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15361

Sigma-Aldrich

Bleomycin sulfate from Streptomyces verticillus

for fluorescence, mixture of bleomycin sulfate salts, lyophilized, powder or crystals, white to off-white

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:
51101500
PubChem Substance ID:
57647391
NACRES:
NA.85

biological source

Streptomyces verticillus

Quality Level

200

grade

for fluorescence

form

powder or crystals

quality

lyophilized

color

white to off-white

solubility

H2O: 20 mg/mL, clear, colorless

cation traces

Cu: ≤0.1%

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 used to study tumor-specific cytotoxic activity in certain cell lines such as human normal oral cells(gingival fibrobast HGF, pulp cell HPC and periodontal ligament fibroblast HPLF), human oral squamous cell carcinoma (HSC-2, HSC-3, HSC-4, Ca9-22 and NA) and human promyelocytic leukemia HL-60 cells. It is used to study free radical-mediated mechanisms of DNA strand scission/breaking and as a transformed cell selection agent, especially for plant transformants. Recommended for use as a selection 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.

Packaging

Packaged in a bottomless glass bottle with its contents inside an inserted fused cone.

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. Keep in a dry place.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H340,H351,H361fd

Hazard Classifications

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

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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R P Hertzberg et al.
Biochemistry, 27(9), 3164-3174 (1988-05-03)
Bleomycin-mediated DNA strand scission has been shown to be diminished at certain sequences in proximity to 5-methylcytidines. We have investigated the molecular basis of this observed diminution using selective bleomycin (BLM) modifications at the C-terminus. Of the four different bleomycin
V Murray et al.
The Journal of biological chemistry, 263(26), 12854-12859 (1988-09-15)
The DNA sequence specificity of the cancer chemotherapeutic agent, bleomycin, has been investigated in three clones of human alpha RI-DNA. The three 340-base pair alpha RI-DNA sequences were almost identical in their nucleotide sequence enabling the study of subtle effects
Mechanism of bleomycin action: in vitro studies.
R M Burger et al.
Life sciences, 28(7), 715-727 (1981-02-16)
Masahiro Sasaki et al.
Anticancer research, 26(5A), 3373-3380 (2006-11-11)
Three antitumor antibiotics, mitomycin C, bleomycin sulfate and peplomycin sulfate, were compared for their tumor-specific cytotoxicity, using human oral squamous cell lines (HSC-2, HSC-3, HSC-4, Ca9-22 and NA), human promyelocytic leukemic cell line HL-60 and human normal oral cell types
Han Yue et al.
The British journal of ophthalmology, 97(6), 739-745 (2013-04-23)
To evaluate the safety and efficacy of intralesional pingyangmycin for treatment of orbital vascular malformations. Thirteen patients received intralesional injections of pingyangmycin at the Eye and ENT Hospital of Fudan University. CT scans of each patient were evaluated with graphic
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