関: macrocyclic lactam、rifabutin

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/03/31 23:18:43」(JST)

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Not to be confused with Annamycin.

Structure of geldanamycin, one of the benzoquinone ansamycins.

Ansamycins is a family of secondary metabolites that show antimicrobial activity against many gram-positive and some gram-negative bacteria and includes various compounds, among which: streptovaricins and rifamycins.^[1] In addition, these compounds demonstrate antiviral activity towards bacteriophages and poxviruses.

Structure

They are named ansamycins (from the Latin ansa, handle) because of their unique structure, which comprises an aromatic moiety bridged by an aliphatic chain.^[2] The main difference between various derivatives of ansamycins is the aromatic moiety, which can be a naphthalene ring or a naphthoquinone ring as in rifamycin and naphthomycin.^[3] Another variation comprises benzene or a benzoquinone ring system as in geldanamycin or ansamitocin. Ansamycins were first discovered in 1959 by Sensi et al. from Amycolatopsis mediterranei, an Actinomycete.^[4]

Examples

Rifamycins are a subclass of ansamycins with high potency against mycobacterial activity. This resulted in their wide use in the treatment of tuberculosis, leprosy, and AIDS-related mycobacterial infections.^[5] Since then various analogues have been isolated from other prokaryotes.

References

^ Wehrli, W.; Staehelin, M. (1971). "Actions of the rifamycins". Bacteriol. Rev. 35 (3): 290. PMC 378391. PMID 5001420. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=378391.
^ Prelog, V.; Oppolzer, W. (1973). "Rifamycins. 4. Ansamycins, a novel class of microbial metabolism products". Helv. Chim. Acta. 56: 2279.
^ Balerna, M.; Keller-Schierlein, W.; Martius, C.; Wolf, H.; Zähner, H. (1969). "Metabolic products of microorganisms. 72. Naphthomycin, an antimetabolite of vitamin K". Arch. Mikrobiol. 65 (4): 303. PMID 4988744.
^ Sensi, P.; Margalith, P.; Timbal, M. T. (1959). "Rifomycin, a new antibiotic; preliminary report". Ed. Sci. 14: 146.
^ Floss, H. G.; Yu, T. (1999). "Lessons from the rifamycin biosynthetic gene cluster". Curr. Opin. Chem. Biol. 3 (5): 592. doi:10.1016/S1367-5931(99)00014-9. PMID 10508670.

UpToDate Contents

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1. Rifamycins (rifampin, rifabutin, rifapentine)
2. HIV感染患者における肺結核の治療 treatment of pulmonary tuberculosis in the hiv infected patient
3. HIV感染患者におけるMycobacterium avium complex (MAC）感染症 mycobacterium avium complex mac infections in hiv infected patients
4. HIV陰性患者における肺非結核性抗酸菌感染症の治療 treatment of nontuberculous mycobacterial infections of the lung in hiv negative patients
5. 小児における播種性非結核性抗酸菌（NTM）感染症およびNTM菌血症の概要 overview of disseminated nontuberculous mycobacterial ntm infections and ntm bacteremia in children

English Journal

NAD(P)H:quinone oxidoreductase 1 (NQO1) in the sensitivity and resistance to antitumor quinones.

Siegel D, Yan C, Ross D.SourceSkaggs School of Pharmacy and Pharmaceutical Sciences, University of Colorado, Anschutz Medical Campus, 12858 East Montview Blvd., Aurora, CO 80045, USA.
Biochemical pharmacology.Biochem Pharmacol.2012 Apr 15;83(8):1033-40. Epub 2011 Dec 24.
Quinones represent a large and diverse class of antitumor drugs and many quinones are approved for clinical use or are currently undergoing evaluation in clinical trials. For many quinones reduction to the hydroquinone has been shown to play a key role in their antitumor activity. The two-electron r
PMID 22209713

Intramolecular proton transfer impact on antibacterial properties of ansamycin antibiotic rifampicin and its new amino analogues.

Pyta K, Przybylski P, Wicher B, Gdaniec M, Stefańska J.SourceFaculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland. piotrp@amu.edu.pl.
Organic & biomolecular chemistry.Org Biomol Chem.2012 Mar 28;10(12):2385-8. Epub 2012 Feb 20.
Intramolecular proton transfer in rifampicin (1) and its analogues 2-9 with the formation of zwitterions has been indicated by multinuclear NMR and crystallographic studies. Biological tests of 1-9 in combination with the analysis of ligand-protein interactions have revealed the relationship between
PMID 22349158

Japanese Journal

Mycotrienin II, a translation inhibitor that prevents ICAM-1 expression induced by pro-inflammatory cytokines

YAMADA Yuriko,TASHIRO Etsu,TAKETANI Shigeru,IMOTO Masaya,KATAOKA Takao
Journal of antibiotics 64(5), 361-366, 2011-05-25
NAID 10030638820

The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC_7N units in ansamycin and mitomycin antibiotics : a review

FLOSS Heinz G,YU Tin-Wein,ARAKAWA Kenji
Journal of antibiotics 64(1), 35-44, 2011-01-25
NAID 10030637355

13 アンサマイシン系抗腫瘍天然物、サイトトリエニンAの全合成(口頭発表の部)

林雄二郎,満庄司,石川勇人,山口潤一郎,田村友裕,今井浩貴,西ケ谷洋輔,高部賢一,掛谷秀昭,長田裕之
天然有機化合物討論会講演要旨集 (50), 101-106, 2008-09-01
… It possesses a (E, E, E)-triene within a 21-membered cyclic lactam which also contains four chiral centers, common structural features of the ansamycin-class of natural products, including the mycotrienins (or ansatrienins), trienomycins, thiazinotrienomycins, and trierixin. …
NAID 110007066767