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Items: 49

1.

An investigation into the pleiotropic activity of metformin. A glimpse of haemostasis.

Markowicz-Piasecka M, Sadkowska A, Huttunen KM, Podsiedlik M, Mikiciuk-Olasik E, Sikora J.

Eur J Pharmacol. 2020 Apr 5;872:172984. doi: 10.1016/j.ejphar.2020.172984. Epub 2020 Feb 1. Review.

PMID:
32017937
2.

Pleiotropic Activity of Metformin and Its Sulfonamide Derivatives on Vascular and Platelet Haemostasis.

Markowicz-Piasecka M, Huttunen KM, Sadkowska A, Sikora J.

Molecules. 2019 Dec 28;25(1). pii: E125. doi: 10.3390/molecules25010125.

3.

Astrocyte-Targeted Transporter-Utilizing Derivatives of Ferulic Acid Can Have Multifunctional Effects Ameliorating Inflammation and Oxidative Stress in the Brain.

Montaser A, Huttunen J, Ibrahim SA, Huttunen KM.

Oxid Med Cell Longev. 2019 Nov 13;2019:3528148. doi: 10.1155/2019/3528148. eCollection 2019.

4.

Novel halogenated sulfonamide biguanides with anti-coagulation properties.

Markowicz-Piasecka M, Sikora J, Zajda A, Huttunen KM.

Bioorg Chem. 2020 Jan;94:103444. doi: 10.1016/j.bioorg.2019.103444. Epub 2019 Nov 19.

PMID:
31776031
5.

L-Type amino acid transporter 1 (LAT1)-utilizing prodrugs are carrier-selective despite having low affinity for organic anion transporting polypeptides (OATPs).

Huttunen J, Gynther M, Vellonen KS, Huttunen KM.

Int J Pharm. 2019 Nov 25;571:118714. doi: 10.1016/j.ijpharm.2019.118714. Epub 2019 Oct 11.

PMID:
31610281
6.

L-Type Amino Acid Transporter 1 (LAT1/Lat1)-Utilizing Prodrugs Can Improve the Delivery of Drugs into Neurons, Astrocytes and Microglia.

Huttunen J, Peltokangas S, Gynther M, Natunen T, Hiltunen M, Auriola S, Ruponen M, Vellonen KS, Huttunen KM.

Sci Rep. 2019 Sep 6;9(1):12860. doi: 10.1038/s41598-019-49009-z.

7.

Mechanistic Study on the Use of the l-Type Amino Acid Transporter 1 for Brain Intracellular Delivery of Ketoprofen via Prodrug: A Novel Approach Supporting the Development of Prodrugs for Intracellular Targets.

Puris E, Gynther M, de Lange ECM, Auriola S, Hammarlund-Udenaes M, Huttunen KM, Loryan I.

Mol Pharm. 2019 Jul 1;16(7):3261-3274. doi: 10.1021/acs.molpharmaceut.9b00502. Epub 2019 Jun 18.

PMID:
31180686
8.

Sulfenamide and Sulfonamide Derivatives of Metformin - A New Option to Improve Endothelial Function and Plasma Haemostasis.

Markowicz-Piasecka M, Huttunen KM, Broncel M, Sikora J.

Sci Rep. 2019 Apr 25;9(1):6573. doi: 10.1038/s41598-019-43083-z.

9.

Sulfenamide derivatives can improve transporter-mediated cellular uptake of metformin and induce cytotoxicity in human breast adenocarcinoma cell lines.

Markowicz-Piasecka M, Huttunen J, Sikora J, Huttunen KM.

Bioorg Chem. 2019 Jun;87:321-334. doi: 10.1016/j.bioorg.2019.03.036. Epub 2019 Mar 19.

PMID:
30913467
10.

L-type amino acid transporter 1 utilizing prodrugs of ferulic acid revealed structural features supporting the design of prodrugs for brain delivery.

Puris E, Gynther M, Huttunen J, Auriola S, Huttunen KM.

