Substituent effects on the ionization and partitioning of p-(aminoethyl)phenols and structurally related compounds: Electrostatic effects dependent on conformation

Journal of Pharmaceutical Sciences

Volumn 98, Issue 12, 2009, Pages 4534-4544

  Tejwani, Ravindra W ^a,b   Stouch, Terry R ^a   Anderson, Bradley D ^a  

^a University of Kentucky   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

Functional group contributions; Hydrophobicity; Ionization constant; Linear free energy relationships (LFERs); Microscopic ionization constant; Partition coefficient

Indexed keywords

1,9 DECADIENE; 4 (AMINOETHYL)PHENOL DERIVATIVE; ALKADIENE; AMPHOLYTE; FUNCTIONAL GROUP; PHENOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTRICITY; IONIZATION; PARTITION COEFFICIENT; PH; PKA;

EID: 71649113810     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21775     Document Type: Article

References (56)

1. van de Waterbeemd H, Gifford E. 2003. ADMET in silico modelling: Towards prediction paradise? Nat Rev Drug Discov 2:192-204.
2. ACD-pKa. 1994-2007. Advanced Chemistry Development/pKa dB, 10.0 edition. Toronto, ON, Canada: Advanced Chemistry Development, Inc.
3. Platts JA, Abraham MH, Butina D, Hersey A. 2000. Estimation of molecular linear free energy relationship descriptors by a group contribution approach. 2. Prediction of partition coefficients. J Chem Inf Comput Sci 40:71-80.
4. Zhang J, Kleinoder T, Gasteiger J. 2006. Prediction of pKa values for aliphatic carboxylic acids and alcohols with empirical atomic charge descriptors. J Chem Inf Model 46:2256-2266. (Pubitemid 46008099)
5. Perrin DD, Dempsey B, Serjeant EP. 1981. pKa prediction for organic acids and bases, 1st edition. London; New York: Chapman and Hall. 146 p.
6. Brandariz I, Fiol S, Herrero R, Vilarino T, Sastre de Vicente M. 1993. Protonation constants of alphaalanine, gamma-aminobutyric acid, and epsilonaminocaproic acid. J Chem Eng Data 38:531-533.
7. Takacs-Novak K, Noszal B, Hermecz I, Kereszturi G, Podanyi B, Szasz G. 1990. Protonation equilibria of quinolone antibacterials. J Pharm Sci 79:1023-1028.
8. Langlois M-H, Montagut M, Dubost J-P, Grellet J, Saux M-C. 2005. Protonation equilibrium and lipophilicity of moxifloxacin. J Pharm Biomed Anal 37:389-393.
9. Szakacs Z, Beni S, Varga Z, Orfi L, Keri G, Noszal B. 2005. Acid-base profiling of imatinib (Gleevec) and its fragments. J Med Chem 48:249-255. (Pubitemid 40105263)
10. Gulyaeva N. 2003. AZPLACBZ pH dependence of the relative hydrophobicity and lipophilicity of amino acids and peptides measured by aqueous two-phase and octanol-buffer partitioning. J Pept Res 61:71-79. (Pubitemid 36152729)
11. Noszal B, Szakacs Z. 2003. Microscopic protonation equilibria of oxidized glutathione. J Phys Chem B 107:5074-5080.
12. Riegelman S, Strait LA, Fischer EZ. 1962. Acid dissociation constants of phenylalkanolamines. J Pharm Sci 51:129-133.
13. Peinhardt G, Wiese M. 2001. Microionization constants: Novel approach for the determination of the zwitterionic equilibrium of hydroxyphenylalkylamines by photometric titration. Int J Pharm 215:83-89. (Pubitemid 32206606)
14. Nagy PI, Takacs-Novak K. 2004. Tautomeric and conformational equilibria of biologically important (hydroxyphenyl)alkylamines in the gas phase and in aqueous solution. Phys Chem Chem Phys 6:2838-2848.
15. Martin RB. 1971. Zwitterion formation upon deprotonation in L-3, 4-dihydroxyphenylalanine and other phenolic amines. J Phys Chem 75:2657-2661.
