Ipertrofan Revisited—The Proposal of the Complete Stereochemistry of Mepartricin A and B - Publication - Bridge of Knowledge

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Ipertrofan Revisited—The Proposal of the Complete Stereochemistry of Mepartricin A and B

Abstract

Being a methyl ester of partricin, the mepartricin complex is the active substance of a drug called Ipertrofan (Tricandil), which was proven to be useful in treatment of benign prostatic hyperplasia and chronic nonbacterial prostatitis/chronic pelvic pain syndrome. Nevertheless, no direct structural evidence on the stereochemistry of its components has been presented to date. In this contribution, we have conducted detailed, NMR-driven stereochemical studies on mepartricins A and B, aided by molecular dynamics simulations. The absolute configuration of all the stereogenic centers of mepartricin A and B was defined as 3R, 7R, 9R, 11S, 13S, 15R, 17S, 18R, 19S, 21R, 36S, 37R, and 38S, and proposed as 41R. The geometry of the heptaenic chromophore of both compounds has been established as 22E, 24E, 26E, 28Z, 30Z, 32E, and 34E. Our studies on mepartricin ultimately proved that partricins A and B are structurally identical to the previously described main components of the aureofacin complex: gedamycin and vacidin, respectively. The knowledge of the stereochemistry of this drug is a fundamental matter not only in terms of studies on its molecular mode of action, but also for potential derivatization, aiming at improvement of its pharmacological properties.

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DOI:
Digital Object Identifier (open in new tab) 10.3390/molecules26185533
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Creative Commons: CC-BY open in new tab

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Details

Category:
Articles
Type:
artykuły w czasopismach
Published in:
MOLECULES no. 26,
ISSN: 1420-3049
Language:
English
Publication year:
2021
Bibliographic description:
Szczeblewski P., Andrałojć W., Polit J., Żabka A., Winnicki K., Laskowski T.: Ipertrofan Revisited—The Proposal of the Complete Stereochemistry of Mepartricin A and B// MOLECULES -Vol. 26,iss. 18 (2021), s.5533-
DOI:
Digital Object Identifier (open in new tab) 10.3390/molecules26185533
Sources of funding:
Verified by:
Gdańsk University of Technology

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