CAS 108212-75-5: Caliquéamicine γ1I

Description : Caliquéamicine γ1I est un antibiotique antitumoral puissant dérivé de la bactérie Micromonospora echinospora. Il appartient à la classe des composés enediyne, connus pour leur capacité à induire des ruptures de brins d'ADN, entraînant des effets cytotoxiques dans les cellules se divisant rapidement. Ce composé présente une structure complexe caractérisée par un noyau bicyclique unique contenant une partie enediyne hautement réactive, qui est cruciale pour son mécanisme d'action. Caliquéamicine γ1I est particulièrement remarquable pour sa sélectivité envers les cellules cancéreuses, ce qui en fait un sujet d'intérêt dans les thérapies ciblées contre le cancer. Sa haute puissance s'accompagne d'une toxicité significative, nécessitant une manipulation et une administration prudentes dans les milieux cliniques. Le composé a été étudié pour son utilisation potentielle dans des conjugués anticorps-médicament, où il peut être lié à des anticorps ciblant spécifiquement les cellules tumorales, améliorant ainsi l'efficacité thérapeutique tout en minimisant les dommages aux tissus normaux. Dans l'ensemble, Caliquéamicine γ1I représente une avancée significative dans le développement d'agents chimiothérapeutiques, en particulier dans le contexte des stratégies de traitement ciblées contre le cancer.

Formule : C₅₅H₇₄IN₃O₂₁S₄

InChI : InChI=1S/C55H74IN3O21S4/c1-12-57-30-24-73-35(22-34(30)68-6)78-48-43(63)40(26(3)75-53(48)77-33-17-15-13-14-16-19-55(67)23-32(61)41(58-54(66)72-10)38(33)29(55)18-20-82-84-81-11)59-80-36-21-31(60)50(28(5)74-36)83-51(65)37-25(2)39(56)46(49(71-9)45(37)69-7)79-52-44(64)47(70-8)42(62)27(4)76-52/h13-14,18,26-28,30-31,33-36,40,42-44,47-48,50,52-53,57,59-60,62-64,67H,12,20-24H2,1-11H3,(H,58,66)/b14-13-,29-18+/t26-,27+,28-,30+,31+,33+,34+,35+,36+,40-,42+,43+,44-,47-,48-,50-,52+,53+,55+/m1/s1

Code InChI : InChIKey=HXCHCVDVKSCDHU-PJKCJEBCSA-N

SMILES : O=C(OC)NC=1C(=O)CC2(O)C#CC=CC#CC(OC3OC(C)C(NOC4OC(C)C(SC(=O)C5=C(OC)C(OC)=C(OC6OC(C)C(O)C(OC)C6O)C(I)=C5C)C(O)C4)C(O)C3OC7OCC(NCC)C(OC)C7)C1C2=CCSSSC

Synonymes :

