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

Abstract

Here, calcium coordination solids were synthesized and evaluated for delivery of olsalazine (H 4olz), an anti-inflammatory compound used for treatment of ulcerative colitis. The materials include one-dimensional Ca(H 2olz)•4H 2O chains, two-dimensional Ca(H 2olz)•2H 2O sheets, and a three-dimensional metal-organic framework Ca(H 2olz)•2DMF (DMF= N,N-dimethylformamide). The framework undergoes structural changes in response to solvent, forming a dense Ca(H 2olz) phase when exposed to aqueous HCl. The compounds Ca(H 2olz)•xH 2O (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 2olz), the commercial formulation, illustrating how formulation of a drug within an extended coordination solid can serve to tune its solubility and performance.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [2];  [3]; ORCiD logo [2]; ORCiD logo [2]; ORCiD logo [3]
  1. Univ. of California, Berkeley, CA (United States); California Inst. of Technology (CalTech), Pasadena, CA (United States)
  2. Univ. of California, Berkeley, CA (United States)
  3. Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1420116
Alternate Identifier(s):
OSTI ID: 1407822
Grant/Contract Number:  
AC02-05CH11231; SC0001015; AC02-06CH11357
Resource Type:
Accepted Manuscript
Journal Name:
ChemMedChem(Print)
Additional Journal Information:
Journal Name: ChemMedChem(Print); Journal Volume: 12; Journal Issue: 21; Journal ID: ISSN 1860-7179
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; calcium; coordination polymers; crystal engineering; drug delivery; metal-organic frameworks

Citation Formats

Levine, Dana J., Gonzalez, Miguel I., Legendre, Christina M., Runcevski, Tomce, Oktawiec, Julia, Colwell, Kristen A., and Long, Jeffrey R. Calcium Coordination Solids for pH-Triggered Release of Olsalazine. United States: N. p., 2017. Web. doi:10.1002/cmdc.201700540.
Levine, Dana J., Gonzalez, Miguel I., Legendre, Christina M., Runcevski, Tomce, Oktawiec, Julia, Colwell, Kristen A., & Long, Jeffrey R. Calcium Coordination Solids for pH-Triggered Release of Olsalazine. United States. doi:10.1002/cmdc.201700540.
Levine, Dana J., Gonzalez, Miguel I., Legendre, Christina M., Runcevski, Tomce, Oktawiec, Julia, Colwell, Kristen A., and Long, Jeffrey R. Tue . "Calcium Coordination Solids for pH-Triggered Release of Olsalazine". United States. doi:10.1002/cmdc.201700540. https://www.osti.gov/servlets/purl/1420116.
@article{osti_1420116,
title = {Calcium Coordination Solids for pH-Triggered Release of Olsalazine},
author = {Levine, Dana J. and Gonzalez, Miguel I. and Legendre, Christina M. and Runcevski, Tomce and Oktawiec, Julia and Colwell, Kristen A. and Long, Jeffrey R.},
abstractNote = {Here, calcium coordination solids were synthesized and evaluated for delivery of olsalazine (H4olz), an anti-inflammatory compound used for treatment of ulcerative colitis. The materials include one-dimensional Ca(H2olz)•4H2O chains, two-dimensional Ca(H2olz)•2H2O sheets, and a three-dimensional metal-organic framework Ca(H2olz)•2DMF (DMF=N,N-dimethylformamide). The framework undergoes structural changes in response to solvent, forming a dense Ca(H2olz) phase when exposed to aqueous HCl. The compounds Ca(H2olz)•xH2O (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 Na2(H2olz), the commercial formulation, illustrating how formulation of a drug within an extended coordination solid can serve to tune its solubility and performance.},
doi = {10.1002/cmdc.201700540},
journal = {ChemMedChem(Print)},
number = 21,
volume = 12,
place = {United States},
year = {2017},
month = {9}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Figures / Tables:

Figure 1 Figure 1: Structure and recommended oral dose2 for (a) 5-ASA and (b) azo-linked prodrugs, which release 5-ASA and a carrier molecule. In olsalazine, the arrier is another equivalent of 5-ASA.

