Online citations, reference lists, and bibliographies.
Please confirm you are human
(Sign Up for free to never see this)
← Back to Search

A Supramolecular Topical Gel Derived From A Non-steroidal Anti-inflammatory Drug, Fenoprofen, Is Capable Of Treating Skin Inflammation In Mice.

J. Majumder, Pavani Yedoti, P. Dastidar
Published 2015 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
A new series of bioconjugates derived from a non-steroidal anti-inflammatory drug (NSAID), namely fenoprofen, has been synthesised by amidation with various biogenic molecules such as β-alanine, aminocaproic acid and tyramine with the aim of converting the NSAID into a supramolecular gelator for plausible biomedical applications. One such bioconjugate (2) showed gelation ability with methylsalicylate (MS) and 1% menthol in methyl salicylate (MMS) solvents. These gels were characterized by table top rheology, high resolution-transmission electron microscopy (HR-TEM) and dynamic rheology. Gelator 2 was found to be biostable both in proteolytic enzymes and in blood serum of BALB/c mouse under physiological conditions. It was also found to be biocompatible, as revealed by the methyl thiazolyldiphenyl tetrazolium bromide (MTT) assay in mouse macrophage RAW 264.7 and mouse myoblast C2C12 cells. The anti-inflammatory response (prostaglandin E2 assay, denoted PGE2 assay) of 2 was comparable to that of the parent drug fenoprofen calcium salt. Finally, a topical gel formulation of 2 displayed in vivo self-delivery application in treating imiquimod (IMQ) induced skin inflammation in BALB/c mice.
This paper references
10.1021/AR0500923
Molecular organogels. Soft matter comprised of low-molecular-mass organic gelators and organic liquids.
M. George (2006)
Org
A. P. Piccionello (2012)
10.1039/c4ob01362j
L-Rhamnose-containing supramolecular nanofibrils as potential immunosuppressive materials.
Fan Zhao (2014)
10.1021/CR0302049
Water gelation by small organic molecules.
L. Estroff (2004)
10.1021/cr9003067
Metal- and anion-binding supramolecular gels.
Marc-Oliver M. Piepenbrock (2010)
10.1039/c2cc17503g
A supramolecular hydrogel containing boronic acid-appended receptor for fluorocolorimetric sensing of polyols with a paper platform.
Masato Ikeda (2012)
Org
F. Zhao (2014)
and P
J. Majumder (2013)
10.1016/j.biomaterials.2012.06.003
Controlled release of dexamethasone from peptide nanofiber gels to modulate inflammatory response.
M. Webber (2012)
10.1021/CR940351U
Polymeric systems for controlled drug release.
K. Uhrich (1999)
10.1295/POLYMJ.12.335
Melting Temperature of Thermally Reversible Gel. VI. Effect of Branching on the Sol–Gel Transition of Polyethylene Gels
A. Takahashi (1980)
10.1007/s00403-012-1272-y
Assessment of an imiquimod-induced psoriatic mouse model in relation to oxidative stress
Jin-Ok Baek (2012)
10.1039/b816192e
L-lysine-based low-molecular-weight gelators.
M. Suzuki (2009)
Angew
Q. Wang (2007)
10.1021/la401929v
β-Amino acid and amino-alcohol conjugation of a nonsteroidal anti-inflammatory drug (NSAID) imparts hydrogelation displaying remarkable biostability, biocompatibility, and anti-inflammatory properties.
J. Majumder (2013)
10.1039/B616563J
D-glucosamine-based supramolecular hydrogels to improve wound healing.
Z. Yang (2007)
10.1039/B507157G
Two-stage enzyme mediated drug release from LMWG hydrogels.
K. V. van Bommel (2005)
10.1039/B9NJ00764D
Supramolecular gels as active media for organic reactions and catalysis
B. Escuder (2010)
Acc
M. George (2006)
10.1021/la400664q
Comparison of dipolar, H-bonding, and dispersive interactions on gelation efficiency of positional isomers of keto and hydroxy substituted octadecanoic acids.
Amrita Pal (2013)
10.1021/ja109269v
Molecular nanofibers of olsalazine form supramolecular hydrogels for reductive release of an anti-inflammatory agent.
