Cover Image

An underestimated factor: the extent of cross-reactions modifying APIs in surface-modified liposomal preparations caused by comprised activated lipids

Despite the nowadays available plentitude of strategies to selectively introduce functional surface modification of liposomes, in preclinical research this process is still primarily performed after liposomal preparation utilizing comprised activated phospholipids with functionalized head groups. Ho...

Full description

Saved in:
Bibliographic Details
Main Authors: Sauter, Max (Author) , Burhenne, Jürgen (Author) , Haefeli, Walter E. (Author) , Uhl, Philipp (Author)
Format: Article (Journal)
Language:English
Published: 27 September 2020
In: Molecules
Year: 2020, Volume: 25, Issue: 19
ISSN:1420-3049
DOI:10.3390/molecules25194436
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.3390/molecules25194436
Verlag, lizenzpflichtig, Volltext: https://www.mdpi.com/1420-3049/25/19/4436
Get full text
Author Notes:Max Sauter, Jürgen Burhenne, Walter E. Haefeli and Philipp Uhl

MARC

LEADER 00000caa a2200000 c 4500
001 1743784821
003 DE-627
005 20230428024258.0
007 cr uuu---uuuuu
008 210104s2020 xx |||||o 00| ||eng c
024 7 |a 10.3390/molecules25194436  |2 doi 
035 |a (DE-627)1743784821 
035 |a (DE-599)KXP1743784821 
035 |a (OCoLC)1341384378 
040 |a DE-627  |b ger  |c DE-627  |e rda 
041 |a eng 
084 |a 30  |2 sdnb 
100 1 |a Sauter, Max  |e VerfasserIn  |0 (DE-588)1103516507  |0 (DE-627)86126813X  |0 (DE-576)470642033  |4 aut 
245 1 3 |a An underestimated factor  |b the extent of cross-reactions modifying APIs in surface-modified liposomal preparations caused by comprised activated lipids  |c Max Sauter, Jürgen Burhenne, Walter E. Haefeli and Philipp Uhl 
264 1 |c 27 September 2020 
336 |a Text  |b txt  |2 rdacontent 
337 |a Computermedien  |b c  |2 rdamedia 
338 |a Online-Ressource  |b cr  |2 rdacarrier 
500 |a Gesehen am 04.01.2021 
520 |a Despite the nowadays available plentitude of strategies to selectively introduce functional surface modification of liposomes, in preclinical research this process is still primarily performed after liposomal preparation utilizing comprised activated phospholipids with functionalized head groups. However, because these activated lipids are present during the liposomal preparation process, they can cross-react with incorporated drugs, especially the particularly often utilized active esters and maleimide groups. Macromolecular drugs, being composed of amino acids, are particularly prone to such cross-reactions due to their often multiple reactive functionalities such as amino and disulfide groups. To demonstrate this impact on the formulation in liposomal surface modification, we assessed the extent of cross-reaction during the liposomal preparation of two activated phospholipids with typically used head group functionalized phospholipids, with the two peptide drugs vancomycin and insulin comprising disulfide and amino functionalities. Both drugs revealed a considerable fraction of covalent modification (estimated 2 to 12%) generated during the liposome preparation process with comprised activated lipids. Modification of the active pharmaceutical ingredients (APIs) was determined by high-resolution mass spectrometric analysis. These findings clearly demonstrate the non-negligibility of potential cross reactions using the post preparation liposomal surface modification strategy in preclinical research. 
650 4 |a API-modification 
650 4 |a cross-reaction 
650 4 |a head group-functionalized phospholipids 
650 4 |a liposomes 
650 4 |a macromolecular drugs 
650 4 |a surface modification 
700 1 |a Burhenne, Jürgen  |d 1963-  |e VerfasserIn  |0 (DE-588)1034228889  |0 (DE-627)745126987  |0 (DE-576)381858197  |4 aut 
