共 73 条
Search for non-nucleoside inhibitors of HIV-1 reverse transcriptase using chemical similarity, molecular docking, and MM-GB/SA scoring
被引:72
作者:

Barreiro, Gabriela
论文数: 0 引用数: 0
h-index: 0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA Yale Univ, Dept Chem, New Haven, CT 06520 USA

Guimaraes, Cristiano R. W.
论文数: 0 引用数: 0
h-index: 0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA Yale Univ, Dept Chem, New Haven, CT 06520 USA

Tubert-Brohman, Ivan
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h-index: 0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA Yale Univ, Dept Chem, New Haven, CT 06520 USA

Lyons, Theresa M.
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h-index: 0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA Yale Univ, Dept Chem, New Haven, CT 06520 USA

Tirado-Rives, Julian
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h-index: 0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA Yale Univ, Dept Chem, New Haven, CT 06520 USA

Jorgensen, William L.
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h-index: 0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA Yale Univ, Dept Chem, New Haven, CT 06520 USA
机构:
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词:
D O I:
10.1021/ci700271z
中图分类号:
R914 [药物化学];
学科分类号:
100701 ;
摘要:
A virtual screening protocol has been applied to seek non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs) and its K103N mutant. First, a chemical similarity search on the Maybridge library was performed using known NNRTIs as reference structures. The top-ranked molecules obtained from this procedure plus 26 known NNRTIs were then docked into the binding sites of the wild-type reverse transcriptase (HIV-RT) and its K103N variant (K103N-RT) using Glide 3.5. The top-ranked 100 compounds from the docking for both proteins were post-scored with a procedure using molecular mechanics and continuum solvation (MM-GB/SA). The validity of the virtual screening protocol was supported by (i) testing of the MM-GB/SA procedure, (ii) agreement between predicted and crystallographic binding poses, (iii) recovery of known potent NNRTIs at the top of both rankings, and (iv) identification of top-scoring library compounds that are close in structure to recently reported NNRTI HTS hits. However, purchase and assaying of selected top-scoring compounds from the library failed to yield active anti-HIV agents. Nevertheless, the highest-ranked database compound, S 10087, was pursued as containing a potentially viable core. Subsequent synthesis and assaying of S10087 analogues proposed by further computational analysis yielded anti-HIV agents with EC50 values as low as 310 nM. Thus, with the aid of computational tools, it was possible to evolve a false positive into a true active.
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页码:2416 / 2428
页数:13
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Novellino, E
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Maga, G
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Spadari, S
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Bergamini, A
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Ventura, L
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Bongiovanni, B
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Capozzi, M
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Bolacchi, F
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Marini, S
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Coletta, M
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h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Guiso, G
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy

Caccia, S
论文数: 0 引用数: 0
h-index: 0
机构: Univ Salerno, Fac Farm, Dipartimento Sci Farmaceut, I-84084 Fisciano, Salerno, Italy
[9]
2-amino-6-arylsulfonylbenzonitriles as non-nucleoside reverse transcriptase inhibitors of HIV-1
[J].
Chan, JH
;
Hong, JS
;
Hunter, RN
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Orr, GF
;
Cowan, JR
;
Sherman, DB
;
Sparks, SM
;
Reitter, BE
;
Andrews, CW
;
Hazen, RJ
;
St Clair, M
;
Boone, LR
;
Ferris, RG
;
Creech, KL
;
Roberts, GB
;
Short, SA
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Weaver, K
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Ott, RJ
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Ren, JS
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Hopkins, A
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Stuart, DI
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Stammers, DK
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JOURNAL OF MEDICINAL CHEMISTRY,
2001, 44 (12)
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Chan, JH
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Hong, JS
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Hunter, RN
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Orr, GF
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Cowan, JR
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Sherman, DB
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Sparks, SM
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Reitter, BE
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Andrews, CW
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Hazen, RJ
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

St Clair, M
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Boone, LR
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Ferris, RG
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Creech, KL
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Roberts, GB
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Short, SA
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Weaver, K
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Ott, RJ
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Ren, JS
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Hopkins, A
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Stuart, DI
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA

Stammers, DK
论文数: 0 引用数: 0
h-index: 0
机构: Glaxo Wellcome Inc, Res Triangle Pk, NC 27709 USA
[10]
Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors
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Corbett, JW
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Ko, SS
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Rodgers, JD
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Gearhart, LA
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Magnus, NA
;
Bacheler, LT
;
Diamond, S
;
Jeffrey, S
;
Klabe, RM
;
Cordova, BC
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Garber, S
;
Logue, K
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Trainor, GL
;
Anderson, PS
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Erickson-Viitanen, SK
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JOURNAL OF MEDICINAL CHEMISTRY,
2000, 43 (10)
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Corbett, JW
论文数: 0 引用数: 0
h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Ko, SS
论文数: 0 引用数: 0
h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Rodgers, JD
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Gearhart, LA
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Magnus, NA
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Bacheler, LT
论文数: 0 引用数: 0
h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Diamond, S
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Jeffrey, S
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Klabe, RM
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Cordova, BC
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机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Garber, S
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Logue, K
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Trainor, GL
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Anderson, PS
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h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA

Erickson-Viitanen, SK
论文数: 0 引用数: 0
h-index: 0
机构:
Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA Dupont Pharmaceut Co, Expt Stn, Wilmington, DE 19880 USA