ENHANCED CHARTREUSIN SOLUBILITY BY HYDROXYBENZOATE HYDROTROPY

被引：62

作者：

POOCHIKIAN, GK

CRADOCK, JC

机构：

[1] Analytical and Product Development Section, Pharmaceutical Resources Branch, National Cancer Institute, National Institutes of Health, Bethesda, Maryland

来源：

JOURNAL OF PHARMACEUTICAL SCIENCES | 1979年 / 68卷 / 06期

关键词：

Antineo‐plastic agents; potential—chartreusin; aqueous solubility enhanced by hydroxybenzoates; Chartreusin—aqueous solubility enhanced by hydroxybenzoates; conformation; Cytotoxic agents—chartreusin; Hydroxybenzoates—electrostatic and hydrophobic interactions; stability constants;

D O I：

10.1002/jps.2600680620

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The apparent aqueous solubility of the water‐insoluble cytotoxic agent, chartreusin, was increased at neutral pH in the presence of hydroxybenzoates. Water molecules play an important role in the chartreusin conformation. Studies included solubility and spectral examinations. The weakest and strongest interactants with chartreusin were sodium benzoate and sodium trihydroxybenzoate, respectively, while the effect of mono‐ and dihydroxybenzoates was intermediate. A plane‐to‐plane orientation of chartreusin and the ligand molecules brought together by electrostatic and hydrophobic interactions is postulated. The dramatic chartreusin aqueous solubility increase relative to its aglycone, chartarin, under similar conditions was best rationalized by micellization. Copyright © 1979 Wiley‐Liss, Inc., A Wiley Company

引用

页码：728 / 732

页数：5

共 30 条

[1]

ADAMSON AW, 1967, PHYSICAL CHEM SURFAC, P73

[2] ISOLATION OF ANTIBIOTIC X-465A AND ITS IDENTIFICATION WITH CHARTREUSIN [J].

BERGER, J ;

STERNBACH, LH ;

POLLOCK, RG ;

LASALA, ER ;

KAISER, S ;

GOLDBERG, MW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (07) :1636-1638

[3]

BIKERMAN JJ, 1970, PHYSICAL SURFACES, P73

[4] ELECTRON AFFINITY OF ORGANIC MOLECULES [J].

BRIEGLEB, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1964, 3 (09) :617-&

[5]

BRIEGLEB G, 1961, MOLEKULVERBINDUNGEN

[6] HYDROGEN BONDING AND CONFORMATION OF GLUCOSE AND POLYGLUCOSES IN DIMETHYLSULPHOXIDE SOLUTION [J].

CASU, B ;

REGGIANI, M ;

GALLO, GG ;

VIGEVANI, A .

TETRAHEDRON, 1966, 22 (09) :3061-+

[7] STABILITY OF SOME MOLECULAR COMPLEXES IN AQUEOUS MIXED SOLVENTS - CORRELATION WITH SOLVENT SURFACE TENSION [J].

CONNORS, KA ;

SUN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (26) :7239-&

[8] EFFECT OF SUBSTITUENT GROUPS ON IONIZATION POTENTIALS OF BENZENES [J].

CRABLE, GF ;

KEARNS, GL .

JOURNAL OF PHYSICAL CHEMISTRY, 1962, 66 (03) :436-&

[9]

DARDEN JC, 1960, CAN J CHEM, V38, P1837

[10] UBER DIE STRUKTUR DES CHARTREUSINS 2 [J].

EISENHUTH, W ;

STAMM, OA ;

SCHMID, H .

HELVETICA CHIMICA ACTA, 1964, 47 (06) :1475-+

← 1 2 3 →