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B5507

Sigma-Aldrich

Bleomycin sulfate from Streptomyces verticillus

crystalline, 1.5-2.0 U/mg

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:
12352200
PubChem Substance ID:
24891839
NACRES:
NA.77

form

crystalline

Quality Level

200

specific activity

1.5-2.0 U/mg

color

white

solubility

H2O: 20 mg/mL

cation traces

Cu: ≤0.10%

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 Sulfate is an atineoplastic antibiotic isolated from Streptomyces verticillus. It is recommended for use as a cell culture agent at 10-100 μg/mL.
Bleomycin sulfate from Streptomyces verticillus has been used:
  • to study the impact of telomere shortening in lung fibrosis
  • to induce lung injury and study its effect on CEACAM6 expression
  • as a DNA-alkylating agent to induce lung injury
  • study its effect on CEACAM6 expression
  • to cause lung injury
  • subsequent fibrosis in animals

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.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Carcinogenicity of bleomycin sulfate and peplomycin sulfate after repeated subcutaneous application to rats
Habs M and Schmahl D
Oncology, 41(2), 114-119 (1984)
Assembly of the Elongin A ubiquitin ligase is regulated by genotoxic and other stresses
Weems JC, et al.
The Journal of Biological Chemistry, 290(24), 15030-15041 (2015)
Loss of CDKN2B promotes fibrosis via increased fibroblast differentiation rather than proliferation
Scruggs AM, et al.
American Journal of Respiratory Cell and Molecular Biology, 59(2), 200-214 (2018)
Telomere shortening activates TGF-betaSmads signaling in lungs and enhances both lipopolysaccharide and bleomycin-induced pulmonary fibrosis
Liu YY, et al.
Acta Pharmacologica Sinica, 39(11), 1735-1735 (2018)
Expression of human carcinoembryonic antigen-related cell adhesion molecule 6 and alveolar progenitor cells in normal and injured lungs of transgenic mice
Lin S, et al.
Physiological Reports, 3(12), e12657-e12657 (2015)
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