Amphotericin B: 50 years of chemistry and biochemistry

被引:90
作者
Cereghetti, DM [1 ]
Carreira, EM [1 ]
机构
[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
来源
SYNTHESIS-STUTTGART | 2006年 / 06期
关键词
amphotericin B; antifungal agents; macrolides; asymmetric synthesis; bioorganic chemistry;
D O I
10.1055/s-2006-926368
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The last century has seen the isolation and synthesis of a multitude of molecules with remarkable biological activity. Some of them represent milestones in chemical space and points of reference in the various disciplines of chemical synthesis, medicine, and biology that they beneficially impact. The notable history of natural products as antibiotics dates back to the 18(th) century. They continue to play an indispensable role in the advances that have been seen in the quality of life for the general population. This has come about because of the rich dialog that can be found at the interfaces between chemistry, biochemistry, biology, and medicine. In this review we examine amphotericin B as an important representative of antibiotics with a long rich history. Its impact continues to be felt today in its use in the clinic to combat fungal infections, In the first part, we review the biochemical efforts aimed at the explanation of amphotericin B's mechanisms of action; in the second part, we take a look at the impact amphotericin B has had on the chemical community in the last two decades. The continuous interest aroused by amphotericin B reveals how much we still do not know about this space.
引用
收藏
页码:914 / 942
页数:29
相关论文
共 286 条
[1]   EFFECT OF AMPHOTERICIN B ON WATER AND NONELECTROLYTE PERMEABILITY OF THIN LIPID MEMBRANES [J].
ANDREOLI, TE ;
DENNIS, VW ;
WEIGL, AM .
JOURNAL OF GENERAL PHYSIOLOGY, 1969, 53 (02) :133-&
[2]   INTERACTION OF POLYENE ANTIBIOTICS WITH THIN LIPID MEMBRANES [J].
ANDREOLI, TE ;
MONAHAN, M .
JOURNAL OF GENERAL PHYSIOLOGY, 1968, 52 (02) :300-+
[3]   STRUCTURE AND FUNCTION OF AMPHOTERICIN B-CHOLESTEROL PORES IN LIPID BILAYER MEMBRANES [J].
ANDREOLI, TE .
ANNALS OF THE NEW YORK ACADEMY OF SCIENCES, 1974, 235 (MAY10) :448-468
[4]  
ANET R, 1961, TETRAHEDRON LETT, P720
[5]  
[Anonymous], [No title captured]
[6]  
Baeyer A., 1899, Ber. Dtsch. Chem. Ges., V32, P3625, DOI 10.1002/cber.189903203151
[7]   Molecular properties of amphotericin B membrane channel: A molecular dynamics simulation [J].
Baginski, M ;
Resat, H ;
McCammon, JA .
MOLECULAR PHARMACOLOGY, 1997, 52 (04) :560-570
[8]   5-ENDO-TRIGONAL REACTIONS - DISFAVORED RING-CLOSURE [J].
BALDWIN, JE ;
CUTTING, J ;
DUPONT, W ;
KRUSE, L ;
SILBERMAN, L ;
THOMAS, RC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :736-738
[9]   APPROACH VECTOR ANALYSIS - STEREOCHEMICAL APPROACH TO REACTIVITY [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :738-741
[10]   RULES FOR RING-CLOSURE - RING FORMATION BY CONJUGATE ADDITION OF OXYGEN NUCLEOPHILES [J].
BALDWIN, JE ;
THOMAS, RC ;
KRUSE, LI ;
SILBERMAN, L .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) :3846-3852