• Benzenecarbothioic acid, 4-((6-deoxy-3-O-methyl-alpha-L-mannopyranosyl)oxy)-3-iodo-5,6-dimethoxy-2-methyl-, 4''-ester with methyl (8-((4,6-dideoxy-2-O-(2,4-dideoxy-4-(ethylamino)-3-O-methyl-alpha-L-threo-pentapyranosyl)-4-(((2,6-dideoxy-4-thio-beta-D-ribo-hexopyranosyl)oxy)amino)-beta-D-glucopyranosyl)oxy)-1-hydroxy-13-(2-(methyltrithio)ethylidene)-11-oxobicyclo(7.3.1)trideca-4,9-diene-2,6-diyn-10-yl)carbamate, (1R-(1R*,4Z,8S*,13E))-
• Benzenecarbothioic acid, 4-[(6-deoxy-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methyl-, 4′′-ester with methyl [8-[[4,6-dideoxy-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-<smallcap>L</smallcap>-threo-pentopyranosyl]-4-[[(2,6-dideoxy-4-thio-β-<smallcap>D</smallcap>-ribo-hexopyranosyl)oxy]amino]-β-<smallcap>D</span>-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]carbamate, [1R-(1R*,4Z,8S*,13E)]-
• Calicheamicin
• Calicheamicin γ₁
• Calicheamicin γ₁^I
• Calicheamicin γ_1α^I
• Calichemicin gamma1
• Calichemicin γ₁
• Carbamic acid, ((1R,4Z,8S,13E)-8-((4,6-dideoxy-4-(((2,6-dideoxy-4-S-(4-((6-deoxy-3-O-methyl-alpha-L-mannopyranopyranosyl)oxy)-3-iodo-5,6-dimethoxy-2-methylbenzoyl)-4-thio-beta-D-ribo-hexopyranosyl)oxy)amino)-2-O-(2,4-dideoxy-4-(ethylamino)-3-O-methyl-alpha-L-threo-pentopyranosyl)-beta-D-glucopyranosyl)oxy)-1-hydroxy-13-(2-(methyltrithio)ethylidene)-11-oxobicyclo(7.3.1)trideca-4,9-diene-2,6-diyn-10-yl)-, methyl ester
• Carbamic acid, N-[(1R,4Z,8S,13E)-8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-<smallcap>D</smallcap>-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-<smallcap>L</smallcap>-threo-pentopyranosyl]-β-<smallcap>D</span>-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-, methyl ester
• Carbamic acid, [(1R,4Z,8S,13E)-8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-<smallcap>D</smallcap>-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-<smallcap>L</smallcap>-threo-pentopyranosyl]-β-<smallcap>D</span>-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-, methyl ester
• Carbamic acid, [8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-<smallcap>D</smallcap>-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-<smallcap>L</smallcap>-threo-pentopyranosyl]-β-<smallcap>D</span>-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-, methyl ester, [1R-(1R*,4Z,8S*,13E)]-
• LL-E 33288γ1-I
• S-(6-{[(5-{[5-(ethylamino)-4-methoxytetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-{[(2S,5Z,9R,13E)-9-hydroxy-12-[(methoxycarbonyl)amino]-13-[2-(methyltrisulfanyl)ethylidene]-11-oxobicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl]oxy}-2-methyltetrahydro-2H-pyran-3-yl)amino]oxy}-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl) 4-[(3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzenecarbothioate (non-preferred name)
• S-[(2R,3S,4S,6S)-6-({[(2R,3S,4S,5R)-5-{[(2S,4S,5S)-5-(ethylamino)-4-methoxytetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-{[(2S,5Z,9S,13E)-9-hydroxy-12-[(methoxycarbonyl)amino]-13-[2-(methyltrisulfanyl)ethylidene]-11-oxobicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl]oxy}-2-methyltetrahydro-2H-pyran-3-yl]amino}oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl] 4-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-3-iodo-5,6-dimethoxy-2-methylbenzenecarbothioate (non-preferred name)
• Benzenecarbothioic acid, 4-[(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methyl-, 4′′-ester with methyl [8-[[4,6-dideoxy-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl]-4-[[(2,6-dideoxy-4-thio-β-D-ribo-hexopyranosyl)oxy]amino]-β-D-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]carbamate, [1R-(1R*,4Z,8S*,13E)]-
• Calicheamicin γ1αI
• Carbamic acid, N-[(1R,4Z,8S,13E)-8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-D-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl]-β-D-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-, methyl ester
• Calichemicin γ1
• Carbamic acid, [(1R,4Z,8S,13E)-8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-D-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl]-β-D-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-, methyl ester

Calicheamicin γ1

CAS : 108212-75-5

• Formule : C₅₅H₇₄IN₃O₂₁S₄
• Masse moléculaire : 1368.37

Calicheamicin γ1

CAS : 108212-75-5

Calicheamicin gamma1 is a cytotoxic agent that exhibits potent antitumor activity. It is a peptide …

• Formule : C₅₅H₇₄IN₃O₂₁S₄
• Degré de pureté : Min. 98 Area-%
• Couleur et forme : Powder
• Masse moléculaire : 1,368.35 g/mol

Calicheamicin

CAS : 108212-75-5

Calicheamicin (Calicheamicin γ1) is an antitumor antibiotic and is a DNA synthesis inhibitor. It also …

• Formule : C₅₅H₇₄IN₃O₂₁S₄
• Degré de pureté : 98.78%
• Couleur et forme : Solid
• Masse moléculaire : 1368.35