700 1 |a Haefeli, Walter E.  |d 1958-  |e VerfasserIn  |0 (DE-588)124572359  |0 (DE-627)656806141  |0 (DE-576)340514221  |4 aut 
700 1 |a Uhl, Philipp  |e VerfasserIn  |0 (DE-588)1112349391  |0 (DE-627)866420797  |0 (DE-576)476575230  |4 aut 
773 0 8 |i Enthalten in  |t Molecules  |d Basel : MDPI, 1996  |g 25(2020,19) Artikel-Nummer 4436, 11 Seiten  |h Online-Ressource  |w (DE-627)311313132  |w (DE-600)2008644-1  |w (DE-576)281192456  |x 1420-3049  |7 nnas  |a An underestimated factor the extent of cross-reactions modifying APIs in surface-modified liposomal preparations caused by comprised activated lipids 
773 1 8 |g volume:25  |g year:2020  |g number:19  |a An underestimated factor the extent of cross-reactions modifying APIs in surface-modified liposomal preparations caused by comprised activated lipids 
856 4 0 |u https://doi.org/10.3390/molecules25194436  |x Verlag  |x Resolving-System  |z lizenzpflichtig  |3 Volltext 
856 4 0 |u https://www.mdpi.com/1420-3049/25/19/4436  |x Verlag  |z lizenzpflichtig  |3 Volltext 
951 |a AR 
992 |a 20210104 
993 |a Article 
994 |a 2020 
998 |g 1112349391  |a Uhl, Philipp  |m 1112349391:Uhl, Philipp  |d 910000  |d 910100  |e 910000PU1112349391  |e 910100PU1112349391  |k 0/910000/  |k 1/910000/910100/  |p 4  |y j 
998 |g 124572359  |a Haefeli, Walter E.  |m 124572359:Haefeli, Walter E.  |d 910000  |d 910100  |e 910000PH124572359  |e 910100PH124572359  |k 0/910000/  |k 1/910000/910100/  |p 3 
998 |g 1034228889  |a Burhenne, Jürgen  |m 1034228889:Burhenne, Jürgen  |d 910000  |d 910100  |e 910000PB1034228889  |e 910100PB1034228889  |k 0/910000/  |k 1/910000/910100/  |p 2 
998 |g 1103516507  |a Sauter, Max  |m 1103516507:Sauter, Max  |d 910000  |d 910100  |e 910000PS1103516507  |e 910100PS1103516507  |k 0/910000/  |k 1/910000/910100/  |p 1  |x j 
999 |a KXP-PPN1743784821  |e 3829769318 
BIB |a Y 
SER |a journal 
JSO |a {"title":[{"title":"An underestimated factor","subtitle":"the extent of cross-reactions modifying APIs in surface-modified liposomal preparations caused by comprised activated lipids","title_sort":"underestimated factor"}],"person":[{"given":"Max","role":"aut","family":"Sauter","display":"Sauter, Max"},{"given":"Jürgen","role":"aut","family":"Burhenne","display":"Burhenne, Jürgen"},{"display":"Haefeli, Walter E.","role":"aut","given":"Walter E.","family":"Haefeli"},{"given":"Philipp","role":"aut","family":"Uhl","display":"Uhl, Philipp"}],"note":["Gesehen am 04.01.2021"],"type":{"media":"Online-Ressource","bibl":"article-journal"},"language":["eng"],"origin":[{"dateIssuedKey":"2020","dateIssuedDisp":"27 September 2020"}],"id":{"eki":["1743784821"],"doi":["10.3390/molecules25194436"]},"relHost":[{"pubHistory":["1.1996 -"],"language":["eng"],"physDesc":[{"extent":"Online-Ressource"}],"type":{"media":"Online-Ressource","bibl":"periodical"},"note":["Gesehen am 25.06.20"],"title":[{"title_sort":"Molecules","title":"Molecules","subtitle":"a journal of synthetic chemistry and natural product chemistry"}],"disp":"An underestimated factor the extent of cross-reactions modifying APIs in surface-modified liposomal preparations caused by comprised activated lipidsMolecules","name":{"displayForm":["Molecular Diversity Preservation International"]},"recId":"311313132","part":{"year":"2020","issue":"19","text":"25(2020,19) Artikel-Nummer 4436, 11 Seiten","volume":"25"},"id":{"eki":["311313132"],"zdb":["2008644-1"],"issn":["1420-3049"]},"origin":[{"publisherPlace":"Basel","dateIssuedDisp":"1996-","dateIssuedKey":"1996","publisher":"MDPI"}]}],"recId":"1743784821","name":{"displayForm":["Max Sauter, Jürgen Burhenne, Walter E. Haefeli and Philipp Uhl"]}} 
SRT |a SAUTERMAXBUNDERESTIM2720 

Similar Items