アスペルリシン

アスペルリシン
	IUPAC名 (S-(2α,9β,9(R*),9α,β))-6,7-Dihydro-7-((2,3,9,9a-tetrahydro-9-hydroxy-2-(2-methylpropyl)-3-oxo-1H-imidazo(1,2-a)indol-9-yl)methyl)quinazolino(3,2-a)(1,4)benzodiazepine-5,13-dione
識別情報
CAS登録番号	93413-04-8
PubChem	3035433
ChemSpider	2299674
ChEMBL	CHEMBL283117
	SMILES O=C1c7ccccc7/N=C3\N1c2ccccc2C(=O)N[C@H]3C[C@]6(O)c4c(cccc4)N5C(=O)[C@@H](N[C@@H]56)CC(C)C;
	InChI InChI=1S/C31H29N5O4/c1-17(2)15-22-29(39)36-25-14-8-5-11-20(25)31(40,30(36)34-22)16-23-26-32-21-12-6-3-9-18(21)28(38)35(26)24-13-7-4-10-19(24)27(37)33-23/h3-14,17,22-23,30,34,40H,15-16H2,1-2H3,(H,33,37)/t22-,23-,30-,31-/m0/s1 Key: MGMRIOLWEROPJY-FPACPZPDSA-N ; InChI=1/C31H29N5O4/c1-17(2)15-22-29(39)36-25-14-8-5-11-20(25)31(40,30(36)34-22)16-23-26-32-21-12-6-3-9-18(21)28(38)35(26)24-13-7-4-10-19(24)27(37)33-23/h3-14,17,22-23,30,34,40H,15-16H2,1-2H3,(H,33,37)/t22-,23-,30-,31-/m0/s1 Key: MGMRIOLWEROPJY-FPACPZPDBR;
特性
化学式	C31H29N5O4
モル質量	535.593
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

アスペルリシン(Asperlicin)は、Aspergillus alliaceusに由来するマイコトキシンである。コレシストキニン受容体CCKAの選択的アゴニストとして作用し^[1]^[2]^[3]、臨床応用される様々なCCKAアンタゴニストのリード化合物として用いられる^[4]^[5]^[6]^[7]。

出典

^ Chang RS, Lotti VJ, Monaghan RL, Birnbaum J, Stapley EO, Goetz MA, Albers-Schönberg G, Patchett AA, Liesch JM, Hensens OD, et al. A potent nonpeptide cholecystokinin antagonist selective for peripheral tissues isolated from Aspergillus alliaceus. Science. 1985 Oct 11;230(4722):177-9. PMID 2994227
^ Goetz MA, Lopez M, Monaghan RL, Chang RS, Lotti VJ, Chen TB. Asperlicin, a novel non-peptidal cholecystokinin antagonist from Aspergillus alliaceus. Fermentation, isolation and biological properties. Journal of Antibiotics (Tokyo). 1985 Dec;38(12):1633-7. PMID 3005212
^ Liesch JM, Hensens OD, Springer JP, Chang RS, Lotti VJ. Asperlicin, a novel non-peptidal cholecystokinin antagonist from Aspergillus alliaceus. Structure elucidation. Journal of Antibiotics (Tokyo). 1985 Dec;38(12):1638-41. PMID 3841533
^ Bock MG, DiPardo RM, Rittle KE, Evans BE, Freidinger RM, Veber DF, Chang RS, Chen TB, Keegan ME, Lotti VJ. Cholecystokinin antagonists. Synthesis of asperlicin analogues with improved potency and water solubility. Journal of Medicinal Chemistry. 1986 Oct;29(10):1941-5. PMID 3761313
^ Evans BE, Rittle KE, Bock MG, DiPardo RM, Freidinger RM, Whitter WL, Gould NP, Lundell GF, Homnick CF, Veber DF, et al. Design of nonpeptidal ligands for a peptide receptor: cholecystokinin antagonists. Journal of Medicinal Chemistry. 1987 Jul;30(7):1229-39. PMID 2885419
^ Van der Bent A, Ter Laak AM, IJzerman AP, Soudijn W. Molecular modelling of asperlicin derived cholecystokinin A receptor antagonists. European Journal of Pharmacology. 1992 Aug 3;226(4):327-34. PMID 1397061
^ Lattmann E, Billington DC, Poyner DR, Howitt SB, Offel M. Synthesis and evaluation of asperlicin analogues as non-peptidal cholecystokinin-antagonists. Drug Design and Discovery. 2001;17(3):219-30. PMID 11469752

[1] Chang RS, Lotti VJ, Monaghan RL, Birnbaum J, Stapley EO, Goetz MA, Albers-Schönberg G, Patchett AA, Liesch JM, Hensens OD, et al. A potent nonpeptide cholecystokinin antagonist selective for peripheral tissues isolated from Aspergillus alliaceus. Science. 1985 Oct 11;230(4722):177-9. PMID 2994227

[2] Goetz MA, Lopez M, Monaghan RL, Chang RS, Lotti VJ, Chen TB. Asperlicin, a novel non-peptidal cholecystokinin antagonist from Aspergillus alliaceus. Fermentation, isolation and biological properties. Journal of Antibiotics (Tokyo). 1985 Dec;38(12):1633-7. PMID 3005212

[3] Liesch JM, Hensens OD, Springer JP, Chang RS, Lotti VJ. Asperlicin, a novel non-peptidal cholecystokinin antagonist from Aspergillus alliaceus. Structure elucidation. Journal of Antibiotics (Tokyo). 1985 Dec;38(12):1638-41. PMID 3841533

[4] Bock MG, DiPardo RM, Rittle KE, Evans BE, Freidinger RM, Veber DF, Chang RS, Chen TB, Keegan ME, Lotti VJ. Cholecystokinin antagonists. Synthesis of asperlicin analogues with improved potency and water solubility. Journal of Medicinal Chemistry. 1986 Oct;29(10):1941-5. PMID 3761313

[5] Evans BE, Rittle KE, Bock MG, DiPardo RM, Freidinger RM, Whitter WL, Gould NP, Lundell GF, Homnick CF, Veber DF, et al. Design of nonpeptidal ligands for a peptide receptor: cholecystokinin antagonists. Journal of Medicinal Chemistry. 1987 Jul;30(7):1229-39. PMID 2885419

[6] Van der Bent A, Ter Laak AM, IJzerman AP, Soudijn W. Molecular modelling of asperlicin derived cholecystokinin A receptor antagonists. European Journal of Pharmacology. 1992 Aug 3;226(4):327-34. PMID 1397061

[7] Lattmann E, Billington DC, Poyner DR, Howitt SB, Offel M. Synthesis and evaluation of asperlicin analogues as non-peptidal cholecystokinin-antagonists. Drug Design and Discovery. 2001;17(3):219-30. PMID 11469752

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