BQ-123

BQ-123
BQ-123[1]
BQ-123 structure.svg
이름
IUPAC 이름
2-[(3R,6R,9S,12R,15S)-6-(1H-indol-3-ylmethyl)-9-(2-methylpropyl)-2,5,8,11,14-pentaoxo-12-propan-2-yl-1,4,7,10,13-pentazabicyclo[13.3.0]octadecan-3-yl]acetic acid
기타 이름
사이클로(D-trP-D-asp-L-pro-D-val-leu)
식별자
3D 모델(JSmol)
켐벨
켐스파이더
펍켐 CID
유니
  • InChI=1S/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)/t21-,22+,23-,24-,26+/m0/s1 ☒N
    키: VYCMAOURFJIHD-AOYLRGSA-N ☒N
  • InChI=1/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)/t21-,22+,23-,24-,26+/m0/s1
    키: VYCMAOURFJIHD-AOYLRGGBG
  • CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(=O)N1)C(C)C)CC(=O)O)CC3=CNC4=CC=CC=C43
특성.
C31H42N6O7
어금질량 610.712 g·190−1
달리 명시된 경우를 제외하고, 표준 상태(25°C [77°F], 100 kPa)의 재료에 대한 데이터가 제공된다.
☒ NVERIFI (?란수표Y☒N?
Infobox 참조 자료

사이클로(-D-TRP-D-Asp-Pro-D-Val-Leu-)로도 알려진 BQ-123은 순환형 펜타펩타이드로, 1991년 스트렙토미세스 미사키엔시스의 발효 육수로부터 처음 격리되었다.[2]NMR 연구에 따르면 폴리펩타이드 백본은 타입 II 베타 턴과 역 감마 턴으로 구성된다.[3][4]측면 체인은 사용하는 용제에 따라 다른 방향을 채택한다.[5][6]베타 턴이 시작될 때 위치한 프로라인 카보닐 산소 원자는 나트륨 이온 결합 지점이다.[7]나트륨 이온에 대한 친화력이 높아 최대 3개까지 조정할 수 있다.[8]연구 결과 BQ123은 이케미아에 의한 급성신부전증을 역전시키는데 효과가 있으며, 이는 BQ123이 근위관세포를 통한 나트륨 이온의 재흡수를 증가시키기 때문일 수 있다고 제안되었다.[9][10][11][12][13]null

BQ-123은 선택적 ETA 내피 수용체 길항제다.[1][14]이와 같이 내인성 수용체 기능 연구에서는 생화학적 도구로 사용된다.BQ-123은 이미 확립된 수축을 ET-1로 역전시킴으로써 ET-1의 대항마로 작용한다.BQ-123이 수용체(ETA)에서 ET-1을 제거하는 길항제 역할을 할 수 있다는 의미다.[15]null

