Theoretical study of a series of phenol derivatives: molecular properties vs. cytotoxicity

Martin Michalík; Lívia Sádecká; Vladimír Lukeš

doi:10.1515/acs-2017-0016

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Theoretical study of a series of phenol derivatives: molecular properties vs. cytotoxicity

Acta Chimica Slovaca

Volume 10 (2017): Issue 2 (December 2017)

By: Martin Michalík, Lívia Sádecká and Vladimír Lukeš

Open Access

|Dec 2017

Abstract

The quantum chemical calculations using DFT were performed for 2-alkyl-4X and 2,6-dialkyl-4-X substituted phenols. Based on the optimal geometries the bond dissociation enthalpies (BDEs), proton enthalpies (PAs) and the lipophilicities were computed. Additionally, simple geometry parameter was found correlating well with experimental leukemia cell toxicity of substituted phenols. Next, we have found no linear dependence between PA or BDE values and log1/C values in gas phase or in water despite the radical toxicity mechanism proposed in the literature.

References

Atkins PW (1998) Physical Chemistry, 6th ed. Oxford University Press, Oxford.
Search in Google Scholar Back to article
Becke AD (1988) Phys Rev A 38: 3098-3100.10.1103/PhysRevA.38.3098
Search in Google Scholar Back to article
Bizarro MM, Cabral BJC, dos Santos RMB, Simões JAM (1999) Pure Appl Chem 71: 1249-1256.10.1351/pac199971071249
Search in Google Scholar Back to article
Borges dos Santos RM, Martinho Simões JA (1998) J Phys Chem Ref Data 27: 707-739. Cheminformatics, Molinspiration. Bratislava, Slovak Republic. 2016.
Search in Google Scholar Back to article
Clark T, Chandrasekhar J, Spitznagel GW, Schleyer PVR (1983) J Comp Chem 4: 294-301.10.1002/jcc.540040303
Search in Google Scholar Back to article
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J and Fox DJ (2009) Gaussian 09, Revision D.01, Gaussian, Inc. Wallingford CT.
Search in Google Scholar Back to article
Ghamali M, Chtita S, Adad A, Hmamouchi R, Bouachrine M, Lakhlifi T (2015) J Mater Environ Sci 6: 280-288.
Search in Google Scholar Back to article
Krishnan RBJS, Binkley JS, Seeger R, Pople JA (1980) J Chem Phys 72: 650-654.10.1063/1.438955
Search in Google Scholar Back to article
Lee C, Yang W, Parr RG (1988) Phys Rev B 37: 785-789.10.1103/PhysRevB.37.785
Search in Google Scholar Back to article
Marenich AV, Cramer CJ, Truhlar DG (2009) J Phys Chem B 113: 6378.10.1021/jp810292n
Search in Google Scholar Back to article
McLean AD, Chandler GS (1980) J Chem Phys 72: 5639-5648.10.1063/1.438980
Search in Google Scholar Back to article
Ong CN, Lee BL, Shi CY, Ong HY, Lee HP (1994) Int J Cancer 59: 177-180.10.1002/ijc.2910590206
Search in Google Scholar Back to article
Parker VD (1992) J Am Chem Soc 114: 7458-7462.10.1021/ja00045a018
Search in Google Scholar Back to article
Selassie CD, De Soyza TV, Rosario M, Gao H, Hansch C (1998) Chem-bio Interact 113: 175-190.10.1016/S0009-2797(98)00027-1
Search in Google Scholar Back to article
Selassie C, Shusterman A, Verma R (1999) J Chem Soc Perk Trans 2: 2729-2733.10.1039/a905764a
Search in Google Scholar Back to article
Selassie CD, Verma RP, Kapur S, Shusterman AJ, Hansch C (2002) J Chem Soc Perk Trans 2: 1112-1117.10.1039/b201478e
Search in Google Scholar Back to article

Articles in this issue

DOI: https://doi.org/10.1515/acs-2017-0016 | Journal eISSN: 1339-3065 | Journal ISSN: 1337-978X

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Language: English

Page range: 91 - 95

Published on: Dec 29, 2017

Published by: Slovak University of Technology in Bratislava

In partnership with: Paradigm Publishing Services

Publication frequency: 1 issue per year

Keywords:

QSAR,

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© 2017 Martin Michalík, Lívia Sádecká, Vladimír Lukeš, published by Slovak University of Technology in Bratislava
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Volume 10 (2017): Issue 2 (December 2017)