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B2434

Sigma-Aldrich

Bleomycin sulfate from Streptomyces verticillus

BioXtra, crystalline

Synonym(s):

Blenoxane, Bleo, Blexane

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About This Item

CAS Number:
EC Number:
MDL number:
UNSPSC Code:
51111733
PubChem Substance ID:
NACRES:
NA.85

product line

BioXtra

Quality Level

form

crystalline

potency

1.5-2.0 units per mg

technique(s)

cell culture | mammalian: suitable

solubility

H2O: 20 mg/mL, clear, colorless

cation traces

Cu: ≤0.10%

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
neoplastics

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

Chemical structure: glycopeptide

Application

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.

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

Signal Word

Danger

Hazard Statements

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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Abdulaleem Alnajar et al.
PloS one, 8(11), e81356-e81356 (2013-11-22)
Fibrogenesis is usually initiated when regenerative processes have failed and/or chronic inflammation occurs. It is characterised by the activation of tissue fibroblasts and dysregulated synthesis of extracellular matrix proteins. FHL2 (four-and-a-half LIM domain protein 2) is a scaffolding protein that
Z G Fridlender et al.
The European respiratory journal, 30(2), 205-213 (2007-05-17)
Epithelial cell injury and apoptosis are recognised as early features in idiopathic pulmonary fibrosis and bleomycin-induced fibrosis in mice. Telomerase is a known apoptosis-alleviating factor. The role of telomerase was studied during bleomycin-induced lung epithelial cell (LEC) apoptosis in vitro
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
Sebastian Willenborg et al.
The Journal of investigative dermatology, 134(7), 2005-2015 (2014-01-11)
Conclusive evidence for the impact of mast cells (MCs) in skin repair is still lacking. Studies in mice examining the role of MC function in the physiology and pathology of skin regenerative processes have obtained contradictory results. To clarify the
Alberto Biggi et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 54(5), 683-690 (2013-03-22)
At present, there are no standard criteria that have been validated for interim PET reporting in lymphoma. In 2009, an international workshop attended by hematologists and nuclear medicine experts in Deauville, France, proposed to develop simple and reproducible rules for

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