Multifunctional lipoic acid conjugates

Current Medicinal Chemistry

Volumn 16, Issue 35, 2009, Pages 4728-4742

  Koufaki, M ^a   Detsi, A ^b   Kiziridi, C ^a  

^a INSTITUTE OF BIOLOGY   (Greece)

^b NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

lipoic acid; Hybrids; Quantum dots; Self assembled monolayers

Indexed keywords

2 (N,N DIMETHYLAMINE)ETHYLAMIDOLIPOATE; 2,4 THIAZOLIDINEDIONE DERIVATIVE; [1 [(1 FORMYL 2 PHENYLETHYL)CARBAMOYL] 2 METHYLPROPYL]CARBAMIC ACID BENZYL ESTER; ALPHA TOCOPHEROL; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; BP 1003; BP 1008; BP 1009; BP 1010; BP 1017; CALPASTATIN; DIHYDROLIPOATE; GOLD NANOPARTICLE; LIPOCRINE; MELATONINOLIPOAMIDE; NANOCRYSTAL; NANOSPHERE; NEUROPROTECTIVE AGENT; PLACEBO; QUANTUM DOT; QUINOLINONE 3 AMINOCARBOXAMIDE DERIVATIVE; ROSIGLITAZONE; THIOCTAMIDE; THIOCTIC ACID; THIOCTIC ACID DERIVATIVE; TRISNORLIPOIC ACID DERIVATIVE; TROLOX C; TROLOX C THIOCTIC ACID CONJUGATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALZHEIMER DISEASE; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ASTHMA; BIOLOGICAL ACTIVITY; CLINICAL TRIAL; CONCENTRATION RESPONSE; COSMETIC INDUSTRY; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HEART PROTECTION; HUMAN; NERVE CELL LESION; NEUROPROTECTION; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; PAW EDEMA; PHARMACOPHORE; PROTEIN FUNCTION; REVIEW; SEMICONDUCTOR; SKIN ALLERGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; COSMETICS; DRUG CARRIERS; HYPOGLYCEMIC AGENTS; NANOSPHERES; NEUROPROTECTIVE AGENTS; QUANTUM DOTS; THIOCTIC ACID;

EID: 72449122926     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986709789878274     Document Type: Review

References (75)

