Loading…
Like Dissolves Like? A Comprehensive Evaluation of Partial Solubility Parameters to Predict Polymer–Drug Compatibility in Ultrahigh Drug-Loaded Polymer Micelles
Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as “like-dissolves-like” or hydrophilic/hydrophobic. However, polymer–drug compatibility strongly affects formulation prop...
Saved in:
Published in: | Biomacromolecules 2019-08, Vol.20 (8), p.3041-3056 |
---|---|
Main Authors: | , , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-a342t-cdc2f173c48ffd414fc8bffbdae860485075ba20a10e07f84606e79ed118cb3f3 |
---|---|
cites | cdi_FETCH-LOGICAL-a342t-cdc2f173c48ffd414fc8bffbdae860485075ba20a10e07f84606e79ed118cb3f3 |
container_end_page | 3056 |
container_issue | 8 |
container_start_page | 3041 |
container_title | Biomacromolecules |
container_volume | 20 |
creator | Lübtow, Michael M Haider, Malik Salman Kirsch, Marius Klisch, Stefanie Luxenhofer, Robert |
description | Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as “like-dissolves-like” or hydrophilic/hydrophobic. However, polymer–drug compatibility strongly affects formulation properties and therefore the translation of a formulation into the clinics. Specific interactions such as hydrogen-bonding, π–π stacking, or coordination interactions can be utilized to increase drug loading. This is commonly based on trial and error and eventually leads to an optimized drug carrier. Unfortunately, due to the unique characteristics of each drug, the deduction of advanced general concepts remains challenging. Furthermore, the introduction of complex moieties or specifically modified polymers hampers systematic investigations regarding polymer–drug compatibility as well as clinical translation. In this study, we reduced the complexity to isolate the crucial factors determining drug loading. Therefore, the compatibility of 18 different amphiphilic polymers for five different hydrophobic drugs was determined empirically. Subsequently, the obtained specificities were compared to theoretical compatibilities derived from either the Flory–Huggins interaction parameters or the Hansen solubility parameters. In general, the Flory–Huggins interaction parameters were less suited to correctly estimate the experimental drug solubilization compared to the Hansen solubility parameters. The latter were able to correctly predict some trend regarding good and poor solubilizers, yet the overall predictive strength of Hansen solubility parameters is clearly unsatisfactory. |
doi_str_mv | 10.1021/acs.biomac.9b00618 |
format | article |
fullrecord | <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acs_biomac_9b00618</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c18091107</sourcerecordid><originalsourceid>FETCH-LOGICAL-a342t-cdc2f173c48ffd414fc8bffbdae860485075ba20a10e07f84606e79ed118cb3f3</originalsourceid><addsrcrecordid>eNp9kEtOwzAURS0EoqWwAQbIG0iw8-8IVaV8pCAqQceR4zy3Lk5c2UmlztgDO2BprISkaRkysv3ePVfyQeiaEpcSj94ybt1c6pJxd5wTEtHkBA1p6EVOEBHvdH8PnTgexwN0Ye2aEDL2g_AcDXzq0yT06RB9p_ID8L20VqstWNw97_AET3W5MbCCysot4NmWqYbVUldYCzxnppZM4TetmlwqWe-6ESuhBmNxrfHcQCF5jeda7UowP59f96ZZ7jvbkgMiK7xQtWEruVzhbu-kmhVQHCn8IjkoBfYSnQmmLFwdzhFaPMzep09O-vr4PJ2kDvMDr3Z4wT1BY58HiRBFQAPBk1yIvGCQRCRIQhKHOfMIowRILJLWUQTxGApKE577wh8hr-_lRltrQGQbI0tmdhklWSc8a4VnvfDsILyFbnpo0-QlFH_I0XAbcPtAB691Y6r2D_81_gLUopN5</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Like Dissolves Like? A Comprehensive Evaluation of Partial Solubility Parameters to Predict Polymer–Drug Compatibility in Ultrahigh Drug-Loaded Polymer Micelles</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><creator>Lübtow, Michael M ; Haider, Malik Salman ; Kirsch, Marius ; Klisch, Stefanie ; Luxenhofer, Robert</creator><creatorcontrib>Lübtow, Michael M ; Haider, Malik Salman ; Kirsch, Marius ; Klisch, Stefanie ; Luxenhofer, Robert</creatorcontrib><description>Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as “like-dissolves-like” or hydrophilic/hydrophobic. However, polymer–drug compatibility strongly affects formulation properties and therefore the translation of a formulation into the clinics. Specific interactions such as hydrogen-bonding, π–π stacking, or coordination interactions can be utilized to increase drug loading. This is commonly based on trial and error and eventually leads to an optimized drug carrier. Unfortunately, due to the unique characteristics of each drug, the deduction of advanced general concepts remains challenging. Furthermore, the introduction