ATR-IR and Raman spectroscopic study of interaction between major calixarene derivatives and oral anticoagulants

Tiuca, Ioana; Saponar, Alina; Bodoki, Andreea; Ziemons, Eric; Bodoki, Ede; Hubert, Philippe; Oprean, Radu

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ATR-IR and Raman spectroscopic study of interaction between major calixarene derivatives and oral anticoagulants

Tiuca, Ioana; Saponar, Alina; Bodoki, Andreea et al.

2013 • In Farmacia, 61 (5), p. 874-882

Peer reviewed

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https://hdl.handle.net/2268/161511

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Keywords :

cali(x)arenes; anticoagulants; Spectroscopy

Abstract :

[en] In this study we analyzed by ATR-IR and Raman spectroscopy the interaction between six major calixarene derivatives and two anticoagulants: warfarin and acenocoumarol. The six calixarene derivatives were: p-tert-butyl-calix[4]arene (C4), p-tert- butyl-calix[6]arene (C6) and p-tert-butyl-calix[8]arene (C8) and their ethyl-ester- derivatives: tetraester-p-tert-butyl-calix[4]arene (C4Es4), hexaester-p-tert-butyl- calix[6]arene (C6Es6), octaester-p-tert-butyl-calix[8]arene (C8Es8). The results showed the most intense interaction in terms of complex formation for the C6-acenocoumarol couple and for the C6-warfarin couple, respectively.

Research Center/Unit :

Centre Interfacultaire de Recherche du Médicament - CIRM

Disciplines :

Pharmacy, pharmacology & toxicology

Author, co-author :

Tiuca, Ioana

Saponar, Alina

Bodoki, Andreea

Ziemons, Eric ; Université de Liège - ULiège > Département de pharmacie > Département de pharmacie

Bodoki, Ede

Hubert, Philippe ; Université de Liège - ULiège > Département de pharmacie > Chimie analytique

Oprean, Radu

Language :

English

Title :

ATR-IR and Raman spectroscopic study of interaction between major calixarene derivatives and oral anticoagulants

Publication date :

2013

Journal title :

Farmacia

ISSN :

0014-8237

eISSN :

2065-0019

Publisher :

Centrul de Documentare Medicală, București, Romania

Volume :

Issue :

Pages :

874-882

Peer reviewed :

Peer reviewed

Available on ORBi :

