Open Access

Journal of Antibiotics, volume 69, issue 7, pages 549-560

New conjugates of polyene macrolide amphotericin B with benzoxaboroles: Synthesis and properties

Tevyashova Anna N ^{1, 2}

Korolev Alexander M ¹

Trenin Aleksey S ¹

Dezhenkova Lyubov G ¹

Shtil Alexander A. ^{1, 2}

Polshakov Vladimir I ³

Savelyev Oleg Yu ³

Olsufyeva Evgenia N ¹

Hide authors affiliations Show authors affiliations: 3 affiliations

Laboratory of Chemical Transformation of Antibiotics, Gause Institute of New Antibiotics, Moscow, Russia |

The National University of Science and Technology MISiS, Moscow, Russia |

Faculty of Fundamental Medicine, MV Lomonosov Moscow State University, Moscow, Russia |

Publication type: Journal Article

Publication date: 2016-03-23

Springer Nature

Journal: Journal of Antibiotics

Quartile SCImago

Quartile WOS

Impact factor: 3.3

ISSN: 00218820, 18811469

DOI: 10.1038/ja.2016.34

Copy DOI

Drug Discovery

Pharmacology

Abstract

A novel series of conjugates of the antifungal antibiotic amphotericin B (AmB) with benzoxaboroles was synthesized. Antifungal activity of new compounds was tested on yeastβ Candida albicans and Cryptococcus humicolus and filamentous fungi Aspergillus niger and Fusarium oxysporum using the broth microdilution method. The potency of di-modified derivatives against the tested strains was similar to that of the parent AmB. New derivatives demonstrated differential toxicity against human cells (colon epithelium or red blood cells). The di-modified conjugate 2-(N,N-dimethylamino)ethylamide of 3′-N-[3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propanoyl] AmB (9) showed the best combination of a high antifungal activity with a low cytotoxic and hemolytic potency.

By date By citations

Citations by journals

	1 2 3
Pharmaceutical Chemistry Journal	Pharmaceutical Chemistry Journal, 3, 12.5% Pharmaceutical Chemistry Journal 3 publications, 12.5%
Russian Chemical Reviews	Russian Chemical Reviews, 3, 12.5% Russian Chemical Reviews 3 publications, 12.5%
Journal of Antibiotics	Journal of Antibiotics, 1, 4.17% Journal of Antibiotics 1 publication, 4.17%
Current Topics in Medicinal Chemistry	Current Topics in Medicinal Chemistry, 1, 4.17% Current Topics in Medicinal Chemistry 1 publication, 4.17%
Journal of Fungi	Journal of Fungi, 1, 4.17% Journal of Fungi 1 publication, 4.17%
Antibiotics	Antibiotics, 1, 4.17% Antibiotics 1 publication, 4.17%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 1, 4.17% Chemistry of Heterocyclic Compounds 1 publication, 4.17%
Bioorganic and Medicinal Chemistry	Bioorganic and Medicinal Chemistry, 1, 4.17% Bioorganic and Medicinal Chemistry 1 publication, 4.17%
PLoS ONE	PLoS ONE, 1, 4.17% PLoS ONE 1 publication, 4.17%
Journal of Organometallic Chemistry	Journal of Organometallic Chemistry, 1, 4.17% Journal of Organometallic Chemistry 1 publication, 4.17%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 4.17% Chemistry - A European Journal 1 publication, 4.17%
Molecules	Molecules, 1, 4.17% Molecules 1 publication, 4.17%
Russian Journal of General Chemistry	Russian Journal of General Chemistry, 1, 4.17% Russian Journal of General Chemistry 1 publication, 4.17%
Chemical Society Reviews	Chemical Society Reviews, 1, 4.17% Chemical Society Reviews 1 publication, 4.17%
Chemical Communications	Chemical Communications, 1, 4.17% Chemical Communications 1 publication, 4.17%
Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry	Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry, 1, 4.17% Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry 1 publication, 4.17%
Biomeditsinskaya Khimiya	Biomeditsinskaya Khimiya, 1, 4.17% Biomeditsinskaya Khimiya 1 publication, 4.17%
Current Computer-Aided Drug Design	Current Computer-Aided Drug Design, 1, 4.17% Current Computer-Aided Drug Design 1 publication, 4.17%
Journal of Medicinal Chemistry	Journal of Medicinal Chemistry, 1, 4.17% Journal of Medicinal Chemistry 1 publication, 4.17%
	1 2 3

Citations by publishers

	1 2 3 4 5
Springer Nature	Springer Nature, 5, 20.83% Springer Nature 5 publications, 20.83%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 3, 12.5% Multidisciplinary Digital Publishing Institute (MDPI) 3 publications, 12.5%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 3, 12.5% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 3 publications, 12.5%
Bentham Science	Bentham Science, 2, 8.33% Bentham Science 2 publications, 8.33%
Elsevier	Elsevier, 2, 8.33% Elsevier 2 publications, 8.33%
Pleiades Publishing	Pleiades Publishing, 2, 8.33% Pleiades Publishing 2 publications, 8.33%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 2, 8.33% Royal Society of Chemistry (RSC) 2 publications, 8.33%
Public Library of Science (PLoS)	Public Library of Science (PLoS), 1, 4.17% Public Library of Science (PLoS) 1 publication, 4.17%
Wiley	Wiley, 1, 4.17% Wiley 1 publication, 4.17%
V. N. Orekhovich Research Institute of Biomedical Chemistry	V. N. Orekhovich Research Institute of Biomedical Chemistry, 1, 4.17% V. N. Orekhovich Research Institute of Biomedical Chemistry 1 publication, 4.17%
American Chemical Society (ACS)	American Chemical Society (ACS), 1, 4.17% American Chemical Society (ACS) 1 publication, 4.17%
	1 2 3 4 5

We do not take into account publications that without a DOI.
Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
Statistics recalculated weekly.

