Host–guest complexes of the antituberculosis drugs pyrazinamide and isoniazid with cucurbit[7]uril View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2010-05-12

AUTHORS

Nial J. Wheate, Virendra Vora, Nahoum G. Anthony, Fiona J. McInnes

ABSTRACT

The potential use of cucurbit[7]uril (CB[7]) as an excipient in oral formulations for improved drug physical stability or for improved drug delivery was examined with the antituberculosis drugs pyrazinamide (pyrazine-2-carboxamide) and isoniazid (isonicotinohydrazide). Both drugs form 1:1 host–guest complexes with CB[7] as determined by 1H nuclear magnetic resonance spectrometry, electrospray ionisation mass spectrometry and molecular modelling. Drug binding is stabilised by hydrophobic effects between the pyridine and pyrazine rings of isoniazid and pyrazinamide, respectively, to the inside cavity of the CB[7] macrocycle as well as hydrogen bonds between the hydrazide and amide groups of each drug to the CB[7] carbonyl portals. At pH 1.5, isoniazid binds CB[7] with a binding constant of 5.6 × 105 M−1, whilst pyrazinamide binds CB[7] at pH 7 with a much smaller binding constant (4.8 × 103 M−1). Finally, CB[7] prevents drug melting through encapsulation. Where previously pyrazinamide displays a typical melting point of 189 °C and isoniazid 171 °C, by differential scanning calorimetry, no melting or degradation at temperatures up to 280 °C is observed for either drug once bound by CB[7]. More... »

PAGES

359-367

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10847-010-9795-3

DOI

http://dx.doi.org/10.1007/s10847-010-9795-3

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1002381817


Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
Incoming Citations Browse incoming citations for this publication using opencitations.net

JSON-LD is the canonical representation for SciGraph data.

TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

[
  {
    "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
    "about": [
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Chemical Sciences", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0302", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Inorganic Chemistry", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0303", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Macromolecular and Materials Chemistry", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0306", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Physical Chemistry (incl. Structural)", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK", 
          "id": "http://www.grid.ac/institutes/grid.11984.35", 
          "name": [
            "Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Wheate", 
        "givenName": "Nial J.", 
        "id": "sg:person.01137526740.20", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01137526740.20"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK", 
          "id": "http://www.grid.ac/institutes/grid.11984.35", 
          "name": [
            "Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Vora", 
        "givenName": "Virendra", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK", 
          "id": "http://www.grid.ac/institutes/grid.11984.35", 
          "name": [
            "Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Anthony", 
        "givenName": "Nahoum G.", 
        "id": "sg:person.01227105351.22", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01227105351.22"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK", 
          "id": "http://www.grid.ac/institutes/grid.11984.35", 
          "name": [
            "Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK"
          ], 
          "type": "Organization"
        }, 
        "familyName": "McInnes", 
        "givenName": "Fiona J.", 
        "id": "sg:person.01322553513.54", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01322553513.54"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "sg:pub.10.1007/s00775-007-0269-z", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1023875792", 
          "https://doi.org/10.1007/s00775-007-0269-z"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1038/nmeth1064", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1005921538", 
          "https://doi.org/10.1038/nmeth1064"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s00604-008-0032-3", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1030704504", 
          "https://doi.org/10.1007/s00604-008-0032-3"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1039/b9pp00041k", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1030784927", 
          "https://doi.org/10.1039/b9pp00041k"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s10847-009-9556-3", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1017127338", 
          "https://doi.org/10.1007/s10847-009-9556-3"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2010-05-12", 
    "datePublishedReg": "2010-05-12", 
    "description": "The potential use of cucurbit[7]uril (CB[7]) as an excipient in oral formulations for improved drug physical stability or for improved drug delivery was examined with the antituberculosis drugs pyrazinamide (pyrazine-2-carboxamide) and isoniazid (isonicotinohydrazide). Both drugs form 1:1 host\u2013guest complexes with CB[7] as determined by 1H nuclear magnetic resonance spectrometry, electrospray ionisation mass spectrometry and molecular modelling. Drug binding is stabilised by hydrophobic effects between the pyridine and pyrazine rings of isoniazid and pyrazinamide, respectively, to the inside cavity of the CB[7] macrocycle as well as hydrogen bonds between the hydrazide and amide groups of each drug to the CB[7] carbonyl portals. At pH 1.5, isoniazid binds CB[7] with a binding constant of 5.6\u00a0\u00d7\u00a0105 M\u22121, whilst pyrazinamide binds CB[7] at pH 7 with a much smaller binding constant (4.8\u00a0\u00d7\u00a0103 M\u22121). Finally, CB[7] prevents drug melting through encapsulation. Where previously pyrazinamide displays a typical melting point of 189\u00a0\u00b0C and isoniazid 171\u00a0\u00b0C, by differential scanning calorimetry, no melting or degradation at temperatures up to 280\u00a0\u00b0C is observed for either drug once bound by CB[7].", 
    "genre": "article", 
    "id": "sg:pub.10.1007/s10847-010-9795-3", 
    "inLanguage": "en", 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1119385", 
        "issn": [
          "0923-0750", 
          "2212-1765"
        ], 
        "name": "Journal of Inclusion Phenomena and Macrocyclic Chemistry", 
        "publisher": "Springer Nature", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "3-4", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "68"
      }
    ], 
    "keywords": [
      "host-guest complexes", 
      "antituberculosis drug pyrazinamide", 
      "nuclear magnetic resonance spectrometry", 
      "drug physical stability", 
      "drug pyrazinamide", 
      "magnetic resonance spectrometry", 
      "ionization mass spectrometry", 
      "differential scanning calorimetry", 
      "typical melting point", 
      "carbonyl portals", 
      "drug melting", 
      "hydrogen bonds", 
      "hydrophobic effect", 
      "resonance spectrometry", 
      "physical stability", 
      "drug delivery", 
      "scanning calorimetry", 
      "mass spectrometry", 
      "molecular modelling", 
      "pyrazine ring", 
      "melting point", 
      "drug binding", 
      "spectrometry", 
      "small binding", 
      "complexes", 
      "isoniazid binds", 
      "macrocycle", 
      "inside cavity", 
      "pyridine", 
      "bonds", 
      "excipients", 
      "hydrazide", 
      "potential use", 
      "calorimetry", 
      "encapsulation", 
      "oral formulation", 
      "ring", 
      "constants", 
      "stability", 
      "binding", 
      "drugs", 
      "degradation", 
      "temperature", 
      "binds", 
      "melting", 
      "isoniazid", 
      "pyrazinamide", 
      "formulation", 
      "delivery", 
      "cavity", 
      "group", 
      "effect", 
      "use", 
      "point", 
      "modelling", 
      "portal", 
      "improved drug physical stability", 
      "pyrazinamide binds", 
      "isoniazid 171"
    ], 
    "name": "Host\u2013guest complexes of the antituberculosis drugs pyrazinamide and isoniazid with cucurbit[7]uril", 
    "pagination": "359-367", 
    "productId": [
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1002381817"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/s10847-010-9795-3"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/s10847-010-9795-3", 
      "https://app.dimensions.ai/details/publication/pub.1002381817"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2021-12-01T19:23", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-springernature-scigraph/baseset/20211201/entities/gbq_results/article/article_518.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://doi.org/10.1007/s10847-010-9795-3"
  }
]
 

Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1007/s10847-010-9795-3'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1007/s10847-010-9795-3'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s10847-010-9795-3'

RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s10847-010-9795-3'


 

This table displays all metadata directly associated to this object as RDF triples.

