Sulfurmycin D
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| Category | Antibiotics |
| Catalog number | BBF-03491 |
| CAS | 83753-74-6 |
| Molecular Weight | 597.61 |
| Molecular Formula | C31H35NO11 |
| Purity | 95% |
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Description
Sulfurmycin D is an anthracycline antibiotic produced by Str. galilaeus OBB-111. It has anti-Gram-positive bacteria and anti-tumor activity.
Specification
| Synonyms | 1-Naphthacenecarboxylic acid, 1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-4-((2,3,6-trideoxy-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-, methyl ester, (1R-(1alpha,2beta,4beta))- |
| IUPAC Name | methyl (1R,2S,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1H-tetracene-1-carboxylate |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(C(C3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5O)C(=O)OC)(CC(=O)C)O)N(C)C)O |
| InChI | InChI=1S/C31H35NO11/c1-13(33)11-31(40)12-20(43-21-10-18(32(3)4)26(35)14(2)42-21)23-16(25(31)30(39)41-5)9-17-24(29(23)38)28(37)22-15(27(17)36)7-6-8-19(22)34/h6-9,14,18,20-21,25-26,34-35,38,40H,10-12H2,1-5H3/t14-,18-,20-,21-,25-,26+,31+/m0/s1 |
| InChI Key | YPHXBUMJGHZUMJ-UCPUWLPESA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 755.1±60.0°C at 760 mmHg |
| Melting Point | 128°C |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1.New anthracycline antibiotics, auramycins and sulfurmycins. II. Isolation and characterization of 10 minor components (C approximately G).
Hoshino T, Tazoe M, Nomura S, Fujiwara A. J Antibiot (Tokyo). 1982 Oct;35(10):1271-9.
Following the discovery of new anthracycline antibiotics, auramycins A and B and sulfurmycins A and B, we found 10 minor analogues of auramycins and sulfurmycins, C, D, E, F and G, from the culture broth of a mutant strain of Streptomyces galilaeus OBB-111 and prepared 2 analogues as the chemical derivatives from auramycin G and sulfurmycin G. All analogues have a sugar moiety at C-7 position of the aglycones. These analogues exhibit activities against Gram-positive bacteria and P388 leukemia.
2.Further examination of 9-alkyl- and sugar-modified anthracyclines in the circumvention of multidrug resistance.
Coley HM1, Twentyman PR, Workman P. Anticancer Drug Des. 1992 Dec;7(6):471-81.
Anthracyclines possessing either a 9-alkyl modification in the A-ring of the tetracyclic aglycone and/or specific changes to the amino sugar moiety retain effective cytotoxic activity against multidrug resistant (MDR) cell lines. To obtain a better understanding of the structural features responsible for this potentially valuable behaviour, we used the MTT tetrazolium dye reduction assay to calculate resistance factors (RF = the ratio of ID50 for the drug-resistant line to that for the parental line) for the EMT6/P mouse mammary tumour and its MDR variant EMT6/AR1.0, and the H69/P human small cell lung cancer line and its MDR counterpart H69/LX4. Both MDR lines exhibit marked resistance to doxorubicin, MDR 1 gene amplification, hyperexpression of the membrane P-glycoprotein and reduced drug accumulation. RF values for doxorubicin were 34 and 131 in the EMT6 and H69 cell line pairs, respectively. The 9-alkyl-substituted anthracyclines were confirmed as having RF values 9- to 15-fold lower than those for doxorubicin.
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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 ╳
