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B8416

Sigma-Aldrich

Bleomycin sulfate from Streptomyces verticillus

crystalline, suitable for cell culture, BioReagent

Synonym(s):

Blenoxane, Bleo, Blexane

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About This Item

CAS Number:
9041-93-4
EC Number:
232-925-2
MDL number:
MFCD00070310
UNSPSC Code:
12352207
PubChem Substance ID:
24891950
NACRES:
NA.76

product name

Bleomycin sulfate from Streptomyces verticillus, 1.5-2.0 units/mg solid, BioReagent, suitable for cell culture

product line

BioReagent

form

powder or crystals

specific activity

1.5-2.0 units/mg solid

technique(s)

cell culture | mammalian: suitable

color

white to off-white

solubility

H2O: 20 mg/mL, clear, colorless

antibiotic activity spectrum

fungi

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

SMILES string

[O-]S([O-])(=O)=O.C[C@@H](O)[C@@H](NC(=O)[C@@H](C)[C@H](O)[C@@H](C)NC(=O)[C@H](NC(=O)c1nc(nc(N)c1C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](O[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@@H]3O[C@H](CO)[C@@H](O)[C@@H](OC(N)=O)[C@@H]3O)c4c[nH]cn4)C(=O)NCCc5nc(cs5)-c6ncc(s6)C(=O)NCCC[S+](C)C.C[C@@H](O)[C@@H](NC(=O)[C@@H](C)[C@H](O)[C@@H](C)NC(=O)[C@H](NC(=O)c7nc(nc(N)c7C)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](O[C@@H]8O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]8O[C@@H]9O[C@H](CO)[C@@H](O)[C@@H](OC(N)=O)[C@@H]9O)c%10c[nH]cn%10)C(=O)NCCc%11nc(cs%11)-c%12ncc(s%12)C(=O)NCCC[S+](C)C

InChI

1S/2C55H83N17O21S3.H2O4S/c2*1-20-33(69-46(72-44(20)58)25(12-31(57)76)64-13-24(56)45(59)82)50(86)71-35(41(26-14-61-19-66-26)91-54-43(39(80)37(78)28(16-73)90-54)92-53-40(81)42(93-55(60)88)38(79)29(17-74)89-53)51(87)67-22(3)36(77)21(2)47(83)70-34(23(4)75)49(85)63-10-8-32-68-27(18-94-32)52-65-15-30(95-52)48(84)62-9-7-11-96(5)6;1-5(2,3)4/h2*14-15,18-19,21-25,28-29,34-43,53-54,64,73-75,77-81H,7-13,16-17,56H2,1-6H3,(H13-,57,58,59,60,61,62,63,66,67,69,70,71,72,76,82,83,84,85,86,87,88);(H2,1,2,3,4)/t2*21-,22+,23+,24-,25-,28-,29+,34+,35+,36-,37+,38+,39-,40-,41-,42+,43-,53-,54-;/m00./s1

InChI key

OOXTWFJZZAJGKA-CNLAFNBISA-N

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General description

Bleomycin Sulfate is an antineoplastic antibiotic isolated from Streptomyces verticillus. It is recommended for use as a cell culture agent at 10-100 μg/mL.
Chemical structure: glycopeptide

Application

Bleomycin is used in combination with Etoposide and Cisplatin to treat testicular, ovarian and cervical cancer. This combination is popular as BEP chemotherapy and has also been demonstrated as effective and most successful chemotherapy regimen in germ-cell tumors. Since it is a cytotoxic agent, bleomycin is known to induce endothelial damage the lung vasculature referred to as bleomycin-induced lung-injury or bleomycin-induced pneumonitis (BIP). Researchers have used this property of bleomycin to induce lung fibrosis in mouse and rat models.

Biochem/physiol Actions

Bleomycin sulfate binds to DNA, causes ssDNA scission at specific base sequences and inhibits DNA synthesis. This inhibitory action requires bleomycin to bind oxygen and a metal ion. It can also cleave RNA, to a lesser degree but more selectively. It acts as an inducer and regulator of apoptosis and inhibits tumor angiogenesis.

Components

This product is a mixture of glycopeptides antibiotics containing Bleomycin A2 (70%) and B2(30%). Bleomycins differ from each other in the terminal amine and show varying biological activity.

Caution

This product should be stored at 2-8°C.

Preparation Note

The product is soluble in water in water at 20 mg/mL and is active for several days. A solution of 2 units/mL in 0.1 M neutral potassium phosphate should be used within 14 days. A solution is active for three months at 3 units/mL in normal saline.

Other Notes

Keep container tightly closed in a dry and well-ventilated place, strongly hygroscopic

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Carc. 2 - Muta. 1B - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Martin Toussaint et al.
Nature protocols, 1(4), 1922-1928 (2007-05-10)
Intracellular metabolites and environmental agents continuously challenge the structural integrity of DNA. In the yeast Saccharomyces cerevisiae, the complete collection of open reading frame deletion mutants, in combination with powerful screening methods, allows for the comprehensive analyses of cellular responses
Donald H Atha et al.
Journal of nucleic acids, 2020, 8810105-8810105 (2020-08-18)
To evaluate methods for analysis of genotoxic effects on mammalian cell lines, we tested the effect of three common genotoxic agents on Chinese hamster ovary (CHO) cells by single-cell gel electrophoresis (comet assay) and gas chromatography-tandem mass spectrometry (GC-MS/MS). Suspension-grown
Ian D Odell et al.
Science immunology, 7(78), eabq6691-eabq6691 (2022-12-10)
Immune cells are fundamental regulators of extracellular matrix (ECM) production by fibroblasts and have important roles in determining extent of fibrosis in response to inflammation. Although much is known about fibroblast signaling in fibrosis, the molecular signals between immune cells
Markus Berger et al.
Journal of medicinal chemistry, 64(17), 12723-12737 (2021-08-25)
Eukaryotes have evolved two major pathways to repair potentially lethal DNA double-strand breaks. Homologous recombination represents a precise, DNA-template-based mechanism available during the S and G2 cell cycle phase, whereas non-homologous end joining, which requires DNA-dependent protein kinase (DNA-PK), allows
Britta Maurer et al.
Annals of the rheumatic diseases, 72(12), 2039-2046 (2013-09-10)
To assess whether the discrepancy between the strong antifibrotic effects of tyrosine kinase inhibitors (TKIs) in animal models and the inconsistent results in clinical studies might be related to the activation levels of drug targets. Skin sections of bleomycin, TSK1
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