筑波大学WPI－IIIS長瀬研究室（創薬化学）では、オレキシン作動薬の開発やオピオイドの研究を行っています。

筑波大学　国際統合睡眠医科学研究機構（WPI-IIIS）長瀬研究室（創薬化学）

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研究業績

1. Yajima, S.; Saitoh, T.; Kawa, K.; Nakamura, K.; Nagase, H.; Einaga, Y.; Nishiyama, S.
   “Asymmetric induction in cyclohexadienones carrying α-D- glucopyranosyl moiety”
   Tetrahedron 2016, 51, 8428-8435. (web)
2. Ioka, S.; Saitoh, T.; Iwano, S.; Maki, S. A.; Imoto, M.; Nishiyama, S.
   “Development of luminescence-controllable a firefly luciferin analogue using selective enzymatic cyclization”
   Tetrahedron 2016, 72, 7505–7508. (web)
3. Kutsumura, N.; Numata, K.; Saito, T.
   “First total synthesis of haplacutine C”
   Tetrahedron Lett.2016, 57, 5581-5583. (web)
4. Kutsumura, N.; Koyama, Y.; Tateno, K.; Yamamoto, N.; Nagase, H.; Saito, T.
   “ZnCl2-Promoted Intramolecular Hetero Diels-Alder Reaction of o-Alkynylphenylcarbodiimides for Synthesis of Dihydrodibenzo[b,g][1,8]naphthyridines”
   Chem. Pharm. Bull. 2016, 64, 1364-1369. (web)
5. Ioka, S.; Saitoh, T.; Iwano, S.; Suzuki, K.; Maki, S. A.; Miyawaki, A.; Imoto, M.; Nishiyama, S.
   “Synthesis of Firefly Luciferin Analogues and Evaluation of the Luminescent Properties”
   Chem. Eur. J. 2016, 22, 9330-9337. (web)
6. Komatsu, T.; Katsuyama, S.; Nagase, H.; Mizoguchi, H.; Sakurada, C.; Tsuzuki, M.; Sakurada, S.; Sakurada, T.
   “Intrathecal morphine-3-glucuronide-induced nociceptive behavior via Delta-2 opioid receptors in the spinal cord”
   Pharmacol. Biochem. Behav. 2016, 140, 68-74. (web)
7. Ardianto, C.; Yonemochi, N.; Yamamoto, S.; Yang, L.; Takenoya, F.; Shioda, S.; Nagase, H.; Ikeda, H.; Kamei, J.
   “OPIOID SYSTEMS IN THE LATERAL HYPOTHALAMUS REGULATE FEEDING BEHAVIOR THROUGH OREXIN AND GABA NEURONS”
   Neuroscience 2016, 320, 183-193. (web)

1. Nagahara, T.; Saitoh, T.; Kutsumura, N.; Irukayama-Tomobe, Y.; Ogawa, Y.; Kuroda, D.; Gouda, H.; Kumagai, H.; Fujii, H.; Yanagisawa, M.; Nagase, H.
   “Design and Synthesis of Non-Peptide, Selective Orexin Receptor 2 Agonists”
   J. Med. Chem. 2015, 58, 7931-7937. (web)  – Featured Article –
   Most Read Article (Sep. 2015)
2. Nakajima, R.; Yamamoto, N.; Hirayama, S.; Iwai, T.; Saitoh, A.; Nagumo, Y.; Fujii, H.; Nagase, H.
   “Synthesis of new opioid derivatives with a propellane skeleton and their pharmacologies: Part 5, novel pentacyclic propellane derivatives with a 6-amide side chain”
   Bioorg. Med. Chem. 2015, 23, 6271-6279. (web)
3. Kutsumura, N.; Nakajima, R.; Koyama, Y.; Miyata, Y.; Saitoh, T.; Yamamoto, N.; Iwata, S.; Fujii, H.; Nagase, H.
   “Investigation of 7-benzylidenenaltrexone derivatives as a novel structural antitrichomonal lead compound”
   Bioorg. Med. Chem. Lett. 2015, 25, 4890-4892. (web) (Invited Paper)
4. Kobayashi, S.; Kudo, K.; Ito, A.; Honjo, T.; Yata, M.; Otani, T.; Kutsumura, N.; Saito, T.; Berrée, F.; Romain, E.; Tripoteau, F.; Carboni, B.
