15 keto 15 f 2t isop

Commercially available IsoPs (2,3-dinor-15-F 2t -IsoP, 15-keto-15-E 2t -IsoP, 15-keto-15-F 2t -IsoP, 15-epi-15-F 2t -IsoP, 15-E 2t -IsoP, 15-F 2t -IsoP), prostaglandins (PGs) (PGE 2 , PGF 2a , 2,3-dinor-11b-PGF 2a , 11b-PGF2a, 6-keto-PGF 1a ), dihomo-PG (1a,1b-dihomo-PGF 2a ) were purchased from Cayman Chemical Company (Ann Arbor, MI, USA), with purities !95% as well as deuterated internal standards (IS, PGF 2a -d 4 and 15-F 2t -IsoP-d 4 ) with purities !98% and incorporation !99% deuterated form (d 1 -d 4 ); <1% d 0 .
Other analytical standards employed were F 2 -IsoPs (5-F 2t -IsoP, 5-epi-5-F 2t -IsoP, 15-epi-2,3-dinor-15-F 2t -IsoP), F 4 -NeuroPs (4-F 4t -NeuroP, 4-epi-4-F 4t -NeuroP, 10-epi-10-F 4t -NeuroP, 10-F 4t -NeuroP, 14(RS)-14-F 4t -NeuroP), Potassium hydroxide (KOH) was from Sigma Aldrich Química SA (Madrid, Spain). LC-MS grade solvents (methanol CH 3 OH, ethanol, heptane and acetonitrile CH 3 CN) were purchased from J.T. Baker (Phillipsburg, NJ, USA). Formic acid (HCOOH, 98%) and ethyl acetate (analytical grade) were from Panreac (Barcelona, Spain). Ultrapure H 2 O was generated on a milliQ system from Merck Millipore (Darmstadt, Germany).

Isoprostanes' standards of 15(R)-15-F 2t -IsoP, 2,3-dinor-15-epi-15-F 2t -IsoP, 5-F 2t -IsoP, 15-keto-15-E 2t -IsoP, 15-keto-15-F 2t -IsoP, 15-E 2t -IsoP, 15-F 2t -IsoP, the prostaglandins PGE 2 and PGF 2α , as well as the deuterated internal standard (IS) PGF 2α -d 4 were purchased from Cayman Chemical Company (Ann Arbor, Michigan, USA). The standards of 7(RS)-ST-Δ 8 -11-dihomo-IsoF, 10-epi-10-F 4t -NeuroP, d 4 -10epi-10-F 4t -NeuroP, 4(RS)-F 4t -NeuroP, 17-epi-17-F 2t -dihomo-IsoP, 17-F 2t -dihomo-IsoP, 17(RS)-10-epi-SC-Δ 15 -11-dihomo-IsoF, Ent-7(RS)-7-F 2t -dihomo-IsoP, and 14(RS)-14-F 4t -NeuroP were synthetized by Durand's team at the Institute des Biomolécules Max Mousseron (IBMM) (Montpellier, France) (Fig. S1 in Electronic Supplementary material) [34] . Methanol (LC-MS grade) and n-heptane (analytical grade) were obtained from J.T. Baker (Avantor Performance Materials B.V., The Netherlands). Chlorhydric acid and acetic acid glacial (99.5%) were purchased from Panreac (Castellar del Vallés, Barcelona, Spain). Ammonium acetate, sodium acetate, sodium hydroxide, and β-glucuronidase (type H2, from Helix pomatia) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Creatinine assay (MicroVue creatinine EIA) from Quidel Corporation (San Diego, CA, USA).