Granaticin | CAS#19879-06-2 | antibiotic

MedKoo Cat#: 599034 | Name: Granaticin

Description:

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

Granaticin is an antibiotic produced by Streptomyces species that is also cytotoxic (ED50 3.2 microgram/ml) against human oral epidermoid carcinoma (KB) cells.

Chemical Structure

Granaticin

CAS#19879-06-2

Theoretical Analysis

MedKoo Cat#: 599034

Name: Granaticin

CAS#: 19879-06-2

Chemical Formula: C22H20O10

Exact Mass: 444.1056

Molecular Weight: 444.39

Elemental Analysis: C, 59.46; H, 4.54; O, 36.00

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

Granaticin; U 19728; U-19728; U19728; NSC 77038; NSC-77038; NSC77038; Antibiotic WR 141;

IUPAC/Chemical Name

(3aS,5S,8S,9R,11S,13bS,15R)-7,8,9,12-tetrahydroxy-5,15-dimethyl-3,3a,5,8,9,10,11,13b-octahydro-2H-11,8-(epoxymethano)furo[3,2-c]naphtho[2,3-g]isochromene-2,6,13-trione

InChi Key

QBQXQYSJPWXZJL-VQJKQLIHSA-N

InChi Code

InChI=1S/C22H20O10/c1-5-11-15(21-8(30-5)4-10(24)32-21)19(27)13-14(17(11)25)20(28)16-12(18(13)26)7-3-9(23)22(16,29)6(2)31-7/h5-9,21,23,26,28-29H,3-4H2,1-2H3/t5-,6+,7-,8-,9+,21+,22+/m0/s1

SMILES Code

O=C(O1)C[C@@]2([H])[C@]1([H])C(C(C3=C4C(O)=C5C([C@@]6([H])O[C@H](C)[C@@]5(O)[C@H](O)C6)=C3O)=O)=C(C4=O)[C@H](C)O2

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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 444.39 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