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    Works referencing / citing this record:

    Linear Azo Polymer Containing Conjugated 5,5′-Azodisalicylic Acid Segments in the Main Chain: Synthesis, Characterization, and Degradation
    journal, October 2005

    • Lai, Junying; Wang, Li-Qun; Tu, Kehua
    • Macromolecular Rapid Communications, Vol. 26, Issue 19
    • DOI: 10.1002/marc.200500550

    Effect of disodium azodisalicylate on electrolyte transport in rabbit ileum and colon in vitro
    journal, October 1988


    Bio-MOFs: Metall-organische Gerüste für biologische und medizinische Anwendungen
    journal, August 2010

    • McKinlay, Alistair C.; Morris, Russell E.; Horcajada, Patricia
    • Angewandte Chemie, Vol. 122, Issue 36
    • DOI: 10.1002/ange.201000048

    Azodisal sodium in the treatment of ulcerative colitis
    journal, April 1986


    Dissolution kinetics and solubilities of p-aminosalicylic acid and its salts
    journal, December 1995


    Recent advances of discrete coordination complexes and coordination polymers in drug delivery
    journal, August 2011


    Metal-Organic Framework-Based Nanomedicine Platforms for Drug Delivery and Molecular Imaging
    journal, July 2015


    Synthesis, characterization and crystal structures of two alkaline-earth metal complexes of olsalazine
    journal, April 2008

    • Tang, Yun-Zhi; Tan, Yu-Hui; Chen, Shao-Hu
    • Journal of Coordination Chemistry, Vol. 61, Issue 8
    • DOI: 10.1080/00958970701572360

    Supramolecular Assembly of Calcium Metal−Organic Frameworks with Structural Transformations
    journal, March 2011

    • Liang, Po-Ching; Liu, Hsin-Kuan; Yeh, Chun-Ting
    • Crystal Growth & Design, Vol. 11, Issue 3
    • DOI: 10.1021/cg101114h

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    • Miller, Stuart R.; Heurtaux, Daniela; Baati, Tarek
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    • DOI: 10.1039/c001181a

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    journal, August 2006

    • Andrews, Philip C.; Deacon, Glen B.; Forsyth, Craig M.
    • Angewandte Chemie International Edition, Vol. 45, Issue 34
    • DOI: 10.1002/anie.200600469

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    • Levine, Dana J.; Runčevski, Tomče; Kapelewski, Matthew T.
    • Journal of the American Chemical Society, Vol. 138, Issue 32
    • DOI: 10.1021/jacs.6b03523

    Supplemental Calcium Attenuates the Colitis-Related Increase in Diarrhea, Intestinal Permeability, and Extracellular Matrix Breakdown in HLA-B27 Transgenic Rats
    journal, June 2006

    • Schepens, Marloes A. A.; Schonewille, Arjan J.; Vink, Carolien
    • The Journal of Nutrition, Vol. 139, Issue 8
    • DOI: 10.3945/jn.109.105205

    On the Colonic Bacterial Metabolism of Azo-Bonded Prodrugsof 5-Aminosalicylic Acid
    journal, October 2014

    • Sousa, Tiago; Yadav, Vipul; Zann, Vanessa
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    • DOI: 10.1002/jps.24103

    Secretory effect of azodisalicylate (azodisal sodium) on the short circuited mucosa of the rat ileum in vitro.
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    Molecular Nanofibers of Olsalazine Form Supramolecular Hydrogels for Reductive Release of an Anti-inflammatory Agent
    journal, December 2010

    • Li, Xinming; Li, Jiayang; Gao, Yuan
    • Journal of the American Chemical Society, Vol. 132, Issue 50
    • DOI: 10.1021/ja109269v

    Verschwundene Polymorphe: eine Neubetrachtung
    journal, June 2015

    • Bučar, Dejan-Krešimir; Lancaster, Robert W.; Bernstein, Joel
    • Angewandte Chemie, Vol. 127, Issue 24
    • DOI: 10.1002/ange.201410356

    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

    • Andrews, Philip C.; Deacon, Glen B.; Forsyth, Craig M.
    • Angewandte Chemie, Vol. 118, Issue 34
    • DOI: 10.1002/ange.200600469

    New forms of old drugs: improving without changing: New forms of old drugs
    journal, February 2015

    • Domingos, Sofia; André, Vânia; Quaresma, Sílvia
    • Journal of Pharmacy and Pharmacology, Vol. 67, Issue 6
    • DOI: 10.1111/jphp.12384