{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2017,2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0,0],"imageUrls":["","","","","","","",""],"datasets":[{"label":"Citations number","data":[1,3,0,6,5,5,3,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["4.17","12.5",0,"25","20.83","20.83","12.5","4.17"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Pharmaceutical Chemistry Journal","Russian Chemical Reviews","Journal of Antibiotics","Current Topics in Medicinal Chemistry","Journal of Fungi","Antibiotics","Chemistry of Heterocyclic Compounds","Bioorganic and Medicinal Chemistry","PLoS ONE","Journal of Organometallic Chemistry","Chemistry - A European Journal","Molecules","Russian Journal of General Chemistry","Chemical Society Reviews","Chemical Communications","Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry","Biomeditsinskaya Khimiya","Current Computer-Aided Drug Design","Journal of Medicinal Chemistry"],"ids":[1261,23802,6099,3277,3021,1488,16828,1162,24963,11834,24708,1770,13581,20586,9073,6894,13607,7366,3673],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/PRGhlgB4OKRltSNtT39eA6wlnOTGRap1QQ6FQHih_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/ORapGEvQagyY4uwGVkDHuIo7YUCJvWzb7YLElWuZ_medium.webp","\/storage\/images\/resized\/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp"],"datasets":[{"label":"","data":[3,3,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[12.5,12.5,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17,4.17],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Springer Nature","Multidisciplinary Digital Publishing Institute (MDPI)","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii","Bentham Science","Elsevier","Pleiades Publishing","Royal Society of Chemistry (RSC)","Public Library of Science (PLoS)","Wiley","V. N. Orekhovich Research Institute of Biomedical Chemistry","American Chemical Society (ACS)"],"ids":[8,202,9422,39,17,101,123,344,11,9340,40],"codes":[0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/doUaFUZdxUEQjLi1TwZjGHi8HXYNWWSk04dSC6Xh_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/oZgeErrVFhuDksyqFURLvYS1wtVSBWczh001igGo_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/PRGhlgB4OKRltSNtT39eA6wlnOTGRap1QQ6FQHih_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/ORapGEvQagyY4uwGVkDHuIo7YUCJvWzb7YLElWuZ_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp"],"datasets":[{"label":"","data":[5,3,3,2,2,2,2,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[20.83,12.5,12.5,8.33,8.33,8.33,8.33,4.17,4.17,4.17,4.17],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}

Metrics

Cite this

GOST |

Cite this

GOST Copy

Tevyashova A. N. et al. New conjugates of polyene macrolide amphotericin B with benzoxaboroles: Synthesis and properties // Journal of Antibiotics. 2016. Vol. 69. No. 7. pp. 549-560.

GOST all authors (up to 50) Copy

Tevyashova A. N., Korolev A. M., Trenin A. S., Dezhenkova L. G., Shtil A. A., Polshakov V. I., Savelyev O. Yu., Olsufyeva E. N. New conjugates of polyene macrolide amphotericin B with benzoxaboroles: Synthesis and properties // Journal of Antibiotics. 2016. Vol. 69. No. 7. pp. 549-560.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1038/ja.2016.34

UR - https://doi.org/10.1038%2Fja.2016.34

TI - New conjugates of polyene macrolide amphotericin B with benzoxaboroles: Synthesis and properties

T2 - Journal of Antibiotics

AU - Tevyashova, Anna N

AU - Korolev, Alexander M

AU - Trenin, Aleksey S

AU - Dezhenkova, Lyubov G

AU - Shtil, Alexander A.

AU - Polshakov, Vladimir I

AU - Savelyev, Oleg Yu

AU - Olsufyeva, Evgenia N

PY - 2016

DA - 2016/03/23 00:00:00

PB - Springer Nature

SP - 549-560

IS - 7

VL - 69

SN - 0021-8820

SN - 1881-1469

ER -

BibTex |

Cite this

BibTex Copy

@article{2016_Tevyashova,

author = {Anna N Tevyashova and Alexander M Korolev and Aleksey S Trenin and Lyubov G Dezhenkova and Alexander A. Shtil and Vladimir I Polshakov and Oleg Yu Savelyev and Evgenia N Olsufyeva},

title = {New conjugates of polyene macrolide amphotericin B with benzoxaboroles: Synthesis and properties},

journal = {Journal of Antibiotics},

year = {2016},

volume = {69},

publisher = {Springer Nature},

month = {mar},

url = {https://doi.org/10.1038%2Fja.2016.34},

number = {7},

pages = {549--560},

doi = {10.1038/ja.2016.34}

}

MLA

Cite this

MLA Copy

Tevyashova, Anna N., et al. “New conjugates of polyene macrolide amphotericin B with benzoxaboroles: Synthesis and properties.” Journal of Antibiotics, vol. 69, no. 7, Mar. 2016, pp. 549-560. https://doi.org/10.1038%2Fja.2016.34.

Found error?

Publisher

Springer Nature

Journal

Journal of Antibiotics

Quartile SCImago

Quartile WOS

Impact factor

3.3

ISSN

00218820 (Print)
18811469 (Electronic)

Labs

Laboratory of Magnetic Tomography and Spectroscopy

Profiles

Polshakov, Vladimir I