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MedKoo Cat#: 565358 | Name: Auromomycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Auromomycin is a natural antibiotic.

Chemical Structure

Auromomycin
Auromomycin
CAS#NONE

Theoretical Analysis

MedKoo Cat#: 565358

Name: Auromomycin

CAS#: NONE

Chemical Formula: C21H24O5

Exact Mass: 356.1624

Molecular Weight: 356.42

Elemental Analysis: C, 70.77; H, 6.79; O, 22.44

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Auromomycin
IUPAC/Chemical Name
2,5,7-Trihydroxy-6-methyl-3-((2,4,4-trimethylcyclohex-1-en-1-yl)methyl)naphthalene-1,4-dione
InChi Key
BXMQOLHYUQUDBY-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H24O5/c1-10-9-21(3,4)6-5-12(10)7-14-18(24)16-13(19(25)20(14)26)8-15(22)11(2)17(16)23/h8,22-23,26H,5-7,9H2,1-4H3
SMILES Code
O=C1C(O)=C(CC2=C(C)CC(C)(C)CC2)C(C3=C1C=C(O)C(C)=C3O)=O
Appearance
Solid powder
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 356.42 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.

Recalculate based on batch purity %
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
1: Peach KC, Cheng AT, Oliver AG, Yildiz FH, Linington RG. Discovery and biological characterization of the auromomycin chromophore as an inhibitor of biofilm formation in Vibrio cholerae. Chembiochem. 2013 Nov 4;14(16):2209-15. doi: 10.1002/cbic.201300131. Epub 2013 Sep 17. PubMed PMID: 24106077; PubMed Central PMCID: PMC3947468. 2: Rauscher FJ 3rd, Beerman TA, Baker RM. Characterization of auromomycin-resistant hamster cell mutants that display a multidrug resistance phenotype. Mol Pharmacol. 1990 Aug;38(2):198-206. PubMed PMID: 2143555. 3: Van Roey P, Beerman TA. Crystal structure analysis of auromomycin apoprotein (macromomycin) shows importance of protein side chains to chromophore binding selectivity. Proc Natl Acad Sci U S A. 1989 Sep;86(17):6587-91. PubMed PMID: 2771945; PubMed Central PMCID: PMC297889. 4: Grimwade JE, Cullinan EB, Beerman TA. Neocarzinostatin and auromomycin preferentially cleave simian virus 40 DNA and chromosomes at a number of discrete locations. Biochim Biophys Acta. 1988 Jul 13;950(2):102-12. PubMed PMID: 2838085. 5: Grimwade JE, Beerman TA. Measurement of bleomycin, neocarzinostatin, and auromomycin cleavage of cell-free and intracellular simian virus 40 DNA and chromatin. Mol Pharmacol. 1986 Oct;30(4):358-63. PubMed PMID: 2429169. 6: Samy TS, Wellham L, Krishan A. Auromomycin-induced DNA damage and repair in human leukemic lymphoblasts (CCRF-CEM cells). Cancer Res. 1986 Feb;46(2):507-12. PubMed PMID: 2934127. 7: Samy TS, Siegel PJ, Hopper WE Jr, Krishan A. Experimental pharmacology of auromomycin in L1210 tumor cells in vitro and in vivo. Cancer Res. 1984 Aug;44(8):3202-7. PubMed PMID: 6589039. 8: Sieker LC, Samy TS. Structural study of crystalline auromomycin. Preliminary X-ray diffraction study of auromomycin and macromomycin. J Mol Biol. 1984 Apr 25;174(4):739-42. PubMed PMID: 6726802. 9: Rauscher F 3rd, Mueller G, Beerman T. The effects of the antitumor protein auromomycin on HeLa S3 nuclei. Release of soluble chromatin. Mol Pharmacol. 1983 Jul;24(1):97-102. PubMed PMID: 6306438. 10: Miwa N, Mizuno S, Okamoto S. Role of pronase-resistant peptide segments of the antitumor protein antibiotics, auromomycin and macromomycin, in stabilizing cytocidal activity of the chromophore moieties to carcinoma cells. J Antibiot (Tokyo). 1983 Jun;36(6):721-7. PubMed PMID: 6307961. 11: Miwa N, Mizuno S, Okamoto S. Differential cytotoxicity to human lung normal diploid, virus-transformed and carcinoma cells by the antitumor antibiotics, auromomycin and macromomycin, and their non-protein chromophores. J Antibiot (Tokyo). 1983 Jun;36(6):715-20. PubMed PMID: 6307960. 12: Suzuki H, Kirino Y, Tanaka N. Evidence for involvement of a free radical in DNA-cleaving reaction by macromomycin and auromomycin. J Antibiot (Tokyo). 1983 May;36(5):583-7. PubMed PMID: 6874573. 13: Suzuki H, Tanaka N. Quantitative analysis of DNA-cleaving activities of macromomycin, auromomycin, and their free chromophores, and some DNA-binding characteristics. J Antibiot (Tokyo). 1983 May;36(5):575-82. PubMed PMID: 6874572. 14: Kumada Y, Miwa T, Naoi N, Watanabe K, Naganawa H, Takita T, Umezawa H, Nakamura H, Iitaka Y. A degradation product of the chromophore of auromomycin. J Antibiot (Tokyo). 1983 Feb;36(2):200-2. PubMed PMID: 6833139. 15: Miwa N. Conformations of protein moieties and chromophore-protein interactions in the antitumor antibiotics, macromomycin and auromomycin, characterized by IR and CD spectral analysis. J Antibiot (Tokyo). 1982 Nov;35(11):1553-60. PubMed PMID: 7161194. 16: Rauscher F 3rd, Mueller G, McHugh M, Beerman T. Degradation of HelA S3 cell chromatin by auromomycin and its chromophore. Biochem Biophys Res Commun. 1982 Sep 16;108(1):355-62. PubMed PMID: 7150293. 17: Vandré DD, Montgomery R. Antitumor proteins of Streptomyces macromomyceticus: purification and characterization of auromomycin, macromomycin A, and macromomycin D. Biochemistry. 1982 Jul 6;21(14):3343-52. PubMed PMID: 6810921. 18: Naoi N, Kumada Y, Yamashita T, Takeuchi T, Umezawa H. DNA strand scission of methanol-extracted chromophores of macromomycin and auromomycin. J Antibiot (Tokyo). 1982 Jul;35(7):934-6. PubMed PMID: 7174544. 19: Naoi N, Miwa T, Okazaki T, Watanabe K, Takeuchi T, Umezawa H. Studies on the reconstitution of macromomycin a d auromomycin from the chromophore and protein moieties. J Antibiot (Tokyo). 1982 Jul;35(7):806-13. PubMed PMID: 7174534. 20: Takeshita M, Kappen LS, Grollman AP, Eisenberg M, Goldberg IH. Strand scission of deoxyribonucleic acid by neocarzinostatin, auromomycin, and bleomycin: studies on base release and nucleotide sequence specificity. Biochemistry. 1981 Dec 22;20(26):7599-606. PubMed PMID: 6173064.

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ELN441958

ELN441958

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