Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates

Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the...

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Published inBioconjugate chemistry Vol. 25; no. 4; pp. 718 - 723
Main Authors Ruhela, Dipali, Kivimäe, Saul, Szoka, Francis C
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 16.04.2014
Subjects
Animals
Cancer
Carbohydrate Conformation
Carbohydrate Sequence
Cattle
Cells, Cultured
Cercopithecus aethiops
Chemistry
COS Cells
Enzymes
Hyaluronic Acid - biosynthesis
Hyaluronic Acid - chemistry
Hyaluronoglucosaminidase - metabolism
Lipids
Lipids - biosynthesis
Lipids - chemistry
Male
Molecular Sequence Data
Molecular weight
Oligosaccharides - biosynthesis
Oligosaccharides - chemistry
Testis - enzymology
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Abstract Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the carboxylate group of the glucuronic acid using carbodiimide chemistry. The HA-lipid conjugate mixture is then digested with bovine testicular hyaluronidase to yield HA-DiPhPE conjugates that have a narrow distribution of moderately sized HA oligosaccharides. These HA-lipid conjugates can be incorporated into liposomes or micelles to selectively target CD44 that is overexpressed on many cancer or cancer initiating cells.
AbstractList Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide-lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the carboxylate group of the glucuronic acid using carbodiimide chemistry. The HA-lipid conjugate mixture is then digested with bovine testicular hyaluronidase to yield HA-DiPhPE conjugates that have a narrow distribution of moderately sized HA oligosaccharides. These HA-lipid conjugates can be incorporated into liposomes or micelles to selectively target CD44 that is overexpressed on many cancer or cancer initiating cells. [PUBLICATION ABSTRACT]
Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide-lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the carboxylate group of the glucuronic acid using carbodiimide chemistry. The HA-lipid conjugate mixture is then digested with bovine testicular hyaluronidase to yield HA-DiPhPE conjugates that have a narrow distribution of moderately sized HA oligosaccharides. These HA-lipid conjugates can be incorporated into liposomes or micelles to selectively target CD44 that is overexpressed on many cancer or cancer initiating cells.
Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently attaching diphytanoyl glycerophosphatidylethanolamine (DiPhPE) to commercially available high molecular weight hyaluronic acid (HA), via the carboxylate group of the glucuronic acid using carbodiimide chemistry. The HA-lipid conjugate mixture is then digested with bovine testicular hyaluronidase to yield HA-DiPhPE conjugates that have a narrow distribution of moderately sized HA oligosaccharides. These HA-lipid conjugates can be incorporated into liposomes or micelles to selectively target CD44 that is overexpressed on many cancer or cancer initiating cells.
Author Ruhela, Dipali
Kivimäe, Saul
Szoka, Francis C
AuthorAffiliation University of California San Francisco
Departments of Bioengineering, Therapeutic Sciences, and Pharmaceutical Chemistry
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Cites_doi 10.1074/jbc.M112.442889
10.1021/bm000283n
10.1016/j.biomaterials.2009.07.024
10.3109/10611869609046255
10.1021/bc9900338
