Bleomycin sulfate Chemical Properties

Melting point:

200-204°C (dec.)

storage temp. 

2-8°C

solubility 

H₂O: 20 mg/mL

form 

powder

color 

white

Water Solubility 

Soluble in water or DMSO

Merck 

14,1318

Stability:

Stable for 1 year from the date of purchase. Solutions in distilled water may be stored at -20°C for up to 3 months.

InChI

InChI=1/2C55H83N17O21S3.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-;/s3

InChIKey

OOXTWFJZZAJGKA-YWZNXBAZNA-N

SMILES

[C@@H](C1N=CNC=1)(O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@@H](OC(=O)N)[C@@H]1O)CO)[C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@H]([C@H](O)C)C(=O)NCCC1SC=C(C2=NC=C(C(=O)NCCC[S+](C)C)S2)N=1)NC(=O)C1=C(C)C(=NC([C@H](CC(=O)N)NC[C@H](N)C(=O)N)=N1)N.[C@@H](C1N=CNC=1)(O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O[C@@H]1O[C@@H]([C@@H](O)[C@@H](OC(=O)N)[C@@H]1O)CO)CO)[C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@H]([C@H](O)C)C(=O)NCCC1SC=C(C2=NC=C(C(=O)NCCC[S+](C)C)S2)N=1)NC(=O)C1=C(C)C(=NC([C@H](CC(=O)N)NC[C@H](N)C(=O)N)=N1)N.S([O-])([O-])(=O)=O |&1:0,7,9,10,12,14,16,18,21,23,28,32,36,38,40,45,46,82,89,96,103,105,106,108,110,112,114,115,117,122,128,132,134,136,141,142,178,185,r|

CAS DataBase Reference

9041-93-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

46-40-36/37/38-63

Safety Statements 

53-36/37-45-36-26

WGK Germany 

3

RTECS 

EC5991990

F 

10

HS Code 

2941906000

MSDS

• Language:English Provider:SigmaAldrich

Bleomycin sulfate Usage And Synthesis

Description

Bleomycin sulfate (9041-93-4) coordinates with metals producing reactive oxygen species which causes oxidative damage to DNA1?and RNA2. Induces double-strand DNA damage.3?Commonly used to induce lung fibrosis in animal disease models.4,5?Anticancer agent in clinical use.6

Chemical Properties

White Powder

Uses

A group of related glycopeptide antibiotics. Bleomycin A2 is the main component of the bleomycin employed clinically. Antineoplastic

Uses

Bleomycin is a complex of 11 glycopeptide antitumour antibiotics originally isolated from Streptomyces verticillus in 1972. The dominant components of the complex are bleomycin A2 and B2, which typically represent >90% of the total weight . Bleomycins have found clinical application in the treatment of a range of tumours. Bleomycins act by intercalation of DNA and RNA. In the presence of oxygen and metal ions, notably copper and iron, bleomycins form a pseudo-enzyme that induces DNA cleavage.

Uses

Bleomycin is a complex of 11 glycopeptide antitumor antibiotics originally isolated from Streptomyces verticillus in 1972. The dominant components of the complex are bleomycin A2 and B2, which typically represent >90% of the total weight. Bleomycins have found clinical application in the treatment of a range of tumors. Bleomycins act by intercalation of DNA and RNA. In the presence of oxygen and metal ions, notably copper and iron, bleomycins form a pseudo-enzyme that induces DNA cleavage.

Uses

Bleomycin sulfate binds to DNA, and can inhibit DNA synthesis and causes scission of DNA. Cleaves DNA, requires binding to oxygen and a metal ion, such as copper or iron. Able to cleave RNA, but at less and more selective degree. Also reported to induce and regulate apoptosis in a variety of cells, and inhibit tumor angiogenesis.

brand name

Blenoxane (Bristol-Myers Squibb).

General Description

Bleomycin occurs as a white powder and is available in 15-and 30-U vials for reconstitution in water. It may be givenintravenously, intramuscularly, or subcutaneously. It is used in the treatment of squamous cell carcinoma of the headneck, cervix, penis, and vulva. It is also used in Hodgkin’sand non-Hodgkin’s lymphoma as well as testicular carcinoma.Unlabeled uses include the treatment of mycosis fungoides,osteosarcoma, and AIDS-related Kaposi sarcoma.

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.

Clinical Use

Bleomycin is used IV in the palliative treatment of squamous cell head and neck cancers, testicular and other genital carcinomas, and Hodgkin's and non-Hodgkin's lymphoma.

Side effects

It is excreted via the kidneys, and serum concentrations of active drug are increased in patients with renal disease. The elimination half-life can rise from 2 to 4 hours to more than 20 hours in renal failure, resulting in significant toxicity, especially pulmonary toxicity.

Veterinary Drugs and Treatments

Bleomycin has occasionally been used as adjunctive treatment of lymphomas, squamous cell carcinomas, teratomas, and nonfunctional thyroid tumors in both dogs and cats. Recent work has demonstrated that bleomycin may be promising for intralesional treatment for a variety of localized tumors with or without concomitant electropermeabilization.

target

UT-SCC-129 cells

References

1) Petering?et al.?(1990),?The role of redox-active metals in the mechanism of action of bleomycin; Chem. Biol. Interact.,?73?133 2) Huttenhofer?et al. (1992),?Cleavage of tRNA by Fe(II)-bleomycin; J. Biol. Chem.,?267?24471 3) Lee?et al.?(2017)?ASF1a Promotes Non-homologous End Joining Repair by facilitating Phosphorylation of MDC1 by ATM at Double-Strand Breaks;?Mol. Cell?68?61 4)?Xie?et al.?(2016), Upregulation of RGS2: a new mechanism for pirfenidone amelioration of pulmonary fibrosis; Respir. Res.,?17?103 5) Inomata?et al. (2014) Pirfenidone inhibits fibrocyte accumulation in the lungs in bleomycin-induced murine pulmonary fibrosis; Respir. Res.,?15?16 6) Tanaka?et al. (2008)?Increased glutathione level is not involved in enhanced bleomycin sensitivity in cisplatin-resistant 2780CP cells; Anticancer Res.,?28?2663

Bleomycin sulfate(9041-93-4)Related Product Information

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