Delaminomycin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00806 |
| CAS | 149779-40-8 |
| Molecular Weight | 485.65 |
| Molecular Formula | C29H43NO5 |
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Description
Delaminomycin C is an extracellular Matrix receptor antagonist and immunomodulator produced by Streptomyces albulus MJ202-72F3. It inhibits cell adhesion ECM (Extracellular matrix), reduces immune response activity, and inhibits Gram-positive bacteria.
Specification
| Synonyms | (3Z)-3-[[2-[(3E,5E)-2,8-dihydroxy-7-methyldeca-3,5-dienyl]-1,6,8-trimethyl-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]pyrrolidine-2,4-dione; 2H-Imidazol-2-one, 3-((2-(2,8-dihydroxy-7-methyl-3,5-decadienyl)-1,2,4a,5,6,7,8,8a-octahydro-1,6,8-trimethyl-1-naphthalenyl)carbonyl)-1,5-dihydro-4-hydroxy- |
| IUPAC Name | (3Z)-3-[[2-[(3E,5E)-2,8-dihydroxy-7-methyldeca-3,5-dienyl]-1,6,8-trimethyl-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]pyrrolidine-2,4-dione |
| Canonical SMILES | CCC(C(C)C=CC=CC(CC1C=CC2CC(CC(C2C1(C)C(=C3C(=O)CNC3=O)O)C)C)O)O |
| InChI | InChI=1S/C29H43NO5/c1-6-23(32)18(3)9-7-8-10-22(31)15-21-12-11-20-14-17(2)13-19(4)26(20)29(21,5)27(34)25-24(33)16-30-28(25)35/h7-12,17-23,26,31-32,34H,6,13-16H2,1-5H3,(H,30,35)/b9-7+,10-8+,27-25- |
| InChI Key | WIRHXGKLHQEIEM-MOROLAGTSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 659°C at 760 mmHg |
| Density | 1.117 g/cm3 |
| Solubility | Soluble in Methanol, DMSO |
Reference Reading
1. Low molecular weight immunomodulators produced by microorganisms
M Ishizuka, M Kawatsu, T Yamashita, M Ueno, T Takeuchi Int J Immunopharmacol. 1995 Feb;17(2):133-39. doi: 10.1016/0192-0561(94)00086-4.
In order to develop a new class of low molecular weight immunomodulators for the treatment of incurable diseases involving cancer, hematologic diseases and inflammation, we have sought cytokine inducers and inhibitors of cell adhesion to the extracellular matrix among the low molecular compounds produced by microorganisms. Cytogenin, cytoblastin (a monokine inducer), conagenin (a lymphokine inducer) and delaminomycins and IC-101 (inhibitors of cell adhesion to extracellular matrices) have been recently found in our institute. In this report, we describe the principles of screening and structures, and discuss their biological activities.
2. Delaminomycins, novel extracellular matrix receptor antagonist. IV. Structure-activity relationships of delaminomycins and derivatives
M Ueno, M Amemiya, K Yamazaki, M Iijima, M Osono, T Someno, H Iinuma, M Hamada, M Ishizuka, T Takeuchi J Antibiot (Tokyo). 1993 Jul;46(7):1156-62. doi: 10.7164/antibiotics.46.1156.
Delaminomycins A, B, C and their derivatives were prepared and investigated biological activities of them. Among these compounds, spiro compounds (A2, B2 and C2) showed stronger inhibitory activity than natural products (A1, B1 and C1) on B16 melanoma cells adhesion assay and Con A-induced proliferation of murine splenic lymphocytes assay. In MLCR and antimicrobial assay, however, A1, B1 and C1 showed more potent inhibitory activity than spiro compounds (A2, B2 and C2). On the other hand, as to C-5' substituents of pyrrolidine ring, the order of inhibitory activity was R = OH > R = OCH3 > R = H on Con A-induced proliferation of murine splenic lymphocytes assay. In MLCR and antimicrobial assay, however, the order of inhibitory activities were R = H > R = OCH3 > R = OH. Inhibitory activities of A4 which was lacked pyrrolidine ring were reduced on B16 melanoma cells adhesion assay and on cytotoxicity against tumor cells in vitro in comparison with those of A1.
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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 ╳