10.1016/j.jconrel.2012.07.015
10.1006/abbi.1994.1387
10.1158/0008-5472.CAN-03-0654
10.1002/(SICI)1097-0215(19980729)77:3<396::AID-IJC15>3.0.CO;2-6
10.1021/bc0600721
10.1016/j.ejpb.2013.06.003
10.1248/bpb.24.535
10.1016/S0021-9258(18)70226-3
10.1593/neo.03460
10.1007/s11095-012-0672-1
10.1021/bc00028a010
10.1002/ijc.11615
10.1042/bj2340653
10.1021/mp800024g
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References 22820451 - J Control Release. 2012 Sep 28;162(3):545-52
8080272 - Arch Biochem Biophys. 1994 Sep;313(2):267-73
11710102 - Biomacromolecules. 2000 Summer;1(2):208-18
18547053 - Mol Pharm. 2008 Jul-Aug;5(4):474-86
8798873 - J Drug Target. 1996;4(1):1-8
13641241 - J Biol Chem. 1959 Mar;234(3):466-8
15256056 - Neoplasia. 2004 Jul-Aug;6(4):343-53
9663602 - Int J Cancer. 1998 Jul 29;77(3):396-401
7948100 - Bioconjug Chem. 1994 Jul-Aug;5(4):339-47
3087347 - Biochem J. 1986 Mar 15;234(3):653-8
14696107 - Int J Cancer. 2004 Feb 20;108(5):780-9
11289136 - Cancer Res. 2001 Mar 15;61(6):2592-601
14744789 - Cancer Res. 2004 Jan 15;64(2):711-8
19647313 - Biomaterials. 2009 Oct;30(30):6026-34
22350800 - Pharm Res. 2012 Apr;29(4):1121-33
23791684 - Eur J Pharm Biopharm. 2013 Nov;85(3 Pt A):373-80
23530033 - J Biol Chem. 2013 May 17;288(20):14068-79
10502340 - Bioconjug Chem. 1999 Sep-Oct;10(5):755-63
16984148 - Bioconjug Chem. 2006 Sep-Oct;17(5):1360-3
11379776 - Biol Pharm Bull. 2001 May;24(5):535-43
Luo Y. (ref12/cit12) 2000; 1
Peer D. (ref7/cit7) 2004; 108
Stern R. (ref1/cit1) 2009
Eliaz R. E. (ref8/cit8) 2004; 64
Journo-Gershfeld G. (ref14/cit14) 2012; 29
Bartlett G. R. (ref21/cit21) 1959; 234
Ruhela D. (ref16/cit16) 2006; 17
Luo Y. (ref11/cit11) 1999
Akima K. (ref4/cit4) 1996; 4
Eliaz R. E. (ref5/cit5) 2001; 61
Oh E. J. (ref20/cit20) 2009; 30
Peer D. (ref6/cit6) 2004; 6
Yerushalmi N. (ref13/cit13) 1994; 313
Pandey M. S. (ref18/cit18) 2013; 288
Laurent T. C. (ref17/cit17) 1986; 234
Pouyani T. (ref3/cit3) 1994; 5
Arpicco S. (ref10/cit10) 2013; 85
Zeng C. (ref15/cit15) 1998; 77
Platt V. M. (ref2/cit2) 2008; 5
Dufaÿ Wojcicki A. (ref9/cit9) 2012; 162
Sugahara S. (ref19/cit19) 2001; 24
References_xml – volume: 288
  start-page: 14068
  year: 2013
  ident: ref18/cit18
  publication-title: J. Biol. Chem.
  doi: 10.1074/jbc.M112.442889
  contributor:
    fullname: Pandey M. S.
– volume: 1
  start-page: 208
  year: 2000
  ident: ref12/cit12
  publication-title: Biomacromolecules
  doi: 10.1021/bm000283n
  contributor:
    fullname: Luo Y.
– volume: 30
  start-page: 6026
  year: 2009
  ident: ref20/cit20
  publication-title: Biomaterials
  doi: 10.1016/j.biomaterials.2009.07.024
  contributor:
    fullname: Oh E. J.
– volume: 4
  start-page: 1
  year: 1996
  ident: ref4/cit4
  publication-title: J. Drug Targeting
  doi: 10.3109/10611869609046255
  contributor:
    fullname: Akima K.
– volume-title: Hyaluronan in Cancer Biology
  year: 2009
  ident: ref1/cit1
  contributor:
    fullname: Stern R.
– volume: 61
  start-page: 2592
  year: 2001
  ident: ref5/cit5
  publication-title: Cancer Res.
  contributor:
    fullname: Eliaz R. E.
– start-page: 755
  year: 1999
  ident: ref11/cit11
  publication-title: Bioconjugate Chem.
  doi: 10.1021/bc9900338
  contributor:
    fullname: Luo Y.
– volume: 162
  start-page: 545
  year: 2012
  ident: ref9/cit9
  publication-title: J. Controlled Release
  doi: 10.1016/j.jconrel.2012.07.015
  contributor:
    fullname: Dufaÿ Wojcicki A.
