Kazusamycin B
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| Category | Antibiotics |
| Catalog number | BBF-01888 |
| CAS | 107140-30-7 |
| Molecular Weight | 542.70 |
| Molecular Formula | C32H46O7 |
| Purity | >95% by HPLC |
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Description
A minor component of the leptomycin complex produced by some streptomyces sp.; an hydroxylated analogue of leptomycin A, a nuclear export inhibitor; displays potent antitumour activity against L1210 and human colon adenocarcinoma, and in vivo activity against P388 lymphocytic leukemia in mice; also possesses strong antibacterial and antifungal activity.
Specification
| Synonyms | PD 124895; 2,10,12,16,18-Nonadecapentaenoic acid, 19-(3,6-dihydro-3-methyl-6-oxo-2H-pyran-2-yl)-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15,17-hexamethyl-8-oxo- |
| Storage | -20 °C |
| IUPAC Name | (2E,10E,12E,16Z,18E)-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15,17-hexamethyl-19-(3-methyl-6-oxo-2,3-dihydropyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid |
| Canonical SMILES | CC1C=CC(=O)OC1C=CC(=CC(C)CC=CC(=CC(CO)C(=O)C(C)C(C(C)CC(=CC(=O)O)C)O)C)C |
| InChI | InChI=1S/C32H46O7/c1-20(15-22(3)11-13-28-24(5)12-14-30(36)39-28)9-8-10-21(2)17-27(19-33)32(38)26(7)31(37)25(6)16-23(4)18-29(34)35/h8,10-15,17-18,20,24-28,31,33,37H,9,16,19H2,1-7H3,(H,34,35)/b10-8+,13-11+,21-17+,22-15-,23-18+ |
| InChI Key | OOQHBJFDAPXZJM-BBHORLQHSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Colourless Film |
| Antibiotic Activity Spectrum | yeast; neoplastics (Tumor) |
| Boiling Point | 754.2°C at 760 mmHg |
| Melting Point | 53-55°C |
| Density | 1.118 g/cm3 |
| Solubility | Soluble in ethanol or methanol. Poor water solubility. Ethanol recommended. Unstable in DMSO |
Reference Reading
1. PD 124,895 and PD 124,966, two new antitumor antibiotics
J C French, G C Hokanson, N E Willmer, R H Bunge, T R Hurley J Antibiot (Tokyo) . 1986 Dec;39(12):1651-6. doi: 10.7164/antibiotics.39.1651.
The isolation and characterization of the title antibiotics, which are produced by the same Streptomyces sp., is described. The potent antitumor agent, PD 124,895, is an analog of hydroxyelactocin (PD 114,721). PD 124,966 is a new member of the depsipeptide family of antibiotics.
2. [Studies on the new antibiotic kazusamycin and related substances]
I Umezawa, K Komiyama Gan To Kagaku Ryoho . 1987 Mar;14(3 Pt 2):858-64.
Kazusamycins A and B and leptomycin B have a structure characteristic of an unsaturated, branched-chain fatty acid with a terminal delta-lactone ring, and show antibacterial activity on some kinds of fungi. Kazusamycin A (KZM-A) showed cytotoxic activity on mammalian cells at very low concentrations (ng/ml) in vitro. The antibiotic inhibited not only the growth of transplantable murine tumors and their metastases to the lung but also human mammary tumors inoculated into nude mice. KZM-A became immediately distributed to the main organs of mice, and a certain quantity of the antibiotic was inactivated by binding to high-molecular-weight substances such as albumin. A large quantity of KZM-A was carried to the liver and excreted into the bile, but was then reabsorbed by the small intestine. The growth of tumor metastases (L5178Y cells) in the liver was suppressed by KZM-A. The antibiotic induced severe diarrhea by causing necrosis and/or lysis of the mucous membrane of the small intestine. In contrast to this, the degree of myelotoxicity was relatively slight. The active site of the fatty acid of KZM-A appeared to consist of conjugated double bonds, carboxylic acid and hydroxyl moieties.
3. The effect of kazusamycin B on the cell cycle and morphology of cultured L1210 cells
K Takamiya, K Komiyama, I Umezawa, M Okanishi, A Okura, T Takahashi, E Yoshida J Antibiot (Tokyo) . 1988 Dec;41(12):1854-61. doi: 10.7164/antibiotics.41.1854.
The effect of a potent antitumor antibiotic, kazusamycin B, on the cell cycle of L1210 cells was examined. Kazusamycin B arrested synchronized L1210 cells at G1 phase. Retardation of metaphase initiation was also observed. Flow cytometric analysis of kazusamycin B-treated asynchronized cells also confirmed G1 arresting effect of kazusamycin B. In addition, an unidentified cell population with lower fluorescence intensity than G1 population was observed when the cells were exposed to the drug longer than 12 hours. Morphology of kazusamycin B-treated L1210 cells revealed that the intranuclear structure changed within 4 hours, and that abnormal condensation of nuclei coincided with the appearance of unidentified population. Kazusamycin B inhibited RNA synthesis moderately but specifically at 2 hours. However, this inhibition might be a secondary effect of the antibiotic-induced structural abnormality of the nuclei.
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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 ╳