   “[3]-1-Azadendralenes as Versatile Building Blocks for the Stereoselective Synthesis of Polysubstituted Hexahydroquinazolin-2-ones and Hexahydrobenzothiazine-2-imines”
   Eur. J. Org. Chem. 2015, 4367-4373. (web)
5. Ikeda, H.; Ardianto, C.; Yonemochi, N.; Yang, L.; Ohashi, T.; Ikegami, M.; Nagase, H.; Kamei, J.
   “INHIBITION OF OPIOID SYSTEMS IN THE HYPOTHALAMUS AS WELL AS THE MESOLIMBIC AREA SUPPRESSES FEEDING BEHAVIOR OF MICE”
   Neuroscience 2015, 311, 9-21. (web)
6. Kutsumura, N.; Matsuo, K.; Saito, T.
   “Total synthesis of aplysinoplide B”
   Tetrahedron Lett. 2015, 56, 2602-2604. (web)
7. Kutsumura, N.; Inagaki, M.; Kiriseko, A.; Saito, T.
   “Novel One-pot Synthetic Method for Propargyl Alcohol Derivatives from Allyl Alcohol Derivatives”
   Synthesis 2015, 47, 1844-1850. (web)
8. Kutsumura, N.; Matsubara, Y.; Honjo, T.; Ohgiya, T.; Nishiyama, S.; Saito, T.
   “Total Synthesis of (―)-5,6-seco-Germacrane Lactone”
   Tetrahedron 2015, 71, 2382-2386. (web)
9. Otani, T.; Jiang, X.; Cho, K.; Araki, R.; Kutsumura, N.; Saito, T.
   “Lewis Acid-Catalyzed or Base-Promoted Regioselective Cycloisomerization of N-Imidoyl-o-alkynylanilines for Synthesis of N-Imidoyl-(1H)-indoles and 4-Alkylidene-3,4-dihydroquinazolines”
   Adv. Synth. Catal. 2015, 357, 1483-1492. (web)
10. Suzuki, M.; Chiwaki, F.; Sawada, Y.; Ashikawa, M.; Aoyagi, K.; Fujita, T.; Yanagihara, K.; Komatsu, M.; Narita, M.; Suzuki, T.; Nagase, H.; Kushima, R.; Sakamoto, H.; Fukagawa, T.; Katai, H.; Nakagama, H.; Yoshida, T.; Uezono, Y.; Sakaki, H.
    “Peripheral Opioid Antagonist Enhances the Effect of Anti-Tumor Drug by Blocking a Cell Growth-Suppressive Pathway In Vivo“
    PLoS One 2015, 10, e0123407. (web)
11. Nemoto, T.; Iihara, Y.; Hirayama, S.; Iwai, T.; Higashi, E.; Fujii, H.; Nagase, H.
    “Naltrindole derivatives with fluorinated ethyl substituents on the 17-nitrogen as δ opioid receptor inverse agonists”
    Bioorg. Med. Chem. Lett. 2015, 25, 2927-2930. (web)
12. Konoura, K.; Fujii, H.; Imaide, S.; Gouda, H.; Hirayama, S.; Hirono, S.; Nagase, H.
    “Transformation of naltrexone into mesembrane and investigation of the binding properties of its intermediate derivatives to opioid receptors”
    Bioorg. Med. Chem.  2015, 23, 439-448. (web)

1. Watanabe, Y.; Kitazawa, S.; Fujii, H.; Nemoto, T.; Hirayama, S.; Iwai, T.; Gouda, H.; Hirono, S.; Nagase, H.
   “Design, synthesis, and structure-activity relationship of novel opioid κ receptor selective agonists: α-Iminoamide derivatives with an azabicyclo[2.2.2]octene skeleton”
   Bioorg. Med. Chem. Lett. 2014, 24, 4980-4983. (web)
