Novel phosphoramidate prodrugs of N-acetyl-(d)-glucosamine with antidegenerative activity on bovine and human cartilage explants

Journal of Medicinal Chemistry

Volumn 55, Issue 10, 2012, Pages 4629-4639

  Serpi, Michaela ^a   Bibbo, Rita ^a   Rat, Stephanie ^a   Roberts, Helen ^a   Hughes, Claire ^a   Caterson, Bruce ^a   Alcaraz, María José ^b   Gibert, Anna Torrent ^c   Verson, Carlos Raul Alaez ^c   McGuigan, Christopher ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b Bioberica SA   (Spain)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 O BENZYL 2 ACETAMIDO 2 DEOXY 4,6 O BENZYLIDENE 3 O (4 METHOXYPHENYL CYCLOHEXYLOXYPROLINYL) PHOSPHATE DEXTRO GLUCOPYRANOSE; 2 ACETAMIDO 2 DEOXY 3 O (4 METHOXYPHENYL CYCLOHEXYLOXYPROLINYL) PHOSPHATE DEXTRO GLUCOPYRANOSE; 2 ACETAMIDO 2 DEOXY 4 O (4 METHOXYPHENYL CYCLOHEXYLOXYPROLINYL) PHOSPHATE DEXTRO GLUCOPYRANOSE; 4 METHOXY PHENYL GROUP; AMINO ACID; ESTER; N ACETYLGLUCOSAMINE; PHENYL GROUP; PHOSPHATE; PHOSPHORAMIDIC ACID DERIVATIVE; PRODRUG; PROLINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CARTILAGE; CARTILAGE CELL; CHONDROPROTECTION; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG STRUCTURE; EXPLANT; HUMAN; HUMAN CELL; HUMAN TISSUE; ISOMER; NONHUMAN; OSTEOARTHRITIS;

ACETYLGLUCOSAMINE; AGGRECANS; ANIMALS; CARTILAGE, ARTICULAR; CATTLE; CHONDROCYTES; DRUG STABILITY; GLYCOSAMINOGLYCANS; GUINEA PIGS; HALF-LIFE; HUMANS; ORGAN CULTURE TECHNIQUES; ORGANOPHOSPHORUS COMPOUNDS; OSTEOARTHRITIS; PRODRUGS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84861503216     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300074y     Document Type: Article

References (33)

