Toxicology - Prof. RNDr. Jiří Patočka, DrSc

Aspiculamycin

Jiří Patočka

Aspiculamycin je nukleosidové antibiotikum, jehož producentem je druh Streptomycety - S. toyocaensis var. aspiculamyceticus. (Arai et al. 1974; Kondo et al., 1974). Je to bazická, ve vodě rozpustná substance, v níž funkci nukleotidu plní cytosin (1-(4-sarkosyl-D-seryl-D-serylamino-4-deoxy-β-D-glukopyranosyluronamid) (Haneishi et al. 1974). Látka je chemicky příbuzná s jiným nukleosidovým antibiotikem – gougerotinem (1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,4-dideoxy-4-[[N-(N-methylglycyl)-D-seryl]amino]-beta-D-glukopyranosyluronamid) (Carrasco a Vázquez, 1984; Du et al., 2013; Niu et al., 2013) nebo bagougeraminy A a B (Takahashi et al., 1986).

Aspiculamycin patří mezi antibiotika, která specificky blokují translaci v buňkách napadených virem (Lacal et al., 1980). Zvýšená účinnost aspiculamycinu v buňkách infikovaných virem, je důsledkem změněné kompártmentalizace a zvýšení propustnosti plazmatické membrány (Cameron et al., 1986). Antibiotikum narušuje 3'-adenosinový konec P/P'-vazebného místa tRNA a oblast peptidyltransferázové smyčky 23S rRNA (Kirillov et al., 1999).

Literatura
Arai M, Haneishi T, Enokita R, Kayamori H. Aspiculamycin, a new cytosine nucleoside antibiotic. I. Producing organism,fermentation and isolation. J Antibiot (Tokyo). 1974; 27(5): 329-333.
Cameron JM, Clemens MJ, Gray MA, Menzies DE, Mills BJ, Warren AP, Pasternak CA. Increased sensitivity of virus-infected cells to inhibitors of protein synthesis does not correlate with changes in plasma membrane permeability. Virology. 1986; 155(2): 534-544.
Carrasco L, Vázquez D. Molecular bases for the action and selectivity of nucleoside antibiotics. Med Res Rev. 1984; 4(4): 471-512.
Du D, Zhu Y, Wei J, Tian Y, Niu G, Tan H. Improvement of gougerotin and nikkomycin production by engineering their biosynthetic gene clusters. Appl Microbiol Biotechnol. 2013; 97(14): 6383-6396.
Haneishi T, Terahara A, Arai M. Aspiculamycin, a new cytosine nucleoside antibiotic. II. Physico-chemical properties and structural elucidation. J Antibiot (Tokyo). 1974; 27(5): 334-338.
Kirillov SV, Porse BT, Garrett RA. Peptidyl transferase antibiotics perturb the relative positioning of the 3'-terminal adenosine of P/P'-site-bound tRNA and 23S rRNA in the ribosome. RNA. 1999; 5(8): 1003-1013.
Kondo F, Kitano N, Domon H, Arai M, Haneishi T. Aspiculamycin, a new cytosine nucleoside antibiotic. IV. Antimycoplasma activity of aspiculamycin in vitro and in vivo. J Antibiot (Tokyo). 1974; 27(7): 529-534.
Lacal JC, Vazquez D, Fernandez-Sousa JM, Carrasco L. Antibiotics that specifically block translation in virus-infected cells. J Antibiot 1980; 33(4): 441-446.
Niu G, Li L, Wei J, Tan H. Cloning, heterologous expression, and characterization of the gene cluster required for gougerotin biosynthesis. Chem Biol. 2013; 20(1): 34-44.
Takahashi A, Ikeda D, Naganawa H, Okami Y, Umezawa H. Bagougeramines A and B, new nucleoside antibiotics produced by a strain of Bacillus circulans. II. Physico-chemical properties and structure determination. J Antibiot (Tokyo). 1986; 39(8): 1041-1046.


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