Structure-activity relationships within a family of selectively cytotoxic macrolide natural products

Organic Letters

Volumn 3, Issue 1, 2001, Pages 57-59

  Salomon, Arthur R ^a   Zhang, Yongbo ^a,b   Seto, Haruo ^a   Khosla, Chaitan ^a  

^a STANFORD UNIVERSITY   (United States)

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC ANTIBIOTIC; APOPTOLIDIN; BIOLOGICAL PRODUCT; CYTOVARICIN; ENZYME INHIBITOR; MACROLIDE; OLIGOMYCIN; OSSAMYCIN; PROTON TRANSPORTING ADENOSINE TRIPHOSPHATASE;

ARTICLE; BACTERIUM; CHEMICAL STRUCTURE; COMPARATIVE STUDY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; STRUCTURE ACTIVITY RELATION; YEAST;

ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTIFUNGAL; ANTIBIOTICS, ANTINEOPLASTIC; BACTERIA; BIOLOGICAL PRODUCTS; ENZYME INHIBITORS; MACROLIDES; MOLECULAR STRUCTURE; OLIGOMYCINS; PROTON-TRANSLOCATING ATPASES; STRUCTURE-ACTIVITY RELATIONSHIP; YEASTS;

EID: 0035843327     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006767d     Document Type: Article

References (11)

1. Kim, J. W.; Adachi, H.; Shin-ya, K.; Hayakawa, Y.; Seto, H. J. Antibiot. 1997, 50, 628-30.
2. Hayakawa, Y.; Kim, J. W.; Adachi, H.; Shinya, K.; Fujita, K.; Seto, H. J. Am. Chem. Soc. 1998, 120, 3524-3525.
3. Salomon, A. R.; Voehringer, D.; Herzenberg, L. A.; Khosla, C. Proc. Natl. Acad. Sci. U.S.A., in press.
4. Salomon, A. R.; Voehringer, D.; Herzenberg, L. A.; Khosla, C. Chem. Biol., in press.
5. Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1968, 974-977.
6. 2, 2 μg/mL antimycin A, 1 mM phosphoenol pyruvate, 5 U/ml lactate dehydrogenase, and 2.5 U/ml pyruvate kinase at 28°C. Oxidation of NADH was followed at 360 nm over time. To establish the mitochondrial origin of the ATPase activity, published procedures were used to measure (mitochondrial) cytochrome c oxidase activity (Wharton, D. C.; Tzagoloff, A. Methods Enzymol. 1967, 10, 245-250).
7. 2, 2 μg/mL antimycin A, 1 mM phosphoenol pyruvate, 5 U/ml lactate dehydrogenase, and 2.5 U/ml pyruvate kinase at 28°C. Oxidation of NADH was followed at 360 nm over time. To establish the mitochondrial origin of the ATPase activity, published procedures were used to measure (mitochondrial) cytochrome c oxidase activity (Wharton, D. C.; Tzagoloff, A. Methods Enzymol. 1967, 10, 245-250).
8. 2, 2 μg/mL antimycin A, 1 mM phosphoenol pyruvate, 5 U/ml lactate dehydrogenase, and 2.5 U/ml pyruvate kinase at 28°C. Oxidation of NADH was followed at 360 nm over time. To establish the mitochondrial origin of the ATPase activity, published procedures were used to measure (mitochondrial) cytochrome c oxidase activity (Wharton, D. C.; Tzagoloff, A. Methods Enzymol. 1967, 10, 245-250).
9. 50 of 1 was 90 nM and 2 was 10 μM.
10. The importance of carbohydrates in relation to the bioactivity of natural products has been reviewed elsewhere. See: Weymouth-Wilson, A. Nat. Prod. Rep. 1997, 14, 99-110.
11. Galanis, M.; Mattoon, J. R.; Nagley, P. FEBS Lett 1989, 249, 333-336.