2. Nozaki, C.; Nagase, H.; Nemoto, T.; Matifas, A.; Kieffer, B. L.; Gaveriaux-Ruff, C.
   “In vivo properties of KNT-127, a novel delta opioid agonist: receptor internalisation, antihyperalgesia and antidepressant effects in mice”
   Br. J. Pharmacol. 2014, 171, 5376-5386. (web)
3. Hirayama, S.; Wada, N.; Kuroda, N.; Iwai, T.; Yamaotsu, N.; Hirono, S.; Fujii, H.; Nagase, H.
   “Synthesis of a novel universal opioid receptor agonist with the 1,3,5-trioxazatriquinane skeleton and its pharmacologies”
   Bioorg. Med. Chem. Lett. 2014, 24, 4895-4898. (web)
4. Hirayama, S.; Wada, N.; Nemoto, T.; Iwai, T.; Fujii, H.; Nagase, H.
   “Synthesis and Pharmacology of a Novel κ Opioid Receptor (KOR) Agonist with a 1,3,5-Trioxazatriquinane Skeleton”
   ACS Med. Chem. Lett. 2014, 5, 868-872. (web)
5. Kutsumura, N.; Toguchi, S.; Iijima, M.; Tanaka, O.; Iwakura, I.; Saito, T.
   “DBU-promoted regioselective HBr-elimination of vicinal dibromides: effects of the adjacent oxygen and/or other heterofunctional groups”
   Tetrahedron 2014, 70, 8004-8009. (web)
6. Saito, T.; Sonoki, Y.; Otani, T.; Kutsumura, N.
   “Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives”
   Org. Biomol. Chem. 2014, 12, 8398-8407. (web)   —Front Cover—
7. Kubo, H.; Matsui, K.; Saitoh, T.; Nishiyama, S.
   “Synthesis and assignment of the absolute stereochemistry of (+)-hemifistularin 3”
   Tetrahedron 2014, 70, 6392-6397. (web)
8. Kashiwagi, T; Fuchigami, T; Saitoh, T; Nishiyama, S; Atobe, M.
   “Sequential paired electrosynthesis of a diary ether derivative using an electrochemical micro reactor”
   Chem. Lett. 2014, 43, 799-801. (web)
9. Nagase, H.; Nakajima, R.; Yamamoto, N.; Hirayama, S.; Iwai, T.; Nemoto, T.; Gouda, H.; Hirono, S.; Fujii, H.
   “Design and synthesis of quinolinopropellane derivatives with selective δ opioid receptor agonism”
   Bioorg. Med. Chem. Lett. 2014, 24, 2851-2854. (web)
10. Kardon, A. P.; Polgar, E.; Hachisuka, J.; Snyder, L. M.; Cameron, D., Savage, S.; Cai, X.; Karnup, S.; Fan, C. R.; Hemenway, G. M.; Bernard, C. S.; Schwartz, E. S.; Nagase, H.; Schwarzer, C.; Watanabe, M.; Furuta, T.; Kaneko, T.; Koerber, H. R.; Todd, A. J.; Ross, S. E.
    “Dynorphin Acts as a Neuromodulator to Inhibit Itch in the Dorsal Horn of the Spinal Cord”
    Neuron 2014, 82, 573-586. (web)
11. Sugiyama, A.; Nagase, H.; Oka, J.; Yamada, M.; Saitoh, A.
    “DOR2-selective but not DOR1-selective antagonist abolishes anxiolytic-like effects of the delta opioid receptor agonist KNT-127”
    Neuropharmacology 2014, 79, 314-320. (web)
12. Fujii, H.; Hayashida, K.; Saitoh, A.; Yokoyama, A.; Hirayama, S.; Iwai, T.; Nakata, E.; Nemoto, T.; Sudo, Y.; Uezono, Y.; Yamada, M.; Nagase, H.
    “Novel Delta Opioid Receptor Agonists with Oxazatricyclodecane Structure”
    ACS Med. Chem. Lett. 2014, 5, 368-372. (web)
13. Kawa, K.; Saitoh, T.; Kaji, E.; Nishiyama, S.
    “Glycosylation of a Newly Functionalized Orthoester Derivative”
    Molecules 2014, 19, 2602-2611. (web)
