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PABA/NO as an anticancer lead: analogue synthesis, structure revision, solution chemistry, reactivity toward glutathione, and in vitro activity.
Saavedra JE, Srinivasan A, Buzard GS, Davies KM, Waterhouse DJ, Inami K, Wilde TC, Citro ML, Cuellar M, Deschamps JR, Parrish D, Shami PJ, Findlay VJ, Townsend DM, Tew KD, Singh S, Jia L, Ji X, Keefer LK. Saavedra JE, et al. J Med Chem. 2006 Feb 9;49(3):1157-64. doi: 10.1021/jm050700k. J Med Chem. 2006. PMID: 16451080 Free PMC article.
Injectable formulation of disodium 1-[2-(carboxylato)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate (PROLI/NO), an ultrafast nitric oxide donor prodrug.
Waterhouse DJ, Saavedra JE, Davies KM, Citro ML, Xu X, Powell DA, Grimes GJ, Potti GK, Keefer LK. Waterhouse DJ, et al. J Pharm Sci. 2006 Jan;95(1):108-15. doi: 10.1002/jps.20486. J Pharm Sci. 2006. PMID: 16315224
Hydrolytic reactivity trends among potential prodrugs of the O2-glycosylated diazeniumdiolate family. Targeting nitric oxide to macrophages for antileishmanial activity.
Valdez CA, Saavedra JE, Showalter BM, Davies KM, Wilde TC, Citro ML, Barchi JJ Jr, Deschamps JR, Parrish D, El-Gayar S, Schleicher U, Bogdan C, Keefer LK. Valdez CA, et al. J Med Chem. 2008 Jul 10;51(13):3961-70. doi: 10.1021/jm8000482. Epub 2008 Jun 6. J Med Chem. 2008. PMID: 18533711 Free PMC article.
The secondary amine/nitric oxide complex ion R(2)N[N(O)NO](-) as nucleophile and leaving group in S9N)Ar reactions.
Saavedra JE, Srinivasan A, Bonifant CL, Chu J, Shanklin AP, Flippen-Anderson JL, Rice WG, Turpin JA, Davies KM, Keefer LK. Saavedra JE, et al. J Org Chem. 2001 May 4;66(9):3090-8. doi: 10.1021/jo0016529. J Org Chem. 2001. PMID: 11325274
Conversion of a polysaccharide to nitric oxide-releasing form. Dual-mechanism anticoagulant activity of diazeniumdiolated heparin.
Saavedra JE, Mooradian DL, Mowery KA, Schoenfisch MH, Citro ML, Davies KM, Meyerhoff ME, Keefer LK. Saavedra JE, et al. Bioorg Med Chem Lett. 2000 Apr 17;10(8):751-3. doi: 10.1016/s0960-894x(00)00086-x. Bioorg Med Chem Lett. 2000. PMID: 10782678
Localizing antithrombotic and vasodilatory activity with a novel, ultrafast nitric oxide donor.
Saavedra JE, Southan GJ, Davies KM, Lundell A, Markou C, Hanson SR, Adrie C, Hurford WE, Zapol WM, Keefer LK. Saavedra JE, et al. J Med Chem. 1996 Oct 25;39(22):4361-5. doi: 10.1021/jm960616s. J Med Chem. 1996. PMID: 8893830
Chemistry of the diazeniumdiolates. 3. Photoreactivity.
Srinivasan A, Kebede N, Saavedra JE, Nikolaitchik AV, Brady DA, Yourd E, Davies KM, Keefer LK, Toscano JP. Srinivasan A, et al. J Am Chem Soc. 2001 Jun 13;123(23):5465-72. doi: 10.1021/ja002898y. J Am Chem Soc. 2001. PMID: 11389628
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