since 19 January 2014

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Bibliography

Andreetti GD, Pochini A, Ungaro R. Molecular inclusion in functionalized macrocycles. Part 6. The crystal and molecular structures of the calix[4]arene from p-(1,1,3,3- tetramethylbutyl)phenol and its 1: 1 complex with toluene. J. Chem. Soc., Perkin Trans. 2, 1983, 1773-79
Bocchinfuso G. et al. Receptors for organochlorine pesticides based on calixarenes. Microchimica Acta 2008; 163:195-202
Bodoki E, Tiuca I, Iacob BC, Hosu O, Oprean R. Determination of enantiomeric ratio of warfarin in tablets by multivariate calibration and modeling of spectroscopic data. Farmacia 2012; 60(3):386-93
Bozkurt S, Durmaz M, Yilmaz M, Sirit A. Calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids. Tetrahedron: Asymmetry 2008; 19(5):618-23
Cieślik-Boczula K, Maniewska J, Grynkiewicz G, Szeja W, Kolla A, Hendrich A. Interaction of quercetin, genistein and its derivatives with lipid bilayers - An ATR IRspectroscopic study. Vibrational Spectroscopy 2012; 62:64-69
Da Silva E, Ficheux D, Coleman AW. Anti-thrombotic Activity of Water-soluble Calix[n]arenas. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2005; 52:201-6
Dale SH, Elsegood MRJ, Redshaw C. Polymorphism and pseudopolymorphism in calixarenes: acetonitrile clathrates of p-But-calix[n]arenes (n= 6 and 8). CrystEngComm, 2003, 5, 368-73
Fehlinger M, Abraham W. Calix[4]arenes bearing a tropylium substituent as hosts for organic cations. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2007;58:263-74
Gutsche CD, Bauer LJ. Calixarenes. 13. The conformational properties of calix[4]arenes, calix[6]arenes, calix[8]arenes, and oxacalixarenes. J. Am. Chem. Soc., 1985, 107, 6052-59
Gutsche CD, Bauer LJ. Calixarenes. 5. Dynamic NMR characteristics of p-tertbutylcalix[ 4]-arene and p-tert-butylcalix[8]arene. Tetrahedron Lett., 1981, 4763-66
Gutsche CD, Dhawan B, Leonis M, Stewart D. p-tert-butylcalix[6]arene. Org.Synthesis, 1989; 68:238-42
Gutsche CD, Iqbal M. p-tert-butylcalix[4]arene. Org.Synthesis. 1989; 68:234-7
Gutsche CD. Calixarenes: an Introduction. London: Royal Society of Chemistry, 2008:24-237
Hubert Joe1 I, Kostova I, Ravikumar C, Amalanathan M, Cînt Pînzaru S. Theoretical and vibrational spectral investigation of sodium salt of acenocoumarol. Journal of Raman Spectroscopy 2009; 40(8):1033-38
Jansen RG, Van Duynhoven JP, Verboom W, Hummel GJ, Harkema S, Reinhouldt DN. Studies on the Dynamics of Phosphorylated p-tert-butyl-Calix[6]arenes by Using 2D NMR Spectroscopy. J. Am. Chem. Soc., 1996, 118, 3666-75
Liu YL, Liu L, Wang YL, Han YC, Wang D, Chen YJ. Calix[n]arene sulfonic acids bearing pendant aliphatic chains as recyclable surfactant-type Brønsted acid catalysts for allylic alkylation with allyl alcohols in water. Green Chem. 2008; 10:635-40
Memon S, Akceylan E, Sap B, Tabakci M, Roundhill DM, Yilmaz M. Polymer Supported Calix[4]Arene Derivatives for the Extraction of Metals and Dichromate Anions. Journal of Polymers and the Environment 2003; 11:67-74
Mohammed-Ziegler I, Grün A. Complex formation between aliphatic amines and chromogenic calix[4]arene derivatives studied by FT-IR spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc 2005; 62:506-17
Motornaya AE, Alimbarova LM, Shokova EA, Kovalev VV. Synthesis and antiherpetic activity of N-(3-amino-1-adamantyl)calix[4]arenes. Pharmaceutical Chemistry Journal 2006; 40:68-72
Munch JH, Gutsche CD. p-tert-butylcalix[8]arene. Org.Synthesis. 1989; 68:243-6
Mutihac L, Buschmann HJ, Diacu E. Calixarene derivatives as carriers in liquid membrane transport. Desalination 2002; 148:253-56
Mutihac L, Buschmann HJ, Mutihac RC, Schollmeyer E. Complexation and Separation of Amines, Amino Acids, and Peptides by Functionalized Calix[n]arenas. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2005; 51:1-10
G. Duţu, C. Cristea, B. Ede, V. Hârceagǎ, A. Saponar, E. Popovici, R. Sǎndulescu, The electrochemical behavior of some local anaesthetics on screen printed electrodes modified with calixarenes, Farmacia, 2011, 59(4), 147-160
Saponar A, Popovici E-J, Grecu R, Silaghi-Dumitrescu I, Popovici N. Synthesis of ester derivatives of calix[n]arene, Studia Universitatis Babeş-Bolyai, Chemia. 2009; 54(4):203-10
Schatz J, Schildbach F, Lentz A, Rastätter S, Debaerdemaeker T. A CH/π interaction at a highly solvated macrocycle in the solid state - the p-tert-butylcalix[8]arene-chloroform 1:8 clathrateZ. Kristallogr., 2001, 216, 182-86
Thamarai Chelvi SK, Yong EL, Gong Y. Preparation and evaluation of calix[4]arenecapped β-cyclodextrin-bonded silica particles as chiral stationary phase for highperformance liquid chromatography. J Chromatogr A 2008; 1203:54-58
Van Hoorn WP, Van Veggel FC, Reinhoudt DN. Conformation of Hexahydroxycalix[6]arene. J. Org. Chem., 1996, 61, 7180-84
Yin T, Miyata T. Warfarin dose and the pharmacogenomics of CYP2C9 and VKORC1 - Rationale and perspectives. Thromb Res 2007; 120(1):1-10.