14. Ishikawa, K.; Tomatsu, M.; Nagase, H.; Fujii, H.
    “Zinc-acetic acid promoted reductive carbon-nitrogen bond cleavage reaction of α-aminoketones”
    Heterocycles 2014, 88, 1051-1063. (web) (Invited Paper)
15. Kawabata, Y.; Naito, Y.; Saitoh, T.; Kawa, K.; Fuchigami, T.; Nishiyama, S.
    “Synthesis of (+)-O-Methylthalibrine Employing a Stereocontrolled Bischler-Napieralski Reaction and an Electrochemically Generated Diaryl Ether”
    Eur. J. Org. Chem. 2014, 99-104. (web)

1. Yamamizu, K.; Furuta, S.; Hamada, Y.; Yamashita, A.; Kuzumaki, N.; Narita, M.; Doi, K.; Katayama, S.; Nagase, H.; Yamashita, J. K.; Narita, M.
   “κ Opioids inhibit tumor angiogenesis by suppressing VEGF signaling”
   Scientific Reports 2013, 3: 3213. (web)
2. Nemoto, T.; Ida, Y.; Iihara, Y.; Nakajima, R.; Hirayama, S.; Iwai, T.; Fujii, H.; Nagase, H.
   “The most effective influence of 17-(3-ethoxypropyl) substituent on the binding affinity and the agonistic activity in KNT-127 derivatives, δ opioid receptor agonists”
   Bioorg. Med. Chem. 2013, 21, 7628-7647. (web)
3. Kawa, K.; Saitoh, T.; Kaji, E.; Nishiyama, S.
   “Development of Glycosylation Using the Glucopyranose 1,2-Orthobenzoate under Electrochemical Conditions”
   Org. Lett. 2013, 15, 5484-5487. (web)
   
4. Kuroda, M.; Funasaki, S.; Saitoh, T.; Sasazawa, Y.; Nishiyama, S.; Umezawa, K.; Shimizu, S.
   “Determination of topological structure of ARL6ip1 in cells: Identification of the essential binding region of ARL6ip1 for conophylline”
   FEBS Letters 2013, 587, 3656-3660. (web)
5. Watanabe, Y.; Kitazawa, S.; Nemoto, T.; Hirayama, S.; Iwai, T.; Fujii, H.; Nagase, H.
   “Design and synthesis of novel opioid ligands with an azabicyclo[2.2.2]octane skeleton having a 7-amide chain and their pharmacologies”
   Bioorg. Med. Chem. 2013, 21, 3032-3050. (web)
   
6. Kajiyama, D.; Saitoh, T.; Yamaguchi, S.; Nishiyama, S.
   “Application of the Hypervalent Iodine Oxidant Electrochemically Generated to Natural Products Synthesis”
   Electrochemistry 2013, 81, 319-324. (web)
7. Kutsumura, N.; Matsubara, Y.; Niwa, K.; Ito, A.; Saito, T.
   “Novel One-pot Method for Regioselective Bromination and Sequential Carbon−Carbon Bond-forming Reactions of Allylic Alcohol Derivatives”
   Eur. J. Org. Chem. 2013, 3337-3346. (web)
8. Ise, Y.; Mori, T.; Katayama, S.; Nagase, H.; Suzuki, T.
   “Rewarding effects of ethanol combined with low doses of morphine through dopamine D1 receptor”
   J. Nippon Medical School 2013, 80, 34-41. (web)
9. Otani, T.; Saito, T.; Sakamoto, R.; Osada, H.; Hirahara, A.; Furukawa, N.; Kutsumura, N.; Matsuo, T.; Tamao, K.
   “Intramolecular [2+2+2] cycloaddition of bis(propargylphenyl)carbodiimides: synthesis of L-shaped π-extended compounds with pyrrolo[1,2-a][1,8]naphthyridine corner units”
   Chem. Commun. 2013, 49, 6206-6208. (web)
10. Saitoh, A.; Sugiyama, A.; Yamada, M.; Inagaki, M.; Oka, J.; Nagase, H.; Yamada, M.
    “The novel δ opioid receptor agonist KNT-127 produces distinct anxiolytic-like effects in rats without producing the adverse effects associated with benzodiazepines”
    Neuropharmacology 2013, 67, 485-493. (web)
11. Nemoto, T.; Yamamoto, N.; Wada, N.; Harada, Y.; Tomatsu, M.; Ishihara, M.; Hirayama, S.; Iwai, T.; Fujii, H.; Nagase, H.