X. Li (2010)
10.1002/cbic.200300827
Probing the Proteolytic Stability of β‐Peptides Containing α‐Fluoro‐ and α‐Hydroxy‐β‐Amino Acids
D. Hook (2004)
10.1002/adma.201200837
A crown ether appended super gelator with multiple stimulus responsiveness.
S. Dong (2012)
10.1016/j.biomaterials.2012.04.047
The inhibition of tumor growth and metastasis by self-assembled nanofibers of taxol.
Huaimin Wang (2012)
10.1016/J.JCONREL.2004.03.012
Entrapment and release of quinoline derivatives using a hydrogel of a low molecular weight gelator.
A. Friggeri (2004)
10.1039/c3ob41449c
Light and acid dual-responsive organogel formation based on m-methyl red derivative.
X. Cao (2013)
Chem
Z. Yang (2007)
10.1016/J.BIOMATERIALS.2007.07.021
Microengineered hydrogels for tissue engineering.
A. Khademhosseini (2007)
10.1001/JAMA.284.10.1247
Gastrointestinal toxicity with celecoxib vs nonsteroidal anti-inflammatory drugs for osteoarthritis and rheumatoid arthritis: the CLASS study: A randomized controlled trial. Celecoxib Long-term Arthritis Safety Study.
F. Silverstein (2000)
10.1021/CR9700282
Low Molecular Mass Gelators of Organic Liquids and the Properties of Their Gels.
P. Terech (1997)
10.1039/c2cs35284b
Peptides and peptidomimetics that behave as low molecular weight gelators.
C. Tomasini (2013)
10.1039/c2cc33486k
Detecting a peroxide-based explosive via molecular gelation.
J. Chen (2012)
Proc
R. N. Shah (2010)
10.1002/ANIE.200700404
A supramolecular-hydrogel-encapsulated hemin as an artificial enzyme to mimic peroxidase.
Q. Wang (2007)
10.1002/ADMA.200502545
Hybrid Biocomposites Based on Calcium Phosphate Mineralization of Self‐Assembled Supramolecular Hydrogels
Z. Schnepp (2006)
10.1021/cr400195e
Functional π-gelators and their applications.
S. S. Babu (2014)
Polym
A. Takahashi (1980)
10.1073/pnas.0906501107
Supramolecular design of self-assembling nanofibers for cartilage regeneration
R. Shah (2010)
10.1021/JA005933+
First phenylenevinylene based organogels: self-assembled nanostructures via cooperative hydrogen bonding and pi-stacking.
A. Ajayaghosh (2001)
10.1023/A:1018976520391
Synthesis and Evaluation of Morpholinoalkyl Ester Prodrugs of Indomethacin and Naproxen
V. Tammara (2004)
10.1021/CS4002282
Pickering Emulsions Based on Supramolecular Hydrogels: Application to Higher Olefins’ Hydroformylation
J. Potier (2013)
10.1021/CR000108X
Hydrogels for tissue engineering.
K. Lee (2001)
10.1038/srep04593
Anion-activated, thermoreversible gelation system for the capture, release, and visual monitoring of CO2
X. Zhang (2014)
10.1002/anie.200904244
Nanoscience for art conservation: oil-in-water microemulsions embedded in a polymeric network for the cleaning of works of art.
E. Carretti (2009)
10.1056/NEJM200011233432103
Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis. VIGOR Study Group.
C. Bombardier (2000)
Molecular Gels: Materials with Self-Assembled Fibrillar Networks
R. Weiss (2005)
10.1002/chem.200800374
Two-component hydrogels comprising fatty acids and amines: structure, properties, and application as a template for the synthesis of metal nanoparticles.
Hajra Basit (2008)
10.1177/001452469000101110
"J."
G.G. Stokes (1890)
10.1039/c1cc12570b
Drug release from hydrazone-containing peptide amphiphiles.