1: Jiang B, Li S, Zhao W, Li T, Zuo L, Nan Y, Wu L, Liu H, Yu L, Shan G, Zuo L. 6-Deoxy-13-hydroxy-8,11-dione-dihydrogranaticin B, an intermediate in granaticin biosynthesis, from Streptomyces sp. CPCC 200532. J Nat Prod. 2014 Sep 26;77(9):2130-3. doi: 10.1021/np500138k. Epub 2014 Aug 25. PubMed PMID: 25153802. 2: Deng MR, Guo J, Ma LY, Li YX, Feng GD, Mo CY, Zhu HH. Complete genome sequence of Streptomyces vietnamensis GIMV4.0001 T, a genetically manipulable producer of the benzoisochromanequinone antibiotic granaticin. J Biotechnol. 2015 Apr 20;200:6-7. doi: 10.1016/j.jbiotec.2015.02.009. Epub 2015 Feb 14. PubMed PMID: 25687102. 3: Deng MR, Guo J, Zhu HH. Streptomyces vietnamensis GIMV4.0001: a granaticin-producing strain that can be readily genetically manipulated. J Antibiot (Tokyo). 2011 Apr;64(4):345-7. doi: 10.1038/ja.2011.3. Epub 2011 Feb 9. PubMed PMID: 21304531. 4: Deng M, Guo J, Huang Y, Zhu H. [Function of the granaticin biosynthetic gene orf20 from Streptomyces vietnamensis]. Wei Sheng Wu Xue Bao. 2011 Mar;51(3):402-9. Chinese. PubMed PMID: 21604555. 5: Ichinose K, Bedford DJ, Tornus D, Bechthold A, Bibb MJ, Revill WP, Floss HG, Hopwood DA. The granaticin biosynthetic gene cluster of Streptomyces violaceoruber Tü22: sequence analysis and expression in a heterologous host. Chem Biol. 1998 Nov;5(11):647-59. PubMed PMID: 9831526. 6: Heinstein P. Mechanism of action of granaticin: inhibition of ribosomal RNA maturation and cell cycle specificity. J Pharm Sci. 1982 Feb;71(2):197-200. PubMed PMID: 7062245. 7: Gibson-Clay G, Byrn SR, Heinstein P. The interaction of granaticin with nucleic acids and pyruvate decarboxylase. J Pharm Sci. 1982 Apr;71(4):467-8. PubMed PMID: 6177848. 8: Ogilvie A, Wiebauer K, Kersten W. Stringent control of ribonucleic acid synthesis in Bacillus subtilis treated with granaticin. Biochem J. 1975 Dec;152(3):517-22. PubMed PMID: 819000; PubMed Central PMCID: PMC1172504. 9: James PD, Edwards C. The effects of temperature on growth and production of the antibiotic granaticin by a thermotolerant streptomycete. J Gen Microbiol. 1989 Jul;135(7):1997-2003. PubMed PMID: 2575655. 10: Sherman DH, Malpartida F, Bibb MJ, Kieser HM, Bibb MJ, Hopwood DA. Structure and deduced function of the granaticin-producing polyketide synthase gene cluster of Streptomyces violaceoruber Tü22. EMBO J. 1989 Sep;8(9):2717-25. PubMed PMID: 2583128; PubMed Central PMCID: PMC401279. 11: Elson AL, Box SJ, Gilpin ML. New quinone antibiotics of the granaticin type, isolated from Streptomyces lateritius. I. Production, isolation and properties. J Antibiot (Tokyo). 1988 Apr;41(4):570-2. PubMed PMID: 3372363. 12: Tornus D, Floss HG. Identification of four genes from the granaticin biosynthetic gene cluster of Streptomyces violaceoruber Tü22 involved in the biosynthesis of L-rhodinose. J Antibiot (Tokyo). 2001 Jan;54(1):91-101. PubMed PMID: 11269719. 13: Bechthold A, Sohng JK, Smith TM, Chu X, Floss HG. Identification of Streptomyces violaceoruber Tü22 genes involved in the biosynthesis of granaticin. Mol Gen Genet. 1995 Sep 20;248(5):610-20. PubMed PMID: 7476861. 14: Kliuev NA, Zhil'nikov VG, Kudinova MK, Shaproĭko ES, Murenets NV. [Mass spectrophotometric study of the antibiotic granaticin]. Antibiot Med Biotekhnol. 1987 Sep;32(9):668-71. Russian. PubMed PMID: 3435095. 15: Ichinose K, Taguchi T, Bedford DJ, Ebizuka Y, Hopwood DA. Functional complementation of pyran ring formation in actinorhodin biosynthesis in Streptomyces coelicolor A3(2) by ketoreductase genes for granaticin biosynthesis. J Bacteriol. 2001 May;183(10):3247-50. PubMed PMID: 11325954; PubMed Central PMCID: PMC95226. 16: Smardová J, Spízek J, Stastná J, Klégr M. Effect of granaticin on the activity of DNA-directed RNA polymerase from Streptomyces granaticolor. Folia Microbiol (Praha). 1989;34(6):536-8. PubMed PMID: 2635132. 17: Weiser J, Janda I, Mikulík K, Tax J. Interaction of granaticin B with the transcription system of Bacillus subtilis. Folia Microbiol (Praha). 1977;22(5):329-38. PubMed PMID: 411719. 18: He XG, Chang CC, Chang CJ, Vederas JC, McInnes AG, Walter JA, Floss HG. Further studies on the biosynthesis of granaticin. Z Naturforsch C. 1986 Jan-Feb;41(1-2):215-21. PubMed PMID: 2939642. 19: Gilpin ML, Box SJ, Elson AL. New quinone antibiotics of the granaticin type, isolated from Streptomyces lateritius. II. Structure determination. J Antibiot (Tokyo). 1988 Apr;41(4):512-8. PubMed PMID: 3372358. 20: Sturdík E, Drobnica L. The cytotoxic action of granaticin, a sulfhydryl-reactive antibiotic, on Ehrlich ascites carcinoma cells. Neoplasma. 1983;30(1):3-6. PubMed PMID: 6835436.