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Glycolipids as treatment for disease

a technology of glycolipids and lipids, applied in the field of glycolipids as treatment for disease, can solve the problems of limiting radiation treatment side effects, brain damage or death, and the remission obtained through chemotherapy is often not durable, and achieves the effect of improving the potency of antagonism of the insulin receptor and affinity for the insulin receptor

Inactive Publication Date: 2012-02-09
SENEB BIOSCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0033]In another embodiment, a compound of the invention utilized in methods and compositions of the present invention exhibits an improvement in a desirable biological property relative to the natural glycolipid. In another embodiment, the biological property is improved biological half-life. In another embodiment, the biological property is improved affinity for the insulin receptor. In another embodiment, the biological property is improved potency for antagonism of the insulin receptor. In another embodiment, the biological property is any other desirable biological property known in the art. Each possibility represents a separate embodiment of the present invention.

Problems solved by technology

However, side effects are a limiting factor in radiation treatments.
Unfortunately, the remissions obtained through chemotherapy are often not durable.
Congenital hyperinsulinism (CHI, OMIM 256450) is a genetic disorder of pancreatic β-cell function characterized by failure to suppress insulin secretion in the presence of hypoglycemia, resulting in brain damage or death if inadequately treated.

Method used

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  • Glycolipids as treatment for disease
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  • Glycolipids as treatment for disease

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of [5-N-acetyl-α-neuraminyl)-(2→3)]-[β-D-galactopyranosyl-(1→4)-O-D-glucopyranose] by Fermentation

[0125]The synthesis of this compound uses the process described by Samain (Samain and Priem, Method for Producing Oligopolysaccharides. WO 01 / 04341 (2001); Priem, Glycobiology, 12:235 (2002); Cottaz, EP Application No. 06291569.9 (2006)) with E. coli JM107-nanA-(Nst-01, pBBnsy) strain using lactose and sialic acid (Kok, J Chem Soc Perkin Trans, 1:2811-2815 (1996)) acid as exogeneous acceptors.

[0126]E. coli JM107-nanA-(Nst-01, pBBnsy) strain was grown at low cell density culture in shake flask fermentation. When the OD540 is about 1, isopropyl 1-thio-β-galactopyranoside (IPTG) and the substrates Neu5Ac and lactose (2 equivalents) were added via a sterile filter and the culture is shaken at 28° C. for 16 hr. After 16 hr, the cells were recovered by centrifugation at 8000 g and 4° C. for 10 min. The supernatant was separated for further TLC analysis while the pellet is resuspende...

example 2

Synthesis of 1-Fluoro-[(5-N-acetyl-α-neuraminyl)-(2→3)]-[β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside]

[0127]The [5-N-acetyl-α-neuraminyl)-(2→3)]-[β-D-galactopyranosyl-(1→4)-β-D-glucopyranose], and DMAP are dissolved in pyridine. Acetic anhydride was added dropwise and then the reaction mixtureis stirred for 2 days. The reaction mixture was concentrated and the residue treated with methanol. After 30 min, the reaction mixture was concetrated again, the residue dissolved in ethyl acetate and the organic solution washed with water, 5% citric acid in water, water and brine. The organic solution was dried with sodium sulfate, filtered and concetrated to dryness yielding a solid used directly for the next step.

[0128]The solid is cooled to −30° C. and then hydrogen fluoride-pyridine was added. The reaction mixture was stirred for 1 hr allowing the reaction to slowly warm to room temperature and then for 4 hrs at room temperature. The reaction mixture was cooled to −10° C. and is then slo...

example 3

Synthesis of [(5-N-acetyl-α-neuraminyl)-(2→3)]-[β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-β-(1→1′)-D-erythro-sphingosine]

[0130]The compound 1-fluoro-[(5-N-acetyl-α-neuraminyl)-(2→3)]-[β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside] and D-erythro-sphingosine are coupled using the procedure as described in Vaughan, J Am Chem Soc, 128:6300-6301 (2006). The reaction was performed in 25 mM NaOAc (pH 5.0) containing 0.2% Triton X-100. A typical reaction mixture contained approximately 10 mM 1-fluoro-[(5-N-acetyl-α-neuraminyl)-(2→3)]-[β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside], 20 mM of the acceptor D-erythro-sphingosine, and 0.5 mg / mL of the appropriate EGC mutant in a total reaction volume. When completed, the product was purified using reversed phase (C-18) chromatography, the eluted product was concentrated to dryness, dissolved in water and freeze-dried to yield a white solid. The product is analyzed by NMR and MS.

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Abstract

This invention provides compounds, compositions, and methods for treating a disorder selected from cancer, hyperinsulinemia, hypoglycemia, hyperinsulinemia with hypoglycemia, atypical Parkinson's disease, Huntington's disease, multiple systems atrophy, GM3 synthase deficiency, GM2 synthase deficiency or tauopathy.

Description

CROSS-REFERENCES TO RELATED APPLICATIONS[0001]This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Patent Application No. 61 / 163,371 filed on Mar. 25, 2009, U.S. Provisional Patent Application No. 61 / 293,200, filed Jan. 7, 2010, U.S. Provisional Patent Application No. 61 / 244,735, filed Sep. 22, 2009, U.S. Provisional Patent Application No. 61 / 220,151, filed Jun. 24, 2009, U.S. Provisional Patent Application No. 61 / 180,346, filed May 21, 2009 and U.S. Provisional Patent Application No. 61 / 180,098, filed May 20, 2009, which are incorporated herein by reference in their entirety for all purposes.FIELD OF THE INVENTION[0002]This invention relates to methods of treating and amliorating diseases of cancer, hyperinsulinemia, hypoglycemia and atypical parkinson's disease, tauopathies, and other neurological diseases, and / or a ganglioside deficiency state or disorder by administering a suitable glycolipid, ganglioside or ganglioside analog.BACKGROUND OF THE INVENTION[...

Claims

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Application Information

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IPC IPC(8): A61K31/7028A61P25/14A61P35/00A61P3/10A61K31/7032A61K31/715
CPCA61K31/70A61K31/715A61K31/7032A61K31/7028A61P3/10A61P25/14A61P25/28A61P35/00
Inventor DEFREES, SHAWN
Owner SENEB BIOSCI
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