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The porphyrin handbook - Kadish K.M.

Kadish K.M. The porphyrin handbook - Academic press, 2000. - 368 p.
Download (direct link): kadishsmishgulilard2000.djvu
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porphyrins containing mono- and di-six-membered ring systems.
Ph
Ph
432
433
434
435
Ph
Ph
R2
436 437
a. R-| = OMe, R2 = H; b. R^ = H, R2 = Me, c. Rj = H, R2 =OMe
220
Pandey and Zheng
Scheme 89. The heme biosynthetic pathway.
Coproporphyrin I Uroporphyrin I
Scheme 90. Cationic dyes as photosensitizers.
0^<N^NH2Cr
C02Et
439 Rhodamine-123
0.5-3.5mg/kg NPe6 followed 4 hours later by 50-100J/ cm2 at 664 nm light.
PDT using NPe6 caused no significant toxicity with the exception of
temporary generalized skin photosensitivity. In all cases, light
treatment caused immediate tissue blanching followed by a marked necrosis
of the tumor mass. Regression of tumor occurred over the course of 24 to
48 hours after the light treatment and was followed by the formation of a
heavy eschar over the tumor site. These data demonstrate that NPe6 is
both an effective and safe photosensitizer for use in PDT.
Lutetium texaphyrin PCI-0123 Lu(Tex) is a water-soluble
photosensitizer with a broad absorption peak centered at 732 nm and
fluorescence emission at 750 nm. Thirty-five patients with cancers
metastatic to the skin or
43 / Porphyrins as Photosensitizers in Photodynamic Therapy
221
Scheme 91. A simple approach for the formation of cationic porphyrins and
chlorins
442
446
Scheme 92. Cationic porphyrins and benzochlorins.
450
Me-
Et Et
vV -Me
V-NH N4 (i) NH2CH2CH2N(CH3)2
F
)= N HN"i. (ii) CH3I
^^co2h
Me Me
452
Et Et
Me

/
v N+ I / \ Me Me
453
222
Pandey and Zheng
Scheme 93. Glycosylated cationic porphyrins.

455 R = Glc OAc
GlcAc =
Glc = (OH
OAc,
OAc
456 R
457 R
458 R
459 R
460 R
461 R'
= Me, R = GlcAc = i-Pr, R = GlcAc = n-Oct, R = GlcAc = Me, R = Glc = i-
Pr, R = Glc = n-Oct, R = Glc
Scheme 94. Cationic phthalocyanines and naphthalocyanines.
464 465
466 X and Y = OPy or H
467 R = GlucOAc, R' = Me
468 R = MaltOAc, R' = Me
469 R = LactOAc, R' = Me
470 R = GlucOAc, R' = bPr
471 R = GlucOAc, R' = n-Oct
43/Porphyrins as Photosensitizers in Photodynamic Therapy
223
Scheme 95. Some novel phthalocyanines and naphthalocyanines.
M = H M = Zn
Nal
CHBr2 NC
CN
CN
NH3
SiCL
474 R = Cl
475 R = OH
476 R = OSi(CH3)2C(CH3)3
477 R = OSi(CH3)2C(CH3)2CH(CH3)2
478 R = OSi(CeH13)3
479 R = OSi(CH3)2C18H37
Table 1. Selected Photosensitizers: Advantages and Disadvantages
Photosensitizer Advantages
Disadvantages Developed by
Photofrin 1. Easy to synthesize 1. Complex
mixture QLT Pharmaceuticals
(porphyrin 2. Easy to formulate 2.
Absorption: 630 nm Vancouver, Canada
Oligomers) 3. Approved worldwide 3. Skin
phototoxicity
m-THPC 1. Easy to synthesize 1. Skin
phototoxicity Scotia Pharmaceuticals
(a chlorin) 2. Very effective Photosensitizer 2. Light
treatment 7-9 Guildford, England
3. Long-wavelength absorption (650 nm) days after
injection.
BPD 1. Long-wavelength absorption (690 nm) 1.
Difficult to synthesize QLT Pharmaceutical
(a chlorin) 2. No skin phototoxicity 2. Clears
rapidly, effective only if the tumors Vancouver, Canada
are
treated with light 3 h post inj. of the drug
NPe6 1. Easy to synthesize 1. Rapidly
cleared from the circulation; Nippon, Japan
(a chlorin) 2. No skin phototoxicity successful
treatment depends on
3. Easy to formulate the
presence of the drug levels in the plasma; levels in
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