Dutomycin
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| Category | Antibiotics |
| Catalog number | BBF-01187 |
| CAS | 146663-67-4 |
| Molecular Weight | 854.89 |
| Molecular Formula | C44H54O17 |
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Description
It is produced by the strain of Streptomyces sp. 1725. Dutomycin has stronger cytotoxicity. 1 μg/mL of Dutomycin can completely inhibit P388 leukemia cells.
Specification
| Synonyms | 1,4,6,7(6aH,10H)-Naphthacenetetrone, 8-acetyl-10-((5-((2,6-dideoxy-4-O-(2,4-dimethyl-1-oxo-2-heptenyl)-3-C-methyl-alpha-L-xylo-hexopyranosyl)oxy)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-10a,11-dihydro-5,6a,9,10a-tetrahydroxy-2-methoxy-12-methyl-, (2S-(2alpha(6aR*,10S*,10aS*),5beta(2Z,4S*),6alpha))- |
| IUPAC Name | [(2S,3R,4R,6S)-6-[(2R,3S,6S)-6-[[(1S,4aS,12aR)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,12-dihydrotetracen-1-yl]oxy]-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] (Z,4R)-2,4-dimethylhept-2-enoate |
| Canonical SMILES | CCCC(C)C=C(C)C(=O)OC1C(OC(CC1(C)O)OC2CCC(OC2C)OC3C(=O)C(=C(C4(C3(CC5=C(C6=C(C(=O)C=C(C6=O)OC)C(=C5C4=O)O)C)O)O)O)C(=O)C)C |
| InChI | InChI=1S/C44H54O17/c1-10-11-18(2)14-19(3)41(52)61-39-23(7)58-29(17-42(39,8)53)59-26-12-13-28(57-22(26)6)60-40-36(49)31(21(5)45)37(50)44(55)38(51)32-24(16-43(40,44)54)20(4)30-33(35(32)48)25(46)15-27(56-9)34(30)47/h14-15,18,22-23,26,28-29,39-40,48,50,53-55H,10-13,16-17H2,1-9H3/b19-14-/t18-,22-,23+,26+,28+,29+,39-,40-,42-,43-,44-/m1/s1 |
| InChI Key | ZYPYHMZLLIDAAL-WNMWLNICSA-N |
Properties
| Appearance | Orange Crystalline Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 1023.6±65.0 °C (Predicted) |
| Melting Point | 237-238 °C |
| Density | 1.43±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol, DMSO |
Reference Reading
1. The Critical Role of 12-Methyl Group of Anthracycline Dutomycin to Its Antiproliferative Activity
Ruoxuan Xu, Dinghang Hu, Jinlian Lin, Jie Tang, Ruoting Zhan, Guiyou Liu, Lei Sun Molecules. 2022 May 23;27(10):3348. doi: 10.3390/molecules27103348.
Anthracycline dutomycin is a tetracyclic quinone glycoside produced by Streptomyces minoensis NRRL B-5482. SW91 is a C-12 demethylated dutomycin derivative, which was identified in our previous research. In vitro cytotoxicity and apoptosis assays of these two compounds were conducted to demonstrate their antiproliferation activities. The results showed that both dutomycin and SW91 block cells at the S phase, whereas dutomycin shows more significant inhibition of cell growth. Their interactions with calf thymus DNA (CT-DNA) were investigated, with dutomycin exhibiting higher binding affinity. The molecular docking demonstrated that the 12-methyl group makes dutomycin attach to the groove of DNA. These findings suggest that dutomycin has binding higher affinity to DNA and impairs DNA replication resulting in more significant antitumor activity.
2. 13-Deoxo-13-iminodutomycin, a new neuroprotective compound from Streptomyces sp. RAP78
Yuta Ibusuki, Shoko Kimata, Yoichi Hayakawa J Antibiot (Tokyo). 2022 Jan;75(1):40-43. doi: 10.1038/s41429-021-00488-1. Epub 2021 Nov 26.
A neuroprotective compound (2) was isolated from the culture broth of the dutomycin (1) producer Streptomyces sp. RAP78. The molecular formula of 2 was established as C44H55NO16 by high-resolution FAB-MS. The structure was determined to be a new dutomycin derivative possessing an acetimidoyl group in place of an acetyl group by NMR spectroscopic analysis. 13-Deoxo-13-iminodutomycin (2) but not dutomycin (1) protected C6 rat glioma cells and N18-RE-105 rat primary retina-mouse neuroblastoma hybrid cells from glutamate-induced toxicity with EC50s of 0.12 µM and 0.72 µM, respectively.
3. Dutomycin Induces Autophagy and Apoptosis by Targeting the Serine Protease Inhibitor SERPINB6
Mina Jang, Shuta Hara, Gun-Hee Kim, Seung Min Kim, Sangkeun Son, Mincheol Kwon, In-Ja Ryoo, Hyemin Seo, Min Jung Kim, Nam-Doo Kim, Nak-Kyun Soung, Yong Tae Kwon, Bo Yeon Kim, Hiroyuki Osada, Jae-Hyuk Jang, Sung-Kyun Ko, Jong Seog Ahn ACS Chem Biol. 2021 Feb 19;16(2):360-370. doi: 10.1021/acschembio.0c00889. Epub 2021 Jan 31.
Autophagy plays an important role in maintaining tumor cell progression and survival in response to metabolic stress. Thus, the regulation of autophagy can be used as a strategy for anticancer therapy. Here, we report dutomycin (DTM) as a novel autophagy enhancer that eventually induces apoptosis due to excessive autophagy. Also, human serine protease inhibitor B6 (SERPINB6) was identified as a target protein of DTM, and its novel function which is involved in autophagy was studied for the first time. We show that DTM directly binds SERPINB6 and then activates intracellular serine proteases, resulting in autophagy induction. Inhibitory effects of DTM on the function of SERPINB6 were confirmed through enzyme- and cell-based approaches, and SERPINB6 was validated as a target protein using siRNA-mediated knockdown and an overexpression test. In a zebrafish xenograft model, DTM showed a significant decrease in tumor area. Furthermore, the present findings will be expected to contribute to the expansion of novel basic knowledge about the correlation of cancer and autophagy by promoting active further research on SERPINB6, which was not previously considered the subject of cancer biology.
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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 ╳
