Structure via PubChem · Public domain (PubChem)
anthramycin
Sign in to saveAnthramycin is a pyrrolobenzodiazepine antibiotic with antitumor activity. First derived from the thermophilic actinomycete Streptomyces refuineus by M. D. Tendler and S Korman in the 1950s, it was first successfully synthesized in a laboratory setting by Leimgruber et al. in 1965. Due to the unstable nature of the chemical structure, characterization of the species was done on its epimer, anthrmycin-11-methyl-ether. This derivative can be formed by recrystallization of anthramycin from hot methanol.
Chemical data
- Formula
- C16H17N3O4
- Molecular weight
- 315.32 g/mol
- IUPAC name
- (E)-3-[(6S,6aS)-4,6-dihydroxy-3-methyl-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]prop-2-enamide
- SMILES
- CC1=C(C2=C(C=C1)C(=O)N3C=C(C[C@H]3[C@@H](N2)O)/C=C/C(=O)N)O
- InChIKey
- VGQOVCHZGQWAOI-HYUHUPJXSA-N
- XLogP
- 0
- Polar surface area
- 116 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
172 papers- From Anthramycin to Pyrrolobenzodiazepine (PBD)-Containing Antibody-Drug Conjugates (ADCs).Angewandte Chemie (International ed. in English) · 2017
- Anthramycin-DNA binding explored by molecular simulations.The journal of physical chemistry. B · 2006
- Pyrrolo(1,4)benzodiazepine antitumor antibiotics. Comparative aspects of anthramycin, tomaymycin and sibiromycin.The Journal of antibiotics · 1977
- Anthramycin inhibition of restriction endonuclease cleavage and its use as a reversible blocking agent in DNA constructions.Nucleic acids research · 1981
- The minor groove covalent reactive drugs anthramycin and (+)-CC-1065 and their interstrand cross-linking derivatives.IARC scientific publications · 1994
via PubMed
Wikidata facts
- Mass
- 315.122
Show 4 more facts
- chemical formula
- C₁₆H₁₇N₃O₄
- isomeric SMILES
- CC1=C(C2=C(C=C1)C(=O)N3C=C(C[C@H]3[C@@H](N2)O)/C=C/C(=O)N)O
- canonical SMILES
- CC1=C(C2=C(C=C1)C(=O)N3C=C(CC3C(N2)O)C=CC(=O)N)O
- different from
- anthracimycin
Sources (1)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Chemical structure
- Medical uses
- Side effects
- See also
- References
Anthramycin is a pyrrolobenzodiazepine antibiotic with antitumor activity. First derived from the thermophilic actinomycete Streptomyces refuineus by M. D. Tendler and S Korman in the 1950s, it was first successfully synthesized in a laboratory setting by Leimgruber et al. in 1965. Due to the unstable nature of the chemical structure, characterization of the species was done on its epimer, anthrmycin-11-methyl-ether. This derivative can be formed by recrystallization of anthramycin from hot methanol.
==Chemical structure== The chemical structure of anthramycin was first elucidated by Leimgruber using nuclear magnetic resonance and ultraviolet spectroscopy. Using another similarly structured fermentation product simply referred to as 'yellow pigment' as a basis of comparison, he was able to identify all major functional groups of the structure. The structure of the species was narrowed down to one of two possible candidates: one with a pyrrolobenzodiazepine nucleus, and another with a pyridoquinazoline skeleton. The first structure was confirmed through the use of mass spectrometry.
Excerpted from Wikipedia’s “anthramycin” article, available under the CC BY-SA 4.0 licence.