1. Reed, L.J.; DeBusk, B.G.; Gansalus, I.C.; Hornberger, C.S. Crystalline α-lipoic acid: a catalytic agent associated with pyruvate dehydrogenase. Science, 1951, 114, 93-94.
2. Reed, L.J.; Gunsalus, I.C.; Schnakenberg, G.H.F., Soper, Q.F.; Boaz, H.E.; Kern, S.F.; Parke, T.V. Isolation, characterization and structure of α-lipoic acid, J. Am. Chem. Soc., 1953, 75, 1267-1270.
3. Elliott, J.D.; Steele, J.; Johnson, W.S. Assymetric synthesis via acetal templates. 12. Highly diastereoselective coupling reactions with a ketene acetal. An efficient, asymmetric synthesis of R-(+)-α-lipoic acid. Tetrahedron Lett., 1985, 26, 2535-2538.
4. Page, P.C.B.; Rayner, C.M.; Sutherland, I.O. Enantioselective synthesis of R-(+)-α -lipoic acid. J. Chem. Soc., Chem. Commun., 1986, 18, 1408-1409.
5. Zimmer, R.; Hain, U.; Berndt, M.; Gewald, R.; Reissig, H.-U. Enantioselective synthesis of (S)- and (R)-6-hydroxy-8-nonenecarboxylates by asymmetric catalysis: a formal synthesis of (R)-α-lipoic acid and its (S)-antipode. Tetrahedron: Asymmetry, 2000, 11, 879-887.
6. Upadhya T.T.; Nikalje M.D.; Sudalai, A. Assymetric dihydroxylation and hydrogenation approaches to the enantioselective synthesis of R-(+)-α-lipoic acid. Tetrahedron Lett., 2001, 42, 4891-4893. (Pubitemid 32588676)
7. Chavan, S.P.; Pravven, C.; Ramakrishna, G.; Kalkote U.R. Enantioselective synthesis of R-(+)-α and S-(-)-α-lipoic acid. Tetrahedron Lett., 2004, 45, 6027-6028.
8. Wei, Z.; Lan, H.-Q.; Zheng, J.-F.; Huang, P.-Q. New and concise approach to (R)-α-lipoic acid. Synth. Commun., 2009, 39, 691-701.
9. Petersen Shay, K.; Moreau, R.F.; Smith, E.J.; Hagen, T.M. Is α-lipoic acid a scavenger of reactive oxygen species in vivo? Evidence for its initiation of stress signaling pathways that promote endogenous antioxidant capacity. IUBMB Life, 2008, 60, 362-367.
10. Packer, L.; Witt, E.H.; Tritschler, H.J. Alpha-lipoic acid as a biological antioxidant. Free Rad. Biol. Med., 1995, 19, 227-250.
11. Moini, H.; Packer, L.; Saris, N.-E.L. Antioxidant and prooxidant activities of a-lipoic acid and dihydrolipoic acid. Toxicol. Applied Pharmacol., 2002, 182, 84-90.
12. Navari-Izzo, F.; Quartacci, M.F.; Sgheri, C. Lipoic acid: a unique antioxidant in the detoxification of activated oxygen species. Plant Physiol. Biochem., 2002, 40, 463-470.
13. Smith, A.R.; Shenvi, S.V.; Widlansky, M.; Suh, J.H.; Hagen, T.M. Lipoic acid as a potential therapy for chronic diseases associated with oxidative stress Curr. Med. Chem., 2004, 11, 1135-1146
14. Meunier, B. Hybrid molecules with a dual mode of action: dream or reality? Acc. Chem. Res., 2008, 41, 69-77.
15. Zhang, L.; Xing, G.Q.; Barker, J.L.; Chang, Y.; Maric, D.; Ma, W.; Li, B-S.; Rubinow, D.R. Alpha-lipoic acid protects rat cortical neurons against cell death induced by amyloid and hydrogen peroxide through the Akt signalling pathway. Neurosci. Lett., 2001, 312, 125-128.
16. Lovell, M.A.; Xie, C.; Xiong, S.; Markesbery, W.R. Protection against amyloid beta peptide and iron/hydrogen peroxide toxicity by alpha lipoic acid. J. Alzheimers. Dis., 2003, 5, 229-239.
17. Holmquist, L.; Stuchbury, G.; Berbaum, K.; Muscat, S.; Young, S.; Hager, K.; Engel, J.; Münch, G. Lipoic acid as a novel treatment for Alzheimer's disease and related dementias. Pharmacol. Ther., 2007, 113, 154-164. (Pubitemid 44969927)
18. Hager, K.; Kenklies, M.; McAfoose, J.; Engel, J.; Münch, G. Alpha-lipoic acid as a new treatment option for Alzheimer's disease - a 48 months follow up analysis. J. Neural. Transm. Suppl., 2007, 72, 189-193.
