Molecular modeling, structure activity relationship and immunomodulatory properties of some lupeol derivatives

Medicinal Chemistry Research

Volumn 22, Issue 4, 2013, Pages 1795-1803

  Shahlaei, Mohsen ^a   Ghanadian, Syed Mustafa ^b   Ayatollahi, Abdul Majid ^c   Mesaik, M Ahmed ^d   Abdalla, Omer Mohamed ^d   Afsharypour, Suleiman ^b   Rabbani, Mohammed ^b  

^a KERMANSHAH UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b ISFAHAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c SHAHID BEHESHTI UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

Biologic screening; Drug design; Molecular modeling; Natural product; Structure activity relationship

Indexed keywords

BETULIC ACID; ETHYL BETULINATE; LUPEOL; LUPEOL ACETATE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; DRUG ISOLATION; DRUG SCREENING; HUMAN; HUMAN CELL; IMMUNE SYSTEM; IMMUNOMODULATION; MOLECULAR DYNAMICS; MOLECULAR MODEL; NONHUMAN; SCIENTIST; SIMULATION; STRUCTURE ACTIVITY RELATION;

EID: 84879691285     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0183-y     Document Type: Article

References (29)

1. Aandahl EM, Moretto WJ, Haslett PA, Vang T, Bryn T, Tasken K, Nixon DF (2002) Inhibition of antigen-specific T cell proliferation and cytokine production by protein kinase A type I. J Immunol 169:802-808
2. Ayatollahi AM, Ghanadian M, Afsharypour S, Abdalla OM, Mirzai M, Askari G (2011) Pentacyclic triterpenes in Euphorbia microsciadia with their t-cell proliferation activity. Iran J Pharm Res 10:287-294
3. Baglin I, Mitaine-Offer AC, Nour M, Tan K, Cave C, Lacaille-Dubois MA (2003) A review of natural and modified betulinic acid, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents. Mini Rev Med Chem 3:525-539
4. Bani S, Kaul A, Khan B, Ahmad SF, Suri KA, Gupta BD, Satti NK, Qazi GN (2006) Suppression of T lymphocyte activity by lupeol isolated from Crataeva religiosa. Phytother Res 20:276-287
5. Berendsen H, Postma J, van Gusteren W, Hermans J (1981) Interaction models for water in relation to protein hydratation. Reidel, Dordrecht
6. Darden T, York D, Pedersen L (1993) Particle mesh Ewald: an N·log(N) method for Ewald sums in large systems. J Chem Phys 98:10089-10092
7. Domínguez-Carmona DB, Escalante-Erosa F, García-Sosa K, Ruiz-Pinell G, Gutierrez-Yapu D, Chan-Bacab MJ, Giménez-Turba A, Pena-Rodriguez LM (2010) Antiprotozoal activity of betulinic acid derivatives. Phytomedicine 17:379-382
8. Einzhammer DA, Xu ZQ (2004) Betulinic acid: a promising anticancer candidate. Idrugs 4:359-373
9. Erickson JA, Jalaie M, Robertson DH, Lewis RA, Vieth M (2004) Lessons in molecular recognition: the effects of ligand and protein flexibility on molecular docking accuracy. J Med Chem 47:45-55
10. Gasteiger J, Marsili M (1980) Iterative partial equalization of orbital electro- negativity-a rapid access to atomic charges. Tetrahedron 36:3219-3228
11. Helen L, Robert J, Roger C, Steven W (2010) Neutrophil function in inflammation and inflammatory diseases. Rheumatology 49:1618-1631
12. Hess B, Bekker H, Berendsen H, Fraahje J (1997) LINCS: a linear constraint solver for molecular interactions. J Comp Chem 18:1463-1472
13. Humphrey W, Dalke A, Schulten K (1996) VMD: Visual molecular dynamics. J Mol Graph 14:33-38
14. Lobstein A, Schoonjans K, Souchet M, Auwerx J, Saladin R, Wagner A (2010) Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes. J Med Chem 53:178-190
15. Macias FA, Simonet AM, Esteban DM (1994) Potential allelopathic lupane triterpenes from bioactive fractions of Melilotus messanensis. Phytochemistry 36:1369-1379
16. Mischak H, Goodnight JA, Kolch W, Martiny-Baron G, Schaechtle C, Kazanietz MG, Blumberg PM, Pierce JH, Mushinski JF (1993) Overexpression of protein kinase C-delta and epsilon in NIH 3T3 cells induces opposite effects on growth, morphology, anchorage dependence, and tumorigenicity. J Biol Chem 268:6090-6096
17. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ (1998) Automated docking using a lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19:1639-1662
18. Nielsen MB, Gerwien J, Nielsen M, Geisler C, Ropke C, Svejgaard A (1998) MHC class II ligation induces CD58 (LFA-3)-mediated adhesion in human T cells. Exp Clin Immunogenet 15:61-68
19. Ottonello L, Morone MP, Dapino P, Dallegri F (1995) Cyclic AMP-elevating agents down-regulate the oxidative burst induced by granulocyte-macrophage colony-stimulating factor (GM-CSF) in adherent neutrophils. Clin Exp Immunol 101:502-506
20. Ruppelt A, Mosenden R, Grönholm M, Aandahl EM, Tobin D, Carlson CR, Abrahamsen H, Herberg FW, Carpén O, Taskén K (2007) Inhibition of T cell activation by cyclic adenosine 5'-monophosphate requires lipid raft targeting of protein kinase A type I by the A-kinase anchoring protein ezrin. J Immunol 179:5159-5168
21. Shahlaei M, Madadkar-Sobhani A, Fassihi A, Saghaie L (2011a) Exploring a model of a chemokine receptor/ligand complex in an explicit membrane environment by molecular dynamics simulation: the human CCR1 receptor. J Chem Inf Model 51:2717-2730
22. Shahlaei M, Madadkar-Sobhani A, Mahnam K, Fassihi A, Saghaie L, Mansourian M (2011b) Homology modeling of human CCR5 and analysis of its binding properties through molecular docking and molecular dynamics simulation. Biochim Biophys Acta Biomembr 1808:802-817
23. Shintyapina AB, Shults EE, Petrenko NI, Uzenkova NV, Tolstikov CA, Pronkina NV, Kozhevnikov VS, Pokrovsky AG (2007) Effect of nitrogen-containing derivatives of the plant triterpenes betulin and glycyrrhetic acid on the growth of MT-4, MOLT-4, CEM, and Hep G2 tumor cells Russ. J Bioorg Chem 33:579-583
24. Solis FJ, Wets JB (1981) Minimization by random search techniques. Math Oper Res 6:19-30
25. Viqar UA, Rahman AU (1994) Handbook of natural products data, vol 2. Elsevier Sciences, Amsterdam
26. Weiner SJ, Kollman PA, Case DA, Singh UC, Ghio C, Alagona G, Profeta S, Weiner PK (1984) A new force-field for molecular mechanical simulation of nucleic-acids and proteins. J Am Chem Soc 6:765-784
27. Yeadon M, Diamant Z (2000) New and exploratory therapeutic agents for asthma. Marcel Dekker, New York
28. Yi JE, Obminska-Mrukowicz B, Yuan LY, Yuan H (2010) Immunomodulatory effects of betulinic acid from the bark of white birch on mice. J Vet Sci 11:305-313
29. Yogeeswari P, Sriram D (2005) Betulinic acid and its derivatives: a review on their biological properties. Curr Med Chem 12:657-666