Reproductive and Developmental Biology

The Korean Society of Animal Reproduction (한국동물번식학회)
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The Search of Pig Pheromonal Odorants for Biostimulation Control System Technologies: Synthesis of $N^1$-allyl-$N^2$-(tetrahydrofuran-2-ylmethyl)oxalamide Molecule and Induction Effect of Pig Estrus

생물학적 자극 통제 수단으로 활용하기 위한 돼지 페르몬 성 냄새 물질의 탐색: $N^1$-allyl-$N^2$-(tetrahydrofuran-2-ylmethyl)oxalamide 분자의 합성과 돼지의 발정 유도효과

  • Park, Chang-Sik (Research Center for Transgenic Cloned Pigs, Chungnam National University) ;
  • Song, Suck-Oh (Chungnam Livestock Technology Research Institute) ;
  • Lim, Jae-Sam (Chungnam Livestock Technology Research Institute) ;
  • Soung, Min-Gyu (Division of Applied Biological Chemistry, Chungnam National University) ;
  • Sung, Nack-Do (Division of Applied Biological Chemistry, Chungnam National University)
  • 박창식 (충남대학교 형질전환복제돼지연구센터) ;
  • 송석오 (충남 축산기술연구소) ;
  • 임재삼 (충남 축산기술연구소) ;
  • 성민규 (충남대학교 농업생명과학대학 응용생물화학부) ;
  • 성낙도 (충남대학교 농업생명과학대학 응용생물화학부)
  • Published : 2009.03.31
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Abstract

To search a new pig pheromonal odorant, the $N^1$-allyl-$N^2$-(tetrahydrofuran-Z-ylmethyl)oxalamide molecule predicted by ligand based approach and molecular docking method was synthesized by nucleophilic addition-elimination reaction ($Ad_{NU-E}$) between N-allyloxalamic acid ethylester and tetrahydrofurlmethylamine. According to the evaluation results for efficiency of pig estrus control, the synthesized pig pheromonal $N^1$-allyl-$N^2$-(tetrahydrofuran-2-ylmethyl)oxalamide molecule advanced the estrus by 11.3 days (p<0.05) compared with the non-pheromone group. And from these results, it is predicted that the synthesized pig pheromonal compound will be able to increase the reproduction efficiency of pig.

Keywords

References

  1. Abeydeera LR, Wang WH, Cantley TC, Prather RS, Day BN (1998): Presence of b-mercaptoethanol can increase the glutathione content of pig oocytes matured in vitro and the rate of blastocyst development after in vitro fertilization. Theriogenology 50: 747-756 https://doi.org/10.1016/S0093-691X(98)00180-0
  2. Akamatsu M (2002): Current state and perspectives of 3D-QSAR. Curr Topics Med Chem 2:1381-1394 https://doi.org/10.2174/1568026023392887
  3. Dal Monte M, Centini M, Anselmi C, Pelosi P (1993): Binding of selected odorants to bovine and porcine odorant-binding proteins. Chem Sences 18:713-721 https://doi.org/10.1093/chemse/18.6.713
  4. Dobrinsky JR, Johnson LA (1994): Cryopreservation of porcine embryos by vitrification: A study of in vitro development. Theriogenology 42:25-35 https://doi.org/10.1016/0093-691X(94)90659-7
  5. Estienne MJ, Harper AF, Horsley BR, Estienne CE, Knight JW (2001): Effects of P.G.600 on the onset of estrus and ovulation rate in gilts treated with Regumate. J Anim Sci 79:2757-2761
  6. Horsley BR, Estienne MJ, Harper AF, Purcell SH, Baitis HK, Beal WE, Knight JW (2005): Effect of P.G.600 on the timing of ovulation in gilts treated with altrenogest. J Anim Sci (Savoy, IL. United States), 83:1690-1695 https://doi.org/10.2527/2005.8371690x
  7. Joerg H, Asai M, Graphodatskaya D, Janett E, Stranzinger F (2004): Validating bovine sexed semen samples using quantitative PCR. J Anim Breeding and Genetics 121:209-215 https://doi.org/10.1111/j.1439-0388.2004.00455.x
  8. Knox RV, Rodriguez-Zas SL, Miller GM, Willenburg KL, Robb JA (2001): Administration of P.G.600 to sows at weaning and time of ovulation as determined by transrectal ultrasound. J Anim Sci 79:796- 802 https://doi.org/10.2527/2001.794796x
  9. Lengauer T, Lemmem C, Rarey M, Zimmermann M (2004): Novel technologies virtual screening. Drug Discovery Today 9:27-34 https://doi.org/10.1016/S1359-6446(04)02939-3
  10. Lowry TH, Richardson KS (1985): Mechanism and Theory in Organic Chemistry (3rd ed.) Harper & Row. Pub., New York, Ch. 7
  11. Lucas X, Martinez EA, Roca J, Vazquez JM, Gil MA, Pastor LM, Alabart JL (2003): Influence of follicle size on the penetrability of immature pig oocytes for homologous in vitro penetration assay. Theriogenology 60:659-667 https://doi.org/10.1016/S0093-691X(03)00077-3
  12. Park CS, Choi YK, Sung ND (2007): The search of pig pheromonal odorants for biostimulation control system technologies: A 2D-QSAR model for binding affinities between ligands of 2-(cyclohexyloxy)tetrahydro furane derivatives and porcine odorant binding protein. Reprod Dev Biol 31:15-20
  13. PBS: The leader in animal health & nutrition, PBS Animal Health, PO Box 9101, Canton, Ohio 44711- 9101. USA
  14. Rewok PI, Ogwu D, Oyedipe EO, Sekoni VO (2001): The role of pheromones and biostimulation in animal reproduction. Anim Reprod Sci 65:157-170 https://doi.org/10.1016/S0378-4320(00)00223-2
  15. SAS (2002): Statistic & Analysis Software on CD- ROM (Ver. 9.1), SAS Institute Inc., Cary NC. 27513 U.S.A
  16. Schneider G, Baringhaus KH (2007): Receptor-ligand interaction. In: Molecular Design, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  17. Shrestha NP, Edwards S, English PR, Robertson JF (2001): An evaluation boar pheromon spray to aid the stimulation and detection of estrus in small farms in Nepal. Asian-Aust J Anim Sci 14:697-700
  18. SOA (Sex odor aerosol): Intervert, Millsboro, DE 1996. Holland
  19. Spinelli S, Vincent R, Pelosi P, Tegoni M, Cambillau C (2002): Boar salivar lipocalin: Three-dimensional X-ray structure and androstenol/androstenone docking simulations. Eur J Biochem, 269:2449-2456 https://doi.org/10.1046/j.1432-1033.2002.02901.x
  20. Soung MG, Cho YG, Park CS, Sung ND (2008): The search of pig pheromonal odorants for biostimulation control system technologies: Prediction of pig pheromonal tetrahydrofuran-2-yl family compounds by means of ligand based approach. Reprod Dev Biol 32: 141-146
  21. Sung ND, Park CS, Park HY, Kim CK (2008a): Docking and virtual screening studies for new leads of boar salivary lipocalin. Bull Korean Chem Soc. 29: 959-962 https://doi.org/10.5012/bkcs.2008.29.5.959
  22. Sung ND, Park CS, Soung MG, Choi KS (2008b): Pig pheromonal compounds, their preparation method and a composite for estrus induction containg it. Korean patent registered; No. 10-0881137, 10- 0883548
  23. Walter WP, Stahl MT, Murcko MA (1998): Virtual screening: An overview. Drug Discovery Today, 3: 160-178 https://doi.org/10.1016/S1359-6446(97)01163-X