19. Maczurek, A.; Hager, K.; Kenklies, M.; Sharman, M.; Martins, R.; Engel, J.; Carlson, D.; Münch, G. Lipoic acid as anti-inflammatory and neuroprotective treatment for Alzheimer's disease. Adv. Drug Deliv. Rev., 2008, 60, 1463-1470.
20. a. Sen, C.K.; Tirosh, O.; Roy, S.; Kobayashi, M.; Packer, L. A positively charged α-lipoic acid analogue with increased cellular uptake and more potent immunomodulatory activity. Biochem. Biophys. Res. Commun., 1998, 247, 223-228.
21. b. Tirosh O.; Sen C.K.; Roy S.; Kobayashi M.S.; Packer L. Neuroprotective effects of α-lipoic acid and its positively charged amide analogue. Free Radic. Biol. Med., 1999, 26, 1418-1426
22. Guillonneau, C.; Charton, Y.; Ginot, Y.-M.; Fouquier- d'Hérouël, M.-V.; Bertrand, M.; Lockhart, B.; Lestage, P.; Goldstein, S. Synthesis and pharmacological evaluation of new 1,2-dithiolane based antioxidants. Eur. J. Med. Chem., 2003, 38, 1-11. (Pubitemid 36197849)
23. Bolognesi, M.L.; Minarini, A.; Tumiatti, V.; Melchiorre, C. Lipoic acid, a lead structure for multi-target-directed drugs for neurodegeneration. Mini Rev. Med. Chem., 2006, 6, 1269-1274. (Pubitemid 44697107)
24. Harnett, J.J.; Auguet, M.; Viossat, I.; Dolo, C.; Bigg, D.; Chabrier, P-E. Novel lipoic acid analogues that inhibit nitric oxide synthase. Bioorg. Med. Chem. Lett., 2002, 12, 1439-1442.
25. Lescop, C.; Herzner, H.; Siendt, H.; Bolliger, R.; Henneböhle, M.; Weyermann, P.; Briguet, A.; Courdier-Fruh, I.; Erb, M.; Foster, M.; Meier, T.; Magyar, J.P.; von Sprecher, A. Novel cell-penetrating a-keto-amide calpain inhibitors as potential treatment for muscular dystrophy. Bioorg. Med. Chem. Lett., 2005, 15, 5176-5181. (Pubitemid 41463642)
26. a. Bognesi, M.L.; Rosini, M.; Andrisano, V.; Bartolini, M.; Minarini, A.; Tumiatti, V.; Melchiorre, C. MTDL design strategy in the context of Alzheimer's disease: from lipocrine to memoquin and beyond Curr. Pharm. Des., 2009, 15, 601-613,
27. b. Rosini, M.; Andrisano, V.; Bartolini, M.; Bolognesi, M. L.; Hrelia, P.; Minarini, A.; Tarozzi, A.; Melchiorre, C. Rational approach to discover multipotent anti-Alzheimer drugs. J. Med. Chem., 2005, 48, 360-363.
28. Decker, M.; Kraus, B.; Heilmann, J. Design, synthesis and pharmacological evaluation of hybrid molecules out of quinazolinimines and lipoic acid lead to highly potent and selective butyrylcholinesterase inhibitors with antioxidant properties. Bioorg. Med. Chem., 2008, 16, 4252-4261.
29. Di Stefano, A.; Sozio, P.; Cocco, A.; Iannitelli, A.; Santucci, E.; Costa, M.; Pecci, L.; Nasuti, C.; Cantalamessa, F.; Pinnen, F. LDopa-and dopamine-(R)-α-lipoic acid conjugates as multifunctional codrugs with antioxidant properties. J. Med. Chem., 2006, 49, 1486-1493. (Pubitemid 43271901)
30. Koufaki, M.; Kiziridi, C.; Nikoloudaki, F.; Alexis, M.N. Design and synthesis of 1,2-dithiolane derivatives and evaluation of their neuroprotective activity. Bioorg. Med. Chem. Lett., 2007, 17, 4223-4227. (Pubitemid 47021397)
31. Coombes, J.S.; Powers, S.K.; Demirel, J.; Jessup, H.K.; Vincent, K.L.; Hamilton, K.L.; Naito, H.; Shanely, R.A.; Sen, C.K.; Packer, L.; Ji, L.L. Effect of combined supplementation with vitamin E and alpha-lipoic acid on myocardial performance during in vivo ischaemia-reperfusion. Acta Physiol. Scand., 2000, 169, 261-269.
32. Koufaki, M.; Calogeropoulou, T.; Detsi, A.; Roditis, A.; Kourounakis, A.P.; Papazafiri, P.; Tsiakitzis, K.; Gaitanaki, C.; Beis, I.; Kourounakis, P.N. Novel potent inhibitors of lipid peroxidation with protective effects against reperfusion arrhythmias. J. Med. Chem., 2001, 44, 4300-4303.
