skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Calcium Coordination Solids for pH-Triggered Release of Olsalazine

Journal Article · · ChemMedChem

Abstract Calcium coordination solids were synthesized and evaluated for delivery of olsalazine (H 4 olz), an anti‐inflammatory compound used for treatment of ulcerative colitis. The materials include one‐dimensional Ca(H 2 olz)⋅4 H 2 O chains, two‐dimensional Ca(H 2 olz)⋅2 H 2 O sheets, and a three‐dimensional metal‐organic framework Ca(H 2 olz)⋅2DMF (DMF= N , N ‐dimethylformamide). The framework undergoes structural changes in response to solvent, forming a dense Ca(H 2 olz) phase when exposed to aqueous HCl. The compounds Ca(H 2 olz)⋅ x  H 2 O ( x =0, 2, 4) were each pressed into pellets and exposed to simulated gastrointestinal fluids to mimic the passage of a pill from the acidic stomach to the pH‐neutral intestines. All three calcium materials exhibited a delayed release of olsalazine relative to Na 2 (H 2 olz), the commercial formulation, illustrating how formulation of a drug within an extended coordination solid can serve to tune its solubility and performance.

Research Organization:
Energy Frontier Research Centers (EFRC) (United States). Center for Gas Separations Relevant to Clean Energy Technologies (CGS); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1420116
Alternate ID(s):
OSTI ID: 1407822
Journal Information:
ChemMedChem, Vol. 12, Issue 21; ISSN 1860-7179
Publisher:
ChemPubSoc EuropeCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 4 works
Citation information provided by
Web of Science

References (51)

Coordination Polymers Based on the 2,5-Dihydroxyterephthalate Ion and Alkaline Earth Metal (Ca, Sr) and Manganese Cations journal October 2009
Supplemental Calcium Attenuates the Colitis-Related Increase in Diarrhea, Intestinal Permeability, and Extracellular Matrix Breakdown in HLA-B27 Transgenic Rats journal June 2006
Trends in Active Pharmaceutical Ingredient Salt Selection based on Analysis of the Orange Book Database journal December 2007
A highly porous medical metal–organic framework constructed from bioactive curcumin journal January 2015
Secretory effect of azodisalicylate (azodisal sodium) on the short circuited mucosa of the rat ileum in vitro. journal March 1988
Optimum dose of olsalazine for maintaining remission in ulcerative colitis. journal September 1994
A Zn azelate MOF: combining antibacterial effect journal January 2015
Systematic Data Set for Structure−Property Investigations: Solubility and Solid-State Structure of Alkaline Earth Metal Salts of Benzoates journal April 2011
Effect of olsalazine on sodium-dependent bile acid transport in rat ileum journal May 1995
pH–Solubility Profiles of Organic Carboxylic Acids and Their Salts journal September 1978
Spectroscopic Studies of Structural Dynamics Induced by Heating and Hydration: A Case of Calcium-Terephthalate Metal–Organic Framework journal April 2013
Azodisal sodium in the treatment of ulcerative colitis journal April 1986
Metal–Organic Frameworks in Biomedicine journal September 2011
Dynamic Calcium Metal-Organic Framework Acts as a Selective Organic Solvent Sponge journal August 2010
Metal-Organic Framework-Based Nanomedicine Platforms for Drug Delivery and Molecular Imaging journal July 2015
An integrated approach to the selection of optimal salt form for a new drug candidate journal May 1994
Biodegradable therapeutic MOFs for the delivery of bioactive molecules journal January 2010
Aminosalicylates journal August 2011
Comparative Analysis of the in Vitro Prosecretory Effects of Balsalazide, Sulfasalazine, Olsalazine, and Mesalamine in Rabbit Distal Ileum journal January 2005
Nanomedicine Applications of Hybrid Nanomaterials Built from Metal–Ligand Coordination Bonds: Nanoscale Metal–Organic Frameworks and Nanoscale Coordination Polymers journal April 2015
Metal organic frameworks based on bioactive components journal January 2017
Towards a Structural Understanding of the Anti-Ulcer and Anti-Gastritis Drug Bismuth Subsalicylate journal August 2006
Protein cages and synthetic polymers: a fruitful symbiosis for drug delivery applications, bionanotechnology and materials science journal January 2016
Mechanochemistry of magnesium oxide revisited: facile derivatisation of pharmaceuticals using coordination and supramolecular chemistry journal January 2010
Olsalazine or sulphasalazine in first attacks of ulcerative colitis? A double blind study. journal May 1989
Crystal structure dependent in vitro antioxidant activity of biocompatible calcium gallate MOFs journal January 2017
Linear Azo Polymer Containing Conjugated 5,5′-Azodisalicylic Acid Segments in the Main Chain: Synthesis, Characterization, and Degradation journal October 2005
Molecular Nanofibers of Olsalazine Form Supramolecular Hydrogels for Reductive Release of an Anti-inflammatory Agent journal December 2010
Dissolution kinetics and solubilities of p-aminosalicylic acid and its salts journal December 1995
Olsalazine sodium in the treatment of ulcerative colitis among patients intolerant of sulfasalazine journal December 1987
Disappearing Polymorphs Revisited journal June 2015
Coercing bisphosphonates to kill cancer cells with nanoscale coordination polymers journal January 2012
On the Colonic Bacterial Metabolism of Azo-Bonded Prodrugsof 5-Aminosalicylic Acid journal October 2014
A biocompatible porous Mg-gallate metal–organic framework as an antioxidant carrier journal January 2015
Supramolecular Assembly of Calcium Metal−Organic Frameworks with Structural Transformations journal March 2011
Bio-MOFs: Metall-organische Gerüste für biologische und medizinische Anwendungen journal August 2010
Small chemical causes drastic structural effects: the case of calcium glutarate journal January 2011
Bioavailability studies on para-aminosalicylic acid and its various salts in man. I. Absorption from solution and suspension journal February 1974
Verschwundene Polymorphe: eine Neubetrachtung journal June 2015
Recent advances of discrete coordination complexes and coordination polymers in drug delivery journal August 2011
Olsalazine-Based Metal–Organic Frameworks as Biocompatible Platforms for H 2 Adsorption and Drug Delivery journal August 2016
Chemoprevention of colon cancer by calcium, vitamin D and folate: molecular mechanisms journal August 2003
Predictive Relationships in the Water Solubility of Salts of a Nonsteroidal Anti-Inflammatory Drug journal August 1985
Effect of disodium azodisalicylate on electrolyte transport in rabbit ileum and colon in vitro journal October 1988
Metal-organic frameworks as potential drug delivery systems journal November 2012
Towards a Structural Understanding of the Anti-Ulcer and Anti-Gastritis Drug Bismuth Subsalicylate journal August 2006
Synthesis, characterization and crystal structures of two alkaline-earth metal complexes of olsalazine journal April 2008
New forms of old drugs: improving without changing: New forms of old drugs journal February 2015
BioMOFs: Metal-Organic Frameworks for Biological and Medical Applications journal July 2010
Contrast and Comparison of Mesalamine Derivatives in the Treatment of Ulcerative Colitis book January 2014
Coercing bisphosphonates to kill cancer cells with nanoscale coordination polymers text January 2012

Cited By (2)



Figures / Tables (5)