Chrysomycin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04099 |
| CAS | 83852-56-6 |
| Molecular Weight | 496.50 |
| Molecular Formula | C27H28O9 |
| Purity | >98% by HPLC |
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Description
Chrysomycin B is a minor analogue in a complex of C-glycoside antitumor active substances isolated from Streptomyces. Its activity is lower than that of its vinyl analogue (Chrysomycin A), but it still has strong anti-tumor activity and is an inhibitor of the catalytic activity of human topoisomerase II. It can be used as a light-activated cross-linking agent for DNA and histones.
Specification
| Synonyms | Chrysomycin M; Virenomycin M; Albacarcin M |
| Storage | Store at -20°C |
| IUPAC Name | 1-hydroxy-10,12-dimethoxy-8-methyl-4-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-4,6-dimethyloxan-2-yl]naphtho[1,2-c]isochromen-6-one |
| Canonical SMILES | CC1C(C(C(C(O1)C2=C3C(=C(C=C2)O)C(=CC4=C3OC(=O)C5=C4C(=CC(=C5)C)OC)OC)O)(C)O)O |
| InChI | InChI=1S/C27H28O9/c1-11-8-15-19(17(9-11)33-4)14-10-18(34-5)21-16(28)7-6-13(20(21)22(14)36-26(15)31)23-25(30)27(3,32)24(29)12(2)35-23/h6-10,12,23-25,28-30,32H,1-5H3/t12-,23+,24+,25+,27-/m1/s1 |
| InChI Key | BJPYMDSMDBCKEP-QSMCFSHASA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Crystals |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 784°C at 760 mmHg |
| Density | 1.41 g/cm3 |
| Solubility | Soluble in DMF, DMSO |
Reference Reading
1. The chemistry of the antibiotics chrysomycin A and B. Antitumor activity of chrysomycin A
K Yoshihira, T T Wei, R J White, U Weiss, R J Highet J Antibiot (Tokyo) . 1982 Sep;35(9):1194-201. doi: 10.7164/antibiotics.35.1194.
The yellow antibiotic chrysomycin, isolated in crystalline form in 1955, is found to consist of two closely related components, a major one, chrysomycin A, and a minor one, chrysomycin B. They differ only through the replacement of a vinyl group of chrysomycin A by methyl in chrysomycin B. The absorption spectrum of chrysomycin A is identical with that of the antitumor antibiotic toromycin (gilvocarcin V, 2064A), while that of chrysomycin B is similarly identical with the one of gilvocarcin M (2064B). The structures of these antibiotics (toromycin, the glivocarcins, and 2064A and B) have been elucidated recently. Chrysomycins A and B thus contain the same chromophores as gilvocarcins V and M, respectively; comparison of 1H and 13C NMR spectra confirms this identity. The chrysomycins differ from these other antibiotics in the C-glycosidic side-chain, which is a methylpentose in the gilvocarcins, a 3,5-dimethylpentose in the chrysomycins. Structure and relative configuration of the latter are given. The biological activity and possible biosynthesis of the chrysomycins are discussed.
2. A colorimetric microassay for the detection of agents that interact with DNA
R R Rasmussen, N S Burres, J B McAlpine, A Frigo J Nat Prod . 1992 Nov;55(11):1582-7. doi: 10.1021/np50089a004.
A simple microtiter assay for the detection of compounds that bind DNA is described. Agents that displace methyl green from DNA are detected spectrophotometrically by a decrease in absorbance at 630 nm. The feasibility of using the assay for detecting DNA-active compounds in fermentation extracts was assessed, and the activities of reference compounds in the methyl green assay and an ethidium bromide displacement method were compared.
3. Biosynthesis of chrysomycins A and B. Origin of the chromophore
R J White, G T Carter, D B Borders, A A Fantini, J C James J Antibiot (Tokyo) . 1985 Feb;38(2):242-8. doi: 10.7164/antibiotics.38.242.
The biosynthetic origin of the carbon atoms in the chromophores of chrysomycins A and B was investigated in feeding experiments using 13C labeled acetates and propionate. A biosynthetic scheme is proposed involving the condensation and rearrangement of a decaketide intermediate which contains either propionate (chrysomycin A) or acetate (chrysomycin B) as the chain initiator.
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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 ╳