1. Mobasheri, A.; Vannucci, S. J.; Bondy, C. A.; Carter, S. D.; Innes, J. F.; Arteaga, M. F.; Trujillo, E.; Ferraz, I.; Shakibaei, M.; Martín-Vasallo, P. Glucose transport and metabolism in chondrocytes: a key to understanding chondrogenesis, skeletal development and cartilage degradation in osteoarthritis Histol. Histopathol. 2002, 17, 1239-1267
2. Kjellen, L.; Lindahl, U. Proteoglycans: Structures and Interactions Annu. Rev. Biochem. 1991, 60, 443-475
3. Ruoslahti, E. Structure and Biology of Proteoglycans Annu. Rev. Cell Biol. 1988, 4, 229-255 (Pubitemid 19139257)
4. Seed, S.; Dunica, K.; Lynch, A. Osteoarthritis: a review of treatment options Geriatrics 2009, 64, 20-29
5. Sofat, N.; Beith, I.; Anikumar, P. G.; Mitchel, P. Recent Clinical Evidence for the Treatment of Osteoarthritis: What We have Learned Rev. Recent Clin. Trials 2011, 6, 114-126
6. Huskisson, E. C. Glucosamine and Chondroitin for Osteoarthritis J. Int. Med. Res. 2008, 36, 1161-1179
7. Miller, K.; Clegg, D. Glucosamine and chondroitin sulfate Rheum. Dis. Clin. North Am. 2011, 37, 103-118
8. Vlad, S. C.; LaValley, M. P.; McAlindon, T. E.; Felson, D. T. Glucosamine for pain in osteoarthritis: Why do trial results differ? Arthritis Rheum. 2007, 56, 2267-2277 (Pubitemid 47173575)
9. Wandel, S.; Juni, P.; Tendal, B.; Nuesch, E.; Villiger, P. M.; Welton, N. J.; Reichenbach, S.; Trelle, S. Effects of glucosamine, chondroitin, or placebo in patients with osteoarthritis of hip or knee: network meta-analysis Br. Med. J. 2010, 341, c4675
10. Sawitzke, A. D.; Shi, H.; Finco, M. F.; Dunlop, D. D.; Harris, C. L.; Singer, N. G.; Bradley, J. D.; Silver, D.; Jackson, C. G.; Lane, N. E.; Oddis, C. V.; Wolfe, F.; Lisse, J.; Furst, D. E.; Bingham, C. O.; Reda, D. J.; Moskowitz, R. W.; Williams, H. J.; Clegg, D. O. Clinical efficacy and safety of glucosamine, chondroitin sulphate, their combination, celecoxib or placebo taken to treat osteoarthritis of the knee: 2-year results from GAIT Ann. Rheum. Dis. 2010, 69, 1459-1464
11. Wildi, L. M.; Raynauld, J.-P.; Martel-Pelletier, J.; Beaulieu, A.; Bessette, L.; Morin, F. D. R.; Abram, F. O.; Dorais, M.; Pelletier, J.-P. Chondroitin sulphate reduces both cartilage volume loss and bone marrow lesions in knee osteoarthritis patients starting as early as 6 months after initiation of therapy: a randomised, double-blind, placebo-controlled pilot study using MRI Ann. Rheum. Dis. 2011, 70, 982-989
12. Bassleer, C.; Rovati, L.; Franchimont, P. Stimulation of proteoglycan production by glucosamine sulfate in chondrocytes isolated from human osteoarthritic articular cartilage in vitro Osteoarthritis Cartilage 1998, 6, 427-434 (Pubitemid 28529800)
13. Uitterlinden, E.; Koevoet, J.; Verkoelen, C.; Bierma-Zeinstra, S.; Jahr, H.; Weinans, H.; Verhaar, J.; van Osch, G. Glucosamine increases hyaluronic acid production in human osteoarthritic synovium explants BMC Musculoskelet. Disord. 2008, 9, 120
14. 35S-sulfate with cultured human chondrocytes to determine the effect of glucosamine concentration on formation of chondroitin sulfate Arthritis Rheum. 2004, 50, 3574-3579 (Pubitemid 39488682)
15. Shikhman, A., R.; Kuhn, K.; Alaaeddine, N.; Lotz, M. N -Acetylglucosamine Prevents IL-1β-Mediated Activation of Human Chondrocytes J. Immunol. 2001, 166, 5155-5160 (Pubitemid 32280730)
16. Ozkan, F. U.; Ozkan, K.; Ramadan, S.; Guven, Z. Chondroprotective effect of N -acetylglucosamine and hyaluronate in early stages of osteoarthritis: an experimental study in rabbits Bull. NYU Hosp. Jt. Dis. 2009, 67, 352-357
17. Aghazadeh-Habashi, A.; Sattari, S.; Pasutto, F.; Jamali, F. Single dose pharmacokinetics and bioavailability of glucosamine in the rat J. Pharm. Pharm. Sci. 2002, 5, 181-184
18. Du, J.; White, N.; Eddington, N. D. The bioavailability and pharmacokinetics of glucosamine hydrochloride and chondroitin sulfate after oral and intravenous single dose administration in the horse Biopharm. Drug Dispos. 2004, 25, 109-116 (Pubitemid 39089553)
