Sperabillin A
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| Category | Antibiotics |
| Catalog number | BBF-02924 |
| CAS | 111337-86-1 |
| Molecular Weight | 325.41 |
| Molecular Formula | C15H27N5O3 |
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Description
It is produced by the strain of Pseudomonas fluorescens YK-437. In vitro it has the effect of anti-pyomonas aeruginosa, alkali-producing faecal bacteria, acinetobacter calcium acetate and staphylococcus aureus. It also has antibacterial effect on Staphylococcus aureus and Pseudomonas aeruginosa resistant to methicillin, streptomycin, kanamycin, gentamicin, erythromycin, lincomycin, etc. It is used in mice infected with Staphylococcus aureus, Streptococcus pyogenes and E. coli O-111 with ED50 (mg/kg, subcutaneous) of 1.31, 8.13 and 67.2, respectively.
Specification
| Related CAS | 111337-87-2 (dihydrochloride) |
| Synonyms | L-threo-Hexonamide, 3-amino-N-(3-amino-3-iminopropyl)-2,3,4,6-tetradeoxy-6-[[(2E,4Z)-1-oxo-2,4-hexadien-1-yl]amino]-; L-threo-Hexonamide, 3-amino-N-(3-amino-3-iminopropyl)-2,3,4,6-tetradeoxy-6-[(1-oxo-2,4-hexadienyl)amino]-, (E,Z)-; Antibiotic TAN 749A |
| IUPAC Name | (3R,5R)-3-amino-N-(3-amino-3-iminopropyl)-6-[[(2E,4Z)-hexa-2,4-dienoyl]amino]-5-hydroxyhexanamide |
| Canonical SMILES | CC=CC=CC(=O)NCC(CC(CC(=O)NCCC(=N)N)N)O |
| InChI | InChI=1S/C15H27N5O3/c1-2-3-4-5-14(22)20-10-12(21)8-11(16)9-15(23)19-7-6-13(17)18/h2-5,11-12,21H,6-10,16H2,1H3,(H3,17,18)(H,19,23)(H,20,22)/b3-2-,5-4+/t11-,12-/m1/s1 |
| InChI Key | OAXPQNCOMDEHMJ-FHNIRRRCSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Density | 1.22 g/cm3 |
| Solubility | Soluble in Water, DMSO, Methanol |
Reference Reading
1. Augmentation of host defense mechanisms against tumor by sperabillin polymers, new basic peptidyl biopolymers, in mice
M Takizawa, T Hida, S Harada, S Tanida Int J Immunopharmacol. 1994 Jan;16(1):67-74. doi: 10.1016/0192-0561(94)90120-1.
Sperabillin polymers, which have been shown recently to have antitumor activity, are new basic peptidyl polymers composed of a pseudo-peptide antibiotic, sperabillin A. The polymers, HP-2 (MW 9990), AP-2 (MW 20,100) and AB-2 (MW 35,000), were found to potently activate murine peritoneal macrophages. The phagocytosis-dependent respiratory burst and Fc gamma receptor expression of peritoneal macrophages from C57BL/6 mice were enhanced after in vitro cultivation with these polymers. When HP-2, a representative of these polymers, was intraperitoneally injected into mice, the number of peritoneal exudate cells increased and phagocytosis-dependent respiratory burst and class II (I-A) antigen expression of peritoneal macrophages were augmented. These macrophages showed strong inhibitory activity against the growth of murine tumor cell lines such as EL4 lymphoma and B16 melanoma. Nitrogen oxide, tumor necrosis factor (TNF) and interleukin 1 (IL-1) might be required for this inhibitory activity. Moreover, in mice treated with HP-2, splenocyte counts also increased and non-specific killer activity of the splenocytes was augmented. These results indicate that sperabillin polymers are new macrophage activators.
2. Synthesis and antimicrobial activity of sperabillin derivatives
T Hida, S Tsubotani, N Katayama, Y Funabashi, H Natsugari, S Harada J Antibiot (Tokyo). 1993 May;46(5):803-12. doi: 10.7164/antibiotics.46.803.
Modification of sperabillins was carried out. The 2-amidinoethylamino moiety was removed by brief acidic hydrolysis. The 2,4-hexadienoyl moiety was hydrogenated to the hexanoyl moiety and this was cleaved by an enzymatic reaction using the cells of Pseudomonas acidovorans IFO 13582. The 2-amidinoethylamino and the 2,4-hexadienoyl moieties were replaced with other groups. The derivative which was prepared by condensation of two molar amounts of dehexadienoylsperabillin A with (E,E)-muconic acid showed better protective effects than sperabillin A against Gram-negative bacteria.
3. Chemistry and anti-tumor activity of sperabillin polymers
T Hida, S Tsubotani, A Hori, M Murakami, H Natsugari, Y Kozai, S Harada Chem Pharm Bull (Tokyo). 1993 May;41(5):889-93. doi: 10.1248/cpb.41.889.
Sperabillin A, 3-[[(3R,5R)-3-amino-6-[(2E,4Z)-2,4-hexadienoylamino]- 5-hydroxyhexanoyl]amino]propanamidine dihydrochloride, was polymerized on standing for several days under a highly humid atmosphere or in the presence of radical initiators. The average molecular weight of the polymers obtained could be regulated by changing the reaction conditions in the latter case. Spectral analyses of the polymers revealed that the 2,4-hexadienoyl moiety of sperabillins was polymerized in a free radical-initiated reaction. The polymers selectively inhibited the proliferation of human umbilical vein endothelial (HUVE) cells. Polymers having higher molecular weight showed stronger inhibition of HUVE cell proliferation. In addition, the polymers showed anti-tumor activity against B16 melanoma in vivo.
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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 ╳