Eur J Pharm Sci. 2019 Mar 1;129:99-109. doi: 10.1016/j.ejps.2019.01.002. Epub 2019 Jan 6.

PMID:
30625368
11.

Alzheimer's Disease Phenotype or Inflammatory Insult Does Not Alter Function of L-Type Amino Acid Transporter 1 in Mouse Blood-Brain Barrier and Primary Astrocytes.

Gynther M, Puris E, Peltokangas S, Auriola S, Kanninen KM, Koistinaho J, Huttunen KM, Ruponen M, Vellonen KS.

Pharm Res. 2018 Nov 28;36(1):17. doi: 10.1007/s11095-018-2546-7.

12.

Metformin and its sulphonamide derivative simultaneously potentiateanti-cholinesterase activity of donepezil and inhibit beta-amyloid aggregation.

Markowicz-Piasecka M, Huttunen KM, Sikora J.

J Enzyme Inhib Med Chem. 2018 Dec;33(1):1309-1322. doi: 10.1080/14756366.2018.1499627.

13.

Identification of human, rat and mouse hydrolyzing enzymes bioconverting amino acid ester prodrug of ketoprofen.

Huttunen KM.

Bioorg Chem. 2018 Dec;81:494-503. doi: 10.1016/j.bioorg.2018.09.018. Epub 2018 Sep 11.

PMID:
30243240
14.

Targeted efflux transporter inhibitors - A solution to improve poor cellular accumulation of anti-cancer agents.

Huttunen J, Gynther M, Huttunen KM.

Int J Pharm. 2018 Oct 25;550(1-2):278-289. doi: 10.1016/j.ijpharm.2018.08.047. Epub 2018 Aug 25.

PMID:
30149128
15.

Secondary carbamate linker can facilitate the sustained release of dopamine from brain-targeted prodrug.

Thiele NA, Kärkkäinen J, Sloan KB, Rautio J, Huttunen KM.

Bioorg Med Chem Lett. 2018 Sep 15;28(17):2856-2860. doi: 10.1016/j.bmcl.2018.07.030. Epub 2018 Jul 18.

PMID:
30055889
16.

Structural properties for selective and efficient l-type amino acid transporter 1 (LAT1) mediated cellular uptake.

Kärkkäinen J, Gynther M, Kokkola T, Petsalo A, Auriola S, Lahtela-Kakkonen M, Laine K, Rautio J, Huttunen KM.

Int J Pharm. 2018 Jun 10;544(1):91-99. doi: 10.1016/j.ijpharm.2018.04.025. Epub 2018 Apr 15.

PMID:
29669256
17.

Sulfenamide and sulfonamide derivatives of metformin can exert anticoagulant and profibrinolytic properties.

Markowicz-Piasecka M, Huttunen KM, Mateusiak Ł, Mikiciuk-Olasik E, Sikora J.

Chem Biol Interact. 2018 Mar 25;284:126-136. doi: 10.1016/j.cbi.2018.02.012. Epub 2018 Feb 16.

PMID:
29458015
18.

Biocompatible sulfenamide and sulfonamide derivatives of metformin can exert beneficial effects on plasma haemostasis.

Markowicz-Piasecka M, Huttunen KM, Mikiciuk-Olasik E, Sikora J.

Chem Biol Interact. 2018 Jan 25;280:15-27. doi: 10.1016/j.cbi.2017.12.005. Epub 2017 Dec 5.

PMID:
29217384
19.

Metformin and Its Sulfenamide Prodrugs Inhibit Human Cholinesterase Activity.

Markowicz-Piasecka M, Sikora J, Mateusiak Ł, Mikiciuk-Olasik E, Huttunen KM.

Oxid Med Cell Longev. 2017;2017:7303096. doi: 10.1155/2017/7303096. Epub 2017 Jul 9.

20.

L-type amino acid transporter 1 utilizing prodrugs: How to achieve effective brain delivery and low systemic exposure of drugs.