of complex moieties or specifically modified polymers hampers systematic investigations regarding polymer–drug compatibility as well as clinical translation. In this study, we reduced the complexity to isolate the crucial factors determining drug loading. Therefore, the compatibility of 18 different amphiphilic polymers for five different hydrophobic drugs was determined empirically. Subsequently, the obtained specificities were compared to theoretical compatibilities derived from either the Flory–Huggins interaction parameters or the Hansen solubility parameters. In general, the Flory–Huggins interaction parameters were less suited to correctly estimate the experimental drug solubilization compared to the Hansen solubility parameters. The latter were able to correctly predict some trend regarding good and poor solubilizers, yet the overall predictive strength of Hansen solubility parameters is clearly unsatisfactory.</description><identifier>ISSN: 1525-7797</identifier><identifier>EISSN: 1526-4602</identifier><identifier>DOI: 10.1021/acs.biomac.9b00618</identifier><identifier>PMID: 31318531</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Biomacromolecules, 2019-08, Vol.20 (8), p.3041-3056</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a342t-cdc2f173c48ffd414fc8bffbdae860485075ba20a10e07f84606e79ed118cb3f3</citedby><cites>FETCH-LOGICAL-a342t-cdc2f173c48ffd414fc8bffbdae860485075ba20a10e07f84606e79ed118cb3f3</cites><orcidid>0000-0001-5567-7404</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31318531$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lübtow, Michael M</creatorcontrib><creatorcontrib>Haider, Malik Salman</creatorcontrib><creatorcontrib>Kirsch, Marius</creatorcontrib><creatorcontrib>Klisch, Stefanie</creatorcontrib><creatorcontrib>Luxenhofer, Robert</creatorcontrib><title>Like Dissolves Like? A Comprehensive Evaluation of Partial Solubility Parameters to Predict Polymer–Drug Compatibility in Ultrahigh Drug-Loaded Polymer Micelles</title><title>Biomacromolecules</title><addtitle>Biomacromolecules</addtitle><description>Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as “like-dissolves-like” or hydrophilic/hydrophobic. However, polymer–drug compatibility strongly affects formulation properties and therefore the translation of a formulation into the clinics. Specific interactions such as hydrogen-bonding, π–π stacking, or coordination interactions can be utilized to increase drug loading. This is commonly based on trial and error and eventually leads to an optimized drug carrier. Unfortunately, due to the unique characteristics of each drug, the deduction of advanced general concepts remains challenging. Furthermore, the introduction of complex moieties or specifically modified polymers hampers systematic investigations regarding polymer–drug compatibility as well as clinical translation. In this study, we reduced the complexity to isolate the crucial factors determining drug loading. Therefore, the compatibility of 18 different amphiphilic polymers for five different hydrophobic drugs was determined empirically. Subsequently, the obtained specificities were compared to theoretical compatibilities derived from either the Flory–Huggins interaction parameters or the Hansen solubility parameters. In general, the Flory–Huggins interaction parameters were less suited to correctly estimate the experimental drug solubilization compared to the Hansen solubility parameters. The latter were able to correctly predict some trend regarding good and poor solubilizers, yet the overall predictive strength of Hansen solubility parameters is clearly unsatisfactory.</description><issn>1525-7797</issn><issn>1526-4602</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kEtOwzAURS0EoqWwAQbIG0iw8-8IVaV8pCAqQceR4zy3Lk5c2UmlztgDO2BprISkaRkysv3ePVfyQeiaEpcSj94ybt1c6pJxd5wTEtHkBA1p6EVOEBHvdH8PnTgexwN0Ye2aEDL2g_AcDXzq0yT06RB9p_ID8L20VqstWNw97_AET3W5MbCCysot4NmWqYbVUldYCzxnppZM4TetmlwqWe-6ESuhBmNxrfHcQCF5jeda7UowP59f96ZZ7jvbkgMiK7xQtWEruVzhbu-kmhVQHCn8IjkoBfYSnQmmLFwdzhFaPMzep09O-vr4PJ2kDvMDr3Z4wT1BY58HiRBFQAPBk1yIvGCQRCRIQhKHOfMIowRILJLWUQTxGApKE577wh8hr-_lRltrQGQbI0tmdhklWSc8a4VnvfDsILyFbnpo0-QlFH_I0XAbcPtAB691Y6r2D_81_gLUopN5</recordid><startdate>20190812</startdate><enddate>20190812</enddate><creator>Lübtow, Michael M</creator><creator>Haider, Malik Salman</creator><creator>Kirsch, Marius</creator><creator>Klisch, Stefanie</creator><creator>Luxenhofer, Robert</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-5567-7404</orcidid></search><sort><creationdate>20190812</creationdate><title>Like