Effects of precocene analogs on the nematode Caenorhabditis remanei (var. bangaloreiensis). I. Structure/activity relations

A. Fodor, Tibor Tímár, I. Kiss, Sándor Hosztafi, Éva Varga, József Soos, Péter Sebök

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Precocenes (PI and PII) and 114 of their analogs (PAs) were synthetized and tested on C. remanei embryos for their precocene-like (P-like) activities resulting in unusual development at sublethal doses. The P-like activity was quantitated by plotting the probit of the percentage of the developmentally affected survivors against the (log) dose to obtain the EC plot and the half effective concentration (EC50). All five PAs (PI, PII, 7-ethoxy-PII, 7-(prop-2-ynyloxy)-PI, and 6-methoxy-7-(prop-2-ynyloxy)-PII) which exert both antiallatal activity in insects and P-like activity in nematodes are 7-alkoxy-substituted 2,2-dimethylchromenes. Both activities can be enhanced by an additional 6-MeO-substitution or by an asymmetric 6,7-dialkoxy-substitution, on condition that R-7 is longer than R-6. There are many more similarities than dissimilarities in the structural requirements needed for antiallatal and P-like activities. All but three nonantiallatal PAs effective in nematodes are 7-prop-2-ynyloxy-substituted; two are symmetrically 6,7-disubstituted, and one is heterosubstituted (thio-PI). All PAs with antiallatal but without P-like activity are 7-monosubstituted with a relatively long alkoxy group. Certain substitutions favor antiallatal activity and others P-like activity. The severe nematocidal effect of 6,7-methylenedioxy-2,2-dimethylchromene (inert in insects) is not accompanied by P-like activity. The present findings lend some indirect support to the supposition that JH-producing cells and/or JH-dependent function(s) might exist in the nematodes.

Original languageEnglish
Pages (from-to)18-31
Number of pages14
JournalGeneral and Comparative Endocrinology
Volume74
Issue number1
DOIs
Publication statusPublished - 1989

Fingerprint

Caenorhabditis
Insects
Nematoda
precocenes
insects
Embryonic Structures
dosage
embryo (animal)
alkoxyl radical
cells

ASJC Scopus subject areas

  • Endocrinology

Cite this

Effects of precocene analogs on the nematode Caenorhabditis remanei (var. bangaloreiensis). I. Structure/activity relations. / Fodor, A.; Tímár, Tibor; Kiss, I.; Hosztafi, Sándor; Varga, Éva; Soos, József; Sebök, Péter.

In: General and Comparative Endocrinology, Vol. 74, No. 1, 1989, p. 18-31.

Research output: Contribution to journalArticle

Fodor, A. ; Tímár, Tibor ; Kiss, I. ; Hosztafi, Sándor ; Varga, Éva ; Soos, József ; Sebök, Péter. / Effects of precocene analogs on the nematode Caenorhabditis remanei (var. bangaloreiensis). I. Structure/activity relations. In: General and Comparative Endocrinology. 1989 ; Vol. 74, No. 1. pp. 18-31.
@article{f624cba7366440c68103e0294a0d7680,
title = "Effects of precocene analogs on the nematode Caenorhabditis remanei (var. bangaloreiensis). I. Structure/activity relations",
abstract = "Precocenes (PI and PII) and 114 of their analogs (PAs) were synthetized and tested on C. remanei embryos for their precocene-like (P-like) activities resulting in unusual development at sublethal doses. The P-like activity was quantitated by plotting the probit of the percentage of the developmentally affected survivors against the (log) dose to obtain the EC plot and the half effective concentration (EC50). All five PAs (PI, PII, 7-ethoxy-PII, 7-(prop-2-ynyloxy)-PI, and 6-methoxy-7-(prop-2-ynyloxy)-PII) which exert both antiallatal activity in insects and P-like activity in nematodes are 7-alkoxy-substituted 2,2-dimethylchromenes. Both activities can be enhanced by an additional 6-MeO-substitution or by an asymmetric 6,7-dialkoxy-substitution, on condition that R-7 is longer than R-6. There are many more similarities than dissimilarities in the structural requirements needed for antiallatal and P-like activities. All but three nonantiallatal PAs effective in nematodes are 7-prop-2-ynyloxy-substituted; two are symmetrically 6,7-disubstituted, and one is heterosubstituted (thio-PI). All PAs with antiallatal but without P-like activity are 7-monosubstituted with a relatively long alkoxy group. Certain substitutions favor antiallatal activity and others P-like activity. The severe nematocidal effect of 6,7-methylenedioxy-2,2-dimethylchromene (inert in insects) is not accompanied by P-like activity. The present findings lend some indirect support to the supposition that JH-producing cells and/or JH-dependent function(s) might exist in the nematodes.",
author = "A. Fodor and Tibor T{\'i}m{\'a}r and I. Kiss and S{\'a}ndor Hosztafi and {\'E}va Varga and J{\'o}zsef Soos and P{\'e}ter Seb{\"o}k",
year = "1989",
doi = "10.1016/0016-6480(89)90110-X",
language = "English",
volume = "74",
pages = "18--31",
journal = "General and Comparative Endocrinology",
issn = "0016-6480",
publisher = "Academic Press Inc.",
number = "1",