Puris E, Gynther M, Huttunen J, Petsalo A, Huttunen KM.

J Control Release. 2017 Sep 10;261:93-104. doi: 10.1016/j.jconrel.2017.06.023. Epub 2017 Jun 27.

PMID:
28662899
21.

New prodrugs of metformin do not influence the overall haemostasis potential and integrity of the erythrocyte membrane.

Markowicz-Piasecka M, Sikora J, Mateusiak Ł, Mikiciuk-Olasik E, Huttunen KM.

Eur J Pharmacol. 2017 Sep 15;811:208-221. doi: 10.1016/j.ejphar.2017.06.011. Epub 2017 Jun 10.

PMID:
28606852
22.

Metformin - a Future Therapy for Neurodegenerative Diseases : Theme: Drug Discovery, Development and Delivery in Alzheimer's Disease Guest Editor: Davide Brambilla.

Markowicz-Piasecka M, Sikora J, Szydłowska A, Skupień A, Mikiciuk-Olasik E, Huttunen KM.

Pharm Res. 2017 Dec;34(12):2614-2627. doi: 10.1007/s11095-017-2199-y. Epub 2017 Jun 6. Review.

23.

Substituted arylsulphonamides as inhibitors of perforin-mediated lysis.

Spicer JA, Miller CK, O'Connor PD, Jose J, Huttunen KM, Jaiswal JK, Denny WA, Akhlaghi H, Browne KA, Trapani JA.

Eur J Med Chem. 2017 Sep 8;137:139-155. doi: 10.1016/j.ejmech.2017.05.048. Epub 2017 May 26.

24.

Benzenesulphonamide inhibitors of the cytolytic protein perforin.

Spicer JA, Miller CK, O'Connor PD, Jose J, Huttunen KM, Jaiswal JK, Denny WA, Akhlaghi H, Browne KA, Trapani JA.

Bioorg Med Chem Lett. 2017 Feb 15;27(4):1050-1054. doi: 10.1016/j.bmcl.2016.12.057. Epub 2016 Dec 23.

25.

Is Metformin a Perfect Drug? Updates in Pharmacokinetics and Pharmacodynamics.

Markowicz-Piasecka M, Huttunen KM, Mateusiak L, Mikiciuk-Olasik E, Sikora J.

Curr Pharm Des. 2017;23(17):2532-2550. doi: 10.2174/1381612822666161201152941. Review.

PMID:
27908266
26.

Amino Acid Promoieties Alter Valproic Acid Pharmacokinetics and Enable Extended Brain Exposure.

Gynther M, Peura L, Vernerová M, Leppänen J, Kärkkäinen J, Lehtonen M, Rautio J, Huttunen KM.

Neurochem Res. 2016 Oct;41(10):2797-2809. Epub 2016 Jul 14.

PMID:
27412117
27.

Systemic and Brain Pharmacokinetics of Perforin Inhibitor Prodrugs.

Gynther M, Pickering DS, Spicer JA, Denny WA, Huttunen KM.

Mol Pharm. 2016 Jul 5;13(7):2484-91. doi: 10.1021/acs.molpharmaceut.6b00217. Epub 2016 Jun 13.

PMID:
27266990
28.

A Selective and Slowly Reversible Inhibitor of l-Type Amino Acid Transporter 1 (LAT1) Potentiates Antiproliferative Drug Efficacy in Cancer Cells.

Huttunen KM, Gynther M, Huttunen J, Puris E, Spicer JA, Denny WA.

J Med Chem. 2016 Jun 23;59(12):5740-51. doi: 10.1021/acs.jmedchem.6b00190. Epub 2016 Jun 8.

PMID:
27253989
29.

Diarylthiophenes as inhibitors of the pore-forming protein perforin.

Miller CK, Huttunen KM, Denny WA, Jaiswal JK, Ciccone A, Browne KA, Trapani JA, Spicer JA.

