WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H130586
CAS#: 81552-36-5
Description: Trioxacarcin A is a natural alkylating agent. Trioxacarcins are a class of novel naturally occurring antitumor agents. Trioxacarcin A targets one flexible guanine in the loops of parallel G-quadruplex DNA (G4-DNA), stabilizing G4-DNA conformation by alkylation on RET G4-DNA.
Hodoodo Cat#: H130586
Name: Trioxacarcin A
CAS#: 81552-36-5
Chemical Formula: C42H52O20
Exact Mass: 876.31
Molecular Weight: 876.860
Elemental Analysis: C, 57.53; H, 5.98; O, 36.49
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Synonym: TXNA, TXN A, TXN-A, Antibiotic DC 45A, DC-45A. DC 45 A
IUPAC/Chemical Name: (2S,3R,4R,6R)-6-(((2S,2'R,4'S,8'S,10'S)-13a'-(((2S,4R,5S,6S)-5-Acetyl-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2'-(dimethoxymethyl)-10',12'-dihydroxy-7'-methoxy-5'-methyl-11'-oxo-3a',8',9',10',11',13a'-hexahydro-2'H,4'H-spiro[oxirane-2,1'-[2,4]epoxyfuro[3,2-b]naphtho[2,3-h]chromen]-8'-yl)oxy)-4-hydroxy-2,4-dimethyltetrahydro-2H-pyran-3-yl acetate
InChi Key: VVCYZYSLUSSELI-JMCWCFQGSA-N
InChi Code: InChI=1S/C42H52O20/c1-15-10-20-27(31(48)29-28(32(20)51-7)22(11-21(45)30(29)47)58-25-13-38(6,49)35(16(2)55-25)57-19(5)44)33-26(15)34-36-41(60-33,39(14-54-39)42(61-34,62-36)37(52-8)53-9)59-24-12-23(46)40(50,17(3)43)18(4)56-24/h10,16,18,21-25,34-37,45-46,48-50H,11-14H2,1-9H3/t16-,18-,21-,22-,23+,24-,25-,34-,35+,36?,38+,39-,40+,41?,42-/m0/s1
SMILES Code: CC(O[C@@H]1[C@H](C)O[C@@H](O[C@H]2C[C@H](O)C(C3=C2C(OC)=C4C=C(C)C([C@@]5([H])C(O[C@]6(C(OC)OC)O5)C([C@@]76OC7)(O[C@H]8C[C@@H](O)[C@@](O)(C(C)=O)[C@H](C)O8)O9)=C9C4=C3O)=O)C[C@]1(O)C)=O
Appearance: To be determined
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 876.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1. Yin S, Lan W, Hou X, Liu Z, Xue H, Wang C, Tang GL, Cao C. Trioxacarcin A Interactions with G-Quadruplex DNA Reveal Its Potential New Targets as an Anticancer Agent. J Med Chem. 2023 May 25;66(10):6798-6810. doi: 10.1021/acs.jmedchem.3c00178. Epub 2023 May 8. PMID: 37154782.
2. Pfoh R, Laatsch H, Sheldrick GM. Crystal structure of trioxacarcin A covalently bound to DNA. Nucleic Acids Res. 2008 Jun;36(10):3508-14. doi: 10.1093/nar/gkn245. Epub 2008 May 3. PMID: 18453630; PMCID: PMC2425490.
3. Pröpper K, Dittrich B, Smaltz DJ, Magauer T, Myers AG. Crystalline guanine adducts of natural and synthetic trioxacarcins suggest a common biological mechanism and reveal a basis for the instability of trioxacarcin A. Bioorg Med Chem Lett. 2014 Sep 15;24(18):4410-4413. doi: 10.1016/j.bmcl.2014.08.016. Epub 2014 Aug 14. PMID: 25176186.
5. Fitzner A, Frauendorf H, Laatsch H, Diederichsen U. Formation of gutingimycin: analytical investigation of trioxacarcin A-mediated alkylation of dsDNA. Anal Bioanal Chem. 2008 Feb;390(4):1139-47. doi: 10.1007/s00216-007-1737-6. Epub 2008 Jan 22. PMID: 18210096; PMCID: PMC2228378.
5. Nicolaou KC, Cai Q, Qin B, Petersen MT, Mikkelsen RJ, Heretsch P. Total synthesis of trioxacarcin DC-45-A2. Angew Chem Int Ed Engl. 2015 Mar 2;54(10):3074-8. doi: 10.1002/anie.201410369. Epub 2015 Jan 12. PMID: 25583408.
6. Chen X, Bradley NP, Lu W, Wahl KL, Zhang M, Yuan H, Hou XF, Eichman BF, Tang GL. Base excision repair system targeting DNA adducts of trioxacarcin/LL-D49194 antibiotics for self-resistance. Nucleic Acids Res. 2022 Mar 21;50(5):2417-2430. doi: 10.1093/nar/gkac085. PMID: 35191495; PMCID: PMC8934636.
7. Yang K, Qi LH, Zhang M, Hou XF, Pan HX, Tang GL, Wang W, Yuan H. The SARP Family Regulator Txn9 and Two-Component Response Regulator Txn11 are Key Activators for Trioxacarcin Biosynthesis in Streptomyces bottropensis. Curr Microbiol. 2015 Oct;71(4):458-64. doi: 10.1007/s00284-015-0868-9. Epub 2015 Jul 16. PMID: 26178900.
8. Hou XF, Song YJ, Zhang M, Lan W, Meng S, Wang C, Pan HX, Cao C, Tang GL. Enzymology of Anthraquinone-γ-Pyrone Ring Formation in Complex Aromatic Polyketide Biosynthesis. Angew Chem Int Ed Engl. 2018 Oct 8;57(41):13475-13479. doi: 10.1002/anie.201806729. Epub 2018 Sep 19. PMID: 30151879.