Dissolves Like? A Comprehensive Evaluation of Partial Solubility Parameters to Predict Polymer–Drug Compatibility in Ultrahigh Drug-Loaded Polymer Micelles</title><author>Lübtow, Michael M ; Haider, Malik Salman ; Kirsch, Marius ; Klisch, Stefanie ; Luxenhofer, Robert</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a342t-cdc2f173c48ffd414fc8bffbdae860485075ba20a10e07f84606e79ed118cb3f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lübtow, Michael M</creatorcontrib><creatorcontrib>Haider, Malik Salman</creatorcontrib><creatorcontrib>Kirsch, Marius</creatorcontrib><creatorcontrib>Klisch, Stefanie</creatorcontrib><creatorcontrib>Luxenhofer, Robert</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Biomacromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lübtow, Michael M</au><au>Haider, Malik Salman</au><au>Kirsch, Marius</au><au>Klisch, Stefanie</au><au>Luxenhofer, Robert</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Like Dissolves Like? A Comprehensive Evaluation of Partial Solubility Parameters to Predict Polymer–Drug Compatibility in Ultrahigh Drug-Loaded Polymer Micelles</atitle><jtitle>Biomacromolecules</jtitle><addtitle>Biomacromolecules</addtitle><date>2019-08-12</date><risdate>2019</risdate><volume>20</volume><issue>8</issue><spage>3041</spage><epage>3056</epage><pages>3041-3056</pages><issn>1525-7797</issn><eissn>1526-4602</eissn><abstract>Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as “like-dissolves-like” or hydrophilic/hydrophobic. However, polymer–drug compatibility strongly affects formulation properties and therefore the translation of a formulation into the clinics. Specific interactions such as hydrogen-bonding, π–π stacking, or coordination interactions can be utilized to increase drug loading. This is commonly based on trial and error and eventually leads to an optimized drug carrier. Unfortunately, due to the unique characteristics of each drug, the deduction of advanced general concepts remains challenging. Furthermore, the introduction of complex moieties or specifically modified polymers hampers systematic investigations regarding polymer–drug compatibility as well as clinical translation. In this study, we reduced the complexity to isolate the crucial factors determining drug loading. Therefore, the compatibility of 18 different amphiphilic polymers for five different hydrophobic drugs was determined empirically. Subsequently, the obtained specificities were compared to theoretical compatibilities derived from either the Flory–Huggins interaction parameters or the Hansen solubility parameters. In general, the Flory–Huggins interaction parameters were less suited to correctly estimate the experimental drug solubilization compared to the Hansen solubility parameters. The latter were able to correctly predict some trend regarding good and poor solubilizers, yet the overall predictive strength of Hansen solubility parameters is clearly unsatisfactory.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31318531</pmid><doi>10.1021/acs.biomac.9b00618</doi><tpages>16</tpages><orcidid>https://orcid.org/0000-0001-5567-7404</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1525-7797 |
ispartof | Biomacromolecules, 2019-08, Vol.20 (8), p.3041-3056 |
issn | 1525-7797 1526-4602 |
language | eng |
recordid | cdi_crossref_primary_10_1021_acs_biomac_9b00618 |
source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
title | Like Dissolves Like? A Comprehensive Evaluation of Partial Solubility Parameters to Predict Polymer–Drug Compatibility in Ultrahigh Drug-Loaded Polymer Micelles |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T00%3A34%3A32IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Like%20Dissolves%20Like?%20A%20Comprehensive%20Evaluation%20of%20Partial%20Solubility%20Parameters%20to%20Predict%20Polymer%E2%80%93Drug%20Compatibility%20in%20Ultrahigh%20Drug-Loaded%20Polymer%20Micelles&rft.jtitle=Biomacromolecules&rft.au=Lu%CC%88btow,%20Michael%20M&rft.date=2019-08-12&rft.volume=20&rft.issue=8&rft.spage=3041&rft.epage=3056&rft.pages=3041-3056&rft.issn=1525-7797&rft.eissn=1526-4602&rft_id=info:doi/10.1021/acs.biomac.9b00618&rft_dat=%3Cacs_cross%3Ec18091107%3C/acs_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a342t-cdc2f173c48ffd414fc8bffbdae860485075ba20a10e07f84606e79ed118cb3f3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/31318531&rfr_iscdi=true |