참조

  1. ^ a b 시그마알드리히 BQ-123
  2. ^ Ihara M, Fukuroda T, Saeki T, Nishikibe M, Kojiri K, Suda H, Yano M (July 1991). "An endothelin receptor (ETA) antagonist isolated from Streptomyces misakiensis". Biochemical and Biophysical Research Communications. 178 (1): 132–7. doi:10.1016/0006-291X(91)91789-F. PMID 1648907.
  3. ^ Atkinson RA, Pelton JT (January 1992). "Conformational study of cyclo[D-Trp-D-Asp-Pro-D-Val-Leu], an endothelin-A receptor-selective antagonist". FEBS Letters. 296 (1): 1–6. doi:10.1016/0014-5793(92)80390-3. PMID 1309703.
  4. ^ Krystek SR, Bassolino DA, Bruccoleri RE, Hunt JT, Porubcan MA, Wandler CF, Andersen NH (March 1992). "Solution conformation of a cyclic pentapeptide endothelin antagonist. Comparison of structures obtained from constrained dynamics and conformational search". FEBS Letters. 299 (3): 255–61. doi:10.1016/0014-5793(92)80127-3. PMID 1544503.
  5. ^ Gonnella NC, Zhang X, Jin Y, Prakash O, Paris CG, Kolossváry I, et al. (May 1994). "Solvent effects on the conformation of cyclo(-D-Trp-D-Asp-Pro-D-Val-Leu-). An NMR spectroscopy and molecular modeling study". International Journal of Peptide and Protein Research. 43 (5): 454–62. doi:10.1111/j.1399-3011.1994.tb00544.x. PMID 8070969.
  6. ^ Bean JW, Peishoff CE, Kopple KD (September 1994). "Conformations of cyclic pentapeptide endothelin receptor antagonists". International Journal of Peptide and Protein Research. 44 (3): 223–32. doi:10.1111/j.1399-3011.1994.tb00164.x. PMID 7822098.
  7. ^ Ngoka LC, Gross ML (February 2000). "Location of alkali metal binding sites in endothelin A selective receptor antagonists, cyclo(D-Trp-D-Asp-Pro-D-Val-Leu) and cyclo(D-Trp-D-Asp-Pro-D-Ile-Leu), from multistep collisionally activated decompositions". Journal of Mass Spectrometry. 35 (2): 265–76. Bibcode:2000JMSp...35..265N. doi:10.1002/(SICI)1096-9888(200002)35:2<265::AID-JMS946>3.0.CO;2-#. PMID 10679990.
  8. ^ Ngoka LC, Gross ML (January 1999). "Novel sodium binding properties of some cyclopentapeptide endothelin A selective receptor antagonists: electrospray and fast-atom-bombardment mass spectrometric studies". Biochemical and Biophysical Research Communications. 254 (3): 713–9. doi:10.1006/bbrc.1998.9772. PMID 9920807.
  9. ^ Büyükgebiz O, Aktan AO, Haklar G, Yalçin AS, Yeğen C, Yalin R, Ercan ZS (1996). "BQ-123, a specific endothelin (ETA) receptor antagonist, prevents ischemia-reperfusion injury in kidney transplantation". Transplant International. 9 (3): 201–7. doi:10.1007/BF00335386. PMID 8723187. S2CID 39612393.
  10. ^ Clozel M, Watanabe H (1993). "BQ-123, a peptidic endothelin ETA receptor antagonist, prevents the early cerebral vasospasm following subarachnoid hemorrhage after intracisternal but not intravenous injection". Life Sciences. 52 (9): 825–34. doi:10.1016/0024-3205(93)90081-d. PMID 8437512.
  11. ^ Clavell AL, Stingo AJ, Margulies KB, Brandt RR, Burnett JC (March 1995). "Role of endothelin receptor subtypes in the in vivo regulation of renal function". The American Journal of Physiology. 268 (3 Pt 2): F455-60. doi:10.1152/ajprenal.1995.268.3.F455. PMID 7900845.
  12. ^ Gellai M, Jugus M, Fletcher T, DeWolf R, Nambi P (February 1994). "Reversal of postischemic acute renal failure with a selective endothelinA receptor antagonist in the rat". The Journal of Clinical Investigation. 93 (2): 900–6. doi:10.1172/JCI117046. PMC 293964. PMID 8113422.
  13. ^ Mino N, Kobayashi M, Nakajima A, Amano H, Shimamoto K, Ishikawa K, et al. (October 1992). "Protective effect of a selective endothelin receptor antagonist, BQ-123, in ischemic acute renal failure in rats". European Journal of Pharmacology. 221 (1): 77–83. doi:10.1016/0014-2999(92)90774-x. PMID 1459192.
  14. ^ Ishikawa K, Fukami T, Nagase T, Fujita K, Hayama T, Niiyama K, et al. (May 1992). "Cyclic pentapeptide endothelin antagonists with high ETA selectivity. Potency- and solubility-enhancing modifications". Journal of Medicinal Chemistry. 35 (11): 2139–42. doi:10.1021/jm00089a028. PMID 1317926.
  15. ^ Berrazueta JR, Bhagat K, Vallance P, MacAllister RJ (December 1997). "Dose- and time-dependency of the dilator effects of the endothelin antagonist, BQ-123, in the human forearm". British Journal of Clinical Pharmacology. 44 (6): 569–71. doi:10.1046/j.1365-2125.1997.t01-1-00631.x. PMC 2042881. PMID 9431833.
Stub icon

이 생화학 기사는 단조롭다.위키피디아를 확장하여 도울 수 있다.