Synthesis, surface properties, and biocompatibility of 1,2,3-triazole- containing alkyl β-D-xylopyranoside surfactants

E. Davis Oldham; Srivenu Seelam; Carolina Lema; Renato J. Aguilera; Jennifer Fiegel; Stephen E. Rankin; Barbara L. Knutson; Hans Joachim Lehmler

doi:10.1016/j.carres.2013.06.020

Synthesis, surface properties, and biocompatibility of 1,2,3-triazole- containing alkyl β-D-xylopyranoside surfactants

E. Davis Oldham, Srivenu Seelam, Carolina Lema, Renato J. Aguilera, Jennifer Fiegel, Stephen E. Rankin, Barbara L. Knutson, Hans Joachim Lehmler

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

27 Scopus citations

Abstract

We are interested in the development of surfactants derived from hemicellulosic biomass, as they are potential components in pharmaceuticals, personal care products, and other detergents. Such surfactants should exhibit low toxicity in mammalian cells. In this study we synthesized a series of alkyl or fluoroalkyl β-xylopyranosides from azides and an alkyne using the copper-catalyzed azide-alkyne (CuAAC) 'click' reaction in 4 steps from xylose. The purified products were evaluated for both their surfactant properties, and for their biocompatibility. Unlike other carbohydrate-based surfactants, liquid-crystalline behavior was not observed by differential scanning calorimetry. The triazole-containing β-xylopyranosides with short (6 carbons) and long (>12 carbons) chains exhibited no toxicity at concentrations ranging from 1 to 1000 μM. Triazole-containing β-xylopyranosides with 8, 10, or 12 carbons caused toxicity via apoptosis, with CC₅₀ values ranging from 26-890 μM. The two longest chain compounds did form stable monolayers at the air-water interface over a range of temperatures, although a brief transition to an the unstable monolayer was observed.

Original language	English
Pages (from-to)	68-77
Number of pages	10
Journal	Carbohydrate Research
Volume	379
DOIs	https://doi.org/10.1016/j.carres.2013.06.020
State	Published - 2013

Bibliographical note

Funding Information:
This work was supported by the National Science Foundation (CBET-0967381/0967390), the U.S. Department of Agriculture Biomass Research and Development Initiative (Grant Agreement 68-3A75-7-608) and the Department of Energy Development and Independence, Energy and Environment Cabinet of The Commonwealth of Kentucky. The cell culture work was performed at the Cell Culture Core of the Border Biomedical Research Center (BBRC) supported by grant 8G12MD007592 from the National Center for Research Resources (NCRR) of the NIH, granted to the University of Texas at El Paso.

Funding

This work was supported by the National Science Foundation (CBET-0967381/0967390), the U.S. Department of Agriculture Biomass Research and Development Initiative (Grant Agreement 68-3A75-7-608) and the Department of Energy Development and Independence, Energy and Environment Cabinet of The Commonwealth of Kentucky. The cell culture work was performed at the Cell Culture Core of the Border Biomedical Research Center (BBRC) supported by grant 8G12MD007592 from the National Center for Research Resources (NCRR) of the NIH, granted to the University of Texas at El Paso.

Funders	Funder number
Border Biomedical Research Center	8G12MD007592
Department of Energy Development and Independence, Energy and Environment Cabinet of The Commonwealth of Kentucky
U.S. Department of Agriculture Biomass Research and Development Initiative	68-3A75-7-608
National Science Foundation Arctic Social Science Program	CBET-0967381/0967390
National Institutes of Health (NIH)
National Center for Research Resources
National Institute on Minority Health and Health Disparities (NIMHD)	G12MD007592
University of Texas at El Paso

Keywords

Carbohydrate surfactants
Click chemistry
Cytotoxicity
Huisgen cycloaddition
Langmuir monolayers

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2013.06.020

Cite this

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title = "Synthesis, surface properties, and biocompatibility of 1,2,3-triazole- containing alkyl β-D-xylopyranoside surfactants",

abstract = "We are interested in the development of surfactants derived from hemicellulosic biomass, as they are potential components in pharmaceuticals, personal care products, and other detergents. Such surfactants should exhibit low toxicity in mammalian cells. In this study we synthesized a series of alkyl or fluoroalkyl β-xylopyranosides from azides and an alkyne using the copper-catalyzed azide-alkyne (CuAAC) 'click' reaction in 4 steps from xylose. The purified products were evaluated for both their surfactant properties, and for their biocompatibility. Unlike other carbohydrate-based surfactants, liquid-crystalline behavior was not observed by differential scanning calorimetry. The triazole-containing β-xylopyranosides with short (6 carbons) and long (>12 carbons) chains exhibited no toxicity at concentrations ranging from 1 to 1000 μM. Triazole-containing β-xylopyranosides with 8, 10, or 12 carbons caused toxicity via apoptosis, with CC50 values ranging from 26-890 μM. The two longest chain compounds did form stable monolayers at the air-water interface over a range of temperatures, although a brief transition to an the unstable monolayer was observed.",