– volume: 313
  start-page: 267
  year: 1994
  ident: ref13/cit13
  publication-title: Arch. Biochem. Biophys.
  doi: 10.1006/abbi.1994.1387
  contributor:
    fullname: Yerushalmi N.
– volume: 64
  start-page: 711
  year: 2004
  ident: ref8/cit8
  publication-title: Cancer Res.
  doi: 10.1158/0008-5472.CAN-03-0654
  contributor:
    fullname: Eliaz R. E.
– volume: 77
  start-page: 396
  year: 1998
  ident: ref15/cit15
  publication-title: Int. J. Cancer
  doi: 10.1002/(SICI)1097-0215(19980729)77:3<396::AID-IJC15>3.0.CO;2-6
  contributor:
    fullname: Zeng C.
– volume: 17
  start-page: 1360
  year: 2006
  ident: ref16/cit16
  publication-title: Bioconjugate Chem.
  doi: 10.1021/bc0600721
  contributor:
    fullname: Ruhela D.
– volume: 85
  start-page: 373
  year: 2013
  ident: ref10/cit10
  publication-title: Eur. J. Pharm. Biopharm.
  doi: 10.1016/j.ejpb.2013.06.003
  contributor:
    fullname: Arpicco S.
– volume: 24
  start-page: 535
  year: 2001
  ident: ref19/cit19
  publication-title: Biol. Pharm. Bull.
  doi: 10.1248/bpb.24.535
  contributor:
    fullname: Sugahara S.
– volume: 234
  start-page: 466
  year: 1959
  ident: ref21/cit21
  publication-title: J. Biol. Chem.
  doi: 10.1016/S0021-9258(18)70226-3
  contributor:
    fullname: Bartlett G. R.
– volume: 6
  start-page: 343
  year: 2004
  ident: ref6/cit6
  publication-title: Neoplasia
  doi: 10.1593/neo.03460
  contributor:
    fullname: Peer D.
– volume: 29
  start-page: 1121
  year: 2012
  ident: ref14/cit14
  publication-title: Pharm. Res.
  doi: 10.1007/s11095-012-0672-1
  contributor:
    fullname: Journo-Gershfeld G.
– volume: 5
  start-page: 339
  year: 1994
  ident: ref3/cit3
  publication-title: Bioconjugate Chem.
  doi: 10.1021/bc00028a010
  contributor:
    fullname: Pouyani T.
– volume: 108
  start-page: 780
  year: 2004
  ident: ref7/cit7
  publication-title: Int. J. Cancer
  doi: 10.1002/ijc.11615
  contributor:
    fullname: Peer D.
– volume: 234
  start-page: 653
  year: 1986
  ident: ref17/cit17
  publication-title: Biochem. J.
  doi: 10.1042/bj2340653
  contributor:
    fullname: Laurent T. C.
– volume: 5
  start-page: 474
  year: 2008
  ident: ref2/cit2
  publication-title: Mol. Pharm.
  doi: 10.1021/mp800024g
  contributor:
    fullname: Platt V. M.
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Snippet Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently...
Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide-lipid conjugates. This strategy is based on first covalently...
Herein, we describe an efficient and high-yielding method to synthesize hyaluronan oligosaccharide–lipid conjugates. This strategy is based on first covalently...
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SubjectTerms Animals
Cancer
Carbohydrate Conformation
Carbohydrate Sequence
Cattle
Cells, Cultured
Cercopithecus aethiops
Chemistry
COS Cells
Enzymes
Hyaluronic Acid - biosynthesis
Hyaluronic Acid - chemistry
Hyaluronoglucosaminidase - metabolism
Lipids
Lipids - biosynthesis
Lipids - chemistry
Male
Molecular Sequence Data
Molecular weight
Oligosaccharides - biosynthesis
Oligosaccharides - chemistry
Testis - enzymology
Title Chemoenzymatic Synthesis of Oligohyaluronan–Lipid Conjugates
URI http://dx.doi.org/10.1021/bc4005975
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