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Preparation and use of steroid-polyanionic polymer-based conjugates targeted to vascular endothelial cells

Assignee: The University of Texas Southwestern Medical Center
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Filing: 1992-03-23
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Granted: 1995-12-12
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Expires: 2012-03-23
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Abstract

Abstract This invention discloses new targeted conjugates for the delivery of a compound, and particularly, a steroid, to vascular endothelial cells. The conjugates comprise two components, preferably linked by a selectively-hydrolyzable bond, such as an acid-labile bond or enzyme-sensitive bond. The first component, a polyanionic polymer, and preferably, a polysulphated polymer such as a heparin-derivative, specifically directs the conjugate to vascular endothelial cells. The second component is a selected agent, such as asteroid, which exerts a specific effect on the target cell following its release. In particular, the present invention provides novel conjugated angiogenesis inhibitors, for use in the treatment of pathogenic conditions including cancer, arthritis, and diabetic blindness. An inhibitor comprising a heparin derivative and the anti-angiogenic steroid, cortisol, is herein shown to be markedly acid-labile, to suppress DNA synthesis and cell migration in human umbilical vein endothelial cells, to retard or abolish (depending on the route of injection) the vascularization of sponges in vivo and to retard lung tumor growth in mice by 65%. No adverse effects of the conjugate were detected, and equivalent treatments with a mixture of heparin plus cortisol were significantly less effective in all cases.

Inventors

  • 👤 Philip E. Thorpe

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 01:08
CPC Classifications
A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/56; A61K47/61; A61K47/58

Claims Analysis

Total Claims: 25
Claim 1
Independent Claim 108 words
A conjugate comprising a polymer, said polymer is a heparin, conjugated to a selected steroidal agent or agents by means of a biologically releasable bond formed between a reactive group on the steroidal agent or agents and: a) a free amino group revealed on the polymer through removal of a sulfate, acetyl or acyl group or groups attached to said amino group; b) a free carboxyl group on the polymer; c) a reactive group derivatized onto the polymer; or d) a combination of a), b) or c); wherein the conjugate is further characterized as having a molar ratio of agent/polymer of greater than 1 mole agent/mole of polymer.
Claim 2
Dependent Claim 108 words
A conjugate comprising a polymer, said polymer is a heparin, conjugated to a selected steroidal agent or agents by means of a biologically releasable bond formed between a reactive group on the steroidal agent or agents and: a) a free amino group revealed on the polymer through removal of a sulfate, acetyl or acyl group or groups attached to said amino group; b) a free carboxyl group on the polymer; c) a reactive group derivatized onto the polymer; or d) a combination of a), b) or c); wherein the conjugate is further characterized as having a molar ratio of agent/polymer of greater than 1 mole agent/mole of polymer.
Claim 3
Dependent Claim 14 words
The conjugate of claim 1, wherein the polymer derivative is a non-anticoagulating heparin derivative.
Claim 4
Dependent Claim 19 words
The conjugate of claim 2, wherein the conjugate has less than 2.5% of the anticoagulating activity of native heparin.
Claim 5
Dependent Claim 26 words
The conjugate of claim 1, wherein the polymer is derivatized to introduce functional groups permitting the attachment of the selected agent through a biologically releasable bond.
Claim 6
Dependent Claim 29 words
The conjugate of claim 4, wherein the polymer is derivatized to introduce functional groups permitting the attachment of the selected agent through a biologically releasable disulfide or trisulfide bond.
Claim 7
Dependent Claim 15 words
The conjugate of claim 1, wherein the biologically releasable bond is a selectively hydrolyzable bond.
Claim 8
Dependent Claim 14 words
The conjugate of claim 6, wherein the selectively hydrolyzable bond is an acid-labile bond.
Claim 9
Dependent Claim 18 words
The conjugate of claim 7, wherein the acid-labile bond is hydrolyzable at a pH of 4.8 or lower.
Claim 10
Dependent Claim 24 words
The conjugate of claim 7, wherein the polymer is derivatized to introduce side chains terminating in hydrazide, hydrazine, primary amine or secondary amine groups.
Claim 11
Dependent Claim 38 words
The conjugate of claim 9, wherein the derivatized polymer is the condensation product of the polymer and adipic dihydrazide, succinic dihydrazide, hydrazine or hydrazine hydrate, and the agent is conjugated to the polymer through a Schiff's base linkage.
Claim 12
Dependent Claim 20 words
The conjugate of claim 10, wherein the agent is conjugated to the polymer through a hydrazone or acyl hydrazone bond.
Claim 13
Dependent Claim 24 words
The conjugate of claim 11, wherein the agent is conjugated to the polymer through a hydrazide linker having the structure R-CO-NH-NH.sub.2 wherein R=the polymer,
Claim 14
Dependent Claim 28 words
The conjugate of claim 10, wherein the agent is conjugated to the polymer by a hydrazide linker having the structure: R-CO-NH-NH-CO-(CH.sub.2).sub.n -CO-NH-NH.sub.2 ; wherein n=1-50; and R=the polymer.
Claim 15
Dependent Claim 14 words
The conjugate of claim 1, wherein the biologically releasable bond is an enzyme-sensitive bond.
Claim 16
Dependent Claim 13 words
The conjugate of claim 14, wherein the enzyme-sensitive bond is a peptide bond.
Claim 17
Dependent Claim 21 words
The conjugate of claim 15, wherein the agent is linked to the polymer through a peptide that includes the sequence Leu-Ala-Leu-Ala.
Claim 18
Dependent Claim 19 words
The conjugate of claim 14, wherein the enzyme-sensitive bond is an ester, an amide, a phosphodiester or a glycoside.
Claim 19
Dependent Claim 17 words
The conjugate of claim 1, wherein the steroidal agent is asteroid from Table II or Table IV.
Claim 20
Dependent Claim 12 words
The conjugate of claim 1, wherein the steroidal agent has anti-angiogenic activity.
Claim 21
Dependent Claim 12 words
The conjugate of claim 1, wherein the steroidal agent has anti-angiostatic activity.
Claim 22
Dependent Claim 15 words
A pharmaceutical preparation comprising the conjugate of claim 1 dispersed in a pharmacologically acceptable vehicle.
Claim 23
Dependent Claim 10 words
The pharmaceutical preparation of claim 21, suitable for parenteral administration.
Claim 24
Dependent Claim 18 words
The conjugate of claim 1, wherein the molar ratio of agent:polymer is at least 5 moles agent/mole polymer.
Claim 25
Dependent Claim 21 words
The conjugate of claim 1, wherein the molar ration of agent:polymer ranges from about 5 to about 80 moles agent/mole polymer.

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Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1998-12-11 1999-06-12 1999-12-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2002-12-11 2003-06-12 2003-12-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2006-12-11 2007-06-12 2007-12-12 $7700.00 Window Closed / Lapsed

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