A versatile strategy for the design and synthesis of novel ADP conjugates and their evaluation as potential poly(ADP-ribose) polymerase 1 inhibitors.
A versatile strategy for the synthesis of [Formula: see text] mimetics was developed, involving an efficient pyrophosphate linkage formation in key conjugates containing a functional amino group which acts as useful reactive anchor for further derivatization. These [Formula: see text] mimetics consist of ADP conjugated through a diphosphate chain to an extended aliphatic linker bearing an aromatic acid residue. A number of conjugates containing aromatic carboxylic acids were found to inhibit poly(ADP-ribose) synthesis catalyzed by poly(ADP-ribose) polymerase-1 (PARP-1). A new class of potential PARP-1 inhibitors mimicking [Formula: see text], a substrate in the PARP-1 catalyzed reaction, was proposed.
Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent'ev Ave., 8, Novosibirsk, 630090, Russia.
Yuliya V
YV
Sherstyuk
Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent'ev Ave., 8, Novosibirsk, 630090, Russia.
Alexandra L
AL
Zakharenko
Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent'ev Ave., 8, Novosibirsk, 630090, Russia.
Mikhail M
MM
Kutuzov
Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent'ev Ave., 8, Novosibirsk, 630090, Russia.|Novosibirsk State University, Pirogova St., 2, Novosibirsk, 630090, Russia.
Polina V
PV
Chalova
Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent'ev Ave., 8, Novosibirsk, 630090, Russia.|Novosibirsk State University, Pirogova St., 2, Novosibirsk, 630090, Russia.
Maria V
MV
Sukhanova
Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent'ev Ave., 8, Novosibirsk, 630090, Russia.|Novosibirsk State University, Pirogova St., 2, Novosibirsk, 630090, Russia.
Olga I
OI
Lavrik
Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent'ev Ave., 8, Novosibirsk, 630090, Russia.
Vladimir N
VN
Silnikov
Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent'ev Ave., 8, Novosibirsk, 630090, Russia. abramova@niboch.nsc.ru.
Tatyana V
http://orcid.org/0000-0003-1187-5542
TV
Abramova
D000244:Adenosine Diphosphate / Q000737:chemistry*; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009243:NAD / Q000737:chemistry; D000071137:Poly (ADP-Ribose) Polymerase-1 / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D009243:NAD; D000244:Adenosine Diphosphate; D000071137:Poly (ADP-Ribose) Polymerase-1
PARP inhibitors; PARP-1; Pyrophosphate synthesis; analogues
J Med Chem. 2010 Jun 24;53(12):4561-84
20364863
Clin Cancer Res. 2003 Jul;9(7):2711-8
12855651
Curr Med Chem. 2003 Feb;10(4):321-40
12570705
J Org Chem. 2007 Sep 14;72(19):7222-8
17715974
Biochem J. 2005 Feb 1;385(Pt 3):667-75
15458385
Chembiochem. 2015 Dec;16(18):2562-70
26420042
Nat Struct Mol Biol. 2009 Sep;16(9):923-9
19680243
Nucleosides Nucleotides Nucleic Acids. 2016;35(1):32-42
26810366
Org Biomol Chem. 2015 Jun 14;13(22):6380-98
25974621
J Med Chem. 2013 Jun 13;56(11):4320-42
23701517
Nucleic Acids Res. 1996 Nov 15;24(22):4387-94
8948628
Expert Opin Ther Pat. 2013 Apr;23(4):503-14
23379721
Cancer Res. 2012 Jun 1;72(11):2822-32
22440753
Biochemistry (Mosc). 2004 May;69(5):558-68
15193131
Bioorg Med Chem. 2011 Mar 1;19(5):1594-605
21324702
Biochem J. 1980 Mar 1;185(3):775-7
6248035
Trends Biochem Sci. 2007 Jan;32(1):12-9
17161604
Nucleosides Nucleotides Nucleic Acids. 2005;24(9):1333-43
16252670
Bioorg Med Chem. 2007 Oct 15;15(20):6549-55
17686631
Nucleosides Nucleotides Nucleic Acids. 2015;34(4):258-76
25774719
J Med Chem. 2012 Feb 9;55(3):1127-36
22260203
Bioorg Med Chem. 2008 Oct 15;16(20):9127-32
18823785
Mol Cell Biol. 1998 Jun;18(6):3563-71
9584196
J Med Chem. 2013 Aug 8;56(15):6175-89
23889609
Mol Neurobiol. 2012 Aug;46(1):55-63
22476980
J Am Chem Soc. 2011 Dec 28;133(51):20857-62
22098020
J Am Chem Soc. 2010 Jul 14;132(27):9363-72
20560583
Nat Rev Clin Oncol. 2013 Dec;10(12):688-96
24129347
J Med Chem. 2007 Nov 15;50(23):5743-51
17958343
Biochem Biophys Res Commun. 1963 Apr 2;11:39-43
14019961
Biochemistry. 1998 Mar 17;37(11):3893-900
9521710
J Biochem. 1975 Jan 1;77(1?):2p
166073
Molecules. 2014 Sep 29;19(10):15754-67
25268725
Nat Biotechnol. 2012 Feb 19;30(3):283-8
22343925
Org Lett. 2014 Jun 6;16(11):2842-5
24820262
Biochim Biophys Acta. 1971 Apr 29;238(1):82-5
4325158
J Biol Chem. 2015 Sep 4;290(36):21811-20
26170451
FEBS J. 2013 Aug;280(15):3563-75
23601167
Biochemistry. 2009 Apr 7;48(13):2878-90
19220062
Bioorg Med Chem Lett. 2007 Mar 15;17(6):1512-5
17258457
Bioorg Med Chem Lett. 2016 Jan 15;26(2):328-333
26706174
Bioorg Med Chem Lett. 2014 Jan 1;24(1):332-6
24269162
Proc Natl Acad Sci U S A. 2009 Aug 18;106(33):13770-4
19666485
Biochem J. 1999 Sep 1;342 ( Pt 2):249-68
10455009
Science. 2009 Sep 4;325(5945):1240-3
19661379
Biochem Biophys Res Commun. 1998 Apr 7;245(1):1-10
9535773
Bioorg Chem. 2007 Jun;35(3):258-75
17303213
Pharmacol Rev. 2002 Sep;54(3):375-429
12223530
J Med Chem. 2011 May 26;54(10):3492-9
21528845
Nucleic Acids Res. 2008 Aug;36(13):4454-64
18603595
Curr Med Chem. 2008;15(7):650-70
18336280
Bioorg Med Chem Lett. 2004 Jan 5;14(1):81-5
14684303
Beilstein J Org Chem. 2013 Dec 18;9:2898-909
24367455
Nucleic Acids Res. 2000 Aug 15;28(16):3125-33
10931928