Bleomycins

from Wikipedia, the free encyclopedia

The bleomycins are a group of structurally closely related antibiotic and cytostatic effective glycopeptide derived from the bacterium Streptomyces verticillus be formed.

Structure and properties

The basic structure of bleomycins is bleomycic acid, a glycopeptide. The peptide part is made up of ten building blocks and linked glycosidically with a disaccharide consisting of L - gulose and 3 - O - carbamoyl - D - mannose . One of the characteristic features is the dithiazole ring system formed from two cysteine units.

The bleomycins are the amides of bleomycin acid, 16 natural representatives are known.

Biogenic and semi-synthetic bleomycins
Basic structure of the bleomycins
Basic structure of the bleomycins
Surname −R CAS number PubChem Molecular formula Molar mass
  • Bleomycin Acid
    (Bleomycin G)
 −OH 37364-66-2 2410 C 50 H 72 N 16 O 22 S 2 1313.33 g mol −1
  • Bleomycin A 1
R Bleomycin A1.svg 58995-26-9 84060 C 54 H 81 N 17 O 22 S 3 1416.52 g mol −1
  • Bleomycin A 2
R Bleomycin A2.svg 11116-31-7 5460769 C 55 H 84 N 17 O 21 S 3 + 1415.55 g mol −1
  • S -Demethylbleomycin A 2
R Bleomycin demethyl A2.svg C 54 H 81 N 17 O 21 S 3 1400.52 g mol −1
R Bleomycin A5.svg 11116-32-8 84046 C 57 H 89 N 19 O 21 S 2 1440.56 g mol −1
  • Bleomycin A 6
37293-17-7 5483658 C 60 H 96 N 20 O 21 S 2 1497.66 g mol −1
  • Bleomycin B ' 1
−NH 2 41138-54-9 84052 C 50 H 73 N 17 O 21 S 2 1312.35 g mol −1
  • Bleomycin B 2
R Bleomycin B2.svg 9060-10-0 5496540 C 55 H 84 N 20 O 21 S 2 1425.51 g mol −1
  • Bleomycin B 4
R Bleomycin B4.svg 9060-11-1 84043 C 68 H 110 N 22 O 27 S 2 1731.86 g mol −1
R peplomycin.svg 68247-85-8 6852373 C 61 H 88 N 18 O 21 S 2 1473.56 g mol −1
88266-67-5 16130954 C 99 H 125 N 19 O 25 S 2 2045.29 g mol −1

Under the generic name Bleomycin , a type mixture produced by fermentation is used as a medicinal substance for the treatment of cancer diseases. It consists of at least 85% bleomycin A 2 + B 2 .

Peplomycin and liblomycin are two semisynthetic bleomycin derivatives that are not used therapeutically. Structurally related to the bleomycins are the cleomycins , talisomycins , phleomycins and zorbamycins .

  • Structure of zorbamycin

  • Structure of talisomycin A

Individual evidence

  1. ^ Theo Dingermann , Karl Hiller, Georg Schneider, Ilse Zündorf: Schneider drug drugs. 5th edition. Elsevier, Munich 2004, p. 488. ISBN 3-8274-1481-4 .