Bioorg Med Chem Lett. 2016 Jan 15;26(2):355-360. doi: 10.1016/j.bmcl.2015.12.003. Epub 2015 Dec 7.

30.

L-Type amino acid transporter 1 (lat1)-mediated targeted delivery of perforin inhibitors.

Huttunen KM, Huttunen J, Aufderhaar I, Gynther M, Denny WA, Spicer JA.

Int J Pharm. 2016 Feb 10;498(1-2):205-16. doi: 10.1016/j.ijpharm.2015.12.034. Epub 2015 Dec 15.

PMID:
26705152
31.

Amino acid ester prodrugs conjugated to the α-carboxylic acid group do not display affinity for the L-type amino acid transporter 1 (LAT1).

Rautio J, Kärkkäinen J, Huttunen KM, Gynther M.

Eur J Pharm Sci. 2015 Jan 23;66:36-40. doi: 10.1016/j.ejps.2014.09.025. Epub 2014 Oct 8.

PMID:
25305508
32.

Glutathione-S-transferase selective release of metformin from its sulfonamide prodrug.

Rautio J, Vernerová M, Aufderhaar I, Huttunen KM.

Bioorg Med Chem Lett. 2014 Nov 1;24(21):5034-6. doi: 10.1016/j.bmcl.2014.09.019. Epub 2014 Sep 16.

PMID:
25248681
33.

Quantitative insight into the design of compounds recognized by the L-type amino acid transporter 1 (LAT1).

Ylikangas H, Malmioja K, Peura L, Gynther M, Nwachukwu EO, Leppänen J, Laine K, Rautio J, Lahtela-Kakkonen M, Huttunen KM, Poso A.

ChemMedChem. 2014 Dec;9(12):2699-707. doi: 10.1002/cmdc.201402281. Epub 2014 Sep 9.

PMID:
25205473
34.

The preclinical pharmacokinetic disposition of a series of perforin-inhibitors as potential immunosuppressive agents.

Bull MR, Spicer JA, Huttunen KM, Denny WA, Ciccone A, Browne KA, Trapani JA, Helsby NA.

Eur J Drug Metab Pharmacokinet. 2015 Dec;40(4):417-25. doi: 10.1007/s13318-014-0220-y. Epub 2014 Aug 26.

PMID:
25155444
35.

Sustained release of metformin via red blood cell accumulated sulfenamide prodrug.

Peura L, Huttunen KM.

J Pharm Sci. 2014 Jul;103(7):2207-2210. doi: 10.1002/jps.24040. Epub 2014 Jun 2.

PMID:
24891115
36.

Exploration of a series of 5-arylidene-2-thioxoimidazolidin-4-ones as inhibitors of the cytolytic protein perforin.

Spicer JA, Lena G, Lyons DM, Huttunen KM, Miller CK, O'Connor PD, Bull M, Helsby N, Jamieson SM, Denny WA, Ciccone A, Browne KA, Lopez JA, Rudd-Schmidt J, Voskoboinik I, Trapani JA.

J Med Chem. 2013 Dec 12;56(23):9542-55. doi: 10.1021/jm401604x. Epub 2013 Nov 19.

37.

Convenient microwave-assisted synthesis of lipophilic sulfenamide prodrugs of metformin.

Huttunen KM, Leppänen J, Laine K, Vepsäläinen J, Rautio J.

Eur J Pharm Sci. 2013 Jul 16;49(4):624-8. doi: 10.1016/j.ejps.2013.05.023. Epub 2013 Jun 1.

PMID:
23732628
38.

Amino acids as promoieties in prodrug design and development.

Vig BS, Huttunen KM, Laine K, Rautio J.

Adv Drug Deliv Rev. 2013 Oct;65(10):1370-85. doi: 10.1016/j.addr.2012.10.001. Epub 2012 Oct 22. Review.

PMID:
23099277
39.

Design, synthesis, and evaluation of novel cyclic phosphates of 5-aminosalicylic acid as cytochrome p450-activated prodrugs.

