Characterization of the antifungal and antiprotozoal antibiotic partricin and structural studies on partricins A and B.

Tweit, Robert C.; Pandey, Ramesh C.; Rinehart, Kenneth L.

doi:10.7164/antibiotics.35.997

Cited by 22 publications

(11 citation statements)

References 17 publications

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“…Although mepartricin is still a registered drug in several countries, only the gross structure of mepartricins A and B were reported [ 12 ] and claimed to be identical with the gross structure of the methyl esters of the antibiotics gedamycin and vacidin, respectively [ 13 ]. No direct stereochemical studies on any of the partricins and/or their derivatives could be traced in the literature.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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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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Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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“…The other member of the AH family, partricin complex (syn. aureofacin, produced by Streptomyces aureofaciens) involves two compounds, differentiated solely by one methyl group at the end of the side chain [6,7]. Both of these molecules also incorporate two cis-type bonds, yet in different positions, i.e., 28Z and 30Z (Figure 1) [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones

et al. 2021

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Partricin is a heptaene macrolide antibiotic complex that exhibits exceptional antifungal activity, yet poor selective toxicity, in the pathogen/host system. It consists of two compounds, namely partricin A and B, and both of these molecules incorporate two cis-type bonds within their heptaenic chromophores: 28Z and 30Z. In this contribution, we have proven that partricins are susceptible to a chromophore-straightening photoisomerization process. The occurring 28Z→28E and 30Z→30E switches are irreversible in given conditions, and they are the only structural changes observed during the experiment. The obtained all-trans partricin’s derivatives, namely iso-partricins A and B, exhibit very promising features, potentially resulting in the improvement of their selective toxicity.

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“…The available structural data comprise levorins, 8,9 trichomycins, 10,11 67-121-A, 67-121-C, 12 perimicin A 13 and aureofacin complex components, vacidin 14 (syn. partricin A 15 ) and gedamycin 16 (syn. partricin B 15 ).…”

Section: Introductionmentioning

confidence: 99%

“…partricin A 15 ) and gedamycin 16 (syn. partricin B 15 ). However, the first discovered and most studied antifungal aromatic heptaenes, candicidins, 2 lack complete stereostructures.…”

Section: Introductionmentioning

confidence: 99%

The stereostructure of candicidin D

et al. 2015

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Characterization of the antifungal and antiprotozoal antibiotic partricin and structural studies on partricins A and B.

Cited by 22 publications

References 17 publications

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

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

Iso-Partricin, an Aromatic Analogue of Amphotericin B: How Shining Light on Old Drugs Might Help Create New Ones

The stereostructure of candicidin D

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