MC-031
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| Category | Antibiotics |
| Catalog number | BBF-03642 |
| CAS | 134637-04-0 |
| Molecular Weight | 941.45 |
| Molecular Formula | C49H61ClO16 |
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Description
MC-031, an inhibitor of cholesterol biosynthesis, is produced by the strain of Streptomyces sp. A3761. It inhibited the synthesis of cholesterol from Mevalonic acid with IC50 of 10.6×10-5 mol/L. It also showed weak anti-gram-positive bacteria activity and inhibited the growth of HL-60 cells.
Specification
| Synonyms | O-Demethylchlorothricin |
| IUPAC Name | (3R,6R,7Z,13R,16S,17S,21R,22R)-17-[(2R,4R,5S,6R)-5-[(2S,4R,5R,6R)-4-(3-chloro-6-hydroxy-2-methylbenzoyl)oxy-5-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-28-hydroxy-3,22-dimethyl-23,26-dioxo-24,27-dioxapentacyclo[23.2.1.01,6.013,22.016,21]octacosa-4,7,14,25(28)-tetraene-4-carboxylic acid |
| Canonical SMILES | CC1CC23C(C=CCCCCC4C=CC5C(C4(C(=O)OC(=C2O)C(=O)O3)C)CCCC5OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC(=O)C8=C(C=CC(=C8C)Cl)O)O)C=C1C(=O)O |
| InChI | InChI=1S/C49H61ClO16/c1-23-22-49-28(19-30(23)44(55)56)12-9-7-6-8-11-27-15-16-29-31(48(27,5)47(59)65-42(43(49)54)46(58)66-49)13-10-14-35(29)62-37-20-34(52)41(26(4)61-37)64-38-21-36(40(53)25(3)60-38)63-45(57)39-24(2)32(50)17-18-33(39)51/h9,12,15-19,23,25-29,31,34-38,40-41,51-54H,6-8,10-11,13-14,20-22H2,1-5H3,(H,55,56)/b12-9-/t23-,25-,26-,27-,28-,29+,31-,34-,35+,36-,37+,38+,40-,41-,48-,49?/m1/s1 |
| InChI Key | KENNYGWGEDSIKQ-LVNKRDKJSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 1011.8°C at 760 mmHg |
| Melting Point | 208-211°C |
| Density | 1.42 g/cm3 |
Reference Reading
1. New cholesterol biosynthesis inhibitors MC-031 (O-demethylchlorothricin), -032 (O-demethylhydroxychlorothricin), -033 and -034
A Kawashima, Y Nakamura, Y Ohta, T Akama, M Yamagishi, K Hanada J Antibiot (Tokyo). 1992 Feb;45(2):207-12. doi: 10.7164/antibiotics.45.207.
In the course of our screening for microbial compounds which possessed inhibitory activities against biosynthesis of cholesterol from mevalonate, we isolated four new compounds from the cultural broth of Streptomyces sp. A7361. They are structurally related to, but distinct from chlorothricin.
2. Bcl-2/Bcl-xL inhibitor ABT-263 overcomes hypoxia-driven radioresistence and improves radiotherapy
Violetta Ritter, Franziska Krautter, Diana Klein, Verena Jendrossek, Justine Rudner Cell Death Dis. 2021 Jul 13;12(7):694. doi: 10.1038/s41419-021-03971-7.
Hypoxia, a characteristic of most human solid tumors, is a major obstacle to successful radiotherapy. While moderate acute hypoxia increases cell survival, chronic cycling hypoxia triggers adaptation processes, leading to the clonal selection of hypoxia-tolerant, apoptosis-resistant cancer cells. Our results demonstrate that exposure to acute and adaptation to chronic cycling hypoxia alters the balance of Bcl-2 family proteins in favor of anti-apoptotic family members, thereby elevating the apoptotic threshold and attenuating the success of radiotherapy. Of note, inhibition of Bcl-2 and Bcl-xL by BH3-mimetic ABT-263 enhanced the sensitivity of HCT116 colon cancer and NCI-H460 lung cancer cells to the cytotoxic action of ionizing radiation. Importantly, we observed this effect not only in normoxia, but also in severe hypoxia to a similar or even higher extent. ABT-263 furthermore enhanced the response of xenograft tumors of control and hypoxia-selected NCI-H460 cells to radiotherapy, thereby confirming the beneficial effect of combined treatment in vivo. Targeting the Bcl-2 rheostat with ABT-263, therefore, is a particularly promising approach to overcome radioresistance of cancer cells exposed to acute or chronic hypoxia with intermittent reoxygenation. Moreover, we found intrinsic as well as ABT-263- and irradiation-induced regulation of Bcl-2 family members to determine therapy sensitivity. In this context, we identified Mcl-1 as a resistance factor that interfered with apoptosis induction by ABT-263, ionizing radiation, and combinatorial treatment. Collectively, our findings provide novel insights into the molecular determinants of hypoxia-mediated resistance to apoptosis and radiotherapy and a rationale for future therapies of hypoxic and hypoxia-selected tumor cell fractions.
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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 ╳
