Hikizimycin

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

MedKoo CAT#: 584549

CAS#: 12706-94-4

Description: Hikizimycin is an antibiotic with antihelmintic properties.

Chemical Structure

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Hikizimycin
CAS# 12706-94-4
Instruction

Theoretical Analysis

MedKoo Cat#: 584549
Name: Hikizimycin
CAS#: 12706-94-4
Chemical Formula: C21H37N5O14
Exact Mass: 583.23
Molecular Weight: 583.548
Elemental Analysis: C, 43.22; H, 6.39; N, 12.00; O, 38.38

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: Hikizimycin; Anthelmycin; L 33876

IUPAC/Chemical Name: 4-amino-1-[5-amino-6-[1-[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6-pentahydroxyhexyl]-3,4-dihydroxyoxan-2-yl]pyrimidin-2-one

InChi Key: VQQSDVBOXQHCHU-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H37N5O14/c22-7-1-2-26(21(37)25-7)19-16(36)12(32)9(24)17(39-19)18(15(35)14(34)10(30)5(29)3-27)40-20-13(33)8(23)11(31)6(4-28)38-20/h1-2,5-6,8-20,27-36H,3-4,23-24H2,(H2,22,25,37)

SMILES Code: O=C1N=C(N)C=CN1C2OC(C(OC3OC(CO)C(O)C(N)C3O)C(O)C(O)C(O)C(O)CO)C(N)C(O)C2O

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 583.55 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: González A, Vázquez D, Jiménez A. Inhibition of translation in bacterial and eukaryotic systems by the antibiotic anthelmycin (hikizimycin). Biochim Biophys Acta. 1979 Feb 27;561(2):403-9. PubMed PMID: 371683.

2: Lacal JC, Vázquez D, Fernandez-Sousa JM, Carrasco L. Antibiotics that specifically block translation in virus-infected cells. J Antibiot (Tokyo). 1980 Apr;33(4):441-6. PubMed PMID: 6251018.

3: Rodriguez-Fonseca C, Amils R, Garrett RA. Fine structure of the peptidyl transferase centre on 23 S-like rRNAs deduced from chemical probing of antibiotic-ribosome complexes. J Mol Biol. 1995 Mar 24;247(2):224-35. PubMed PMID: 7707371.

4: Fürstner A, Wuchrer M. Concise approach to the "higher sugar" core of the nucleoside antibiotic hikizimycin. Chemistry. 2005 Dec 16;12(1):76-89. PubMed PMID: 16196060.

5: Vuilhorgne M, Ennifar S, Das BC, Paschal JW, Nagarajan R, Hagaman EW, Wenkert E. Structure analysis of the nucleoside disaccharide antibiotic anthelmycin by carbon-13 nuclear magnetic resonance spectroscopy. A structural revision of hikizimycin and its identity with anthelmycin. J Org Chem. 1977 Sep 30;42(20):3289-91. PubMed PMID: 903851.

6: Fernández-Puentes C. Permeability to inhibitors of protein synthesis in virus infected cells. Mol Biol Rep. 1984 Dec;10(2):65-8. PubMed PMID: 6527684.

7: Uchida K, Ichikawa T, Shimauchi Y, Ishikura T, Ozaki A. Hikizimycin, a new antibiotic. J Antibiot (Tokyo). 1971 Apr;24(4):259-62. PubMed PMID: 5572754.

8: Uchida K, Das BC. Hikosamine, a novel C11 aminosugar component of the antibiotic hikizimycin. Biochimie. 1973 May;55(5):635-6. PubMed PMID: 4754193.

9: Das BC, Defaye J, Uchida K. The structure of hikizimycin. I. Identification of 3-amino-3-deoxy-D-glucose and cytosine as structural components. Carbohydr Res. 1972 May;22(2):293-9. PubMed PMID: 5047747.

10: HAMMILL RL, HOEHN M. ANTHELMYCIN, A NEW ANTIBIOTIC WITH ANTHELMINTIC PROPERTIES. J Antibiot (Tokyo). 1964 May;17:100-3. PubMed PMID: 14171214.

11: Uchida K, Wolf H. Metabolic products of microorganisms 133. Inhibition of ribosomal peptidyl transferase by hikizimycin, a nucleoside antibiotic. J Antibiot (Tokyo). 1974 Oct;27(10):783-7. PubMed PMID: 4616934.

12: Masuda K, Nagatomo M, Inoue M. Direct assembly of multiply oxygenated carbon chains by decarbonylative radical-radical coupling reactions. Nat Chem. 2017 Mar;9(3):207-212. doi: 10.1038/nchem.2639. Epub 2016 Oct 31. PubMed PMID: 28221357.