Structure-activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells

W. Matthew Leevy; Seth T. Gammon; Tatiana Levchenko; David D. Daranciang; Oscar Murillo; Vladimir Torchilin; David Piwnica-Worms; James E. Huettner; George W. Gokel

doi:10.1039/b508157b

Structure-activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells

W. Matthew Leevy, Seth T. Gammon, Tatiana Levchenko, David D. Daranciang, Oscar Murillo, Vladimir Torchilin, David Piwnica-Worms, James E. Huettner, George W. Gokel

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

Hydraphile compounds are shown to be cytotoxic to Gram-negative and Gram-positive bacteria, yeast, and mammalian cells. Their cellular toxicity compares favorably with other synthetic ionophores and rivals that potency of natural antibiotics. The effects of structural variations on toxicity are described. The effects of these variations correlate well with previous studies of ion transport in liposomes. Whole cell patch clamping with mammalian cells confirms a channel mechanism in living cells suggesting that this family may comprise novel and flexible pharmacological agents.

Original language	English (US)
Pages (from-to)	3544-3550
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	3
Issue number	19
DOIs	https://doi.org/10.1039/b508157b
State	Published - Oct 7 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/b508157b

Cite this

Leevy, W. M., Gammon, S. T., Levchenko, T., Daranciang, D. D., Murillo, O., Torchilin, V., Piwnica-Worms, D., Huettner, J. E., & Gokel, G. W. (2005). Structure-activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells. Organic and Biomolecular Chemistry, 3(19), 3544-3550. https://doi.org/10.1039/b508157b

Leevy, WM, Gammon, ST, Levchenko, T, Daranciang, DD, Murillo, O, Torchilin, V, Piwnica-Worms, D, Huettner, JE & Gokel, GW 2005, 'Structure-activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells', Organic and Biomolecular Chemistry, vol. 3, no. 19, pp. 3544-3550. https://doi.org/10.1039/b508157b

@article{037740918e9c4f56aae04bcc09cbba1b,

title = "Structure-activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells",

abstract = "Hydraphile compounds are shown to be cytotoxic to Gram-negative and Gram-positive bacteria, yeast, and mammalian cells. Their cellular toxicity compares favorably with other synthetic ionophores and rivals that potency of natural antibiotics. The effects of structural variations on toxicity are described. The effects of these variations correlate well with previous studies of ion transport in liposomes. Whole cell patch clamping with mammalian cells confirms a channel mechanism in living cells suggesting that this family may comprise novel and flexible pharmacological agents.",

author = "Leevy, {W. Matthew} and Gammon, {Seth T.} and Tatiana Levchenko and Daranciang, {David D.} and Oscar Murillo and Vladimir Torchilin and David Piwnica-Worms and Huettner, {James E.} and Gokel, {George W.}",

year = "2005",

month = oct,

day = "7",

doi = "10.1039/b508157b",

language = "English (US)",

volume = "3",

pages = "3544--3550",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "19",

}

TY - JOUR

T1 - Structure-activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells

AU - Leevy, W. Matthew

AU - Gammon, Seth T.

AU - Levchenko, Tatiana

AU - Daranciang, David D.

AU - Murillo, Oscar

AU - Torchilin, Vladimir

AU - Piwnica-Worms, David

AU - Huettner, James E.

AU - Gokel, George W.

PY - 2005/10/7

Y1 - 2005/10/7

N2 - Hydraphile compounds are shown to be cytotoxic to Gram-negative and Gram-positive bacteria, yeast, and mammalian cells. Their cellular toxicity compares favorably with other synthetic ionophores and rivals that potency of natural antibiotics. The effects of structural variations on toxicity are described. The effects of these variations correlate well with previous studies of ion transport in liposomes. Whole cell patch clamping with mammalian cells confirms a channel mechanism in living cells suggesting that this family may comprise novel and flexible pharmacological agents.

AB - Hydraphile compounds are shown to be cytotoxic to Gram-negative and Gram-positive bacteria, yeast, and mammalian cells. Their cellular toxicity compares favorably with other synthetic ionophores and rivals that potency of natural antibiotics. The effects of structural variations on toxicity are described. The effects of these variations correlate well with previous studies of ion transport in liposomes. Whole cell patch clamping with mammalian cells confirms a channel mechanism in living cells suggesting that this family may comprise novel and flexible pharmacological agents.

UR - http://www.scopus.com/inward/record.url?scp=27144523746&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=27144523746&partnerID=8YFLogxK

U2 - 10.1039/b508157b

DO - 10.1039/b508157b

M3 - Article

C2 - 16172693

AN - SCOPUS:27144523746

SN - 1477-0520

VL - 3

SP - 3544

EP - 3550

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 19

ER -

Structure-activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this