16. Kappe T, Armstrong MD. 1965. Ultraviolet absorption spectra and apparent acidic dissociation constants of some phenolic amines. J Med Chem 8:368-374.
17. Armstrong J, Barlow RB. 1976. The ionization of phenolic amines, including apomorphine, dopamine, and catecholamines and an assessment of zwitterion constants. Br J Pharmacol 57:501-516.
18. Granot J. 1976. NMR studies of catecholamines, Acid dissociation equilibria in aqueous solutions. FEBS Lett 67:271-275.
19. Kiefer EF. 1972. Rapid, convenient preparative procedure for phenethylamines. J Med Chem 15:214.
20. Borgman RJ, McPhillips JJ, Stitzel RE, Goodman IJ. 1973. Synthesis and pharmacology of centrally acting dopamine derivatives and analogs in relation to Parkinson's disease. J Med Chem 16:630-633.
21. Tejwani RW, Anderson BD. 2008. Influence of intravesicular pH drift and membrane binding on the liposomal release of a model amine-containing permeant. J Pharm Sci 97:381-399.
22. Anderson BD, Rytting JH, Higuchi T. 1980. Solubility of polar organic solutes in nonaqueous systems: Role of specific interactions. J Pharm Sci 69:676-680. (Pubitemid 10002950)
23. Anderson BD, Rytting JH, Higuchi T. 1979. Influence of self-association on the solubility of phenol in isooctane and cyclohexane. J Am Chem Soc 101:5194-5197.
24. Rytting JH, Anderson BD, Higuchi T. 1978. Vapor pressure studies of the self-association of alcohols in isooctane. 2. The effect of chain branching. J Phys Chem 82:2240-2245. (Pubitemid 9040616)
25. Anderson BD, Rytting JH, Higuchi T. 1978. Vapor pressure studies of self-association of alcohols in isooctane. I. The effect of chain length. Int J Pharm 1:15-31. (Pubitemid 9040616)
26. Anderson BD, Rytting JH, Lindenbaum S, Higuchi T. 1975. Calorimetric study of the self-association of primary alcohols in isooctane. J Phys Chem 79:2340-2344.
27. Munson MSB. 1965. Proton affinities and the methyl inductive effect. J Am Chem Soc 87:2332-2336.
28. Hall NF, Sprinkle MR. 1932. Relations between the structure and strength of certain organic bases in aqueous solution. J Am Chem Soc 54:3469-3485.
29. Harned HS, Owen BB. 1930. The thermodynamic properties of weak acids and bases in salt solutions, and an exact method of determining their dissociation constants. J Am Chem Soc 52:5079-5091.
30. Harned HS, Robinson RA. 1928. The ionic concentrations and activity coefficients of weak electrolytes in certain salt solutions. J Am Chem Soc 50:3157-3178.
31. Coetzee JF, Padmanabhan GR. 1965. Properties of bases in acetonitrile as solvent. IV. Proton acceptor power and homoconjugation of mono- and diamines. J Am Chem Soc 87:5005-5010.
32. Brown HC, Bartholomay H, Taylor MD. 1944. Acidbase studies in gaseous systems. II. The anomalous base strength of the methylamines; a new manifestation of steric strain. J Am Chem Soc 66:435-442.
33. Aue DH, Webb HM, Bowers MT. 1976. A thermodynamic analysis of solvation effects on the basicities of alkylamines. An electrostatic analysis of substituent effects. J Am Chem Soc 98:318-329.
34. Bowers MT, Aue DH, Webb HM, McIver RT. 1971. Equilibrium constants for gas-phase ionic reactions. Accurate determination of relative proton affinities. J Am Chem Soc 93:4314-4315.
35. Arnett EM, Jones FM, Taagepera M, Henderson WG, Beauchamp JL, Holtz D, Taft RW. 1972. Complete thermodynamic analysis of the "anomalous order" of amine basicities in solution. J Am Chem Soc 94:4724-4726.
36. Aue DH, Webb HM, Bowers MT. 1972. Quantitative relative gas-phase basicities of alkylamines. Correlation with solution basicity. J Am Chem Soc 94:4726-4728.
