TAN-1030A. The new compounds inhibited protein kinase C with IC50 values in the micromolar range with the exception of those compounds that are alkylated at the lactam nitrogen.
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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 ╳