    Metal–Organic Frameworks in Biomedicine
    journal, September 2011

    • Horcajada, Patricia; Gref, Ruxandra; Baati, Tarek
    • Chemical Reviews, Vol. 112, Issue 2, p. 1232-1268
    • DOI: 10.1021/cr200256v

    BioMOFs: Metal-Organic Frameworks for Biological and Medical Applications
    journal, July 2010

    • McKinlay, Alistair C.; Morris, Russell E.; Horcajada, Patricia
    • Angewandte Chemie International Edition, Vol. 49, Issue 36, p. 6260-6266
    • DOI: 10.1002/anie.201000048

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    dataset, June 2017


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    journal, August 2011

    • Campregher, Christoph; Gasche, Christoph
    • Best Practice & Research Clinical Gastroenterology, Vol. 25, Issue 4-5
    • DOI: 10.1016/j.bpg.2011.10.013

    Predictive Relationships in the Water Solubility of Salts of a Nonsteroidal Anti-Inflammatory Drug
    journal, August 1985

    • Anderson, B. D.; Conradi, R. A.
    • Journal of Pharmaceutical Sciences, Vol. 74, Issue 8
    • DOI: 10.1002/jps.2600740803

    Mechanochemistry of magnesium oxide revisited: facile derivatisation of pharmaceuticals using coordination and supramolecular chemistry
    journal, January 2010

    • Chow, Ernest H. H.; Strobridge, Fiona C.; Friščić, Tomislav
    • Chemical Communications, Vol. 46, Issue 34
    • DOI: 10.1039/c0cc01337d

    Olsalazine or sulphasalazine in first attacks of ulcerative colitis? A double blind study.
    journal, May 1989


    Olsalazine sodium in the treatment of ulcerative colitis among patients intolerant of sulfasalazine
    journal, December 1987


    Optimum dose of olsalazine for maintaining remission in ulcerative colitis.
    journal, September 1994


    Coercing bisphosphonates to kill cancer cells with nanoscale coordination polymers
    journal, January 2012

    • Liu, Demin; Kramer, Stephanie A.; Huxford-Phillips, Rachel C.
    • Chemical Communications, Vol. 48, Issue 21
    • DOI: 10.1039/c2cc17635a

    Coordination Polymers Based on the 2,5-Dihydroxyterephthalate Ion and Alkaline Earth Metal (Ca, Sr) and Manganese Cations
    journal, October 2009

    • Dietzel, Pascal C.; Blom, Richard; Fjellvåg, Helmer
    • Zeitschrift für anorganische und allgemeine Chemie, Vol. 635, Issue 12
    • DOI: 10.1002/zaac.200900348

    Trends in Active Pharmaceutical Ingredient Salt Selection based on Analysis of the Orange Book Database
    journal, December 2007

    • Paulekuhn, G. Steffen; Dressman, Jennifer B.; Saal, Christoph
    • Journal of Medicinal Chemistry, Vol. 50, Issue 26
    • DOI: 10.1021/jm701032y

    Spectroscopic Studies of Structural Dynamics Induced by Heating and Hydration: A Case of Calcium-Terephthalate Metal–Organic Framework
    journal, April 2013

    • Mazaj, Matjaž; Mali, Gregor; Rangus, Mojca
    • The Journal of Physical Chemistry C, Vol. 117, Issue 15
    • DOI: 10.1021/jp311529e

    Dynamic Calcium Metal-Organic Framework Acts as a Selective Organic Solvent Sponge
    journal, August 2010

    • Platero-Prats, Ana E.; de la Peña-O'Shea, Víctor A.; Snejko, Natalia
    • Chemistry - A European Journal, Vol. 16, Issue 38
    • DOI: 10.1002/chem.201001218

    Disappearing Polymorphs Revisited
    journal, June 2015

    • Bučar, Dejan-Krešimir; Lancaster, Robert W.; Bernstein, Joel
    • Angewandte Chemie International Edition, Vol. 54, Issue 24
    • DOI: 10.1002/anie.201410356

    Systematic Data Set for Structure−Property Investigations: Solubility and Solid-State Structure of Alkaline Earth Metal Salts of Benzoates
    journal, April 2011

    • Arlin, Jean-Baptiste; Florence, Alastair J.; Johnston, Andrea
    • Crystal Growth & Design, Vol. 11, Issue 4
    • DOI: 10.1021/cg101547r

    pH–Solubility Profiles of Organic Carboxylic Acids and Their Salts
    journal, September 1978


      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.