33. Koufaki, M.; Detsi, A.; Theodorou, E.; Kiziridi, C.; Calogeropoulou, T.; Vassilopoulos, A.; Kourounakis, A.P.; Rekka, E.; Kourounakis, P.N.; Gaitanaki, C.; Papazafiri, P. Synthesis of chroman analogues of lipoic acid and evaluation of their activity against reperfusion arrhythmias. Bioorg. Med. Chem,. 2004, 12, 4835-4841. (Pubitemid 39164391)
34. Vassilopoulos, A.; Papazafiri, P. Attenuation of oxidative stress in HL-1 cardiomyocytes improves mitochondrial function and stabilizes Hif-1a. Free Radic. Res., 2005, 39, 1273-1284. (Pubitemid 43023792)
35. Antonello, A.; Hrelia, P.; Leonardi, A.; Marucci, G.; Rosini, M.; Tarozzi, A.; Tumiatti, V.; Melchiorre, C. Design, synthesis and biological evaluation of prazosin-related derivatives as multipotent compounds. J. Med. Chem., 2005, 48, 28-31. (Pubitemid 40105246)
36. Antonello, A.; Tarozzi, A.; Morroni, F.; Cavalli, A.; Rosini, M.; Hrelia, P.; Bolognesi, M.L.; Melchiorre, C. Multitarget-directed drug design strategy: A novel molecule designed to block Epidermal Growth Factor Receptor (EGFR) and to exert proapoptotic effects. J. Med. Chem., 2006, 49, 6642-6645. (Pubitemid 44749729)
37. Kaskiw, M.J.; Tassotto, M.L.; Th'ng, J.; Jiang Z.-H. Synthesis and cytotoxic activity of diosgenyl saponin analogues. Bioorg. Med. Chem., 2008, 16, 3209-3217.
38. Fuchs, J.; Milbradt, R. Antioxidant inhibition of skin inflammation induced by reactive oxidants: Evaluation of the redox couple dihydrolipoate/lipoate. Skin Pharmacol., 1994, 7, 278-284. (Pubitemid 24127758)
39. Cho, Y.S.; Lee, J.; Lee, T.-H.; Lee, E.Y.; Lee, K.-U.; Park, J.Y.; Moon, H.-B. R-Lipoic acid inhibits airway inflammation and hyperresponsiveness in a mouse model of asthma. J. Allergy Clin. Immunol., 2004, 114, 429-435. (Pubitemid 39119048)
40. Venkatraman, M.S.; Chittiboyina, A.; Meingassner, J.; Ho, C.I.; Varani, J.; Ellis, C.N.; Avery, M.A.; Pershadsingh, H.A.; Kurtz, T.W.; Benson, S.C. α-Lipoic acid-based PPARγ agonists for treating inflammatory skin diseases. Arch. Dermatol. Res., 2004, 296, 97-104.
41. Detsi, A.; Bouloumbasi, D.; Prousis, K. C.; Koufaki, M.; Athanasselis, G.; Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J. Design and synthesis of novel quinolinone-3- aminoamides and their α-lipoic acid adducts as antioxidant and anti-inflammatory agents. J. Med. Chem., 2007, 50, 2450-2458.
42. Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Detsi, A.; Koufaki, M.; Kontogiorgis, C.; Hadjipavlou-Litina, D.; Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3- aminoamides and their alpha-lipoic acid adducts, Eur. J. Med. Chem., 2009, 44, 3020-3026
43. Ziegler, D.; Nowak, H.; Kempler, P.; Vargha, P.; Low, P.A. Treatment of symptomatic diabetic polyneuropathy with the antioxidant alpha-lipoic acid: a meta-analysis. Diabetes Med., 2004, 21, 114-121. (Pubitemid 38221809)
44. Singh, U.; Jialal, I. Alpha-lipoic acid supplementation and diabetes. Nutr. Rev., 2008, 66, 646-657.
45. Gruzman, A.; Hidmi, A.; Katzhendler, J.; Haj-Yehiec, A.; Sasson, S. Synthesis and characterization of new and potent α-lipoic acid derivatives. Bioorg. Med. Chem., 2004 12, 1183-1190. (Pubitemid 38251308)
46. Chittiboyina, A.; Venkatraman, M.S.; Mizuno, C.S.; Desai, P.V.; Patny, A.; Benson, S.C.; Ho, C.I.; Kurtz, T.W.; Pershadsingh, H.A.; Avery, M.A. Design and synthesis of the first generation of dithiolane thiazolidinedione- and phenylacetic acid-based PPARγ agonists. J. Med. Chem., 2006, 49, 4072-4084.
