Design, synthesis, and biological evaluation of new (2E,6E)-10-(dimethylamino)-3,7-dimethyl-2,6-decadien-1-ol ethers as inhibitors of human and Trypanosoma cruzi oxidosqualene cyclase

Ubaldina Galli; Simonetta Oliaro-Bosso; Silvia Taramino; Serena Venegoni; Emanuele Pastore; Gian Cesare Tron; Gianni Balliano; Franca Viola; Giovanni Sorba

doi:10.1016/j.bmcl.2006.09.058

Design, synthesis, and biological evaluation of new (2E,6E)-10-(dimethylamino)-3,7-dimethyl-2,6-decadien-1-ol ethers as inhibitors of human and Trypanosoma cruzi oxidosqualene cyclase

Ubaldina Galli
, Simonetta Oliaro-Bosso
, Silvia Taramino
, Serena Venegoni
, Emanuele Pastore
, Gian Cesare Tron
, Gianni Balliano
, Franca Viola
, Giovanni Sorba

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

New dimethylamino truncated squalene ether derivatives containing a different aromatic moiety (phenyl, naphthyl, and biphenyl) or a simple alkyl (n-hexylic) group were synthesized as inhibitors of the oxidosqualene cyclase (OSC) and of the sterol biosynthetic pathway. The activity against human OSC was compared with the activity against the OSCs of pathogenic organisms such as Pneumocystis carinii and Trypanosoma cruzi. The phenyl derivative was the most potent inhibitor of T. cruzi OSC.

Lingua originale	Inglese
pagine (da-a)	220-224
Numero di pagine	5
Rivista	Bioorganic and Medicinal Chemistry Letters
Volume	17
Numero di pubblicazione	1
DOI	https://doi.org/10.1016/j.bmcl.2006.09.058
Stato di pubblicazione	Pubblicato - 1 gen 2007

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10.1016/j.bmcl.2006.09.058

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Galli, U., Oliaro-Bosso, S., Taramino, S., Venegoni, S., Pastore, E., Tron, G. C., Balliano, G., Viola, F., & Sorba, G. (2007). Design, synthesis, and biological evaluation of new (2E,6E)-10-(dimethylamino)-3,7-dimethyl-2,6-decadien-1-ol ethers as inhibitors of human and Trypanosoma cruzi oxidosqualene cyclase. Bioorganic and Medicinal Chemistry Letters, 17(1), 220-224. https://doi.org/10.1016/j.bmcl.2006.09.058

@article{ff7a1e15e278499da77838cdbdc158c0,

title = "Design, synthesis, and biological evaluation of new (2E,6E)-10-(dimethylamino)-3,7-dimethyl-2,6-decadien-1-ol ethers as inhibitors of human and Trypanosoma cruzi oxidosqualene cyclase",

abstract = "New dimethylamino truncated squalene ether derivatives containing a different aromatic moiety (phenyl, naphthyl, and biphenyl) or a simple alkyl (n-hexylic) group were synthesized as inhibitors of the oxidosqualene cyclase (OSC) and of the sterol biosynthetic pathway. The activity against human OSC was compared with the activity against the OSCs of pathogenic organisms such as Pneumocystis carinii and Trypanosoma cruzi. The phenyl derivative was the most potent inhibitor of T. cruzi OSC.",

keywords = "Chagas disease, Lanosterol synthase, Oxidosqualene cyclase, Truncated squalene derivatives, Trypanosoma cruzi",

author = "Ubaldina Galli and Simonetta Oliaro-Bosso and Silvia Taramino and Serena Venegoni and Emanuele Pastore and Tron, \{Gian Cesare\} and Gianni Balliano and Franca Viola and Giovanni Sorba",

note = "Funding Information: Financial support from Universit{\`a} del Piemonte Orientale and the Ministero dell{\textquoteright}Istruzione, Universit{\`a} e Ricerca (MIUR), Italy (ex 60\%), is gratefully acknowledged. Thanks are due to Professor Seiichi Matsuda (Rice University, Houston, TX, USA) for supplying S. cerevisiae strains SMY8[pBJ1.21], expressing the OSC of T. cruzi; SMY8[pSM61.21], expressing the wild-type yeast OSC; SMY8[pBJ4.21] expressing the P. carinii OSC and to Ralf Thoma (Hoffmann-La Roche Ltd, Pharma Discovery Research CH 4070, Basel, Switzerland) for supplying the Pichia pastoris strain expressing the human OSC.",