keywords = "Carbohydrate surfactants, Click chemistry, Cytotoxicity, Huisgen cycloaddition, Langmuir monolayers",

author = "{Davis Oldham}, E. and Srivenu Seelam and Carolina Lema and Aguilera, {Renato J.} and Jennifer Fiegel and Rankin, {Stephen E.} and Knutson, {Barbara L.} and Lehmler, {Hans Joachim}",

note = "Funding Information: This work was supported by the National Science Foundation (CBET-0967381/0967390), the U.S. Department of Agriculture Biomass Research and Development Initiative (Grant Agreement 68-3A75-7-608) and the Department of Energy Development and Independence, Energy and Environment Cabinet of The Commonwealth of Kentucky. The cell culture work was performed at the Cell Culture Core of the Border Biomedical Research Center (BBRC) supported by grant 8G12MD007592 from the National Center for Research Resources (NCRR) of the NIH, granted to the University of Texas at El Paso.",

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doi = "10.1016/j.carres.2013.06.020",

language = "English",

volume = "379",

pages = "68--77",

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AU - Davis Oldham, E.

AU - Seelam, Srivenu

AU - Lema, Carolina

AU - Aguilera, Renato J.

AU - Fiegel, Jennifer

AU - Rankin, Stephen E.

AU - Knutson, Barbara L.

AU - Lehmler, Hans Joachim

N1 - Funding Information: This work was supported by the National Science Foundation (CBET-0967381/0967390), the U.S. Department of Agriculture Biomass Research and Development Initiative (Grant Agreement 68-3A75-7-608) and the Department of Energy Development and Independence, Energy and Environment Cabinet of The Commonwealth of Kentucky. The cell culture work was performed at the Cell Culture Core of the Border Biomedical Research Center (BBRC) supported by grant 8G12MD007592 from the National Center for Research Resources (NCRR) of the NIH, granted to the University of Texas at El Paso.

PY - 2013

Y1 - 2013

N2 - We are interested in the development of surfactants derived from hemicellulosic biomass, as they are potential components in pharmaceuticals, personal care products, and other detergents. Such surfactants should exhibit low toxicity in mammalian cells. In this study we synthesized a series of alkyl or fluoroalkyl β-xylopyranosides from azides and an alkyne using the copper-catalyzed azide-alkyne (CuAAC) 'click' reaction in 4 steps from xylose. The purified products were evaluated for both their surfactant properties, and for their biocompatibility. Unlike other carbohydrate-based surfactants, liquid-crystalline behavior was not observed by differential scanning calorimetry. The triazole-containing β-xylopyranosides with short (6 carbons) and long (>12 carbons) chains exhibited no toxicity at concentrations ranging from 1 to 1000 μM. Triazole-containing β-xylopyranosides with 8, 10, or 12 carbons caused toxicity via apoptosis, with CC50 values ranging from 26-890 μM. The two longest chain compounds did form stable monolayers at the air-water interface over a range of temperatures, although a brief transition to an the unstable monolayer was observed.

AB - We are interested in the development of surfactants derived from hemicellulosic biomass, as they are potential components in pharmaceuticals, personal care products, and other detergents. Such surfactants should exhibit low toxicity in mammalian cells. In this study we synthesized a series of alkyl or fluoroalkyl β-xylopyranosides from azides and an alkyne using the copper-catalyzed azide-alkyne (CuAAC) 'click' reaction in 4 steps from xylose. The purified products were evaluated for both their surfactant properties, and for their biocompatibility. Unlike other carbohydrate-based surfactants, liquid-crystalline behavior was not observed by differential scanning calorimetry. The triazole-containing β-xylopyranosides with short (6 carbons) and long (>12 carbons) chains exhibited no toxicity at concentrations ranging from 1 to 1000 μM. Triazole-containing β-xylopyranosides with 8, 10, or 12 carbons caused toxicity via apoptosis, with CC50 values ranging from 26-890 μM. The two longest chain compounds did form stable monolayers at the air-water interface over a range of temperatures, although a brief transition to an the unstable monolayer was observed.

KW - Carbohydrate surfactants

KW - Click chemistry

KW - Cytotoxicity

KW - Huisgen cycloaddition

KW - Langmuir monolayers

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VL - 379

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JO - Carbohydrate Research

JF - Carbohydrate Research

ER -

Synthesis, surface properties, and biocompatibility of 1,2,3-triazole- containing alkyl β-D-xylopyranoside surfactants

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

Access to Document

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