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Volumn 2, Issue 6, 2002, Pages 553-562

Quinoline Binding Site on Malaria Pigment Crystal: A Rational Pathway for Antimalaria Drug Design

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Indexed keywords


EID: 0042139505     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg025550i     Document Type: Article
Times cited : (162)

References (78)
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    • note
    • a3 of the secondary aniline amine nitrogen is estimated at 5.0 (refs 73-75). Calculating the extent of ionization of weak base in the two pH environments using the Henderson-Hasselblach equation for the various amines of chloroquine, we obtain for physiological pH = 7.4: 0.4% (5.0), 83.4% (8.1), 99.8% (10.2), and in the acidic vacuole pH = 4.8: 61.3% (5.0), 99.9% (8.1), and 100% (10.2).
  • 26
    • 0347604118 scopus 로고    scopus 로고
    • note
    • The reported cell constants are a = 12.20 Å, b = 14.68 Å, c = 8.04 Å, a = 90.2°, β = 96.8°, γ = 97.9°, space group P1.
  • 42
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    • Accelrys Inc., San Diego, CA
    • Cerius2 v. 4.5, Accelrys Inc., San Diego, CA, 2000.
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  • 43
    • 0346343262 scopus 로고    scopus 로고
    • note
    • {h, k, l} denotes both (h, k, l) and (-h, -k, -l) faces.
  • 44
    • 0346973151 scopus 로고    scopus 로고
    • note
    • To reduce errors due to the possibility that the specimen crystals may not lie exactly parallel to the plane of the {100} face we had made use of crystals with different azimuths, as well as the projected thickness of the {011} face.
  • 45
    • 0346343260 scopus 로고    scopus 로고
    • note
    • Extended polymer chains would most likely lie parallel to the long axis of the crystal, in this case the c-axis, even though such a crystal would grow by side-to-side juxtaposition of the polymer chains. Since such chains will not be of the same length their ends cannot form a smooth obliquely oriented {011} face.
  • 55
    • 0347604116 scopus 로고    scopus 로고
    • note
    • 2(carboxylate) hydrogen bond, which occurs in several zwitterionic α-amino acid crystal structures, must be no less than 6 kcal/mol.
  • 56
    • 0037016451 scopus 로고    scopus 로고
    • Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76. In this review OH···C=C interactions were referred to, rather than NH···C=C.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 48-76
    • Steiner, T.1
  • 57
    • 0346343261 scopus 로고    scopus 로고
    • note
    • It is noteworthy that the γ-crystalline form of glycine, which is in a zwitterionic state, is obtained from an aqueous solution of glycine made acidic with acetic acid or basic with ammonium hydroxide (ref 76).
  • 58
    • 0346973148 scopus 로고    scopus 로고
    • note
    • 50 (effective dose 50) is the amount of material required to produce a specified effect in 50% of an animal population.
  • 60
    • 0346343257 scopus 로고    scopus 로고
    • note
    • 50 values (ref 58) for drug-mediated crystal inhibition in vitro experiments was usually higher than for in-vivo experiments (using chloroquine sensitive parasites). This difference may be attributed to the ability of the molecule to accumulate within the food vacuole, increasing its local concentration at the target site.
  • 61
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    • note
    • Thermodynamic parameters for various quinolines were also calculated for neutral pH ∼ 7.5 by Egan et al. (refs 27 and 77) in 407% DMSO, while Dorn et al. (ref 22) measured at pH ∼ 6.5 in water, with similar results.
  • 63
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    • note
    • 50 values.
  • 65
    • 0000857071 scopus 로고
    • Jacquemain, D.; Wolf, S. G.; Levieiller, F.; Frolow, F.; Eisenstein, M.; Lahav, M.; Leiserowitz, L. J. Am. Chem. Soc. 1992, 114, 9983-9989. In this reference the net charge of -0.14e units on F atoms was determined experimentally from a deformation electron density analysis of low-temperature X-ray diffraction data. The net charge on the H atom is about +0.06 e units.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9983-9989
    • Jacquemain, D.1    Wolf, S.G.2    Levieiller, F.3    Frolow, F.4    Eisenstein, M.5    Lahav, M.6    Leiserowitz, L.7
  • 67
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    • note
    • 3 and H groups attached to the asymmetric C atom, does not appear to embody poor intramolecular contacts, nor introduce a noticeable change in intermolecular contacts.
  • 68
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    • note
    • 3. However, whether the X-ray powder diffraction analysis can reveal atomic disorder between the vinyl and methyl groups as low as 5-10% is a moot point.
  • 74
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    • a, http://www.chem.wisc.edu/ areas/reich/pkatable/index.htm, 2002.
    • (2002) a
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    • Harvard
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.