Rubromycin

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

MedKoo CAT#: 462654

CAS#: 1393-16-4

Description: Rubromycin is a human telomerase inhibitor

Chemical Structure

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Rubromycin
CAS# 1393-16-4
Instruction

Theoretical Analysis

MedKoo Cat#: 462654
Name: Rubromycin
CAS#: 1393-16-4
Chemical Formula: C27H20O12
Exact Mass: 536.10
Molecular Weight: 536.445
Elemental Analysis: C, 60.45; H, 3.76; O, 35.79

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Wakita F, Ando Y, Ohmori K, Suzuki K. Model Reactions for the Enantioselective Synthesis of γ-Rubromycin: Stereospecific Intramolecular Photoredox Cyclization of an ortho-Quinone Ether to a Spiroacetal. Org Lett. 2018 Jul 6;20(13):3928-3932. doi: 10.1021/acs.orglett.8b01475. Epub 2018 Jun 22. PMID: 29932661.

2: Wei L, Xue J, Liu H, Wang W, Li Y. Synthesis of (±)-γ-rubromycin via a new hypoiodite-catalytic oxidative cycloetherification. Org Lett. 2012 Oct 19;14(20):5302-5. doi: 10.1021/ol3024874. Epub 2012 Oct 10. PMID: 23050595.

3: Bernardo CE, Silva PJ. Computational development of rubromycin-based lead compounds for HIV-1 reverse transcriptase inhibition. PeerJ. 2014 Jul 10;2:e470. doi: 10.7717/peerj.470. PMID: 25071993; PMCID: PMC4103094.

4: Wang W, Xue J, Tian T, Zhang J, Wei L, Shao J, Xie Z, Li Y. Total synthesis of (±)-δ-rubromycin. Org Lett. 2013 May 17;15(10):2402-5. doi: 10.1021/ol400864f. Epub 2013 May 1. PMID: 23635026.

5: Mizushina Y, Takeuchi T, Sugawara F, Yoshida H. 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.