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Synthesis of 2,11-bis(methylidene)spermine, a new inhibitor of spermine oxidase

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Abstract

Earlier unknown 1,12-diamino-2,11-bis(methylidene)-4,9-diazadodecane, which may be considered as an enzyme-activated inhibitor of spermine oxidase, was synthesized in 6 steps starting from 2-chloromethyl-3-chloropropene-1 in a high yield. Application of newly synthesized spermine analogue for the inhibition of spermine oxidase was discussed.

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Abbreviations

APAO:

acetylpolyamine oxidase

2,11-bis(methylidene)-Spm:

1,12-diamino-2,11-bis(methylidene)-4,9-diazadodecane

LSD1:

lysine specific demethylase

Ms:

methanesulfonyl

Ns:

o-nitrophenylsulfonyl

Put:

putrescine (1,4-diaminobutane)

SMO:

spermine oxidase

Spd:

spermidine (1,8diamino-4-azaoctane)

α-MeSpd:

(1,8-diamino-5-azanonane)

β-MeSpd:

(1,8-diamino-2-methyl-4-azaoctane)

Spm:

spermine (1,12-diamino-4,9-diazadodecane)

α,α'Me2Spm:

2,13-diamino-5,10-diazatetradecane

β,β'-Me2Spm:

1,12-diamino-2,11-dimethyl-4,9-diazadodecane

SSAT:

spermidine/spermine N 1-acetyltransferase

Pht:

phtaloyl

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Author notes

  1. N. A. Grigorenko

    Present address: BASF Schweiz AG, Klybeckstrasse 141, Basel, CH4057, Switzerland

Authors and Affiliations

  1. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 119991, Russia

    N. A. Grigorenko, M. A. Khomutov, A. R. Simonian, S. N. Kochetkov & A. R. Khomutov

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  1. N. A. Grigorenko
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  2. M. A. Khomutov
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  3. A. R. Simonian
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  4. S. N. Kochetkov
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Correspondence to A. R. Khomutov.

Additional information

Original Russian Text © N.A. Grigorenko, M.A. Khomutov, A.R. Simonian, S.N. Kochetkov, A.R. Khomutov, 2016, published in Bioorganicheskaya Khimiya, 2016, Vol. 42, No. 4, pp. 469–474.

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Grigorenko, N.A., Khomutov, M.A., Simonian, A.R. et al. Synthesis of 2,11-bis(methylidene)spermine, a new inhibitor of spermine oxidase. Russ J Bioorg Chem 42, 423–427 (2016). https://doi.org/10.1134/S1068162016030080

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  • DOI: https://doi.org/10.1134/S1068162016030080

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