HCID 178435490, compound → HCID 178435498, compound

HRID 548537Notes

Reaction equation

HRID 548537 reaction equation
[CH3:1][CH2:2][C:3]1[C:21]2=[N:22][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[CH:34]([CH3:35])[CH:33]([CH2:36][CH2:37][C:38]([O:40]C)=[O:39])[C:15]([C:16]5[CH:27](C(OC)=O)[C:25](=[O:26])[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:32])=[CH:20]2)=[N:14]4)=[C:9]([CH3:42])[C:8]=3[CH:43]=[CH2:44])[C:4]=1[CH3:45].CCC1C(C)=C2NC=1C=C1N=C3C(C(C(C(OC)=O)C3=C3N=C(C=C4NC(=C2)C(C=C)=C4C)C(C)C3CCC(OC)=O)=O)=C1C>>[CH3:1][CH2:2][C:3]1[C:4]([CH3:45])=[C:5]2[NH:22][C:21]=1[CH:20]=[C:19]1[C:23]([CH3:32])=[C:24]3[C:25]([CH2:27][C:16]([C:17]3=[N:18]1)=[C:15]1[C@@H:33]([CH2:36][CH2:37][C:38]([OH:40])=[O:39])[C@H:34]([CH3:35])[C:13]([NH:14]1)=[CH:12][C:10]1=[N:11][C:7]([C:8]([CH:43]=[CH2:44])=[C:9]1[CH3:42])=[CH:6]2)=[O:26]

Participants

3

Reactant 2

HCID 178435490HCID 178435490, compoundHCID 178435494HCID 178435494, compound

Product 1

HCID 178435498HCID 178435498, compound

Procedure

Materials and General Methods. Melting points are uncorrected. UV-vis spectra were recorded on a Beckman DU-600 or a Perkin-Elmer Lambda spectrophotometer. Fluorescence emission was measured with a Perkin-Elmer LS-50B fluorometer. 1H NMR spectra were recorded on a Bruker ASPECT 360 MHz instrument. ESI-MS and HRMS spectrometry analysis were performed at the Mass Spectrometry Facility of the Department of Chemistry, University of Pennsylvania. Methyl pheophorbide a was obtained from Spirulina pacifica algae available from Cyanotech Corp., Hawaii. Purpurin-18 methyl ester (1) was synthesized from methyl pheophorbide according to a literature procedure. (Zheng, G.; Li, H.; Zhang, M.; Lund-Katz, S.; Chance, B.; Glickson, J. D., Low-density lipoprotein reconstituted by pyropheophorbide cholesteryl oleate as target-specific photosensitizer. Bioconjugate Chemistry 2002, 13, (3), 392-396.) Bacteriochlorophyll a (BChl) was extracted from R. Sphaeroides biomass purchased from Frontier Science, Utah. Bacteriopurpurin-18 methyl ester (6) and bacteriopheophorbide a methyl ester (11) were synthesized from BChl according to previously described procedures. (Kozyrev, A. N.; Zheng, G.; Zhu, C. F.; Dougherty, T. J.; Smith, K. M.; Pandey, R. K., Syntheses of stable bacteriochlorophyll-a derivatives as potential photosensitizers for photodynamic therapy. Tetrahedron Letters 1996, 37, (36), 6431-6434; Hartwich, G.; Fiedor, L.; Simonin, I.; Cmiel, E.; Schafer, W.; Noy, D.; Scherz, A.; Scheer, H., Metal-substituted bacteriochlorophylls. 1. Preparation and influence of metal and coordination on spectra. Journal of the American Chemical Society 1998, 120, (15), 3675-3683). Other chemicals were purchased from Aldrich. Where necessary, solvents were dried before use. For TLC, EM Science TLC plates (silica gel 60 F254) were used. Purity of the final conjugates was validated by reverse phase HPLC using a Waters Delta-600 analytical/semi-preparation system equipped with photodiode array and fluorescence detectors.

Workup

  1. extraction(Zheng, G.; Li, H.; Zhang, M.; Lund-Katz, S.; Chance, B.; Glickson, J. D., Low-density lipoprotein reconstituted by pyropheophorbide cholesteryl oleate as target-specific photosensitizer. Bioconjugate Chemistry 2002, 13, (3), 392-396.) Bacteriochlorophyll a (BChl) was extracted from R
  2. customPreparation and influence of metal and coordination on spectra
  3. customWhere necessary, solvents were dried before use
  4. customequipped with photodiode array and fluorescence detectors

Sources & evidence

ORD record
ord-78782f0dd6414fbaad6964a973483c71
Source dataset
uspto-grants-2011_05
Patent number
US07943586B2

Reaction notes

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