Rubromycin | CAS#1393-16-4

MedKoo Cat#: 462654 | Name: Rubromycin

Description:

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

Rubromycin is a human telomerase inhibitor

Chemical Structure

Rubromycin

CAS#1393-16-4

Theoretical Analysis

MedKoo Cat#: 462654

Name: Rubromycin

CAS#: 1393-16-4

Chemical Formula: C27H20O12

Exact Mass: 536.0955

Molecular Weight: 536.45

Elemental Analysis: C, 60.45; H, 3.76; O, 35.79

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

Tuoromycin;

IUPAC/Chemical Name

methyl 7,8-dihydroxy-6-(2-(8-hydroxy-5,7-dimethoxy-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-2-yl)ethyl)-1-oxo-1H-isochromene-3-carboxylate

InChi Key

LQNGOIZVRFNQLO-UHFFFAOYSA-N

InChi Code

InChI=1S/C27H20O12/c1-35-14-9-15(36-2)22(30)19-18(14)21(29)13-8-12(38-25(13)24(19)32)5-4-10-6-11-7-16(26(33)37-3)39-27(34)17(11)23(31)20(10)28/h6-9,28,30-31H,4-5H2,1-3H3

SMILES Code

COC(C1=Cc2c(C(O1)=O)c(O)c(O)c(CCc3cc4c(C(c5c(C4=O)c(OC)cc(OC)c5O)=O)o3)c2)=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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 536.45 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

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Anti-cancer targeting telomerase inhibitors: β-rubromycin and oleic acid. Mini Rev Med Chem. 2012 Oct;12(11):1135-43. doi: 10.2174/138955712802762220. PMID: 22876944. 6: Mizushina Y, Ueno T, Oda M, Yamaguchi T, Saneyoshi M, Sakaguchi K. The biochemical mode of inhibition of DNA polymerase beta by alpha-rubromycin. Biochim Biophys Acta. 2000 Oct 18;1523(2-3):172-81. doi: 10.1016/s0304-4165(00)00119-7. PMID: 11042381. 7: Wilsdorf M, Reissig HU. A convergent total synthesis of the telomerase inhibitor (±)-γ-rubromycin. Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4332-6. doi: 10.1002/anie.201400315. Epub 2014 Mar 12. PMID: 24623604. 8: Atkinson DJ, Brimble MA. Isolation, biological activity, biosynthesis and synthetic studies towards the rubromycin family of natural products. Nat Prod Rep. 2015 Jun;32(6):811-40. doi: 10.1039/c4np00153b. PMID: 25798711. 9: Rathwell DC, Yang SH, Tsang KY, Brimble MA. An efficient formal synthesis of the human telomerase inhibitor (+/-)-gamma-rubromycin. Angew Chem Int Ed Engl. 2009;48(43):7996-8000. doi: 10.1002/anie.200903316. PMID: 19644991. 10: Metsä-Ketelä M, Ylihonko K, Mäntsälä P. Partial activation of a silent angucycline-type gene cluster from a rubromycin beta producing Streptomyces sp. PGA64. J Antibiot (Tokyo). 2004 Aug;57(8):502-10. doi: 10.7164/antibiotics.57.502. PMID: 15515887. 11: Wang X, Elshahawi SI, Ponomareva LV, Ye Q, Liu Y, Copley GC, Hower JC, Hatcher BE, Kharel MK, Van Lanen SG, She QB, Voss SR, Thorson JS, Shaaban KA. Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated Streptomyces. J Nat Prod. 2019 Dec 27;82(12):3469-3476. doi: 10.1021/acs.jnatprod.9b01015. Epub 2019 Dec 13. PMID: 31833370; PMCID: PMC7084111. 12: Brockmann H, Zeeck A. Rubromycine. 3. Die Konstitution von alpha-Rubromycin, beta-Rubromycin, gamma-Rubromycin und gamma-iso-Rubromycin [Rubromycins. 3. The constitution of alpha-rubromycin, beta-rubromycin, gamma-rubromycin, and gamma- iso-rubromycin]. Chem Ber. 1970;103(6):1709-26. German. doi: 10.1002/cber.19701030607. PMID: 5447178. 13: Wu KL, Mercado EV, Pettus TR. A convergent total synthesis of (±)-γ-rubromycin. J Am Chem Soc. 2011 Apr 27;133(16):6114-7. doi: 10.1021/ja1115524. Epub 2011 Mar 31. PMID: 21452818. 14: Ueno T, Takahashi H, Oda M, Mizunuma M, Yokoyama A, Goto Y, Mizushina Y, Sakaguchi K, Hayashi H. Inhibition of human telomerase by rubromycins: implication of spiroketal system of the compounds as an active moiety. Biochemistry. 2000 May 23;39(20):5995-6002. doi: 10.1021/bi992661i. PMID: 10821671. 15: Tsang KY, Brimble MA, Bremner JB. Use of a sonogashira-acetylide coupling strategy for the synthesis of the aromatic spiroketal skeleton of gamma- rubromycin. Org Lett. 2003 Nov 13;5(23):4425-7. doi: 10.1021/ol035723c. PMID: 14602016. 16: Akai S, Kakiguchi K, Nakamura Y, Kuriwaki I, Dohi T, Harada S, Kubo O, Morita N, Kita Y. Total synthesis of (+/-)-gamma-rubromycin on the basis of two aromatic Pummerer-type reactions. Angew Chem Int Ed Engl. 2007;46(39):7458-61. doi: 10.1002/anie.200702382. PMID: 17702074. 17: Brockmann H, Lenk W, Schwantje G, Zeeck A. Rubromycine, II [Rubromycin II]. Chem Ber. 1969;102(1):126-51. German. doi: 10.1002/cber.19691020118. PMID: 5764292. 18: Harunari E, Imada C, Igarashi Y, Fukuda T, Terahara T, Kobayashi T. Hyaluromycin, a new hyaluronidase inhibitor of polyketide origin from marine Streptomyces sp. Mar Drugs. 2014 Jan 21;12(1):491-507. doi: 10.3390/md12010491. PMID: 24451191; PMCID: PMC3917283. 19: Ortega HE, Batista JM Jr, Melo WGP, Clardy J, Pupo MT. Absolute Configurations of Griseorhodins A and C. Tetrahedron Lett. 2017 Dec 13;58(50):4721-4723. doi: 10.1016/j.tetlet.2017.11.008. Epub 2017 Nov 7. PMID: 29503481; PMCID: PMC5828249. 20: Harunari E, Imada C, Igarashi Y. Konamycins A and B and Rubromycins CA1 and CA2, Aromatic Polyketides from the Tunicate-Derived Streptomyces hyaluromycini MB-PO13T. J Nat Prod. 2019 Jun 28;82(6):1609-1615. doi: 10.1021/acs.jnatprod.9b00107. Epub 2019 Jun 7. PMID: 31181919.