Indoleamine 2,3-Dioxygenase Inhibitory Activity of Derivatives of Marine Alkaloid Tsitsikammamine A

E. Dolušić; P. Larrieu; C. Meinguet; D. Colette; A. Rives; S. Blanc; T. Ferain; L. Pilotte; V. Stroobant; J. Wouters; B. Van Den Eynde; B. Masereel; E. Delfourne; R. Frédérick

doi:10.1016/j.bmcl.2012.11.036

Indoleamine 2,3-Dioxygenase Inhibitory Activity of Derivatives of Marine Alkaloid Tsitsikammamine A

E. Dolušić, P. Larrieu, C. Meinguet, D. Colette, A. Rives, S. Blanc, T. Ferain, L. Pilotte, V. Stroobant, J. Wouters, B. Van Den Eynde, B. Masereel, E. Delfourne, R. Frédérick

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Résumé

Tsitsikammamines are marine alkaloids whose structure is based on the pyrroloiminoquinone scaffold. These and related compounds have attracted attention due to various interesting biological properties, including cytotoxicity, topoisomerase inhibition, antimicrobial, antifungal and antimalarial activity. Indoleamine 2,3-dioxygenase (IDO1) is a well-established therapeutic target as an important factor in the tumor immune evasion mechanism. In this preliminary communication, we report the inhibitory activity of tsitsikammamine derivatives against IDO1. Tsitsikammamine A analogue 11b displays submicromolar potency in an enzymatic assay. A number of derivatives are also active in a cellular assay while showing little or no activity towards tryptophan 2,3-dioxygenase (TDO), a functionally related enzyme. This IDO1 inhibitory activity is rationalized by molecular modeling studies. An interest is thus established in this class of compounds as a potential source of lead compounds for the development of new pharmaceutically useful IDO1 inhibitors.

langue originale	Anglais
Pages (de - à)	47-54
Nombre de pages	8
journal	Bioorganic & Medicinal Chemistry Letters
Volume	23
Numéro de publication	1
Date de mise en ligne précoce	24 nov. 2012
Les DOIs	https://doi.org/10.1016/j.bmcl.2012.11.036
Etat de la publication	Publié - 1 janv. 2013
Evénement	JFB 2011. - Liege, Belgique Durée: 19 mai 2011 → …

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10.1016/j.bmcl.2012.11.036

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Dolusic tsitsikammamines BMCL 2013 final
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27 Citations
5 Poster
3 Revue de documentation
2 Article
1 Article dans les actes d'une conférence/un colloque

Indoleamine 2,3-dioxygenase inhibitors: a patent review (2008-2012)
Dolušić, E. & Frédérick, R., 1 oct. 2013, Dans: Expert opinion on therapeutic targets. 23, 10, p. 1367-1381 15 p.
Résultats de recherche: Contribution à un journal/une revue › Revue de documentation › Revue par des pairs
Discovery and preliminary SARs of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors
Dolušić, E., Larrieu, P., Blanc, S., Sapunaric, F., Pouyez, J., Moineaux, L., Colette, D., Stroobant, V., Pilotte, L., Colau, D., Ferain, T., Fraser, G., Galleni, M., Frère, J.-M., Masereel, B., Van Den Eynde, B., Wouters, J. & Frédérick, R., 2011, Dans: European Journal of Medicinal Chemistry. 46, 7, p. 3058-3065 8 p.
Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs
Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors
Dolušić, E., Larrieu, P., Blanc, S., Sapunaric, F., Norberg, B., Moineaux, L., Colette, D., Stroobant, V., Pilotte, L., Colau, D., Ferain, T., Fraser, G., Galeni, M., Frre, J. M., Masereel, B., Van Den Eynde, B., Wouters, J. & Frédérick, R., 15 févr. 2011, Dans: Bioorganic and Medicinal Chemistry. 19, 4, p. 1550-1561 12 p.
Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

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1 Terminé

CANTOL: Conception et synthèse d'inhibiteurs de l'indolaminedioxygénase (IDO) pour le traitement du cancer
Masereel, B. (Responsable du Projet), Wouters, J. (Responsable du Projet), Dolušić, E. (Chercheur), FREDERICK, R. (Chercheur), POUYEZ, J. (Chercheur), Van den Eynde, B. J. (Co-investigateur), Frère, J.-M. (Co-investigateur), Moser, M. (Co-investigateur), Jean-Marie, B. (Co-investigateur), Combalbert, J. (Responsable du Projet) & Stephenne, J. (Co-investigateur)
1/04/08 → 31/03/12
Projet: Recherche

Physico-chimie et caractérisation (PC2)
Wouters, J. (!!Manager) & Aprile, C. (!!Manager)
Plateforme technologique Caracterisation physico-chimiques
Equipement/installations: Plateforme technolgique

5 Participation à une conférence, un congrès

47th RICT: Drug Discovery and Selection.
Dolusic, E. (Poster)
6 juil. 2011 → 8 juil. 2011
Activité: Participation ou organisation d'un événement › Participation à une conférence, un congrès
JFB 2011.
Dolusic, E. (Conférencier)
19 mai 2011 → 20 mai 2011
Activité: Participation ou organisation d'un événement › Participation à une conférence, un congrès
XVIIIeme JOURNEE JEUNES CHERCHEURS
Dolusic, E. (Poster)
4 févr. 2011
Activité: Participation ou organisation d'un événement › Participation à une conférence, un congrès

Contient cette citation

Dolušić, E., Larrieu, P., Meinguet, C., Colette, D., Rives, A., Blanc, S., Ferain, T., Pilotte, L., Stroobant, V., Wouters, J., Van Den Eynde, B., Masereel, B., Delfourne, E., & Frédérick, R. (2013). Indoleamine 2,3-Dioxygenase Inhibitory Activity of Derivatives of Marine Alkaloid Tsitsikammamine A. Bioorganic & Medicinal Chemistry Letters, 23(1), 47-54. https://doi.org/10.1016/j.bmcl.2012.11.036

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title = "Indoleamine 2,3-Dioxygenase Inhibitory Activity of Derivatives of Marine Alkaloid Tsitsikammamine A",

abstract = "Tsitsikammamines are marine alkaloids whose structure is based on the pyrroloiminoquinone scaffold. These and related compounds have attracted attention due to various interesting biological properties, including cytotoxicity, topoisomerase inhibition, antimicrobial, antifungal and antimalarial activity. Indoleamine 2,3-dioxygenase (IDO1) is a well-established therapeutic target as an important factor in the tumor immune evasion mechanism. In this preliminary communication, we report the inhibitory activity of tsitsikammamine derivatives against IDO1. Tsitsikammamine A analogue 11b displays submicromolar potency in an enzymatic assay. A number of derivatives are also active in a cellular assay while showing little or no activity towards tryptophan 2,3-dioxygenase (TDO), a functionally related enzyme. This IDO1 inhibitory activity is rationalized by molecular modeling studies. An interest is thus established in this class of compounds as a potential source of lead compounds for the development of new pharmaceutically useful IDO1 inhibitors.",

keywords = "Cancer immunology, Indoleamine 2,3-dioxygenase, Molecular modeling, Pyrroloiminoquinones, Tsitsikammamines",

author = "E. Dolu{\v s}i{\'c} and P. Larrieu and C. Meinguet and D. Colette and A. Rives and S. Blanc and T. Ferain and L. Pilotte and V. Stroobant and J. Wouters and {Van Den Eynde}, B. and B. Masereel and E. Delfourne and R. Fr{\'e}d{\'e}rick",

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doi = "10.1016/j.bmcl.2012.11.036",

language = "English",

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journal = "Bioorganic & Medicinal Chemistry Letters",

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Dolušić, E, Larrieu, P, Meinguet, C, Colette, D, Rives, A, Blanc, S, Ferain, T, Pilotte, L, Stroobant, V, Wouters, J, Van Den Eynde, B, Masereel, B, Delfourne, E & Frédérick, R 2013, 'Indoleamine 2,3-Dioxygenase Inhibitory Activity of Derivatives of Marine Alkaloid Tsitsikammamine A', Bioorganic & Medicinal Chemistry Letters, VOL. 23, Numéro 1, p. 47-54. https://doi.org/10.1016/j.bmcl.2012.11.036

TY - JOUR

T1 - Indoleamine 2,3-Dioxygenase Inhibitory Activity of Derivatives of Marine Alkaloid Tsitsikammamine A

AU - Dolušić, E.

AU - Larrieu, P.

AU - Meinguet, C.

AU - Colette, D.

AU - Rives, A.

AU - Blanc, S.

AU - Ferain, T.

AU - Pilotte, L.

AU - Stroobant, V.

AU - Wouters, J.

AU - Van Den Eynde, B.

AU - Masereel, B.

AU - Delfourne, E.

AU - Frédérick, R.

PY - 2013/1/1

Y1 - 2013/1/1

N2 - Tsitsikammamines are marine alkaloids whose structure is based on the pyrroloiminoquinone scaffold. These and related compounds have attracted attention due to various interesting biological properties, including cytotoxicity, topoisomerase inhibition, antimicrobial, antifungal and antimalarial activity. Indoleamine 2,3-dioxygenase (IDO1) is a well-established therapeutic target as an important factor in the tumor immune evasion mechanism. In this preliminary communication, we report the inhibitory activity of tsitsikammamine derivatives against IDO1. Tsitsikammamine A analogue 11b displays submicromolar potency in an enzymatic assay. A number of derivatives are also active in a cellular assay while showing little or no activity towards tryptophan 2,3-dioxygenase (TDO), a functionally related enzyme. This IDO1 inhibitory activity is rationalized by molecular modeling studies. An interest is thus established in this class of compounds as a potential source of lead compounds for the development of new pharmaceutically useful IDO1 inhibitors.

AB - Tsitsikammamines are marine alkaloids whose structure is based on the pyrroloiminoquinone scaffold. These and related compounds have attracted attention due to various interesting biological properties, including cytotoxicity, topoisomerase inhibition, antimicrobial, antifungal and antimalarial activity. Indoleamine 2,3-dioxygenase (IDO1) is a well-established therapeutic target as an important factor in the tumor immune evasion mechanism. In this preliminary communication, we report the inhibitory activity of tsitsikammamine derivatives against IDO1. Tsitsikammamine A analogue 11b displays submicromolar potency in an enzymatic assay. A number of derivatives are also active in a cellular assay while showing little or no activity towards tryptophan 2,3-dioxygenase (TDO), a functionally related enzyme. This IDO1 inhibitory activity is rationalized by molecular modeling studies. An interest is thus established in this class of compounds as a potential source of lead compounds for the development of new pharmaceutically useful IDO1 inhibitors.

KW - Cancer immunology

KW - Indoleamine 2,3-dioxygenase

KW - Molecular modeling

KW - Pyrroloiminoquinones

KW - Tsitsikammamines

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DO - 10.1016/j.bmcl.2012.11.036

M3 - Article

C2 - 23218716

AN - SCOPUS:84871024705

SN - 0960-894X

VL - 23

SP - 47

EP - 54

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 1

T2 - JFB 2011.

Y2 - 19 May 2011

ER -

Indoleamine 2,3-Dioxygenase Inhibitory Activity of Derivatives of Marine Alkaloid Tsitsikammamine A

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