Phleomycin
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| Category | Antineoplastic |
| Catalog number | BBF-02677 |
| CAS | 11006-33-0 |
| Molecular Weight | 1326.37 |
| Molecular Formula | C51H75N17O21S2 |
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Description
It is produced by the strain of Streptoverticillium verticillum 843-1. It's a heteropeptide antibiotic. It has anti-gram-positive bacteria, negative bacteria and mycobacterium effects. The therapeutic index of the complex for Solid Adenocarcinoma and Sarcoma-180 are 16. The therapeutic index of Ehrlician ascites cancer is 4-8. It acts an antibiotic originally, an anticancer agent and a selection agent for transformed algae, protista, animal and fungal cells.
Specification
| Synonyms | Bleomycin; phleomycin complex; Phleomycins |
| Storage | Store at 2-8°C |
| IUPAC Name | 2-[2-[2-[[2-[[4-[[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2R,3S,4S,5S,6S)-3-[(2S,3R,4R,5S)-4-carbamoyl-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)-3-methyloxan-2-yl]oxy-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxy-2-methylpentanoyl]amino]-3-oxobutanoyl]amino]ethyl]-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazole-4-carboxamide |
| Canonical SMILES | CC1=C(N=C(N=C1N)C(CC(=O)N)NCC(C(=O)N)N)C(=O)NC(C(C2=CN=CN2)OC3C(C(C(C(O3)CO)O)O)(C)OC4C(C(C(C(O4)CO)O)(C(=O)N)O)O)C(=O)NC(C)C(C(C)C(=O)NC(C(=O)C)C(=O)NCCC5=NC(CS5)C6=NC(=CS6)C(=O)N)O |
| InChI | InChI=1S/C51H75N17O21S2/c1-16-29(65-41(68-38(16)54)21(8-27(53)72)60-9-20(52)39(55)78)44(82)67-31(34(22-10-58-15-61-22)88-49-50(5,36(76)33(74)25(11-69)87-49)89-47-37(77)51(85,48(57)84)35(75)26(12-70)86-47)45(83)62-18(3)32(73)17(2)42(80)66-30(19(4)71)43(81)59-7-6-28-63-24(14-90-28)46-64-23(13-91-46)40(56)79/h10,13,15,17-18,20-21,24-26,30-37,47,49,60,69-70,73-77,85H,6-9,11-12,14,52H2,1-5H3,(H2,53,72)(H2,55,78)(H2,56,79)(H2,57,84)(H,58,61)(H,59,81)(H,62,83)(H,66,80)(H,67,82)(H2,54,65,68)/t17?,18?,20?,21?,24?,25-,26?,30?,31?,32?,33+,34?,35-,36-,37-,47-,49-,50-,51+/m0/s1 |
| InChI Key | QRBLKGHRWFGINE-UGWAGOLRSA-N |
Properties
| Appearance | Light Blue Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor); Mycobacteria |
| Boiling Point | 1718.8°C at 760 mmHg |
| Melting Point | 195-197°C (dec.) |
| Density | 1.83 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Differential effect of phleomycin on the infectivity of poliovirus and poliovirus-induced ribonucleic acids
G Koch J Virol . 1971 Jul;8(1):28-34. doi: 10.1128/JVI.8.1.28-34.1971.
The infectivity of intact poliovirus was not affected by exposure to the antibiotic phleomycin at concentrations as high as 200 mug/ml, whereas that of the singlestranded poliovirus ribonucleic acid (RNA) was inactivated to 99% by pretreatment of the RNA with phleomycin at a concentration of 2 mug/ml. The infectivity of double and multistranded RNA was 10 times less sensitive than that of singlestranded RNA to the action of this antibiotic. Preincubation of HeLa cells for 30 min with 10 to 50 mug of phleomycin reduced the sensitivity of the cells to infection by viral RNA and intact virus, indicating that phleomycin interferes with cellular functions necessary for virus replication. When phleomycin was added to cells at different times after infection with single- or double-stranded RNA, the highest inactivation of infective centers was observed immediately after infection. With time of incubation at 37 C, the infective centers became more resistant to the action of phleomycin.
2. Phleomycin resistance as a dominant selectable marker in CHO cells
M Dalens, P Mulsant, A Gatignol, G Tiraby Somat Cell Mol Genet . 1988 May;14(3):243-52. doi: 10.1007/BF01534585.
The Tn5 and the Streptoalloteichus hindustanus (Sh) ble genes conferring resistance to bleomycin-phleomycin antibiotics have been cloned into a mammalian vector under the RSV-LTR promoter. The resulting plasmids, pUT506 and pUT507 respectively, were used to transfect CHO cells by either the calcium phosphate or the recently described polybrene-DMSO method. Phleomycin- or bleomycin-resistant clones arose with a higher frequency after transfection with pUT507, and pUT507 transfectants were more resistant to both antibiotics than pUT506 transfectants. Phleomycin resistance in pUT507 transfectants was stable and associated with integration of plasmid sequences in genomic DNA. The Sh ble gene, which confers a dominant phleomycin-resistance phenotype, should provide a useful transferable selectable marker in CHO cells as well as in other animal cell lines.
3. Phleomycin complex - Coordination mode and in vitro cleavage of DNA
Małgorzata Jeżowska-Bojczuk, Robert Wieczorek, Valentyn Dzyhovskyi, Kamila Stokowa-Sołtys J Inorg Biochem . 2019 Jun;195:71-82. doi: 10.1016/j.jinorgbio.2019.03.010.
Phleomycin is one of the anticancer glycopeptide antibiotics which cause DNA cleavage. It is commonly used as a copper(II) complex. Therefore, it is important to study the metal ion binding process and to define the coordination mode. In this paper, we describe the acid-base properties of phleomycin and the coordination sphere of the Cu(II) cation. In the metal binding process up to five nitrogen donor atoms can be involved. Four of them in the same plane deriving from: the pyrimidine ring, secondary amine of β-aminoalanine, imidazole and amide of the nearest peptide bond (from β-hydroxyhistidine) and in the apical position from the α-amino functional group of β-aminoalanine, resulting complex has a square-pyramidal geometry. Phleomycin complexes are able to induce single- and double-stranded DNA damage when they are accompanied by one-electron reductants, such as dithiothreitol, glutathione, 2-mercaptoethanol or ascorbic acid. In such conditions they produce reactive oxygen species which are responsible for DNA cleavage. The metal ion binding site is relatively close to the nucleic acid interacting moiety. This supports the hypothesis that copper ion is important in the anticancer activity which involves DNA degradation.
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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 ╳
