Variamycin

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

MedKoo CAT#: 585362

CAS#: 12677-11-1

Description: Variamycin is a glycoside antibiotic from aureolic acid group that disrupts RNA synthesis in Staph aureus and HeLa cells.

Chemical Structure

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Variamycin
CAS# 12677-11-1
Instruction

Theoretical Analysis

MedKoo Cat#: 585362
Name: Variamycin
CAS#: 12677-11-1
Chemical Formula: C52H76O24
Exact Mass: 1,084.47
Molecular Weight: 1,085.156
Elemental Analysis: C, 57.56; H, 7.06; O, 35.38

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: Variamycin; Variamitsin; Antibiotic 6604-9A

IUPAC/Chemical Name: (2S,3S)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[4-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-2-[5-hydroxy-4-[5-hydroxy-4-(4-hydroxy-5-methoxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-7-methyl-3,4-dihydro-2H-anthracen-1-one

InChi Key: NKGFIFLSQXHQOK-QGZUPYPISA-N

InChi Code: InChI=1S/C52H76O24/c1-18-30(72-36-15-31(44(59)21(4)68-36)73-34-13-28(54)43(58)20(3)67-34)12-26-10-25-11-27(51(66-9)49(64)42(57)19(2)53)52(48(63)40(25)47(62)39(26)41(18)56)76-38-17-33(46(61)23(6)70-38)75-37-16-32(45(60)22(5)69-37)74-35-14-29(55)50(65-8)24(7)71-35/h10,12,19-24,27-29,31-38,42-46,50-62H,11,13-17H2,1-9H3/t19-,20?,21?,22?,23?,24?,27+,28?,29?,31?,32?,33?,34?,35?,36?,37?,38?,42+,43?,44?,45?,46?,50?,51+,52+/m1/s1

SMILES Code: O=C1[C@@H](OC2OC(C)C(O)C(OC3OC(C)C(O)C(OC4OC(C)C(OC)C(O)C4)C3)C2)[C@H]([C@H](OC)C([C@@H](O)[C@H](O)C)=O)CC5=C1C(O)=C6C(O)=C(C)C(OC7OC(C)C(O)C(OC8OC(C)C(O)C(O)C8)C7)=CC6=C5

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 1,085.16 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: Shashkov AS, Iashunskiĭ DV, Zhdanovich IuV, Lokshin GB. [Structure of the antineoplastic antibiotic variamycin]. Bioorg Khim. 1991 Mar;17(3):410-6. Russian. PubMed PMID: 1829608.

2: Gupta RS, Murray W, Gupta R. Cross resistance pattern towards anticancer drugs of a human carcinoma multidrug-resistant cell line. Br J Cancer. 1988 Oct;58(4):441-7. PubMed PMID: 3207599; PubMed Central PMCID: PMC2246790.

3: Romodanov SA, Annin EA, Verkhogliadova TP, Semenova VM, Egorenko GG. [Toxicity of anti-tumor preparations after intracranial, subarachnoid and suboccipital administration (experimental study)]. Zh Vopr Neirokhir Im N N Burdenko. 1987 Mar-Apr;(2):38-40. Russian. PubMed PMID: 2954348.

4: Kondakov LI, Khalanskiĭ AS, Terent'eva TG, Iablonovskaia LIa. [Effect of the antibiotic variamycin on the growth of a rabbit brain tumor]. Antibiot Med Biotekhnol. 1986 Aug;31(8):620-4. Russian. PubMed PMID: 2945512.

5: Maĭdanov VV, Egutkin NL, Nikitin IuE. [Surface-active properties of antibiotics]. Antibiotiki. 1983 Sep;28(9):663-5. Russian. PubMed PMID: 6638981.

6: Zhdanovich IuV, Kuzovkov AD, Veselova SI, Vagina IM, Sapozhnikov IuM. [Isolation of the new antibiotic variamycin B from the biosynthetic products of a Streptomyces olivovariabilis sp. nov. culture]. Antibiotiki. 1982 Feb;27(2):83-7. Russian. PubMed PMID: 6461290.

7: Terent'eva TG, Sokolov AB, Navashin SM. [Comparative experimental antitumor activity of the antibiotics variamycin and mitramycin]. Antibiotiki. 1978 Apr;23(4):349-51. Russian. PubMed PMID: 148238.

8: Radzievskaia VV, Terent'eva TG, Sokolov AB. [Action of aureolic acid and dactinomycin group antibiotics on human brain tumors in culture]. Antibiotiki. 1978 Feb;23(2):103-9. Russian. PubMed PMID: 204247.

9: Solov'ev VN, Egorenko GG. [Parameters of the toxic action of antibiotic derivatives of aureolic acid in acute and subchronic experiments]. Antibiotiki. 1976 Mar;21(3):258-61. Russian. PubMed PMID: 132138.

10: Terent'eva TG, Torbochkina LI, Bobikov EV, Sokolov AB, Aniskina RI. [C14-variamycin content in normal and tumorous brain tissues of white rats]. Antibiotiki. 1975 Nov;20(11):1032-5. Russian. PubMed PMID: 178269.

11: Bobikov EV, Terent'eva TG, Torbochkina LI, Sokolov AB, Sazykin IuO. [Study of the distribution of C14-variamycin and C14-mitramycim after intravenous administration to mice]. Antibiotiki. 1975 Aug;20(8):705-9. Russian. PubMed PMID: 132892.

12: Dzegilenko NB, Korchagin VB, Zhdanovich IV, Petrakushina ZV. [Quantitative method for determining variamycin]. Antibiotiki. 1975 Feb;20(2):154-8. Russian. PubMed PMID: 235239.

13: Zhdanovich IuV, Lokshin GB, Petrakushina ZV. [Method of determining variamycin using thin-layer chromatography]. Antibiotiki. 1974 Aug;19(8):687. Russian. PubMed PMID: 4455118.

14: Eselevich MM, Torbochkina LI, Bobikov EV, Sazykin IuO. [Complex formation of variamycin with DNA]. Antibiotiki. 1973 Jan;18(1):15-9. Russian. PubMed PMID: 4265402.

15: Eselevich MM, Torbochkina LI, Sazykin IuO. [Comparative study of the action of variamycin and its degradation products on the synthesis of nucleic acids and protein]. Antibiotiki. 1972 Nov;17(11):975-8. Russian. PubMed PMID: 4664267.

16: Rubtsova GV, Eselevich MM, Votrin II, Debov SS, Sazykin IuO. [Effect of variamycin on RNA biosynthesis in isolated cell nuclei of rat M-1 sarcoma and liver]. Biokhimiia. 1972 May-Jun;37(3):531-6. Russian. PubMed PMID: 4261537.

17: Rudaia SM, Singal EM, Il'inskaia SA, Solov'eva NK. [Act. olivovariabilis sp.nov., an organism producing variamycin, a new antitumor antibiotic]. Antibiotiki. 1971 Nov;16(11):969-76. Russian. PubMed PMID: 4947970.

18: Eselevich MM, Sazykin IuO, Torbochkina LI. [Study of the mechanism of action of variamycin]. Antibiotiki. 1971 May;16(5):400-4. Russian. PubMed PMID: 5002220.