Compound UCH9

Details Compound UCH9 Compound UCH9

1995-04-21

1997-08-12

Peselev, Elli

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 63, 536 64, 536 181, C07H 1500

Patent

active

056567367

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to the compound UCH9 which has antibacterial and anti-tumor activity and is useful as antibacterial and anti-tumor agents.


BACKGROUND ART

Heretofore, many compounds such as chromomycin-type compounds, olivomycin-type compounds, and mithramycin-type compounds have been reported as anti-tumor antibiotics belonging to the group of aureolic acids [CRC Handbook of Antibiotic Compounds, CRC Press, vol. 1, 325-348, U.S.A. (1981)].
Chromomycin A.sub.3 is known which has a skeleton related to the present compound and which is represented by the following formula (A) [Tetrahedron, 23, 421 (1967)]. ##STR2##
It is known that these aureolic acids form dimeric complexes having divalent metal ions, e.g., 1/2 magnesium salt [Biochemistry, 28, 751 (1989); 32, 463 (1993); 32, 6588 (1993)].


DISCLOSURE OF THE INVENTION

The present invention provides the compound UCH9 having antibacterial and anti-tumor activity which is represented by the following formula: ##STR3## and pharmaceutically acceptable salts thereof.
The pharmaceutically acceptable salts of the compound UCH9 include alkaline earth metal salts such as magnesium salt and calcium salt, nickel salt, etc.
Compound UCH9 forms a dimeric complex having divalent metal ions like other aureolic acids.
Compound UCH9 can be produced by culturing a microorganism belonging to the genus Streptomyces.
The present invention is described in detail below.
The physicochemical properties of UCH9.multidot.1/2 magnesium salt provided by the present invention are shown below. 432.5(113) (1126)=M] solution]: 4.63(1H), 4.51(1H), 4.38(1H), 4.22(1H), 4.08(1H), 3.99(1H), 3.68(1H), 3.62(3H), 3.60(1H), 3.57(1H), 3.50(1H), 3.48(3H), 3.47(1H), 3.45(1H), 3.42(1H), 3.37(1H), 3.28(1H), 3.16(1H), 3.01(1H), 2.97(1H), 2.83(1H), 2.82(1H), 2.76(1H), 2.64(1H), 2.46(1H), 2.28(1H), 2.16(1H), 2.13(1H), 2.12(1H), 1.85(1H), 1.72(1H), 1.62(1H), 1.52(2H), 1.41(1H), 1.40(3H), 1.38(3H), 1.34(3H), 1.33(3H), 1.32(3H), 1.30(3H), 1.29(3H), 1.28(3H), 0.88(3H) solution]: 160.9(s), 139.3(s), 138.9(s), 116.7(s), 112.5(s), 111.6(s), 110.7(s), 100.8(d), 100.5(d), 100.3(d), 99.9(d), 99.7(d), 95.7(d), 84.8(d), 83.6(d), 82.1(d), 79.6(d), 78.0(d), 77.5(d), 77.4(d), 77.2(d), 75.4(d), 75.3(d), 72.7(d), 72.6(d), 72.4(d), 71.6(d), 71.55(d), 71.4(d), 70.3(d), 67.9(d), 68.1(d), 61.1(q), 59.6(q), 43.1(d), 40.1(t), 39.6(t), 37.3(t), 36.7(t), 32.4(t), 31.5(d), 29.0(t), 28.3(d), 19.7(q), 19.1(q), 18.6(q), 18.4(q), 18.0(q), 17.9(q), 16.6(q), 13.4(q) water and chloroform.
The Rf value obtained by using chloroform:methanol:aqueous ammonia (70:26:4 v/v) as a developing solvent was 0.32.
The Rf value obtained by using ethyl acetate:methanol (3:1 v/v) as a developing solvent was 0.67.
The biological activities of UCH9 are described below.
The minimum inhibitory concentration (MIC) of the compound obtained in Example 1 against the growth of various bacteria is shown in Table 1.
The antibacterial activity was determined by the agar dilution method using a medium (pH 7) which comprises 3 g/l Bacto-tryptone (Difco Laboratories), 3 g/l meat extract, 1 g/l yeast extract, 1 g/l glucose and 16 g/l agar.


TABLE 1 ______________________________________ MIC (.mu.g/ml) Bacteria tested UCH9 ______________________________________ Staphylococcus aureus ATCC 6538P 5.2 Bacillus subtilis No. 10707 0.04 Enterococcus faecium ATCC 10541 41.6 ______________________________________
HeLa S.sub.3 cells (ATCC HTB22) were suspended in a medium comprising 10% fetal calf serum, 2 mM glutamine and MEM medium (Nippon Pharmaceutical Co., Ltd.) (hereinafter referred to as medium A) to a concentration of 3.times.10.sup.4 cells/mi. The cell suspension was put into wells of a 96-well microtiter plate in an amount of 0.1 ml per well. The cells in the plate were cultured at 37.degree. C. for 20 hours in a CO.sub.2 -incubator. Subsequently, the test compound obtained in Example 1 which was appropriately diluted with medium A was added to the wells in an amount of 0.1 ml/well. The cells were further cultured

REFERENCES:
patent: 3821085 (1974-06-01), Zhdanovich et al.
Tetrahedron, 1967, vol. 23, pp. 421 to 437.
Biochemistry, 1989, vol. 28, pp. 751 to 762.
Biochemistry, 1993, vol. 32, pp. 463 to 471.
Biochemistry, 1993, vol. 32, pp. 6588 to 6604.

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