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Biogenic Amine-Ionophore Interactions Proc. Nati. Acad. Scl. USA Vol. 74, No. 11, pp. 4734-4738, November 1977 Chemistry Biogenic amine-ionophore interactions: Structure and dynamics of lasalocid (X537A) complexes with phenethylamines and catecholamines in nonpolar solution (nuclear magnetic resonance/solution conformation/exchange kinetics) CYNTHIA SHEN AND DINSHAW J. PATEL Bell Laboratories, Murray Hill, New Jersey 07974 Communicated by F. A. Bovey, August 12,1977 ABSTRACT The ionophore lasalocid A forms 1:1 complexes alkaline earth ions are sandwiched between the polar faces of with phenethylamines (1-amino-1-phenylethane and 1-amino- two lasalocid anions in nonpolar solution (3, 12, 13) and in 2-phenylethane) and catecholamines (dopamine and norepi- nephrine) in nonpolar solution. We have undertaken high-res- crystals grown from the same medium (7-10). By contrast, olution proton nuclear magnetic resonance studies to deduce monomeric structures, in which the metal ion chelates to the structural and kinetic information on the ionophore-biogenic polar face of one lasalocid anion and solvent, are observed in amine complexes in chloroform solution. The coupling constant, polar media (4, 14). chemical shift, and relaxation time data demonstrate that the A number of biological studies have implicated the ability lasalocid backbone conformation and the primary amine of lasalocid to affect the distribution of biogenic amines across binding sites in the complexes are similar to those determined earlier for the alkali and alkaline earth complexes of this iono- the membrane (18-21). Westley and coworkers have demon- phore in solution. The exchange of lasalocid between the free strated that lasalocid A forms crystalline complexes with pri- acid (HX) and the primary amine complexes (RNH3X) in chlo- mary biogenic amines (22) and this has led us to undertake roform solution have been evaluated from the temperature- structural and kinetic investigations of these complexes in so- dependent line shapes at superconducting fields. The kinetic lution. These amines include 2-aminoheptane (1), the phen- parameters associated with the unimolecular dissociation ethylamines [1-amino-l-phenylethane (2), and 1-amino-2- phenylethane (3a)], and the catecholamines [dopamine (3b) and (RNH3X T RNH2 + HX) norepinephrine (3c)] (Fig. 2). and the bimolecular exchange (RNH3X + HX* k2 RNH3X* + HX) EXPERIMENTAL Materials. Lasalocid (ethanol-free) and R(+)- and S(-)- reactions have been deduced from an analysis of the lifetime 1-amino-l-phenylethanes were generous gifts from J. W. of the complex as a function of the reactant concentrations. The relative stability of the complex decreases in the order phenyl Westley and R. Evans, Jr., of Hoffman-La Roche, Nutley, NJ. > n-pentyl for substituents on the carbon a to the amino group Dopamine and R(+)-norepinephrine were purchased as their (1-amino-l-phenylethane and 2-aminoheptane) and phenyl > hydrochloride salts from Norse Laboratories, Santa Barbara, 3,4-dihydroxyphenyl for substituents on the carbon # to the CA. Deuterated chloroform, deuterated methylene chloride, amino group (l-amino-2-phenylethane and dopamine). These and 1-amino-2-phenylethane were purchased from Aldrich results suggest that nonpolar interactions between the biogenic Chemical Co. The solvents were dried over molecular sieves amine side chain and the lasalocid molecule contribute to the prior to use. stability of the complex in solution. Methods. Proton nuclear magnetic resonance (NMR) spectra Lasalocid A [see Fig. 1, for chemical sequence (1) and revised (360 MHz) were obtained in the Fourier transform mode on numbering system (2)] belongs to the family of linear carboxylic a Bruker HX-360 spectrometer interfaced with a Nicolet polyether antibiotics that transport alkali ions across membranes BNC-12 computer system. Proton longitudinal relaxation times (5, 6). The backbone of these ionophores adopts a folded (T1) were measured by using the (ir,r, ir/2) pulse sequence. head-to-tail conformation stabilized by intramolecular hy- The amine-lasalocid complexes of 1, 2, and 3a were gener- drogen bonds between the carboxylic and hydroxyl groups (refs. ated by mixing equimolar ratios of the amine and lasalocid in 5 and 6 and the references therein). The ionophores complex methylene chloride solution, followed by gradual addition of the alkali ions through their hydroxyl, ether, carbonyl, and n-hexane to precipitate the complexes. We followed the pro- carboxylate groups, resulting in a hydrophobic exterior which cedure of Westley et al. (22) to generate the lasalocid complexes facilitates the transport of metal ions across membranes. The of dopamine (3b) and R(+)-norepinephrine (3c). conformation of lasalocid resembles a flat disc with a polar and a nonpolar face (7-10), and it differs from the other carboxylic RESULTS AND DISCUSSION polyether antibiotics of larger dimensions which can form polar Stoichiometry. We have monitored the interaction of lasa- cavities for metal ion coordination. This permits the polar face locid with biogenic amines by following the chemical shift of lasalocid to coordinate ions with different radii and charges, changes of the ionophore proton NMR resonances on addition including alkali, alkaline earth (3, 4, 11-14), rare earth (15), and of amines to saturation concentrations. The exchange rate be- transition (16) metal ions as well as amines (17). The alkali and tween the free and complexed states (as monitored at the H5, The costs of publication of this article were defrayed in part by the H6, and HI1 resonances) was slow on the NMR time scale for payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U. S. C. §1734 solely to indicate Abbreviations: NMR, nuclear magnetic resonance; T1, proton longi- this fact. tudinal relaxation times. 4734 Downloaded by guest on October 1, 2021 Chemistry: Shen and Patel Proc. Natl. Acad. Sci. USA 74 (1977) 4735 .CH 3, [4] L5J L,/ J CH3 24 CH3 FIG. 1. Formula of lasalocid A. We have adopted the recently proposed numbering system (2), which differs from that was used in our previous papers (3, 4). from a comparison of the relative areas for a given resonance and at H5, H6, and H23 (located on the periphery of the folded in each state. By contrast, fast exchange between free and ionophore structure) (Table 2). complexed states was observed for amines 3b and 3c so that the The lasalocid H8 and HI, protons located on the polar face stoichiometry of the complex could be evaluated from the av- of the ionophore exhibited the largest decrease in T1 values on erage chemical shift changes for a given resonance of lasalocid complex formation (Table 2). This suggests that the biogenic on the gradual addition of amine (23). These studies establish amine binds to the polar face as observed in the crystalline state the formation of 1:1 complexes between lasalocid and the pri- (22), and the short T1 values for H8 and HI1 in the complexes mary amines 1, 2, 3a, 3b, and 3c in chloroform solution. The reflect proton-proton dipolar contributions to the relaxation complexation shifts are summarized in Table 1. time from proximal biogenic amine protons. Molecular Dimensions. X-ray studies have demonstrated We have also evaluated T1 for the biogenic amine protons that lasalocid forms 1:1 monomeric complexes with 1-amino- in these complexes and found them to be much shorter than the 1-phenylethane (2) for crystals grown from nonpolar solvents corresponding values expected for the free amines in solution. (22). This is in contrast to the dimeric structures (Na2X2, BaX2) For example, the relaxation times are 0.59 sec (NHS+ protons), observed in the crystalline state with the less bulky alkali and 0.54 ± 0.02 sec (CaH proton), 0.40 sec (CaCH3 protons), and alkaline earth ions (4, 15). The 360-MHz T1 values for lasalocid 1.1 + 0.2 sec (aromatic protons) in the 1-amino-1-phenyleth- A and its complexes with 2, 3a, 3b, and 3c in chloroform solu- ane-lasalocid A complex in chloroform solution at 20°. tion are summarized in Table 2. Structural Aspects. The x-ray structure of the 1:1 complex Previous studies have established a monomeric structure for of R(+)-l-amino-l-p-bromophenylethane and lasalocid es- lasalocid in nonpolar solution (3) so that the molecular weight tablishes that the amine nitrogen coordinates the ionophore by increases from 590 for the free acid to 711 for its complexes with hydrogen bonding at carboxylate 02, ether 06, and hydroxyl 2 and 3a and to 750 10 for its complexes with 3b and 3c. The 08 located on the polar face of the folded backbone of lasalocid increased value of the rotational correlation time in the 1:1 in the crystalline state (22). complexes should result in shorter T1 values compared to the The vicinal proton-proton coupling constants across C10-C11, values for the free acid. This was observed for the ionophore C11-C12, C14-CI5, and C15-CI6 single bonds were evaluated resonances at H12, H14, and H19 (located on the nonpolar face) for the 1:1 biogenic amine-lasalocid complexes and were similar Table 1. Lasalocid proton chemical shift changes upon complex formation with biogenic amines in chloroform at 270* HX-RNH3X H5 H6 H8 Hi, H12 H14 H15 Hi9 H23 For RNH2 1 -0.15 -0.14 +0.82 +0.22 -0.08 -0.14 +0.27 -0.03 -0.19 2a -0.13 -0.12 +0.81 +0.27 -0.09 -0.17 +0.21 -0.15 -0.40 3a -0.15 -0.14 +0.79 +0.19 -0.09 -0.14 +0.25 -0.03 -0.28 3b -0.13 -0.11 +0.57 +0.20 +0.01 -0.14 +0.13 -0.07 -0.59 3c -0.11 -0.09 +0.69 +0.31 +0.01 -0.10 +0.16 -0.03 -0.27 HXt 7.15 6.61 3.32 4.08 2.81 2.60 3.87 3.47 3.95 * (-) For upfield shifts, (+) for downfield shifts.
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