37. Henderson WG, Taagepera M, Holtz D, McIver RT, Beauchamp JL, Taft RW. 1972. Methyl substituent effects in protonated aliphatic amines and their radical cations. J Am Chem Soc 94:4728-4729.
38. Hammett LP. 1937. Effect of structure upon the reactions of organic compounds. Benzene derivatives. J Am Chem Soc 59:96-103.
39. Taft RW, Jr. 1953. The general nature of the proportionality of polar effects of substituent groups in organic chemistry. J Am Chem Soc 75:4231-4238.
40. Ishimitsu T, Hirose S, Sakurai H. 1979. Microscopic acid dissociation constants of 3,4-dihydroxyphenylbutyric acid and 3,4-dihydroxybenzoic acid. Chem Pharm Bull 27:247-251. (Pubitemid 9114524)
41. Demirelli H, Koeseoglu F. 2004. Solvent and substituent effects on the protonation of anilines in dioxane-water mixtures. J Solut Chem 33:1501-1515. (Pubitemid 40385404)
42. Bjerrum N. 1923. Dissociation constants of polybasic acids and their application to the calculation of molecular dimensions. Z Physik Chem 106:219-242.
43. Edsall JT, Martin RB, Hollingworth BR. 1958. Ionization of individual groups in dibasic acids, with application to the amino and hydroxyl groups of tyrosine. Proc Natl Acad Sci USA 44:505-518.
44. Kirkwood JG, Westheimer FH. 1938. The electrostatic influence of substituents on the dissociation constants of organic acids. I. J Chem Phys 6:506-512.
45. Westheimer FH, Kirkwood JG. 1938. The electrostatic influence of substituents on the dissociation constants of organic acids. II. J Chem Phys 6:513-517.
46. Ehrenson S. 1976. Transmission of substituent effects. Generalization of the ellipsoidal cavity field effect model. J Am Chem Soc 98:7510-7514.
47. Robertson EG, Simons JP, Mons M. 2001. Comment on "structural and vibrational assignment of p-methoxyphenethylamine conformers". J Phys Chem A 105:9990-9992.
48. Melandri S, Maris A. 2004. Intramolecular hydrogen bonds and conformational properties of biogenic amines: A free-jet microwave study of tyramine. Phys Chem Chem Phys 6:2863-2866.
49. Cao Y, Marra M, Anderson BD. 2004. Predictive relationships for the effects of triglyceride ester concentration and water uptake on solubility and partitioning of small molecules into lipid vehicles. J Pharm Sci 93:2768-2779. (Pubitemid 39506627)
50. Aue DH, Webb HM, Bowers MT. 1976. A thermodynamic analysis of solvation effects on the basicities of alkylamines. An electrostatic analysis of substituent effects. J Am Chem Soc 98:318-329.
51. Lambert WJ, Wright LA, Stevens JK. 1990. Development of a preformulation lipophilicity screen utilizing a C-18-derivatized polystyrenedivinylbenzene high-performance liquid chromatographic (HPLC) column. Pharm Res 7:577-586.
52. Abraham MH, Chadha HS, Whiting GS, Mitchell RC. 1994. Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the Δlog P parameter of seiler. J Pharm Sci 83:1085-1100.
53. Yamazaki F, Fujiki K, Murata Y. 1965. The ionization constants of organic compounds. I. The microscopic ionization constants of tyrosine and related compounds. Bull Chem Soc Jpn 38:8-12.
54. Mack F, Boenisch H. 1979. Dissociation constants and lipophilicity of catecholamines and related compounds. Naunyn Schmiedebergs Arch Pharmakol 310:1-9. (Pubitemid 10176177)
55. Gluck SJ, Cleveland JA, Jr. 1994. Capillary zone electrophoresis for the determination of dissociation constants. J Chromatogr A 680:43-48.
56. Wehry EL, Rogers LB. 1965. Application of linear free energy relations to electronically excited states of monosubstituted phenols. J Am Chem Soc 87:4234-4238.