gamma-Actinorhodin

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MedKoo CAT#: 565551

CAS#: 172886-23-6

Description: Actinorhodin is a benzoisochromanequinone dimer polyketide antibiotic produced by Streptomyces coelicolor.[2][3] The gene cluster responsible for actinorhodin production contains the biosynthetic enzymes and genes responsible for export of the antibiotic.[4] The antibiotic also has the effect of being a pH indicator due to its pH-dependent color change.[5]

Chemical Structure

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gamma-Actinorhodin
CAS# 172886-23-6
Instruction

Theoretical Analysis

MedKoo Cat#: 565551
Name: gamma-Actinorhodin
CAS#: 172886-23-6
Chemical Formula: C32H22O14
Exact Mass: 630.10
Molecular Weight: 630.514
Elemental Analysis: C, 60.96; H, 3.52; O, 35.52

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.
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Related CAS #: 1397-77-9  

Synonym: gamma-Actinorhodin; gamma Actinorhodin; Actinorhodin

IUPAC/Chemical Name: 17-Methyl-5-(2,4,7,9-tetrahydroxy-17-methyl-13-oxo-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1,3,5,7,9-pentaen-5-yl)-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),5-triene-2,4,7,9,13-pentone

InChi Key: XETDAWMNFAQXQO-UHFFFAOYSA-N

InChi Code: InChI=1S/C32H22O14/c1-7-17-23(31-13(43-7)5-15(35)45-31)29(41)19-11(33)3-9(25(37)21(19)27(17)39)10-4-12(34)20-22(26(10)38)28(40)18-8(2)44-14-6-16(36)46-32(14)24(18)30(20)42/h3-4,7-8,13-14,31-33,37,39,41H,5-6H2,1-2H3

SMILES Code: O=C(C(C(C(C1=CC(O)=C2C(O)=C(C3=C(O)C2=C1O)C4OC(CC4OC3C)=O)=C5)=O)=C6C5=O)C7=C(C8OC(CC8OC7C)=O)C6=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 630.51 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: Nass NM, Farooque S, Hind C, Wand ME, Randall CP, Sutton JM, Seipke RF, Rayner CM, O'Neill AJ. Revisiting unexploited antibiotics in search of new antibacterial drug candidates: the case of γ-actinorhodin. Sci Rep. 2017 Dec 12;7(1):17419. doi: 10.1038/s41598-017-17232-1. PubMed PMID: 29234001; PubMed Central PMCID: PMC5727142.

2: Neumeyer M, Brückner R. First Stereoselective Total Synthesis of a Dimeric Naphthoquinonopyrano-γ-lactone: (+)-γ-Actinorhodin. Angew Chem Int Ed Engl. 2017 Mar 13;56(12):3383-3388. doi: 10.1002/anie.201611183. Epub 2017 Feb 17. PubMed PMID: 28211203.

3: Mulay SV, Fernandes RA. Synthetic studies on actinorhodin and γ-actinorhodin: synthesis of deoxyactinorhodin and deoxy-γ-actinorhodin/crisamicin A isomer. Chemistry. 2015 Mar 16;21(12):4842-52. doi: 10.1002/chem.201406431. Epub 2015 Feb 11. PubMed PMID: 25677470.

4: Galet J, Deveau A, Hôtel L, Leblond P, Frey-Klett P, Aigle B. Gluconic acid-producing Pseudomonas sp. prevent γ-actinorhodin biosynthesis by Streptomyces coelicolor A3(2). Arch Microbiol. 2014 Sep;196(9):619-27. doi: 10.1007/s00203-014-1000-4. Epub 2014 Jun 7. PubMed PMID: 24906569.

5: Manikprabhu D, Lingappa K. γ Actinorhodin a natural and attorney source for synthetic dye to detect acid production of fungi. Saudi J Biol Sci. 2013 Apr;20(2):163-8. doi: 10.1016/j.sjbs.2013.01.004. Epub 2013 Feb 1. PubMed PMID: 23961232; PubMed Central PMCID: PMC3730729.

6: Mao XM, Sun ZH, Liang BR, Wang ZB, Feng WH, Huang FL, Li YQ. Positive feedback regulation of stgR expression for secondary metabolism in Streptomyces coelicolor. J Bacteriol. 2013 May;195(9):2072-8. doi: 10.1128/JB.00040-13. Epub 2013 Mar 1. PubMed PMID: 23457252; PubMed Central PMCID: PMC3624600.

7: Shin JH, Singh AK, Cheon DJ, Roe JH. Activation of the SoxR regulon in Streptomyces coelicolor by the extracellular form of the pigmented antibiotic actinorhodin. J Bacteriol. 2011 Jan;193(1):75-81. doi: 10.1128/JB.00965-10. Epub 2010 Oct 29. PubMed PMID: 21037009; PubMed Central PMCID: PMC3019960.

8: Parajuli N, Viet HT, Ishida K, Tong HT, Lee HC, Liou K, Sohng JK. Identification and characterization of the afsR homologue regulatory gene from Streptomyces peucetius ATCC 27952. Res Microbiol. 2005 Jun-Jul;156(5-6):707-12. Epub 2005 Apr 21. PubMed PMID: 15921897.

9: Verma S, Bhatia Y, Valappil SP, Roy I. A possible role of poly-3-hydroxybutyric acid in antibiotic production in Streptomyces. Arch Microbiol. 2002 Dec;179(1):66-9. Epub 2002 Nov 9. PubMed PMID: 12471506.

10: Coisne S, Béchet M, Blondeau R. Actinorhodin production by Streptomyces coelicolor A3(2) in iron-restricted media. Lett Appl Microbiol. 1999 Mar;28(3):199-202. PubMed PMID: 10196768.

11: Bystrykh LV, Fernández-Moreno MA, Herrema JK, Malpartida F, Hopwood DA, Dijkhuizen L. Production of actinorhodin-related "blue pigments" by Streptomyces coelicolor A3(2). J Bacteriol. 1996 Apr;178(8):2238-44. PubMed PMID: 8636024; PubMed Central PMCID: PMC177931.