165 TRIPLES      22 PREDICATES      91 URIs      76 LITERALS      6 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/s10847-010-9795-3 schema:about anzsrc-for:03
2 anzsrc-for:0302
3 anzsrc-for:0303
4 anzsrc-for:0306
5 schema:author N058494522d3d48bfb6aab7beaa360d97
6 schema:citation sg:pub.10.1007/s00604-008-0032-3
7 sg:pub.10.1007/s00775-007-0269-z
8 sg:pub.10.1007/s10847-009-9556-3
9 sg:pub.10.1038/nmeth1064
10 sg:pub.10.1039/b9pp00041k
11 schema:datePublished 2010-05-12
12 schema:datePublishedReg 2010-05-12
13 schema:description The potential use of cucurbit[7]uril (CB[7]) as an excipient in oral formulations for improved drug physical stability or for improved drug delivery was examined with the antituberculosis drugs pyrazinamide (pyrazine-2-carboxamide) and isoniazid (isonicotinohydrazide). Both drugs form 1:1 host–guest complexes with CB[7] as determined by 1H nuclear magnetic resonance spectrometry, electrospray ionisation mass spectrometry and molecular modelling. Drug binding is stabilised by hydrophobic effects between the pyridine and pyrazine rings of isoniazid and pyrazinamide, respectively, to the inside cavity of the CB[7] macrocycle as well as hydrogen bonds between the hydrazide and amide groups of each drug to the CB[7] carbonyl portals. At pH 1.5, isoniazid binds CB[7] with a binding constant of 5.6 × 105 M−1, whilst pyrazinamide binds CB[7] at pH 7 with a much smaller binding constant (4.8 × 103 M−1). Finally, CB[7] prevents drug melting through encapsulation. Where previously pyrazinamide displays a typical melting point of 189 °C and isoniazid 171 °C, by differential scanning calorimetry, no melting or degradation at temperatures up to 280 °C is observed for either drug once bound by CB[7].
14 schema:genre article
15 schema:inLanguage en
16 schema:isAccessibleForFree false
17 schema:isPartOf N094f8f8651114a3f828c5a3892343173
18 Nc1d38323994948569bdb7dd6dc5181cf
19 sg:journal.1119385
20 schema:keywords antituberculosis drug pyrazinamide
21 binding
22 binds
23 bonds
24 calorimetry
25 carbonyl portals
26 cavity
27 complexes
28 constants
29 degradation
30 delivery
31 differential scanning calorimetry
32 drug binding
33 drug delivery
34 drug melting
35 drug physical stability
36 drug pyrazinamide
37 drugs
38 effect
39 encapsulation
40 excipients
41 formulation
42 group
43 host-guest complexes
44 hydrazide
45 hydrogen bonds
46 hydrophobic effect
47 improved drug physical stability
48 inside cavity
49 ionization mass spectrometry
50 isoniazid
51 isoniazid 171
52 isoniazid binds
53 macrocycle
54 magnetic resonance spectrometry
55 mass spectrometry
56 melting
57 melting point
58 modelling
59 molecular modelling
60 nuclear magnetic resonance spectrometry
61 oral formulation
62 physical stability
63 point
64 portal
65 potential use
66 pyrazinamide
67 pyrazinamide binds
68 pyrazine ring
69 pyridine
70 resonance spectrometry
71 ring
72 scanning calorimetry
73 small binding
74 spectrometry
75 stability
76 temperature
77 typical melting point
78 use
79 schema:name Host–guest complexes of the antituberculosis drugs pyrazinamide and isoniazid with cucurbit[7]uril
80 schema:pagination 359-367
81 schema:productId N3e3aaa4c5b6f477e85aadc33f75ae480
82 Nfa2045296b3e4831bfe415d932437e9e
83 schema:sameAs https://app.dimensions.ai/details/publication/pub.1002381817
84 https://doi.org/10.1007/s10847-010-9795-3
85 schema:sdDatePublished 2021-12-01T19:23
86 schema:sdLicense https://scigraph.springernature.com/explorer/license/
87 schema:sdPublisher Ne1ed84f0a1484076b9890c1e4682e8a4
88 schema:url https://doi.org/10.1007/s10847-010-9795-3
89 sgo:license sg:explorer/license/
90 sgo:sdDataset articles
91 rdf:type schema:ScholarlyArticle
92 N058494522d3d48bfb6aab7beaa360d97 rdf:first sg:person.01137526740.20
93 rdf:rest Nd2a8c518d9be4c48b4d4761e9b116555