47. Venkatachalam, S.R.; Salaskar, A.; Chattopadhyay, A.; Barik, A.; Mishra, B.; Gangabhagirathi, R.; Priyadarsini, K.I. Synthesis, pulse radiolysis, and in vitro radioprotection studies of melatoninolipoamide, a novel conjugate of melatonin and α-lipoic acid. Bioorg. Med. Chem., 2006, 14, 6414-6419.
48. Durand, G.; Polidori, A.; Salles, J. P.; Prost, M.; Durand, P.; Pucci, B. Synthesis and antioxidant efficiency of a new amphiphilic spintrap derived from PBN and lipoic acid. Bioorg. Med. Chem. Lett., 2003, 13, 2673-2676.
49. Saah, M.; Wu, W.M.; Eberst, K.; Marvanyos, E.; Bodor, N. Design, synthesis, pharmacokinetic evaluation of a chemical delivery system for drug targeting to lung tissue. J. Pharm. Sci., 1996, 85, 496-504.
50. Ortial, S.; Durand, G.; Poeggeler, B.; Polidori, A.; Pappolla, M.A.; Böker, J. Hardeland, R.; Pucci, B. Fluorinated amphiphilic amino acid derivatives as antioxidant carriers: a new class of protective agents J. Med. Chem., 2006, 49, 2812-2820.
51. Prasad, P. D.; Wang, H.; Kekuda, R.; Fujita, T.; Fei, Y.-J.; Devoe, L.D.; Leibach, F. H.; Ganapathy, V. Cloning and functional expression of a cDNA encoding a mammalian sodium-dependent vitamin transporter mediating the uptake of pantothenate, biotin, and lipoate. J. Biol. Chem. 1998, 273, 7501-7506.
52. Luo, S.; Kansara, V. S.; Zhu, X.; Pal, D.; Mitra, A.K. Functional characterization of sodium-dependent multivitamin transporter (SMVT) in MDCK-MDR1 cells and its utilization as a target for drug delivery. Mol. Pharm. 2006, 3, 329-339.
53. Dobson, P. D.; Kell D. B. Carrier-mediated cellular uptake of pharmaceutical drugs:an exception or the rule? Nat. Rev. Drug Discov., 2008, 7, 205-220. (Pubitemid 351321232)
54. Neuberger, M.; Polidori, A.M.; Piètre, E.; Faure, M.; Jourdain, A.; Bourgouignon, J.; Pucci, B.; Douce, R. Interaction between the lipoamide-containing H-protein and the lipoamide-dehydrogenase (L-protein) of the glycine decarboxylase multienzyme system. Eur. J. Biochem., 2000, 267, 2882-2889. (Pubitemid 30321333)
55. Tsuji-Naito, K.; Hatani, T.; Okada, T.; Tehara, T. Modulating effects of a novel skin-lightening agent, α-lipoic acid derivative, on melanin production by the formation of DOPA conjugate products. Bioorg. Med. Chem., 2007, 15, 1967-1975. (Pubitemid 46176634)
56. Gelo-Pujic, M.; Desmurs, J.-R.; Delaire, S.; Adao, A.; Tawil, D. Synthesis of new antioxidant conjugates and their in vitro hydrolysis with Stratum corneum enzymes. Int. J. Cosmet. Sci., 2008, 30, 195-204. (Pubitemid 351623839)
57. Lee, B.-S.; Yuan, X.; Xu, Q.; McLafferty, F. S.; Petersen, B. A.; Collette, J. C.;. Black, K. L.; Yu, J. S. Stimuli-responsive antioxidant nanoprodrugs of NSAIDs. Int. J. Pharm., 2009, 372, 112-124.
58. Lee, B.S.; Yuan, X.; Xu, Q.; McLafferty, F.S.; Petersen, B.A.; Collette, J.C.; Black, K.L.; Yu, J.S. Preparation and characterization of antioxidant nanospheres from multiple α-lipoic acidcontaining compounds Bioorg. Med. Chem. Lett., 2009, 19, 1678-1681.
59. Miura, Y.; Kimura, S.; Imanishi, Y.; Umemura, J. Formation of oriented helical peptide layers on a gold surface due to the self-assembling properties of peptides. Langmuir, 1998, 14, 6935-6940. (Pubitemid 128585006)
60. Morita, T.; Kimura, S.; Kobayashi, S.; Imanishi, Y. Photocurrent generation under a large dipole moment formed by self-assembled monolayers of helical peptides having an N-ethylcarbazolyl group. J. Am. Chem. Soc., 2000, 122, 2850-2859. (Pubitemid 30191045)
