Second basic pKa: An overlooked parameter in predicting phospholipidosis-inducing potential of diamines.

In this paper, we present the phospholipidosis-inducing potential (PLIP) of forty fragment-sized diamines derived from N-benzyl-4-(methylamino)piperidine and discuss the relationship between their PLIP and the physicochemical properties. Our results demonstrate that the previously reported methods are not suitable for predicting the PLIP of fragment-sized diamines; the second basic pKa can distinguish PLIP-positive diamines from PLIP-negative diamines more accurately than ClogP or most basic pKa. To the best of our knowledge, this is the first report describing the relationship between PLIP and second basic pKa. Copyright © 2019 Elsevier Ltd. All rights reserved.

Citation

Hiroki Sakai, Hidekazu Inoue, Kenji Murata, Tetsuya Toba, Naohiro Takemoto, Takahiro Matsumoto, Takeo Kawabata. Second basic pKa: An overlooked parameter in predicting phospholipidosis-inducing potential of diamines. Bioorganic & medicinal chemistry letters. 2020 May 01;30(9):126933

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PMID: 32044185

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