202
S. D. Shnyder and C. W. Wright
60. Ansah C, Mensah KB (2013) A review of the anticancer potential of the antimalarial herbal
Cryptolepis sanguinolenta and its major alkaloid cryptolepine. Ghana Med J 47:137
61. Ahmed F, Toume K, Ohtsuki T, Rahman M, Sadhu SK, Ishibashi M (2011) Cryptolepine,
isolated from Sida acuta, sensitizes human gastric adenocarcinoma cells to TRAIL-induced
apoptosis. Phytother Res 25:147
62. Pal HC, Katiyar SK (2016) Cryptolepine, a plant alkaloid, inhibits the growth of non-melanoma
skin cancer cells through inhibition of topoisomerase and induction of DNA damage. Molecules
21:1758
63. Ladame S, Schouten JA, Stuart J, Roldan J, Neidle S, Balasubramanian S (2004) Tetrapeptides
induce selective recognition for G-quadruplexes when conjugated to a DNA-binding platform.
Org Biomol Chem 2:2925
64. Long Y, Li Z, Tan JH, Ou TM, Li D, Gu LQ, Huang ZS (2012) Benzofuroquinoline derivatives
had remarkable improvement of their selectivity for telomeric G-quadruplex DNA over duplex
DNA upon introduction of peptidyl group. Bioconjug Chem 23:1821
65. Lavrado J, Reszka AP, Moreira R, Neidle S, Paulo A (2010) C-11 diamino cryptolepine
derivatives NSC748392, NSC748393, and NSC748394: anticancer profile and G-quadruplex
stabilization. Bioorg Med Chem Lett 20:7042
66. Lavrado J, Borralho PM, Ohnmacht SA, Castro RE, Rodrigues CM, Moreira R, dos Santos
DJ, Neidle S, Paulo A (2013) Synthesis, G-quadruplex stabilization, docking studies, and
effect on cancer cells of indolo[3,2-b]quinolines with one, two, or three basic side chains.
ChemMedChem 8:1648
67. Shen FH, Jin J, Li J, Wang Y, Zhu SH, Lu YJ, Ou TM, Huang ZS, Huang M, Huang ZY
(2013) The G-quadruplex ligand, SYUIQ-FM05, targets proto-oncogene c-kit transcription
and induces apoptosis in K562 cells. Pharm Biol 51:447
68. Le Gresley A, Gudivaka V, Carrington S, Sinclair A, Brown JE (2016) Synthesis, analysis and
biological evaluation of novel indolquinonecryptolepine analogues as potential anti-tumour
agents. Org Biomol Chem 14:3069
69. Zhou WJ, Deng R, Feng GK, Zhu XF (2009) A G-quadruplex ligand SYUIQ-5 induces
autophagy by inhibiting the Akt-FOXO3, a pathway in nasopharyngeal cancer cells. Chin
J Cancer 28:1049
70. Kuntworbe N, Alany RG, Brimble M, Al-Kassas R (2013) Determination of pKa and forced
degradation of the indoloquinoline antimalarial compound cryptolepine hydrochloride. Pharm
Dev Tech 18:866
71. Kwakye RA, Kuntworbe N, Ofori-Kwakye K, Osei YA (2018) Detection, quantification
and investigation of the red blood cell partitioning of cryptolepine hydrochloride. J Pharm
Pharmacogn Res 6:260
72. Stell JGP, Wheelhouse RT, Wright CW (2011) Metabolism of cryptolepine and 2fluorocryptolepine by aldehyde oxidase. J Pharm Pharmac 64:237
73. Forkuo AD, Ansah C, Pearson D, Gertsch W, Cirello A, Amaral A, Spear J, Wright CW, Rynn C
(2017) Identification of cryptolepine metabolites in rat and human hepatocytes and metabolism
and pharmacokinetics of cryptolepine in Sprague Dawley rats. BMC Pharmacol Toxicol 18:84
74. Rojas M, Wright CW, Piña B, Portugal J (2008) Genomewide expression profiling of
cryptolepine-induced toxicity in Saccharomyces cerevisiae. Antimicrob Agents Chemother
52:3844
75. Ansah C, Khan A, Gooderham NJ (2005) In vitro genotoxicity of the West African anti-malarial
herbal Cryptolepis sanguinolenta and its major alkaloid cryptolepine. Toxicology 298:141
76. Gopalan R, Emerce E, Wright CW, Karahalil B, Larakaya AE, Anderson D (2011) Effects of
the anti-malarial compound cryptolepine and its analogues in human lymphocytes and sperm
in the Comet assay. Toxicol Lett 207:322
77. Mensah KB, Benneh C, Forkuo AD, Ansah C (2019) Cryptolepine, the main alkaloid of the antimalarial Cryptolepis sanguinolenta (Lindl.) Schlechter, induces malformations in zebrafish
embryos. Biochem Res Int 2019:7076986
78. Mariz IFA, Pinto S, Lavrado J, Paulo A, Martinho JMG, Maçôas EMS (2017) Cryptolepine
and quindoline: understanding their photophysics. PhysChem Chem Phys 19:10255
S. D. Shnyder and C. W. Wright
60. Ansah C, Mensah KB (2013) A review of the anticancer potential of the antimalarial herbal
Cryptolepis sanguinolenta and its major alkaloid cryptolepine. Ghana Med J 47:137
61. Ahmed F, Toume K, Ohtsuki T, Rahman M, Sadhu SK, Ishibashi M (2011) Cryptolepine,
isolated from Sida acuta, sensitizes human gastric adenocarcinoma cells to TRAIL-induced
apoptosis. Phytother Res 25:147
62. Pal HC, Katiyar SK (2016) Cryptolepine, a plant alkaloid, inhibits the growth of non-melanoma
skin cancer cells through inhibition of topoisomerase and induction of DNA damage. Molecules
21:1758
63. Ladame S, Schouten JA, Stuart J, Roldan J, Neidle S, Balasubramanian S (2004) Tetrapeptides
induce selective recognition for G-quadruplexes when conjugated to a DNA-binding platform.