61. Yoshiko, M.; Shunsaku, K.; Kobayashi, S.; Imanishi, Y.; Umemura, J. Cation recognition by self-assembled monolayers of oriented helical peptides having a crown ether unit. Biopolymers (Peptide Science), 2000, 55, 391-398. (Pubitemid 32248745)
62. Wen, X.; Linton, R.W.; Formaggio, F.; Toniolo, C.; Samulski E.T. Self-assembled monolayers of hexapeptides on gold: surface characterization and orientation distribution analysis. J. Phys. Chem. A, 2004, 108, 9673-9681.
63. Sieczkowska, B.; Millaruelo, M.; Messerschmidt, M.; Voit, B. New photolabile functional polymers for patterning onto gold obtained by click chemistry. Macromolecules, 2007, 40, 2361-2370. (Pubitemid 46608262)
64. Gatto, E.; Stella, L.; Formaggio, F.; Toniolo, C.; Lorenzelli, L.; Venanzi, M. Electroconductive and photocurrent generation properties of self-assembled monolayers formed by functionalized, conformationally-constrained peptides on gold electrodes. J. Pept. Sci., 2008, 14, 184-191.
65. Bunjes, N.E.; Schmidt, K.; Jonczyk, A.; Rippmann, F.; Beyer, D.; Ringsdorf, H.; Gräber, P.; Knoll, W.; Naumann, R. Thiopeptide-supported lipid layers on solid substrates. Langmuir, 1997, 13, 6188-6194. (Pubitemid 127592018)
66. Schiller, S. M.; Naumann, R.; Lovejoy, K.; Kunz, H.; Knoll, W. Archaea analogue thiolipids for tethered bilayer lipid membranes on ultrasmooth gold surfaces. Angew. Chem. Int. Ed., 2003, 42, 208-211. (Pubitemid 36125579)
67. Liebert, T.; Hussain, M. A.; Tahir, M. N.; Heinze, T. Synthesis and characterization of cellulose α-lipoates: a novel material for adsorption onto gold. Polymer Bull., 2006, 57, 857-863.
68. Karamanska, R.; Mukhopadhyay, B.; Russell, D.A.; Field R.A. Thioctic acid amides: convenient tethers for achieving low nonspecific protein binding to carbohydrates presented on gold surfaces. Chem. Commun., 2005, 3334-3336.
69. Kadalbajoo, M.; Park, J.; Opdahl, A.; Suda, H.; Kitchens, C.A.; Garno, J.C.; Batteas, J.D.; Tarlov, M.J.; DeShong, P. Synthesis and structural characterization of glucopyranosylamide films on gold. Langmuir, 2007, 23, 700-707. (Pubitemid 46226582)
70. Dondapati, S. K.; Montornes, J.M.; Sanchez, P.L.; Sanchez, J.L.A.; O'Sullivan, C.; Katakis, I. Site-directed immobilization of proteins through electrochemical deprotection on electroactive self-assembled monolayers. Electroanalysis, 2006, 18, 1879-1884.
71. Hahn, C.D.; Leitner, C.; Weinbrenner, T.; Schlapak, R.; Tinazli, A.; Tampe, R.; Lackner, B.; Steindl, C.; Hinterdorfer, P.; Gruber, H.J.; Hölzl, M. Self-assembled monolayers with latent aldehydes for protein immobilization Bioconjug. Chem., 2007, 18, 247-253. (Pubitemid 46146016)
72. Dougan, J.A.; Karlsson, C.; Smith W.E.; Graham, D. Enhanced oligonucleotide-nanoparticle conjugate stability using thioctic acid modified oligonucleotides. Nucleic Acids Res., 2007, 35, 3668-3675. (Pubitemid 47244661)
73. Vikholm-Lundin, I.; Pulli, T.; Albers, W.M. Tappura K. A comparative evaluation of molecular recognition by monolayers composed of synthetic receptors or oriented antibodies. Biosens. Bioelectron., 2008, 24, 1036-1038.
74. Susumu, K.; Uyeda, T.H.; Medintz, I.L.; Pons, T.; Delehanty, J.B.; Mattoussi, H. Enhancing the stability and biological functionalities of quantum dots via compact multifunctional ligands. J. Am. Chem. Soc. 2007, 129, 13987-13996. (Pubitemid 350106090)
75. Han, G.; Mokari, T.; Ajo-Franklin, C.; Cohen, B.E. Caged quantum dots. J. Am. Chem. Soc., 2008, 130, 15811-15813.