Bleomycin

June 29, 2020
An award-winning researcher studied me.
What molecule am I?

The term “bleomycin” represents a group of glycopeptides used as cancer drugs and antibiotics. It was discovered in 1962 by microbiologist Hamao Umezawa at the Institute of Microbial Chemistry (Tokyo), who observed that culture filtrates of the bacterium Streptomyces verticillus had anticancer activity.

All bleomycins have the same general structure; they differ only by the functional group attached to the terminal amine. The most prominent member, bleomycin A2 (shown), contains a (dimethylsulfonio)propyl cation on the amine. It is marketed in the form of a sulfate salt that contains other bleomycins. The total synthesis of bleomycin A2 was reported in 1981 by Umezawa and colleagues at several Japanese research institutions. The commercial product, however, is obtained from S. verticillus.

Bleomycin sulfate is used primarily to treat Hodgkin and non-Hodgkin lymphoma; testicular and cervical cancers; squamous cell carcinomas; and cancer-related pleural effusion. It is administered via intravenous and intramuscular injection.

Biochemist JoAnne Stubbe at MIT (Cambridge, MA) was awarded the 2020 Priestley Medal for her work on enzyme mechanisms and for uncovering the details of the mechanism of action of bleomycin, which cleaves double-stranded DNA. Stephen J. Lippard, also at MIT, calls Stubbe “the top mechanistic biochemist of her generation”. The Priestley Medal for lifetime achievement in chemistry is the highest award given by ACS.

Bleomycin hazard information

Hazard class* Hazard statement
Germ cell mutagenicity, category 1B H340—May cause genetic defects  Chemical Safety Warning
Carcinogenicity, category 2 H351—Suspected of causing cancer Chemical Safety Warning
Reproductive toxicity, category 2 H361—Suspected of damaging fertility or the unborn child Chemical Safety Warning

*Data for mixed bleomycin sulfate.
**Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

Bleomycin fast facts

CAS Reg. No. 11116-31-7
SciFinder
nomenclature
Bleomycinamide, N1-[3-(dimethylsulfonio)-propyl]-
Empirical formula C55H84N17O21S3+
Molar mass 1415.55 g/mol
Appearance White to yellowish powdera
Melting point 200–204 ºC (dec.)a
Water solubility 20 g/La

a. Data for mixed bleomycin sulfate, CAS Reg. No. 9041-93-4.

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