Atebrine

Q lllllflCrillC [Atebrine, 3-chloro-9(4-diethylamino-l-methyl)butylamino-7-methoxy)acridine] dihydrochloride. [69-05-6] M 472.9, m 248-250 (dec), pK -6.49 (aq H2SO4), pKj 7.73 (ring NH ), pKj 10.18 (Et2N). Cryst from H2O (sol 2.8% at room temp) as yellow crystals. Slightly sol in MeOH and EtOH. Antimalarial, antiprotozoal and intercalates DNA. [Wolfe Antibiot 3 (Springer-Verlag) 203 1975.]... 

Initially approved in the 1930s as antimalarial drug, quinacrine (2) became one of the first potential substitutes to quinine. The total synthesis of quinacrine would be achieved in 1931 by German scientists at Bayer,and it would be subsequently marketed as Mepacrine or Atebrine. However, quinacrine would soon be replaced by another synthetic and more efficient antimalarial drug, chloroquine (3). 

Dip the slides into distilled water for a few seconds. Transfer to staining solution (0.5% w/v quinacrine dihydrochloride in 0.1 M phosphate buffer pH 4.5. The stain may be obtained from G.T. Gurr Ltd. Appendix 3 — under the name Atebrin ). 

Viallet, P., Kohen, E., Schactschabel, D.0., Marty, A., Salmon, J.M., Kohen, C., Leising, H.B. and Thorell, B. The effect of atebrine and an acridine analog (BCMA) on the coenzyme fluorescence spectra of cultured melanoma and Ehrlich ascites cells (EL2 cells). Histochemistry 57,... 

A special problem arose with respect to the antiplasmodial drugs chloroquine (Resochin) and quinacrine (Atebrin). Plasmodia can not be propagated in cell-free lifeless media and the limited availability of erythrocytic plasmodial cultures severely limits biochemical or molecular pharmacological studies on the action of antimalarials. The actions of chloroquine and quinacrine were, therefore, studied in Bacillus megaterium or E. coli, respectively 22 ... 

Synonyms. Acrichinum Acrinamine Atebrine Chinacrina Quinacrine. 

The true chemotherapeutic significance of this phenomenon is not defined at the moment but it requires careful scrutiny since it involves so many drugs and so many organisms (Coli, Salmonella, Klebsiella, Shigella, Vibrio). Perhaps, by means of this new look at a bacterially old process, we will now be able to devise a cure for this "infectious disease" of bacteria which will be effective in vivo and will finally enable us to deal with the important problem of bacterial resistance (cf. a clinical study9 of atebrin in combination therapy of multi-drug-resistant urinary infections). 

Atebrin 37 was used as an antimalarial during World War II, but is no longer important because of its side-effects. Acriflavine hydrochloride A 38 is an antiseptic. 

Christophers SR, Dissociation constants and solubilities of bases of anti-malarial compoimds. 1. Quinine. II. Atebrin, Ann. Trop. Med. Parasitol. 31,43-69 (1937). CA 31 58602. Cited in Perrin Bases no. 2958 ref. C30. NB This paper reported pKb values of 5.70 (equivalent to pXa = 8.47) and 9.85 (equivalent to pK = 4.32), using pKyf = 14.167 at 20 °C. These do not corre ond exactly wid the values quoted by Perrin. Also reported die solubility-temperature dependence. 

W G Christophers SR, Dissociation constants and solubilities of bases of anti-malarial compounds. I. Quinine. II. Atebrin, Ann. Trap. Med. Parasitol, 31,43-69 (1937). CA 31 58602. NB Results were reported as pJCb values. 

Shown in Table II are I q values for inhibition of electron transport in spinach thylakoids (water to ferricyanide) and the associated phosphorylation reaction by the test compounds. Also included are I5Q values for inhibition of the light-dependent quenching of atebrin fluorescence and the ratio obtained by dividing the Icq for the atebrin response by the I q for inhibition of photophosphorylation. The relative order of inhibitory potency for some of the compounds for inhibition of ferricyanide reduction has been reported previously (12). For the herbicides,... 

The atebrin/phosphorylation ratio (Table II, last column) relates inhibition of photophosphorylation to dissipation of the postulated energized state (A pH) of the thylakoid membrane. A low ratio suggests that the two responses are correlated. However, the high ratios obtained for ioxynil and propanil suggest that these two herbicides act as electron transport inhibitors rather than as uncouplers. 

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