}

TY - JOUR

T1 - Effects of precocene analogs on the nematode Caenorhabditis remanei (var. bangaloreiensis). I. Structure/activity relations

AU - Fodor, A.

AU - Tímár, Tibor

AU - Kiss, I.

AU - Hosztafi, Sándor

AU - Varga, Éva

AU - Soos, József

AU - Sebök, Péter

PY - 1989

Y1 - 1989

N2 - Precocenes (PI and PII) and 114 of their analogs (PAs) were synthetized and tested on C. remanei embryos for their precocene-like (P-like) activities resulting in unusual development at sublethal doses. The P-like activity was quantitated by plotting the probit of the percentage of the developmentally affected survivors against the (log) dose to obtain the EC plot and the half effective concentration (EC50). All five PAs (PI, PII, 7-ethoxy-PII, 7-(prop-2-ynyloxy)-PI, and 6-methoxy-7-(prop-2-ynyloxy)-PII) which exert both antiallatal activity in insects and P-like activity in nematodes are 7-alkoxy-substituted 2,2-dimethylchromenes. Both activities can be enhanced by an additional 6-MeO-substitution or by an asymmetric 6,7-dialkoxy-substitution, on condition that R-7 is longer than R-6. There are many more similarities than dissimilarities in the structural requirements needed for antiallatal and P-like activities. All but three nonantiallatal PAs effective in nematodes are 7-prop-2-ynyloxy-substituted; two are symmetrically 6,7-disubstituted, and one is heterosubstituted (thio-PI). All PAs with antiallatal but without P-like activity are 7-monosubstituted with a relatively long alkoxy group. Certain substitutions favor antiallatal activity and others P-like activity. The severe nematocidal effect of 6,7-methylenedioxy-2,2-dimethylchromene (inert in insects) is not accompanied by P-like activity. The present findings lend some indirect support to the supposition that JH-producing cells and/or JH-dependent function(s) might exist in the nematodes.

AB - Precocenes (PI and PII) and 114 of their analogs (PAs) were synthetized and tested on C. remanei embryos for their precocene-like (P-like) activities resulting in unusual development at sublethal doses. The P-like activity was quantitated by plotting the probit of the percentage of the developmentally affected survivors against the (log) dose to obtain the EC plot and the half effective concentration (EC50). All five PAs (PI, PII, 7-ethoxy-PII, 7-(prop-2-ynyloxy)-PI, and 6-methoxy-7-(prop-2-ynyloxy)-PII) which exert both antiallatal activity in insects and P-like activity in nematodes are 7-alkoxy-substituted 2,2-dimethylchromenes. Both activities can be enhanced by an additional 6-MeO-substitution or by an asymmetric 6,7-dialkoxy-substitution, on condition that R-7 is longer than R-6. There are many more similarities than dissimilarities in the structural requirements needed for antiallatal and P-like activities. All but three nonantiallatal PAs effective in nematodes are 7-prop-2-ynyloxy-substituted; two are symmetrically 6,7-disubstituted, and one is heterosubstituted (thio-PI). All PAs with antiallatal but without P-like activity are 7-monosubstituted with a relatively long alkoxy group. Certain substitutions favor antiallatal activity and others P-like activity. The severe nematocidal effect of 6,7-methylenedioxy-2,2-dimethylchromene (inert in insects) is not accompanied by P-like activity. The present findings lend some indirect support to the supposition that JH-producing cells and/or JH-dependent function(s) might exist in the nematodes.

UR - http://www.scopus.com/inward/record.url?scp=0024558154&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0024558154&partnerID=8YFLogxK

U2 - 10.1016/0016-6480(89)90110-X

DO - 10.1016/0016-6480(89)90110-X

M3 - Article

C2 - 2737452

AN - SCOPUS:0024558154

VL - 74

SP - 18

EP - 31

JO - General and Comparative Endocrinology

JF - General and Comparative Endocrinology

SN - 0016-6480

IS - 1

ER -