Org Biomol Chem 2:2925
64. Long Y, Li Z, Tan JH, Ou TM, Li D, Gu LQ, Huang ZS (2012) Benzofuroquinoline derivatives
had remarkable improvement of their selectivity for telomeric G-quadruplex DNA over duplex
DNA upon introduction of peptidyl group. Bioconjug Chem 23:1821
65. Lavrado J, Reszka AP, Moreira R, Neidle S, Paulo A (2010) C-11 diamino cryptolepine
derivatives NSC748392, NSC748393, and NSC748394: anticancer profile and G-quadruplex
stabilization. Bioorg Med Chem Lett 20:7042
66. Lavrado J, Borralho PM, Ohnmacht SA, Castro RE, Rodrigues CM, Moreira R, dos Santos
DJ, Neidle S, Paulo A (2013) Synthesis, G-quadruplex stabilization, docking studies, and
effect on cancer cells of indolo[3,2-b]quinolines with one, two, or three basic side chains.
ChemMedChem 8:1648
67. Shen FH, Jin J, Li J, Wang Y, Zhu SH, Lu YJ, Ou TM, Huang ZS, Huang M, Huang ZY
(2013) The G-quadruplex ligand, SYUIQ-FM05, targets proto-oncogene c-kit transcription
and induces apoptosis in K562 cells. Pharm Biol 51:447
68. Le Gresley A, Gudivaka V, Carrington S, Sinclair A, Brown JE (2016) Synthesis, analysis and
biological evaluation of novel indolquinonecryptolepine analogues as potential anti-tumour
agents. Org Biomol Chem 14:3069
69. Zhou WJ, Deng R, Feng GK, Zhu XF (2009) A G-quadruplex ligand SYUIQ-5 induces
autophagy by inhibiting the Akt-FOXO3, a pathway in nasopharyngeal cancer cells. Chin
J Cancer 28:1049
70. Kuntworbe N, Alany RG, Brimble M, Al-Kassas R (2013) Determination of pKa and forced
degradation of the indoloquinoline antimalarial compound cryptolepine hydrochloride. Pharm
Dev Tech 18:866
71. Kwakye RA, Kuntworbe N, Ofori-Kwakye K, Osei YA (2018) Detection, quantification
and investigation of the red blood cell partitioning of cryptolepine hydrochloride. J Pharm
Pharmacogn Res 6:260
72. Stell JGP, Wheelhouse RT, Wright CW (2011) Metabolism of cryptolepine and 2fluorocryptolepine by aldehyde oxidase. J Pharm Pharmac 64:237
73. Forkuo AD, Ansah C, Pearson D, Gertsch W, Cirello A, Amaral A, Spear J, Wright CW, Rynn C
(2017) Identification of cryptolepine metabolites in rat and human hepatocytes and metabolism
and pharmacokinetics of cryptolepine in Sprague Dawley rats. BMC Pharmacol Toxicol 18:84
74. Rojas M, Wright CW, Piña B, Portugal J (2008) Genomewide expression profiling of
cryptolepine-induced toxicity in Saccharomyces cerevisiae. Antimicrob Agents Chemother
52:3844
75. Ansah C, Khan A, Gooderham NJ (2005) In vitro genotoxicity of the West African anti-malarial
herbal Cryptolepis sanguinolenta and its major alkaloid cryptolepine. Toxicology 298:141
76. Gopalan R, Emerce E, Wright CW, Karahalil B, Larakaya AE, Anderson D (2011) Effects of
the anti-malarial compound cryptolepine and its analogues in human lymphocytes and sperm
in the Comet assay. Toxicol Lett 207:322
77. Mensah KB, Benneh C, Forkuo AD, Ansah C (2019) Cryptolepine, the main alkaloid of the antimalarial Cryptolepis sanguinolenta (Lindl.) Schlechter, induces malformations in zebrafish
embryos. Biochem Res Int 2019:7076986
78. Mariz IFA, Pinto S, Lavrado J, Paulo A, Martinho JMG, Maçôas EMS (2017) Cryptolepine
and quindoline: understanding their photophysics. PhysChem Chem Phys 19:10255