    “The effect of 17-N substituents on the activity of the opioid kappa receptor in nalfurafine derivatives”
    Bioorg. Med. Chem. Lett. 2013, 23, 268-272. (web)

1. Hara, A.; Morimoto, R.; Iwasaki, Y.; Saitoh, T.; Ishikawa, Y.; Nishiyama, S.
   Total Syntheses of Amphidinolides B, G, and H
   Angew. Chem. Int. Ed. 2012, 51, 9877-9880.
2. Fujii, H.; Nakajima, R.; Akiyama, J.; Yamamoto, N.; Hirayama, S.; Nemoto, T.; Gouda, H.; Hirono, S.; Nagase, H.
   Synthesis of new opioid derivatives with a propellane skeleton and their pharmacologies: Part 3, novel propellane derivatives with pentacyclic skeletons
   Bioorg. Med. Chem. Lett. 2012, 21, 7697-7701.
3. Nakano, H.; Kutsumura, N.; Saito, T.
   Functionalized Carbodiimide Mediated Synthesis of 2,3-Disubstituted Quinazolin-4(3H)-ones via the Tandem Strategy of C-Nucleophilic Addition and Intramolecular NH-Substitution Cyclization
   Synthesis 2012, 44, 3179-3184.
4. Kajiyama, D.; Saitoh, T.; Yamaguchi, S.; Nishiyama, S.
   Oxidative Cyclization of Tryptamine by means of Hypervalent Iodobenzene toward Pyrroloindole Alkaloid Synthesis
   Synthesis 2012, 44, 1667-1671.
5. Nagase, H.; Akiyama, J.; Nakajima, R.; Hirayama, S.; Nemoto, T.; Gouda, H.; Hirono, S.; Fujii, H.
   Synthesis of new opioid derivatives with a propellane skeleton and their pharmacology. Part 2: Propellane derivatives with an amide side chain
   Bioorg. Med. Chem. Lett. 2012, 22, 2775-2779.
6. Kutsumura, N.; Kiriseko, A.; Saito, T.
   Total Synthesis of (+)-Heteroplexisolide E
   Heterocycles 2012, 86, 1367-1378.
7. Fujii, H.; Yamada, T.; Hayashida, K.; Kuwada, M.; Hamasaki, A.; Nobuhara, K.; Ozeki, S.; Nagase, H.
   Application of SO3H Silica gel to Deprotection of Silyl Ethers
   Heterocycles 2012, 85, 2685-2691.
8. Sumi, T.; Saitoh, T.; Natsui, K.; Yamamoto, T.; Atobe, M.; Einaga, Y.; Nishiyama, S.
   Anodic oxidation on a boron-doped diamond electrode mediated by methoxy radicals
   Angew. Chem. Int. Ed. 2012, 51, 5443-5446.
9. Ohyoshi, T.; Funakubo, S.; Miyazawa, Y.; Niida, K.; Hayakawa, I.; Kigoshi, H.
   Total Synthesis of (–)-13-Oxyingenol and its Natural Derivative
   Angew. Chem. Int. Ed. 2012, 51, 4972-4975.
10. Ida, Y.; Matsubara, A.; Nemoto, T.; Saito, M.; Hirayama, S.; Fujii, H.; Nagase, H.
    Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands
    Bioorg. Med. Chem. 2012, 20, 5810-5831.
11. Kutsumura, N.; Kiriseko, A.; Saito, T.
    First total synthesis of (+)-heteroplexisolide E
    Tetrahedron Lett. 2012, 53, 3274-3276.
12. Fujii, H.; Imaide, S.; Hirayama, S.; Nemoto, T.; Gouda, H.; Hirono, S.; Nagase, H.
    Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 3: Synthesis of decahydro(iminoethano)phenanthorene derivatives with an oxygen functionality at the 3-position and their pharmacologies
    Bioorg. Med. Chem. Lett. 2012, 22, 7711-7714.
13. Wada, N,; Fujii, H.; Koyano, K.; Hirayama, S.; Iwai, T.; Nemoto, T.; Nagase, H.
    Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. 3: Synthesis of novel triplet drugs with the bis(epoxymethano) or bis(dimethylepoxymethano) structure (double-capped triplet)
    Bioorg. Med. Chem. Lett. 2012, 22, 7551-7554.