John B. Matson (2011)
10.1017/CBO9781139207249.009
I and J
William M. Marsden (2012)
Nat
S. Kiyonaka (2004)
10.1002/ADMA.200501522
Nanostructured hydrogels for three-dimensional cell culture through self-assembly of fluorenylmethoxycarbonyl-dipeptides
Vineetha Jayawarna (2006)
Chem
J. B. Matson (2011)
10.1038/nchem.859
Anion-switchable supramolecular gels for controlling pharmaceutical crystal growth
J. A. Foster (2010)
10.1002/anie.201306787
White-light-emitting supramolecular gels.
V. K. Praveen (2014)
10.1039/c3cc48513g
Designing a simple organic salt-based supramolecular topical gel capable of displaying in vivo self-delivery application.
J. Majumder (2014)
Chem
H. Basit (2008)
Adv
Z.A.C. Schnepp (2006)
( a ) A . Ajayaghosh and S . J . George
D. Byamba
10.1039/c2ob07024c
Synthesis of fluorinated oxadiazoles with gelation and oxygen storage ability.
A. Palumbo Piccionello (2012)
10.1158/0008-5472.CAN-09-3267
Induction of cancer cell death by self-assembling nanostructures incorporating a cytotoxic peptide.
Stephany M. Standley (2010)
10.1039/B307149A
A new urea gelator: incorporation of intra- and intermolecular hydrogen bonding for stable 1D self-assembly.
K. Yabuuchi (2003)
10.1021/JA062650U
Enzyme catalysis: tool to make and break amygdalin hydrogelators from renewable resources: a delivery model for hydrophobic drugs.
P. Vemula (2006)
10.1038/NMAT1034
Semi-wet peptide/protein array using supramolecular hydrogel
S. Kiyonaka (2004)
Arch
J. O. Baek (2012)
10.1111/j.2042-7158.1994.tb03871.x
Menthol and Related Cooling Compounds
R. Eccles (1994)
10.1039/b807346e
Supramolecular gelling agents: can they be designed?
P. Dastidar (2008)
10.1039/c3ob00041a
Photoresponsive two-component organogelators based on trisphenylisoxazolylbenzene.
T. Haino (2013)
10.2174/156720112801323053
Polymers and drug delivery systems.
G. Vilar (2012)
10.1007/BF02976502
Enhancement of solubility and dissolution rate of poorly water-soluble naproxen by complexation with 2-hydroxypropyl-β-cyclodextrin
B. Lee (1995)
10.1021/ja903938g
Supramolecular gel based on a perylene diimide dye: multiple stimuli responsiveness, robustness, and photofunction.
Elisha Krieg (2009)
10.1021/ar900282h
New frontiers in materials science for art conservation: responsive gels and beyond.
E. Carretti (2010)
10.1016/J.TETLET.2006.08.002
(S)-(+)-Ibuprofen-based hydrogelators: an approach toward anti-inflammatory drug delivery
S. Bhuniya (2006)
10.1039/c3cs60080g
Characterization of supramolecular gels.
Guocan Yu (2013)
10.1021/JO052293Q
Direct synthesis of esters and amides from unprotected hydroxyaromatic and -aliphatic carboxylic acids.
A. Katritzky (2006)
10.5406/j.ctvpj7hjj.15
What are “ A ” and “ B ” ?
A. News
Nat
J. A. Foster (2010)
Chem
D. F. Hook (2004)
10.1021/ja310019x
D-amino acids boost the selectivity and confer supramolecular hydrogels of a nonsteroidal anti-inflammatory drug (NSAID).
Jiayang Li (2013)
Chem
J. Li (2013)
10.1039/C3TB20155D
RGD anchored C2-benzene based PEG-like hydrogels as scaffolds for two and three dimensional cell cultures.
Xiaoqiu Dou (2013)
10.1039/c3ob40969d
Disulfide bond reduction-triggered molecular hydrogels of folic acid-Taxol conjugates.
C. Yang (2013)
10.1080/095466302317584403
An effective, cosmetically acceptable, novel hydro-gel emollient for the management of dry skin conditions
A. Wynne (2002)
10.1021/JA060573X
Self-assembly of peptide-amphiphile nanofibers: the roles of hydrogen bonding and amphiphilic packing.
S. E. Paramonov (2006)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar