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(12) Patent Application Publication (10) Pub. No.: US 2004/0077731A1 Wilkemeyer Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2004/0077731A1 Wilkemeyer Et Al US 2004OO77731A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0077731A1 Wilkemeyer et al. (43) Pub. Date: Apr. 22, 2004 (54) METHOD AND COMPOUND FOR (22) Filed: Oct. 16, 2002 ANTAGONIZING INHIBITION EFFECTS OF ALCOHOL ON CELLADHESION Publication Classification (76) Inventors: Michael F. Wilkemeyer, Allston, MA (51) Int. Cl.' ........................ A61 K 31/045; A61K 31/05 (US); Michael E. Charness, Waban, (52) U.S. Cl. ........................... 514/724; 514/729; 514/731 MA (US) (57) ABSTRACT Correspondence Address: A method of antagonizing inhibition effects of alcohol on Dinesh Agarwal, P.C. cell adhesion, includes contacting a cell-adhesion molecule Law Office expressing cell with an effective amount of a compound, Suite 330 wherein the compound comprises an alcohol with five or 5350 Shawnee Road more carbons. More particularly, the compound comprises Alexandria, VA 22312 (US) 3-pentanol, 2-pentanol, cyclopentanol, 4-methyl-1-pentanol, 2-methyl-2-pentanol, decanol, 2,6-diisopropylphenol, or a (21) Appl. No.: 10/270,551 structural derivative thereof. Patent Application Publication Apr. 22, 2004 Sheet 1 of 8 US 2004/0077731A1 AGONSTS ANTAGONSTS 1-pentanol (C5) methanol HO Ho1N1,N1 . (C6. C 12) ethanol HO1N HO 1-propanol HON1 1-tridecanol (C13) OH 2-butanol - N-N- 3-pentanol cyclopropylmethanol HO -( ) benzyl alcohol 1Y 7 HO 1-butanol HO1N1N HO1N1S 3-buten-1-ol oo: OCD cyclobutanol HO-C) H O cyclopentano 2-methvi-2-butanolmethyl-2-butano X. 2-pentanol 3-methyl-1-butanol HO to-l. 4-methyl-1-pentanol 3,3-dimethyl-1-butanol or-X 2-methyl-2-pentanol 2-ethyl-1-butanol )-/ 2,6-di-isopropylphenol H OH MIXED AGONIST- INACTIVE O ANTAGONIST II HO-N-A e s 2-buten-1 ol H o1a1n cyclopropylethanol dimethylsulfoxide o1N1N1N1N1-1N1 1-tetradecanol (C14) o1N1a1a1a1a1a1a1 1-pentadecanol (C15) FIG. 1 Patent Application Publication Apr. 22, 2004 Sheet 2 of 8 US 2004/0077731A1 g s | o s s Patent Application Publication Apr. 22, 2004 Sheet 3 of 8 US 2004/0077731A1 Patent Application Publication Apr. 22, 2004 Sheet 4 of 8 US 2004/0077731 A1 O W7 08 09 07 Patent Application Publication Apr. 22, 2004 Sheet 5 of 8 US 2004/0077731 A1 | ‘Ioue?nq-L6o|(Wuu) "SDIV79 | |Ou?uO3-O- £---WuuL-u??nq-£|O- G-7–Wn|Oue?OO-). 0//+ 0/- 09| 0 Patent Application Publication Apr. 22, 2004 Sheet 6 of 8 US 2004/0077731 A1 HIH Ioud.dodost-P9'. H 1999" 1999. in 1999 III I'k oueue d-2-Aupou-z 10-kuence it is 1991 it. I've ueoued "MAOe Suofeue Patent Application Publication Apr. 22, 2004 Sheet 7 of 8 US 2004/0077731 A1 Patent Application Publication Apr. 22, 2004 Sheet 8 of 8 US 2004/0077731 A1 US 2004/0077731 A1 Apr. 22, 2004 METHOD AND COMPOUND FOR membrane-buffer partition coefficient (Charness et al., 1994; ANTAGONZING INHIBITION EFFECTS OF Ramanathan et al., 1996). In contrast, 1-pentanol and higher ALCOHOL ON CELL ADHESION 1-alcohols had no effect on L1-mediated cell-cell adhesion. The activity of 1-butanol, a four-carbon 1-alcohol, was BACKGROUND OF THE INVENTION abolished by the presence of a double bond between the 3 and 4 carbons; however, the presence of methyl groups at the 0001. The present invention is directed to inhibiting 2 or 3 carbons was associated with an increase in potency alcohol effects on cell adhesion, and more particularly to (Wilkemeyer et al., 2000). These findings indicate that method and compound for antagonizing inhibition effects of ethanol and other Small alcohols inhibit L1-mediated cell alcohol on cell adhesion, and further to the use of alcohol cell adhesion by binding within a well-defined, hydrophobic inhibition antagonists in prophylaxis or treatment of toxic pocket of a target protein, possibly L1. effects of alcohol. 0006 We believe that the existence of a specific binding 0002 Ethanol is a pleiotropic, weak central nervous pocket for ethanol would lead to the development of drugs system (CNS) drug (Charness et al., 1989). Ethanol potency that can block ethanol's effects. Strikingly, very low con is orders of magnitude less than that of other psychoactive centrations of both the five-carbon alcohol 1-pentanol and drugs. This low potency indicates that the brain does not the eight-carbon alcohol 1-octanol abolished the effects of express a high-affinity ethanol receptor; rather, ethanol is ethanol on L1-mediated cell-cell adhesion (Wilkemeyer et believed to produce its CNS effects by interacting at milli al., 2000). 1-Octanol also blocked the effects of ethanol on molar concentrations with components of diverse neu the morphology of dividing neural cells (Wilkemeyer et al., rotransmitter systems (Diamond and Gordon, 1997). For 2000) and prevented apoptosis and dysmorphology in cul many years, the prevailing view was that ethanol modified tured mouse embryos (Chen et al., 2001). 1-Octanol is a Synaptic activity by altering the biophysical properties of toxic compound that could not be used clinically. However, neuronal membranes, thereby disrupting indirectly the func the identification of a Single compound that blocks ethanol tion of various membrane proteins (Goldstein, 1983). Recent teratogenesis indicates the possibility of Safer alcohol research, however, Suggests that ethanol interacts directly antagonists. with Small regions of Selective neuronal proteins (Slater et al., 1993; Franks and Lieb, 1994; Harris, 1999). 0007. In U.S. Pat. No. 6,359,015 B1-Charness et al. (incorporated herein in its entirety by reference) a method 0003. The immunoglobulin neural cell adhesion mol and composition for antagonizing inhibition effects of alco ecule L1 is a multifunctional, transmembrane protein that hol on cell adhesion using 1-pentanol, 1-octanol, and deriva binds to L1 molecules on adjacent cells and to selective proteins in the extracellular matrix, cell membrane, and tives thereof, was disclosed. The present invention identifies cytoskeleton (Crossin and Krushel, 2000). L1 interactions a new Series of alcohol antagonists and examines their control cell-cell and cell-matrix events that are essential for Structure activity relation and mechanism of action. growth cone mobility, axon pathfinding, axon fasciculation, 0008 U.S. Pat. Nos. 5,496,851; 6,169,071; and 6,169, and neuronal migration. L1 binding also triggers a Series of 072, are directed to method and compounds for modulating transmembrane Signaling events, resulting in neurite out or inhibiting cell-cell-adhesion. growth and changes in growth cone morphology. L1 is expressed in the developing nervous System, where it playS OBJECTS AND SUMMARY OF THE a critical role in CNS development (Fransen et al., 1995; INVENTION Fransen et al., 1998; Demyanenko et al., 1999), and in the 0009. The principal object of the present invention is to mature CNS, where it may be involved in learning and provide a method and compound for antagonizing inhibition memory (Lithi et al., 1994; Rose, 1995). effects of alcohol on cell adhesion. This is based on the 0004 Mutations in the gene for L1 are associated with discovery that Straight, branched, and cyclic alcohols act on hydrocephalus, agenesis of the corpus calloSum, cerebellar multiple, discrete Sites to antagonize the actions of ethanol dysplasia and a variety of other brain malformations and 1-butanol on L1-mediated cell-cell adhesion. (Fransen et al., 1995). Because children with fetal alcohol Syndrome have neuropathology similar to that of children 0010 Another object of the present invention is to pro with L1 mutations, we studied the effects of ethanol on vide a method and compound for the prophylaxis or treat L1-mediated cell-cell adhesion (Charness et al., 1994; ment of neurotoxic effects of alcohol, particularly beverage Ramanathan et al., 1996). Clinically-relevant concentrations alcohol, i.e., ethanol. of ethanol inhibited L1-mediated cell adhesion in NG108-15 0011. An additional object of the present invention is to neuroblastomaxglioma hybrid cells, cerebellar granule cells, provide a method and compound for the prophylaxis or and selected human L1-transfected murine fibroblasts (Char treatment of fetal alcohol Syndrome, memory disorders, ness et al., 1994; Ramanathan et al., 1996; Wilkemeyer and malformations of the brain, cognitive learning disorders, Charness, 1998; Wilkemeyer et al., 1999). Similar concen neuro-behavioral disorders, neurological disorders, terato trations of ethanol also inhibited L1-mediated neurite out genesis, and alcohol-related memory disorder, and alcohol growth in cerebellar granule cells (Bearer et al., 1999). addiction in adults. 0005 Structure activity analysis of various straight 0012. In accordance with the present invention, a method chain, branched-chain, and cyclic alcohols revealed Surpris of antagonizing inhibition effects of alcohol on cell adhe ingly Strict Structural requirements for alcohol inhibition of Sion, includes contacting a cell-adhesion molecule express L1-mediated cell-cell adhesion (Wilkemeyer et al., 2000). ing cell with an effective amount of a compound, wherein The potency of methanol, ethanol, 1-propanol, and 1-bu the compound comprises an alcohol with five or more tanol increased as a function of carbon chain length and carbons. More particularly, the compound comprises 3-pen US 2004/0077731 A1 Apr. 22, 2004 tanol, 2-pentanol, cyclopentanol, 4-methyl-1-pentanol, declined from 1-dodecanol (C12) to 1-tridecanol (C13), and 2-methyl-2-pentanol, decanol, 2,6-diisopropylphenol, or a 1-tetradecanol (C14) and 1-pentadecanol (C15) were inac structural derivative thereof. tive. 0027. The presence and position of a double bond in the BRIEF DESCRIPTION OF THE DRAWINGS 1-butanol molecule determined whether a compound was a 0013 The above and other objects, novel features and full agonist (1-butanol), a mixed agonist-antagonist advantages of the present invention will become apparent (2-buten-1-ol), or an antagonist (3-buten-1-ol). Increasing from the following detailed description of the invention, as the concentration of agonist (1-butanol or ethanol) overcame illustrated in the drawings, in which: the antagonism of 3-buten-1-ol, benzyl alcohol, cyclopen tanol and 3-pentanol, but not that of 4-methyl-1-pentanol, 0.014 FIG.
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