year = "2007",

month = jan,

day = "1",

doi = "10.1016/j.bmcl.2006.09.058",

language = "English",

volume = "17",

pages = "220--224",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd.",

number = "1",

}

Galli, U, Oliaro-Bosso, S, Taramino, S, Venegoni, S, Pastore, E, Tron, GC, Balliano, G, Viola, F & Sorba, G 2007, 'Design, synthesis, and biological evaluation of new (2E,6E)-10-(dimethylamino)-3,7-dimethyl-2,6-decadien-1-ol ethers as inhibitors of human and Trypanosoma cruzi oxidosqualene cyclase', Bioorganic and Medicinal Chemistry Letters, vol. 17, n. 1, pagg. 220-224. https://doi.org/10.1016/j.bmcl.2006.09.058

Design, synthesis, and biological evaluation of new (2E,6E)-10-(dimethylamino)-3,7-dimethyl-2,6-decadien-1-ol ethers as inhibitors of human and Trypanosoma cruzi oxidosqualene cyclase. / Galli, Ubaldina; Oliaro-Bosso, Simonetta; Taramino, Silvia et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 17, N. 1, 01.01.2007, pag. 220-224.

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

TY - JOUR

T1 - Design, synthesis, and biological evaluation of new (2E,6E)-10-(dimethylamino)-3,7-dimethyl-2,6-decadien-1-ol ethers as inhibitors of human and Trypanosoma cruzi oxidosqualene cyclase

AU - Galli, Ubaldina

AU - Oliaro-Bosso, Simonetta

AU - Taramino, Silvia

AU - Venegoni, Serena

AU - Pastore, Emanuele

AU - Tron, Gian Cesare

AU - Balliano, Gianni

AU - Viola, Franca

AU - Sorba, Giovanni

N1 - Funding Information: Financial support from Università del Piemonte Orientale and the Ministero dell’Istruzione, Università e Ricerca (MIUR), Italy (ex 60%), is gratefully acknowledged. Thanks are due to Professor Seiichi Matsuda (Rice University, Houston, TX, USA) for supplying S. cerevisiae strains SMY8[pBJ1.21], expressing the OSC of T. cruzi; SMY8[pSM61.21], expressing the wild-type yeast OSC; SMY8[pBJ4.21] expressing the P. carinii OSC and to Ralf Thoma (Hoffmann-La Roche Ltd, Pharma Discovery Research CH 4070, Basel, Switzerland) for supplying the Pichia pastoris strain expressing the human OSC.

PY - 2007/1/1

Y1 - 2007/1/1

N2 - New dimethylamino truncated squalene ether derivatives containing a different aromatic moiety (phenyl, naphthyl, and biphenyl) or a simple alkyl (n-hexylic) group were synthesized as inhibitors of the oxidosqualene cyclase (OSC) and of the sterol biosynthetic pathway. The activity against human OSC was compared with the activity against the OSCs of pathogenic organisms such as Pneumocystis carinii and Trypanosoma cruzi. The phenyl derivative was the most potent inhibitor of T. cruzi OSC.

AB - New dimethylamino truncated squalene ether derivatives containing a different aromatic moiety (phenyl, naphthyl, and biphenyl) or a simple alkyl (n-hexylic) group were synthesized as inhibitors of the oxidosqualene cyclase (OSC) and of the sterol biosynthetic pathway. The activity against human OSC was compared with the activity against the OSCs of pathogenic organisms such as Pneumocystis carinii and Trypanosoma cruzi. The phenyl derivative was the most potent inhibitor of T. cruzi OSC.

KW - Chagas disease

KW - Lanosterol synthase

KW - Oxidosqualene cyclase

KW - Truncated squalene derivatives

KW - Trypanosoma cruzi

UR - https://www.scopus.com/pages/publications/33845789647

U2 - 10.1016/j.bmcl.2006.09.058

DO - 10.1016/j.bmcl.2006.09.058

M3 - Article

SN - 0960-894X

VL - 17

SP - 220

EP - 224

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 1

ER -

Design, synthesis, and biological evaluation of new (2E,6E)-10-(dimethylamino)-3,7-dimethyl-2,6-decadien-1-ol ethers as inhibitors of human and Trypanosoma cruzi oxidosqualene cyclase

Abstract

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