AdipoGen Life Sciences

Rifamycin AF-O13

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AG-CN2-0336-M01010 mgCHF 150.00

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Specifications / Handling

More Information
Product Details
Synonyms	3-Formylrifamycin SV O-n-octyloxime; 3- Formylrifamycin SV O-octyloxime; AF 013; NCI 143-483; NSC 143483; Rifampicin AF 013; Rifamycin AF 013
Product Type	Chemical
Properties
Formula	C₄₆H₆₄N₂O₁₃
MW	853.0
CAS	35225-13-9
Source/Host Chemicals	Semisynthetic.
Purity Chemicals	≥95% (HPLC)
Appearance	Red powder.
Solubility	Soluble in DMSO, aqueous acetonitrile or ethanol.
Identity	Determined by ¹H-NMR and MS.
InChi Key	DTEDDHSJILGOKQ-RIPXLWFGSA-N
Smiles	OC1=C(NC(/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@H]([C@H]2C)O)=O)C(/C=N/OCCCCCCCC)=C(O)C3=C4C(O[C@@](O/C=C/[C@H](OC)[C@H]([C@H]2OC(C)=O)C)(C)C4=O)=C(C)C(O)=C31
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light. Protect from light when in solution.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Scientific Background Information

Product Description

Ansamycin antibiotic.
Potent inhibitor of nucleic acid polymerizing enzymes and of some hormone receptors.
Selective inhibitor of bacterial DNA-dependent RNA polymerase (RNAP).
Inhibitor of RNA-dependent DNA polymerase of MSV.
Effective against mycobacteria and therefore might be used in research of tuberculosis, leprosy and Mycobacterium avium complex (MAC) infections.

Product-specific References

Reverse transcriptase, RNA tumor virus transformation, and derivatives of rifamycin SV: R.C. Ting, et al.; Nat. New Biol. 236, 163 (1972)
Selective toxicity of rifamycin derivatives for leukaemic human leucocytes: R.G. Smith, et al.; Nat. New Biol. 236, 1166 (1972)
Rifamycin antibiotics: inhibitors of Rauscher murine leukemia virus reverse transcriptase and of purified DNA polymerases from human normal and leukemic lymphoblasts: S.S. Yang, et al.; J. Natl. Cancer Inst. 49, 7 (1972)
Rifamycin Derivatives Strongly Inhibiting RNA>DNA Polymerase (Reverse Transcriptase) of Murine Sarcoma Viruses: C. Gurgo, et al.; J. Natl. Cancer Inst. 49, 61 (1972)
Selective inhibition of Rous sarcoma virus production in transformed chick fibroblasts by two rifamycin derivatives: S. Barlati & P. Vigier; FEBS Lett. 24, 343 (1972)
Inhibition of RNA polymerases from rat liver by the semi-synthetic rifampicin derivatives: P.P. Juhasz, et al.; FEBS Lett. 27, 30 (1972)
Mechanism of action of a rifamycin derivative (AF-013) which is active on the nucleic acid polymerases insensitive to rifampicin: S. Riva, et al.; BBRC 49, 1263 (1972)
Action of rifamycin derivatives on RNA polymerase of human leukemic lymphocytes: M.J. Tsai & G.F. Saunders; PNAS 70, 2072 (1973)
Activation of DNA polymerase of murine leukemia virus by rifamycin derivatives: S. Barlati, et al.; Intervirol. 2, 33 (1974)
Specific inhibition of a primer-dependent nucleotide chain elongation reaction by the rifamycin derivative AF/013; S.T. Jacob, et al.; Arch. Biochem. Biophys. 164, 771 (1974)
Oximes of 3-formylrifamycin SV. Synthesis, antibacterial activity, and other biological properties: R. Cricchio, et al.; J. Med. Chem. 17, 396 (1974)
The inhibition of nuclear RNA synthesis by the rifampicin derivative AF/013 in living cells: E. Egyhazi; Biochim. Biophys. Acta 378, 205 (1975)
Mechanism of inhibition of RNA polymerase II and poly(adenylic acid) polymerase by the O-n-octyloxime of 3-formylrifamycin SV: K.M. Rose, et al.; Biochemistry 14, 3598 (1975)
The rifamycin derivative AF/013 is cytolytic: U. Scheer; Mol. Pharmacol. 11, 883 (1975)
Differential susceptibility of spleen focus-forming virus and murine leukemia viruses to ansamycin antibiotics: J.S. Horoszewicz, et al.; Antimicrob. Agents Chemother. 12, 4 (1977)
Different modes of inhibition of purified ribonucleic acid directed deoxyribonucleic acid polymerase of avian myeloblastosis virus by rifamycin SV derivatives: C. Gurgo & D.P.Grandgenett; Biochemistry. 16, 786 (1977)
Inhibition of DNA polymerases alpha and gamma by rifamycin derivative AF/013: T. Yagura, et al.; J. Biochem. 90, 1397 (1981)
Inhibitory action of aurintricarboxylic acid and rifamycin AF/013 at the polynucleotide domain of 1,25-dihydroxyvitamin D3-receptor complexes: W.S. Mellon; Biochem. Pharmacol. 33, 1047 (1984)
Inhibition by rifamycin AF/013 of thyroid hormone binding to the nuclear receptor: A. Inoue, et al.; J. Biochem. 102, 1365 (1987)
Effects of antibiotics on RNA polymerase III transcription: K. Logan & S. Ackerman; DNA 7, 483 (1988)

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