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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

specific activity

1.5-2.0 U/mg

color

white to off-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

Signal Word

Danger

Hazard Statements

H340,H351,H361fd

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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