14. Miyata, Y.; Fujii, H.; Uenohara, Y.; Kobayashi, S.; Takeuchi, T.; Nagase, H.
    Investigation of 7-benzylidenenaltrexone derivatives as reverser of resitance for chliroquine-resistant Plasmodium chabaudi
    Bioorg. Med. Chem. Lett. 2012, 22, 5174-5176.
15. Honda, T.; Arai, H.; Yamamoto, N.; Takahashi, K.
    Formal synthesis of sceletium alkaloids, (±)-mesembrine and (±)-mesembranol
    Heterocycles 2012, 84, 327-331.
16. Saito, T.; Nakano, H.; Terada, H.; Kutsumura, N.; Otani, T.
    Expedient Synthesis of 3,4-Dihydro-quinazolines via Tandem Addition―Conjugate Addition Cyclization of Carbodiimides Bearing a Michael Acceptor
    Heterocycles 2012, 84, 893-911.
17. Nagase, H.; Imaide, S.; Hirayama, S.; Nemoto, T.; Fujii, H.
    Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 2: Synthesis of decahydroiminoethano)phenanthoren derivatives and their pharmacologies
    Bioorg. Med. Chem. Lett. 2012, 22, 5071-5074.
18. Al-Mekhlafi, N. A.; Shaari, K.; Abas, F.; Kneer, R.; Jeyaraj, E. J.; Stanslas, J.; Yamamoto, N.; Honda, T.; Lajis, N. H.
    Alkenylresorcinols and cytotoxic activity of the constituents isolated from Labisia pumila
    Phytochemistry 2012, 80, 42-49.
19. Nagase, H.; Imaide, S.; Yamada, T.; Hirayama, S.; Nemoto, T.; Yamaotsu, N.; Hirono, S.; Fujii, H.
    Essential Structure of Opioid κ Receptor Agonist Nalfurafine for Binding to κ Receptor 1: Synthesis of Decahydroisoquinoline Derivatives and Their Pharmacologies
    Chem. Pharm. Bull. 2012, 60, 945-948.
20. Watanabe, Y.; Kitazawa, S.; Fujii, H.; Nemoto, T.; Hirayama, S.; Nagase, H.
    Design and synthesis of novel opioid ligands with anazabicyclo[2.2.2]octane skeleton and their pharmacologies
    Bioorg. Med. Chem. 2012, 22, 2689-2692.
21. Ida, Y.; Nemoto, T.; Hirayama, S.; Fujii, H.; Osa, Y.; Imai, M.; Nakamura, T.; Kanemasa, T.; Kato, T.; Nagase, H.
    Synthesis of quinolinomorphinan-4-ol derivatives as delta opioid receptor agonist
    Bioorg. Med. Chem. 2012, 20, 949-961.
22. Torigoe, K.; Nakahara, K.; Rahmadi, M.; Yoshizawa, K.; Horiuchi, H.; Hirayama, S.; Imai, S.; Kuzumaki, N.; Ito, T.; Yamashita, T.; Shakunaga, K.; Yamasaki, M.; Nagase, H.; Matoba, M.; Suzuki, T.; Narita, M.
    Usefulness of Olanzapine as an Adjunct to Opioid Treatment and for the Treatment of Neuropathic pain
    Anesthesiology 2012, 116, 159-169.
23. Tanahashi, S.; Ueda, Y.; Yamamura, S.; Nagase, H.; Okada, M.
    Novel δ 1-receptor agonist KNT-127 increases releases of dopamine and L-Glutamate in striatum, nucleus accumbens and median prefrontal cortex
    Neurpharmacology 2012, 62, 2057-2067.
24. Kuzumaki, N,; Suzuki, A.; Narita, M.; Hosoya, T.; Nagasawa, A.; Imai, S.; Yamamizu, K.; Morita, H.; Nagase, H.; Okada, Y.; Okano, H. J.; Yamashita, J. K.; Okano, H.; Suzuki, T.; Narita, M.
    Effect of κ-opioid, receptor agonist on the growth of non-small-cell lung cancer (NSCLC) cells
    British J. Cancer 2012, 106, 1148-1152.