11-Deoxydoxorubicin
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| Category | Antibiotics |
| Catalog number | BBF-01344 |
| CAS | 71800-89-0 |
| Molecular Weight | 527.52 |
| Molecular Formula | C27H29NO10 |
| Purity | ≥95% |
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Description
11-Deoxydoxorubicin is an impurity of Doxorubicin, which is an anthracycline antibiotic with anti-Gram-positive bacterial activity and a broad antitumor spectrum.
Specification
| Related CAS | 73952-94-0 (monohydrochloride) |
| Synonyms | 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-8,11-dihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-; (1S,3S)-3-Glycoloyl-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside; (8S-cis)-10-((3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-8,11-dihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione; 11-Deoxyadriamycin |
| Storage | Store at 2-8°C |
| IUPAC Name | (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9-dihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(CC3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)(C(=O)CO)O)N)O |
| InChI | InChI=1S/C27H29NO10/c1-11-23(31)15(28)7-19(37-11)38-17-9-27(35,18(30)10-29)8-12-6-14-22(25(33)20(12)17)26(34)21-13(24(14)32)4-3-5-16(21)36-2/h3-6,11,15,17,19,23,29,31,33,35H,7-10,28H2,1-2H3/t11-,15-,17-,19-,23+,27-/m0/s1 |
| InChI Key | JBVCUZWDGRKRKU-CYMFRXPCSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor) |
| Boiling Point | 791.8±60.0°C at 760 mmHg |
| Density | 1.6±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Hydroxyl radical production and DNA damage induced by anthracycline-iron complex
J R Muindi, B K Sinha, L Gianni, C E Myers FEBS Lett. 1984 Jul 9;172(2):226-30. doi: 10.1016/0014-5793(84)81130-8.
Adriamycin-Fe3+ complex catalyzes the formation of hydroxyl radical from hydrogen peroxide but the DNA-adriamycin-iron ternary complex is much more effective. 11-Deoxyadriamycin, which shows no spectral evidence of complex formation with iron, was ineffective. The generation of hydroxyl radical by adriamycin-Fe3+ complex in the presence of DNA correlates with its ability to cleave DNA. Hydroxyl radicals are thus implicated as the reactive oxygen species involved in the DNA damage caused by the adriamycin-Fe3+ complex.
2. Influence of aglycone modifications on the binding of anthracycline drugs to DNA: the molecular structure of idarubicin and 4-O-demethyl-11-deoxydoxorubicin complexed to d(CGATCG)
Y G Gao, A H Wang Anticancer Drug Des. 1991 Jul;6(3):137-49.
X-ray diffraction analyses of the complexes between two anthracycline antitumor compounds, idarubicin (IDR) and 4-O-demethyl-11-deoxydoxorubicin (ddDOX), with the DNA hexamer d(CGATCG) provided the detailed three-dimensional molecular structures at 1.7 A and 1.8 A resolution, respectively. Their structures have been refined with the constrained refinement procedure to final R-factors of 0.188 (1724 reflections for IDR) and 0.179 (1247 reflections for ddDOX). The overall structures of both complexes are similar to those of the previously studied DAU- and DOX-DNA complexes. In both complexes, two IDR (and ddDOX) molecules bind to the DNA hexamer double helix with the elongated aglycone chromophore intercalated between the CpG steps at both ends of the helix. The aglycone chromophore spans the GC Watson-Crick base pairs with its amino sugar lying in the minor groove where little structural difference is seen, compared with the daunorubicin-d(CGATCG) and doxorubicin-d(CGATCG) complexes. In contrast, the missing C4 methoxy of IDR and the missing methyl group at the O4 position of ddDOX result in a different binding surface in the major groove. The O4 hydroxyl group is capable of receiving and/or donating a hydrogen bond to proteins that bind to the drug-DNA complex. The missing O11 hydroxyl group in ring B creates an empty space in the intercalation cavity between the two GC base pairs, which appears to affect the stacking interactions between the aglycone and the DNA base pairs. Those structural changes in the major groove of the drug-DNA complexes due to the modifications of the aglycone chromophore may be responsible in part for the difference in their biological activities.
3. New anthracycline glycosides: 4-O-demethyl-11-deoxydoxorubicin and analogues from Streptomyces peucetius var. aureus
G Cassinelli, G Rivola, D Ruggieri, F Arcamone, A Grein, S Merli, C Spalla, A M Casazza, A Di Marco, G Pratesi J Antibiot (Tokyo). 1982 Feb;35(2):176-83. doi: 10.7164/antibiotics.35.176.
The new anthracyclines 4-O-demethyl-11-deoxydoxorubicin, 4-O-demethyl-11-deoxydaunorubicin along with its 13-dihydro and 13-deoxo analogues are the main components of the anthracycline complex produced by cultures of Streptomyces peucetius var. aureus. They were isolated by solvent partition, separated by column chromatography and characterized by chemical and physical methods. Among these new anthracyclines, displaying antibacterial and cytotoxic activity "in vitro", 4-O-demethyl-11-deoxydoxorubicin and the corresponding daunorubicin analogue were also active against experimental tumors.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