19. Adebowale, A.; Du, J.; Liang, Z.; Leslie, J. L.; Eddington, N. D. The bioavailability and pharmacokinetics of glucosamine hydrochloride and low molecular weight chondroitin sulfate after single and multiple doses to beagle dogs Biopharm. Drug Dispos. 2002, 23, 217-225
20. McGuigan, C.; Serpi, M.; Bibbo, R.; Roberts, H.; Hughes, C.; Caterson, B.; Gibert, A. T.; Verson, C. R. A. Phosphate Prodrugs Derived from N -Acetylglucosamine Have Enhanced Chondroprotective Activity in Explant Cultures and Represent a New Lead in Antiosteoarthritis Drug Discovery J. Med. Chem. 2008, 51, 5807-5812
21. Paulsen, H. Advances in Selective Chemical Syntheses of Complex Oligosaccharides Angew. Chem., Int. Ed. 1982, 21, 155-173 (Pubitemid 12510861)
22. Crich, D.; Dudkin, V. Why Are the Hydroxy Groups of Partially Protected N -Acetylglucosamine Derivatives Such Poor Glycosyl Acceptors, and What Can Be Done about It? A Comparative Study of the Reactivity of N -Acetyl-, N -Phthalimido-, and 2-Azido-2-deoxy-glucosamine Derivatives in Glycosylation. 2-Picolinyl Ethers as Reactivity-Enhancing Replacements for Benzyl Ethers J. Am. Chem. Soc. 2001, 123, 6819-6825 (Pubitemid 32884542)
23. Liao, L.; Auzanneau, F.-I. Glycosylation of N -Acetylglucosamine: Imidate Formation and Unexpected Conformation Org. Lett. 2003, 5, 2607-2610 (Pubitemid 37140822)
24. Colombo, M. I.; Stortz, C. A.; Rúveda, E. A. A comparative study of the O-3 reactivity of isomeric N -dimethylmaleoyl-protected d -glucosamine and d -allosamine acceptors Carbohydr. Res. 2011, 346, 569-576
25. Bohn, M. L.; Colombo, M. I.; Pisano, P. L.; Stortz, C. A.; Rúveda, E. A. Differential O-3/O-4 regioselectivity in the glycosylation of [alpha] and [beta] anomers of 6-O-substituted N -dimethylmaleoyl-protected d-glucosamine acceptors Carbohydr. Res. 2007, 342, 2522-2536 (Pubitemid 47633521)
26. Bohn, M. L.; Colombo, M. I.; Ruveda, E. A.; Stortz, C. A. Conformational and electronic effects on the regioselectivity of the glycosylation of different anomers of N -dimethylmaleoyl-protected glucosamine acceptors Org. Biomol. Chem. 2008, 6, 554-561 (Pubitemid 351161746)
27. Cao, S.; Gan, Z.; Roy, R. Active-latent glycosylation strategy toward Lewis X pentasaccharide in a form suitable for neoglycoconjugate syntheses Carbohydr. Res. 1999, 318, 75-81 (Pubitemid 29421785)
28. Gan, Z.; Cao, S.; Wu.; Roy, R. Regiospecific Syntheses of N -Acetyllactosamine Derivatives and Application Toward a Highly Practical Synthesis of Lewis X Trisaccharide J. Carbohydr. Chem. 1999, 18, 755-773 (Pubitemid 129331229)
29. Figueroa-Pérez, S.; Verez-Bencomo, V. Synthesis of dimeric Lewis X antigenic determinant with azido-type spacer arm by a sequence of regioselective glycosylation steps Tetrahedron Lett. 1998, 39, 9143-9146 (Pubitemid 28539248)
30. Spijker, N. M.; Keuning, C. A.; Hooglugt, M.; Veeneman, G. H.; van Boeckel, C. A. A. Synthesis of a hexasaccharide corresponding to a porcine zona pellucida fragment that inhibits porcine sperm-oocyte interaction in vitro Tetrahedron 1996, 52, 5945-5960 (Pubitemid 26116192)
31. Ssarek, W. A.; Zamojski, A.; Tiwari, K. N.; Ison, E. R. A new facile method for cleavage of actals and dithioacetals in carbohydrate derivatives Tetrahedron Lett. 1986, 27, 3827-3830
32. Mio, T.; Yamada-Okabe, T.; Arisawa, M.; Yamada-Okabe, H. Functional cloning and mutational analysis of the human cDNA for phosphoacetylglucosamine mutase: identification of the amino acid residues essential for the catalysis Biochim. Biophys. Acta 2000, 1492, 369-376 (Pubitemid 30427348)
33. McGuigan, C.; Sutton, P. W.; Cahard, D.; Turner, K.; O'Leary, G.; Wang, Y.; Gumbleton, M.; De Clercq, E.; Balzarini, J. Synthesis, anti-human immunodefeficency virus activity and esterase lability of some novel carboxylic ester-modified phosphoramidate derivatives of stavudine (d4T) Antivir. Chem. Chemother. 1998, 9, 473-479 (Pubitemid 28556662)