94 N094f8f8651114a3f828c5a3892343173 schema:volumeNumber 68
95 rdf:type schema:PublicationVolume
96 N15d9b0a3cc22402988072139a2d32589 schema:affiliation grid-institutes:grid.11984.35
97 schema:familyName Vora
98 schema:givenName Virendra
99 rdf:type schema:Person
100 N3e3aaa4c5b6f477e85aadc33f75ae480 schema:name dimensions_id
101 schema:value pub.1002381817
102 rdf:type schema:PropertyValue
103 N54134a946ef341c0a9abdb433448c833 rdf:first sg:person.01322553513.54
104 rdf:rest rdf:nil
105 Nc1d38323994948569bdb7dd6dc5181cf schema:issueNumber 3-4
106 rdf:type schema:PublicationIssue
107 Nd2a8c518d9be4c48b4d4761e9b116555 rdf:first N15d9b0a3cc22402988072139a2d32589
108 rdf:rest Nf5a87755d35c41f98565c0be9bd90b3e
109 Ne1ed84f0a1484076b9890c1e4682e8a4 schema:name Springer Nature - SN SciGraph project
110 rdf:type schema:Organization
111 Nf5a87755d35c41f98565c0be9bd90b3e rdf:first sg:person.01227105351.22
112 rdf:rest N54134a946ef341c0a9abdb433448c833
113 Nfa2045296b3e4831bfe415d932437e9e schema:name doi
114 schema:value 10.1007/s10847-010-9795-3
115 rdf:type schema:PropertyValue
116 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
117 schema:name Chemical Sciences
118 rdf:type schema:DefinedTerm
119 anzsrc-for:0302 schema:inDefinedTermSet anzsrc-for:
120 schema:name Inorganic Chemistry
121 rdf:type schema:DefinedTerm
122 anzsrc-for:0303 schema:inDefinedTermSet anzsrc-for:
123 schema:name Macromolecular and Materials Chemistry
124 rdf:type schema:DefinedTerm
125 anzsrc-for:0306 schema:inDefinedTermSet anzsrc-for:
126 schema:name Physical Chemistry (incl. Structural)
127 rdf:type schema:DefinedTerm
128 sg:journal.1119385 schema:issn 0923-0750
129 2212-1765
130 schema:name Journal of Inclusion Phenomena and Macrocyclic Chemistry
131 schema:publisher Springer Nature
132 rdf:type schema:Periodical
133 sg:person.01137526740.20 schema:affiliation grid-institutes:grid.11984.35
134 schema:familyName Wheate
135 schema:givenName Nial J.
136 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01137526740.20
137 rdf:type schema:Person
138 sg:person.01227105351.22 schema:affiliation grid-institutes:grid.11984.35
139 schema:familyName Anthony
140 schema:givenName Nahoum G.
141 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01227105351.22
142 rdf:type schema:Person
143 sg:person.01322553513.54 schema:affiliation grid-institutes:grid.11984.35
144 schema:familyName McInnes
145 schema:givenName Fiona J.
146 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01322553513.54
147 rdf:type schema:Person
148 sg:pub.10.1007/s00604-008-0032-3 schema:sameAs https://app.dimensions.ai/details/publication/pub.1030704504
149 https://doi.org/10.1007/s00604-008-0032-3
150 rdf:type schema:CreativeWork
151 sg:pub.10.1007/s00775-007-0269-z schema:sameAs https://app.dimensions.ai/details/publication/pub.1023875792
152 https://doi.org/10.1007/s00775-007-0269-z
153 rdf:type schema:CreativeWork
154 sg:pub.10.1007/s10847-009-9556-3 schema:sameAs https://app.dimensions.ai/details/publication/pub.1017127338
155 https://doi.org/10.1007/s10847-009-9556-3
156 rdf:type schema:CreativeWork
157 sg:pub.10.1038/nmeth1064 schema:sameAs https://app.dimensions.ai/details/publication/pub.1005921538
158 https://doi.org/10.1038/nmeth1064
159 rdf:type schema:CreativeWork
160 sg:pub.10.1039/b9pp00041k schema:sameAs https://app.dimensions.ai/details/publication/pub.1030784927
161 https://doi.org/10.1039/b9pp00041k
162 rdf:type schema:CreativeWork
163 grid-institutes:grid.11984.35 schema:alternateName Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK
164 schema:name Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, John Arbuthnott Building, 27 Taylor Street, G4 0NR, Glasgow, UK
165 rdf:type schema:Organization
 




Preview window. Press ESC to close (or click here)


...