Huttunen KM, Tani N, Juvonen RO, Raunio H, Rautio J.

Mol Pharm. 2013 Feb 4;10(2):532-7. doi: 10.1021/mp300330v. Epub 2012 Aug 31.

PMID:
22937971
40.

In vitro and in vivo evaluation of a sulfenamide prodrug of basic metformin.

Huttunen KM, Leppänen J, Vepsäläinen J, Sirviö J, Laine K, Rautio J.

J Pharm Sci. 2012 Aug;101(8):2854-60. doi: 10.1002/jps.23221. Epub 2012 May 30.

PMID:
22648910
41.

Inhibition of the pore-forming protein perforin by a series of aryl-substituted isobenzofuran-1(3H)-ones.

Spicer JA, Huttunen KM, Miller CK, Denny WA, Ciccone A, Browne KA, Trapani JA.

Bioorg Med Chem. 2012 Feb 1;20(3):1319-36. doi: 10.1016/j.bmc.2011.12.011. Epub 2011 Dec 22.

PMID:
22244072
42.

Prodrugs--from serendipity to rational design.

Huttunen KM, Raunio H, Rautio J.

Pharmacol Rev. 2011 Sep;63(3):750-71. doi: 10.1124/pr.110.003459. Epub 2011 Jul 7. Review.

PMID:
21737530
43.

Prodrugs - an efficient way to breach delivery and targeting barriers.

Huttunen KM, Rautio J.

Curr Top Med Chem. 2011;11(18):2265-87. Review.

PMID:
21671868
44.

Inhibition of the cellular function of perforin by 1-amino-2,4-dicyanopyrido[1,2-a]benzimidazoles.

Lyons DM, Huttunen KM, Browne KA, Ciccone A, Trapani JA, Denny WA, Spicer JA.

Bioorg Med Chem. 2011 Jul 1;19(13):4091-100. doi: 10.1016/j.bmc.2011.05.013. Epub 2011 May 18.

PMID:
21664824
45.

The first bioreversible prodrug of metformin with improved lipophilicity and enhanced intestinal absorption.

Huttunen KM, Mannila A, Laine K, Kemppainen E, Leppänen J, Vepsäläinen J, Järvinen T, Rautio J.

J Med Chem. 2009 Jul 23;52(14):4142-8. doi: 10.1021/jm900274q.

PMID:
19522462
46.

Determination of metformin and its prodrugs in human and rat blood by hydrophilic interaction liquid chromatography.

Huttunen KM, Rautio J, Leppänen J, Vepsäläinen J, Keski-Rahkonen P.

J Pharm Biomed Anal. 2009 Oct 15;50(3):469-74. doi: 10.1016/j.jpba.2009.04.033. Epub 2009 May 7.

PMID:
19481899
47.

Cytochrome P450-activated prodrugs: targeted drug delivery.

Huttunen KM, Mähönen N, Raunio H, Rautio J.

Curr Med Chem. 2008;15(23):2346-65. Review.

PMID:
18855665
48.

Novel cyclic phosphate prodrug approach for cytochrome P450-activated drugs containing an alcohol functionality.

Huttunen KM, Mähönen N, Leppänen J, Vepsäläinen J, Juvonen RO, Raunio H, Kumpulainen H, Järvinen T, Rautio J.

Pharm Res. 2007 Apr;24(4):679-87. Epub 2007 Feb 15.

PMID:
17372695
49.

Synthesis and CB1 receptor activities of dimethylheptyl derivatives of 2-arachidonoyl glycerol (2-AG) and 2-arachidonyl glyceryl ether (2-AGE).

Parkkari T, Salo OM, Huttunen KM, Savinainen JR, Laitinen JT, Poso A, Nevalainen T, Järvinen T.

Bioorg Med Chem. 2006 Apr 15;14(8):2850-8. Epub 2006 Jan 5.

PMID:
16403642

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