Aranciamycin A | CAS#960622-70-2 | Anthracyclic antibiotic

MedKoo Cat#: 464401 | Name: Aranciamycin A

Description:

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

Aranciamycin A is an anthracyclic antibiotic that has been found in Streptomyces. It is active against M. bovis and B. subtilis (MICs = 30 and 7.5 µM, respectively) but not S. aureus, E. coli, P. aeruginosa, or C. albicans (MICs = >30 µM for all).

Chemical Structure

Aranciamycin A

CAS#960622-70-2

Theoretical Analysis

MedKoo Cat#: 464401

Name: Aranciamycin A

CAS#: 960622-70-2

Chemical Formula: C26H28O10

Exact Mass: 500.1682

Molecular Weight: 500.50

Elemental Analysis: C, 62.39; H, 5.64; O, 31.97

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Synonym

Aranciamycin A; Aranciamycin-A;

IUPAC/Chemical Name

(8R,10S)-10-(((2R,3R,4R,5R,6S)-4,5-dihydroxy-3-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-1,8,11-trihydroxy-8-methyl-7,8,9,10-tetrahydrotetracene-5,12-dione

InChi Key

DEPMSUJGYKZLRC-ZCUANGBISA-N

InChi Code

InChI=1S/C26H28O10/c1-10-19(28)23(32)24(34-3)25(35-10)36-15-9-26(2,33)8-11-7-13-18(21(30)16(11)15)22(31)17-12(20(13)29)5-4-6-14(17)27/h4-7,10,15,19,23-25,27-28,30,32-33H,8-9H2,1-3H3/t10-,15-,19-,23+,24+,25-,26+/m0/s1

SMILES Code

OC1=C(C2=CC3=C1[C@@H](O[C@H]4[C@H](OC)[C@H](O)[C@@H](O)[C@H](C)O4)C[C@@](O)(C)C3)C(C5=C(C=CC=C5C2=O)O)=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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 500.50 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: Cong Z, Huang X, Liu Y, Liu Y, Wang P, Liao S, Yang B, Zhou X, Huang D, Wang J. Cytotoxic anthracycline and antibacterial tirandamycin analogues from a marine-derived Streptomyces sp. SCSIO 41399. J Antibiot (Tokyo). 2019 Jan;72(1):45-49. doi: 10.1038/s41429-018-0103-6. Epub 2018 Sep 26. PMID: 30258222. 2: Koshla O, Lopatniuk M, Rokytskyy I, Yushchuk O, Dacyuk Y, Fedorenko V, Luzhetskyy A, Ostash B. Properties of Streptomyces albus J1074 mutant deficient in tRNALeuUAA gene bldA. Arch Microbiol. 2017 Oct;199(8):1175-1183. doi: 10.1007/s00203-017-1389-7. Epub 2017 May 20. PMID: 28528473. 3: Bilyk B, Horbal L, Luzhetskyy A. Chromosomal position effect influences the heterologous expression of genes and biosynthetic gene clusters in Streptomyces albus J1074. Microb Cell Fact. 2017 Jan 4;16(1):5. doi: 10.1186/s12934-016-0619-z. PMID: 28052753; PMCID: PMC5209838. 4: Khalil ZG, Raju R, Piggott AM, Salim AA, Blumenthal A, Capon RJ. Aranciamycins I and J, Antimycobacterial Anthracyclines from an Australian Marine-Derived Streptomyces sp. J Nat Prod. 2015 Apr 24;78(4):949-52. doi: 10.1021/acs.jnatprod.5b00095. Epub 2015 Mar 19. PMID: 25789410. 5: Nachtigall J, Schulz D, Beil W, Süssmuth RD, Fiedler HP. Aranciamycin anhydride, a new anthracycline-type antibiotic isolated from Streptomyces sp. Tü 6384(*). J Antibiot (Tokyo). 2010 Jul;63(7):397-9. doi: 10.1038/ja.2010.59. Epub 2010 Jun 16. PMID: 20551987. 6: Motohashi K, Takagi M, Shin-Ya K. Tetracenoquinocin and 5-iminoaranciamycin from a sponge-derived Streptomyces sp. Sp080513GE-26. J Nat Prod. 2010 Apr 23;73(4):755-8. doi: 10.1021/np9007409. PMID: 20192240. 7: Luzhetskyy A, Hoffmann J, Pelzer S, Wohlert SE, Vente A, Bechthold A. Aranciamycin analogs generated by combinatorial biosynthesis show improved antitumor activity. Appl Microbiol Biotechnol. 2008 Aug;80(1):15-9. doi: 10.1007/s00253-008-1515-1. Epub 2008 Jun 13. PMID: 18553079. 8: Luzhetskyy A, Mayer A, Hoffmann J, Pelzer S, Holzenkämper M, Schmitt B, Wohlert SE, Vente A, Bechthold A. Cloning and heterologous expression of the aranciamycin biosynthetic gene cluster revealed a new flexible glycosyltransferase. Chembiochem. 2007 Apr 16;8(6):599-602. doi: 10.1002/cbic.200600529. PMID: 17357167. 9: Sianidis G, Wohlert SE, Pozidis C, Karamanou S, Luzhetskyy A, Vente A, Economou A. Cloning, purification and characterization of a functional anthracycline glycosyltransferase. J Biotechnol. 2006 Sep 18;125(3):425-33. doi: 10.1016/j.jbiotec.2006.03.035. Epub 2006 May 19. PMID: 16713002. 10: Bols M, Binderup L, Hansen J, Rasmussen P. Synthesis and collagenase inhibition of new glycosides of aranciamycinone: the aglycon of the naturally occurring antibiotic aranciamycin. Carbohydr Res. 1992 Nov 4;235:141-9. doi: 10.1016/0008-6215(92)80084-e. PMID: 1335359. 11: Bols M, Binderup L, Hansen J, Rasmussen P. Inhibition of collagenase by aranciamycin and aranciamycin derivatives. J Med Chem. 1992 Jul 24;35(15):2768-71. doi: 10.1021/jm00093a008. PMID: 1322986. 12: Keller-Schierlein W, Müller A. The sugar component of aranciamycin: 2-0-methyl-L-rhamnose. Experientia. 1970 Sep 26;26(9):929-30. doi: 10.1007/BF02114109. PMID: 5478623. 13: Keller-Schierlein W, Sauerbier J, Vogler U, Zähner H. Stoffwechselprodukte von Mikroorganismen. Aranciamycin [Metabolites of microorganisms. Aranciamycin]. Helv Chim Acta. 1970;53(4):779-89. German. doi: 10.1002/hlca.19700530413. PMID: 5433438.