Phleomycin E

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Category Antibiotics
Catalog number BBF-02403
CAS 11031-13-3
Molecular Weight 1540.68
Molecular Formula C60H97N23O21S2

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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. It extends the survival time of mice transplanted with Ehrman's ascites cancer by 300 percent with MED of 12.5-25 μg/mL. It inhibits airy entity carcinoma in mice with IC50 of 0.31 μg/mL.

Specification

Synonyms N1-[4-[[[[4-[[Aminoiminomethyl]amino]butyl]amino](imino)methyl]amino]butyl]-7,8-dihydrobleomycinamide; Bleomycinamide, N1-[4-[[[[4-[(aminoiminomethyl)amino]butyl]amino]iminomethyl]amino]butyl]-7,8-dihydro-
IUPAC Name [(2R,3S,4S,5R,6R)-2-[(2R,3S,4S,5S,6S)-2-[(1R,2S)-2-[[6-amino-2-[(1S)-3-amino-1-[[(2S)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[(2R,3S,4S)-5-[[(2S,3R)-1-[2-[4-[4-[4-[[N'-[4-(diaminomethylideneamino)butyl]carbamimidoyl]amino]butylcarbamoyl]-1,3-thiazol-2-yl]-4,5-dihydro-1,3-thiazol-2-yl]ethylamino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-hydroxy-4-methyl-5-oxopentan-2-yl]amino]-1-(1H-imidazol-5-yl)-3-oxopropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] carbamate
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)OC4C(C(C(C(O4)CO)O)OC(=O)N)O)C(=O)NC(C)C(C(C)C(=O)NC(C(C)O)C(=O)NCCC5=NC(CS5)C6=NC(=CS6)C(=O)NCCCCNC(=NCCCCN=C(N)N)N)O
InChI InChI=1S/C60H97N23O21S2/c1-23-36(80-49(83-47(23)63)28(15-34(62)87)75-16-27(61)48(64)93)53(97)82-38(44(29-17-69-22-76-29)102-57-46(42(91)40(89)32(18-84)101-57)103-56-43(92)45(104-60(68)99)41(90)33(19-85)100-56)54(98)77-25(3)39(88)24(2)50(94)81-37(26(4)86)52(96)71-14-9-35-78-31(21-105-35)55-79-30(20-106-55)51(95)70-10-5-7-12-73-59(67)74-13-8-6-11-72-58(65)66/h17,20,22,24-28,31-33,37-46,56-57,75,84-86,88-92H,5-16,18-19,21,61H2,1-4H3,(H2,62,87)(H2,64,93)(H2,68,99)(H,69,76)(H,70,95)(H,71,96)(H,77,98)(H,81,94)(H,82,97)(H2,63,80,83)(H4,65,66,72)(H3,67,73,74)/t24-,25+,26+,27-,28-,31?,32-,33+,37-,38-,39-,40+,41+,42-,43-,44-,45-,46-,56+,57-/m0/s1
InChI Key NVEXEWYGCXIGOY-FFZWGXSXSA-N

Properties

Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor); Mycobacteria
Density 1.75±0.1 g/cm3 (Predicted)
Solubility Soluble in Water

Reference Reading

1. Identification and mapping of regions of the plasmid pKM101 which influence the growth rate and resistance to phleomycin E of Escherichia coli WP2
R M Hall J Bacteriol. 1985 Sep;163(3):1142-6. doi: 10.1128/jb.163.3.1142-1146.1985.
The effects of deletion of various regions of the pKM101 genome on several phenotypes conferred by pKM101 in Escherichia coli WP2 cells were investigated. Differences in the response of cells carrying pKM101 or various pKM101 deletion derivatives to the mutagenic effects of phleomycin E can be attributed to differences in sensitivity to the lethal effects of phleomycin E. Resistance to phleomycin E is conferred by the pKM101 mucAB genes (or an adjacent gene) but observed only with pKM101 derivatives which have lost a 2.2-kilobase (BalI-KpnI-2) segment which completely includes the pKM101 endonuclease gene nuc. A pKM101 slow-growth determinant, distinct from the slo gene, has also been identified and localized in the 2.4-kilobase (BalI-KpnI-3) segment which is adjacent to the nuc gene. Loss of this region does not appear to substantially influence the toxic or mutagenic effects of phleomycin E.
2. Sequence-selective binding of phleomycin to DNA
K R Fox, G W Grigg, M J Waring Biochem J. 1987 May 1;243(3):847-51. doi: 10.1042/bj2430847.
The binding of phleomycin and bleomycin to DNA has been investigated by studying their effects on cleavage by DNAase I and micrococcal nuclease. In the presence of cobalt, cleavage of DNA by the antibiotics is suppressed, yet they still provide protection from nuclease attack in regions surrounding the drug cleavage sites. We conclude that cleavage by phleomycin occurs at bonds around which the antibiotic is already selectively bound.

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