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Didemnin antiviral activity

Considerable effort has gone into investigating compounds from tunicates over the past two decades. For unknown reasons these chemicals are often potent antiviral agents, whereas clinicians have few drugs active against viruses. Didemnin B was the first of these candidate compounds to be examined and initially it showed promise against a broad spectrum of viruses. After lengthy clinical trials, however, it was finally abandoned as too toxic for safe human use. [Pg.176]

Didemnin B (347) is a cyclic depsipeptide isolated from the Caribbean tunicate Trididemnum solidum and is currently in phase II clinical trials as an anticancer agent. Didemnin B also shows antiviral and immunosuppressive activity. The structure of didemnin B was revised to 347 containing... [Pg.89]

Bugula neritina) and related organisms produce substances with antibacterial, antitumor (e.g. bryostatins, didemnin B, dolastatin, girodazol, halichondrin B), anti-inflammatory (e.g. pseudopterosin E, manoalide derivatives), antifungal, antiviral, or immuno-suppressive (e.g. microcolin A and B) activity [399,400]. These compounds and/or their synthetic derivatives may be important novel bioactive pharmaceutical substances. It is also very Hkely that some new natural marine substances or their derivatives can be used as antifouling compounds, insecticides, or fungicides. [Pg.152]

Didemnins were isolated from a Caribbean tunicate Trididemnum solidum. These structurally unique cyclic depsipeptides have quite interesting cytotoxic, antiviral, and immunosuppressive activities. The synthesis of the didemnins A, B, and C (173-175) involves the key component 178, which is prepared from acid 176 and amine 177 using the coupling agent DEPC.69... [Pg.526]

Tunicates (ascidians) are an excellent source of novel biologically active compounds of varied biosynthetic origin, particularly nitrogen-containing amino-acid-derived metabolites [146], The most important compounds discovered to date from tunicates may be the didemnins, potent cytotoxic and antiviral cyclic... [Pg.84]

Dtdemnins, Biologically active depsipeptides extracted from a Caribbean tunicate (sea squirt) family Didem-nidae. genus Trididemnum. The three components, didem-nins A, B and C are weakly basic compds with antiviral, antitumor activity. Didemnin A is the most abundant, whereas didemnin B is generally the most active. Extraction and purification K., L. Rinehart. Jr., Eur. pat. Appl. 48,149 and U.S. pat. 4,493,796 (1982, 1985 both to Univ. Illinois). Structure determn K, L. Rinehart. Jr. et ah, J. Am. Chem. Soc. 103, 1857 (1981). Revised structure and total synthesis K. L. Rinehart, Jr- et ah. ibid. 109, 6846 (1987). See also U. Sebmidt et ah. Tetrahedron Letters 29, 3057 (1988) eidem, ibid. 4407. Crystal structure of B M. B. Hossain el ah. Proc. Nat. Acad. Sci. USA 85, 4118 (1988). Efficient total synthesis of A and B Y. Hamada et ah. J. [Pg.489]

The didemnins are cyclic molecules composed of amino acids that were isolated from the marine invertebrate Trididemnum solidum. One of the amino acids is proline. The didemnins exhibit antitumor, antiviral, and i m m u n osu ppressi ve activity. The group labeled "R" in the structure is a side chain that contains additional amino acids. [Pg.1117]

One of the methods used currently is to broaden the source of the screens hence, companies are now searching for new compounds from samples obtained fiom tropical rain forests to deserts and oceans. The didemnins, which displayed potent antiviral and antitumor activities, were the first pharmaceuticals obtained from a marine source to be tested in the clinic (59). These, and other marine-derived dru have relatively unusual structures that eventually may provide new activities against atypical targets (59). [Pg.15]

With more than 350 original structures, almost all of which contain nitrogen, Didemnidae may be regarded as the richest family of the class Ascidiacea, with several molecules that are undergoing clinical trials for their antiviral and anti-tumor activity. Most of the structures isolated from Didemnidae derive from only three genera, Didemnum, Trididemnum and Lissoclinum, which each contain families of active substances (didemnins, eudis-tomins, lamellarins, lissoclinamides and Hssodimides). Table 28.3 shows the main types of structure encountered in the main genera of the order. [Pg.827]

Like didemnins, most eudistomins are powerful antiviral agents (HSV-1, herpesvirus) and antitumor agents (many human cancer lines colon, melanoma, ovarian, lung, kidney, breast). Structure-activity relationships have been studied for natural eudistomins and several synthetic derivatives. The most active molecules are eudistomins with an oxathiazepine ring, and the main results are srunmarized in Figure 28.20 (Van Maarseveen et al, 1992, 1997 Kurihara et al, 1996). [Pg.859]


See other pages where Didemnin antiviral activity is mentioned: [Pg.528]    [Pg.851]    [Pg.219]    [Pg.714]    [Pg.355]    [Pg.464]    [Pg.119]    [Pg.74]    [Pg.103]    [Pg.106]    [Pg.326]    [Pg.286]    [Pg.392]    [Pg.309]   
See also in sourсe #XX -- [ Pg.5 , Pg.421 ]

See also in sourсe #XX -- [ Pg.5 , Pg.421 ]




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